- Pd-carbene catalyzed carbonylation reactions of aryl iodides
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A series of carbene complexes [PdBr2(iPr 2-bimy)L] (C2-C13) with different types of co-ligands (L) have been tested for their catalytic activities in the carbonylative annulation of 2-iodophenol with phenylacetylene in DMF to afford the respective flavone 2a. Complex C12 with an N-phenylimidazole co-ligand showed the best activity and also afforded high yields when the substrate scope was extended to other aryl or pyridyl acetylenes. In addition, catalyst C12 was also efficient in the carbonylative annulation of 2-iodoaniline with acid chlorides giving the desirable 2-substituted 4H-3,1-benzoxazin-4-ones (4) in good yields. Additionally, this Pd-NHC complex also proved to be a very efficient catalyst for the hydroxycarbonylation of iodobenzene derivatives at low catalyst loading and under low CO pressure. These results demonstrate the versatility and efficiency of this phosphine-free Pd(ii)-NHC complex in different types of carbonylations of aryl iodides under mild conditions. The Royal Society of Chemistry 2011.
- Xue, Liqin,Shi, Lijun,Han, Yuan,Xia, Chungu,Huynh, Han Vinh,Li, Fuwei
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- Visible Light Photocatalytic Aerobic Oxygenation of Indoles and pH as a Chemoselective Switch
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An efficient chemodivergent strategy for visible light photocatalysis is developed. In the presence of a dicyanopyrazine-derived chromophore (DPZ) photocatalyst, aerobic photooxygenation of indoles could produce either isatins or formylformanilides in satisfactory yields by judiciously selecting inorganic salts or modulating the reaction pH. The current chemodivergent method is also effective with 2-substituted indoles, opening straightforward synthetic routes to valuable 2,2-disubstituted 3-oxindoles, formylformanilide derivatives, and benzoxazinones. Mechanistic investigations involving cyclic voltammetry studies further confirm that reaction pH influences the electrochemical properties of DPZ, thus affecting the oxidative pathway by which indoles are being transformed.
- Zhang, Chenhao,Li, Sanliang,Bure?, Filip,Lee, Richmond,Ye, Xinyi,Jiang, Zhiyong
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- Reaction of Anthranilic Acid with Orthoesters: A New Facile One-pot Synthesis of 2-Substituted 4H-3,1-Benzoxazin4-ones
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The synthesis of 2-substituted 4H-3,1-benzoxazin-4-ones by the condensation of anthranilic acid and orthoesters under classical heating and microwave irradiation is described.
- Khajavi, Mohammad S.,Montazari, Nasser,Sadat Hosseini
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- Design, synthesis and in vivo screening of some novel quinazoline analogs as anti-hyperlipidemic and hypoglycemic agents
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A novel series of substituted quinazoline derivatives were designed, synthesized and evaluated for their hypolipidemic activity in cholesterol induced hyperlipidemic rats. In vivo screening concluded that compounds A-4, C-5 and C-6 have shown potent antihyperlipidemic activity by decreasing the plasma level of triglycerides (TG), very low density lipoprotein (VLDL), low density lipoprotein (LDL), followed by increase in level of high density lipoprotein (HDL).
- Mokale, Santosh N.,Palkar, Akash D.,Dube, Pritam N.,Sakle, Nikhil S.,Miniyar, Pankaj B.
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- Synthesis of some new benzoxazine derivatives of biological interest
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The synthesis of a number of biologically important imino-quinazolones has been achieved by the condensation of 3-amino-2-aryl-4-quinazolone and aromatic aldehydes.
- Verma, Manjusha,Singh, Sundaram,Singh
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- A new series of Schiff base derivatives bearing 1,2,3-triazole: Design, synthesis, molecular docking, and α-glucosidase inhibition
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A series of new Schiff bases bearing 1,2,3-triazole 12a?o was designed, synthesized, and evaluated as α-glucosidase inhibitors. All the synthesized compounds showed promising inhibition against α-glucosidase and were more potent than the standard drug aca
- Nasli-Esfahani, Ensieh,Mohammadi-Khanaposhtani, Maryam,Rezaei, Sepideh,Sarrafi, Yaghoub,Sharafi, Zeinab,Samadi, Nasser,Faramarzi, Mohammad Ali,Bandarian, Fatemeh,Hamedifar, Haleh,Larijani, Bagher,Hajimiri, Mirhamed,Mahdavi, Mohammad
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- 4H-Benzo[d][1,3]oxazin-4-ones and Dihydro analogs from substituted anthranilic acids and orthoesters
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A one-pot route to 2-alkyl and 2-aryl-4H-benzo[d][1,3]oxazin-4-ones (also known as 4H-3,1-benzoxazin-4-ones) has been developed and studied. The method involves the reaction of aryl-substitutedanthranilic acidswithorthoesters inethanol catalyzedby acetic acid. Additionally,wehave also investigated the reaction under microwave conditions. Not all of the substrates were successful in yielding the target heterocycles as some of the reactions failed to undergo the final elimination. This process led to the isolation of (±)-2-alkyl/aryl-2-ethoxy-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-ones. The formation of the dihydro analogs correlated with the electron density on the aromatic ring: Electron-donating groups favored the 4H- benzo[d][1,3]oxazin-4-ones, while electron-withdrawing groups tended to favor the dihydro product. Substituting a pyridine ring for the benzene ring in the substrate acid suppressed the reaction.
- Annor-Gyamfi, Joel K.,Bunce, Richard A.
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- In vitro bacteriostatic and DNA interaction studies of drug-based mixed-ligand complexes of cobalt(II)
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The dinuclear cobalt(II) complexes with ciprofloxacin and bidentate ligands were synthesized and characterized using infrared spectra, electronic spectra, magnetic measurements, elemental analyses, thermal investigation, and mass spectroscopy. Here in we
- Patel, Mohan,Chhasatia, Mehul,Bhatt, Bhupesh
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- Synthesis, characterization, and screening for analgesic and anti-inflammatory activities of new 1,3,4-oxadiazole derivatives linked to quinazolin-4-one ring
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In the present study, several new 1,3,4-oxadiazole derivatives linked with quinazolin-4-one moiety were synthesized by following steps. 2-methyl -4H-3, 1-benzoxazin-4-one, and 2-phenyl -4H-3, 1-benzoxazin-4-one were synthesized in the first and second step by stirring anthranilic acid in pyridine with benzoyl chloride and with an acetic anhydride for 30 min at room temperature. On treatment with semicarbazide with the above synthesized intermediates, that is, 2-methyl-4H-3,1-benzoxazin-4-one, and 2-phenyl-4H-3,1-benzoxazin-4-one in the third step afforded 2-methyl-4-oxoquinazoline-3(4H)-carbohydrazide and 2-phenyl-4-oxoquinazoline-3(4H)-carbohydrazide. These were introduced in cyclization reaction with different aromatic acids, aromatic aldehydes, and carbon disulfide in the next step, producing the corresponding 3-(4-acetyl-5-aryl-4,5-dihydro-1,3,4-oxadiazol-2-yl)-2-phenyl-quinazolin-4(3H)-one derivatives, 3-(4-acetyl-5-aryl-4,5-dihydro-1,3,4-oxadiazol-2-yl)-2-methyl-quinazolin-4(3H)-one derivatives, 3-(5-aryl-1,3,4-oxadiazol-2-yl)-2-phenylquinazolin-4(3H)-one derivatives and 3-(5-aryl-1,3,4-oxadiazol-2-yl)-2-methylquinazolin-4(3H)-one derivatives. Purity of these synthesized derivatives was confirmed by thin layer chromatography, melting point. Structure of the derivatives was set up by determining infrared spectroscopy, nuclear magnetic resonance, and mass spectroscopy. All the synthesized derivatives were evaluated for their analgesic and anti-inflammatory activities in mice and rats. In animal studies, the derivatives 3-[4-acetyl-5-(2-hydroxyphenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-2-phenylquinazolin-4(3H)-one and 3-[4-acetyl-5-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-2-phenylquinazolin-4(3H)-one shown more potent analgesic activity and the derivatives 3-[4-acetyl-5-(4-methoxyphenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-2-phenylquinazolin-4(3H)-one and 3-[4-acetyl-5-(4-methoxyphenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-2-methylquinazolin-4(3H)-one shown more potent anti-inflammatory activity as compared to other derivatives. The results of current study indicate that cyclization of carbohydrazide group of intermediate 2-methyl-4-oxoquinazoline-3(4H)-carbohydrazide and 2-phenyl-4-oxoquinazoline-3(4H)-carbohydrazide with different aromatic acids, aromatic aldehydes, and carbon disulfide produces novel quinazolin-4-one linked oxadiazole derivatives with potent analgesic and anti-inflammatory activities.
- Dewangan, Dhansay,Verma, Vinay Sagar,Nakhate, Kartik T.,Tripathi, Dulal Krishna,Kashyap, Pranita,Dhongade, Hemant
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- Silica-bound benzoyl chloride mediated the solid-phase synthesis of 4H-3, 1-benzoxazin-4-ones
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The solid-phase synthesis of 4H-3, 1-benzoxazin-4-ones was achieved using silica-bound benzoyl chloride (SBBC) as dehydrating agent in reaction with 2-acylaminobenzoic acids. The silica-grafted reagent (SBBC) was simply recovered after reaction and reused several times.
- Rad-Moghadam, Kurosh,Rouhi, Somayeh
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- Palladium (0)-catalyzed C(sp2)-H oxygenation with carboxylic acids
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Palladium (0)-catalyzed Ortho-benzoxylation of the sp2 C–H bond of arylbenzoxazinones with carboxylic acid is reported. With benzoxazinone as directing group, the reaction went smoothly under the benign condition and gave the desired product wi
- Gong, Ai-Jun,Li, Xu-Qin,Vu, Huu-Manh,Yong, Jia-Yuan
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- Design, synthesis and assessment of new series of quinazolinone derivatives as EGFR inhibitors along with their cytotoxic evaluation against MCF7 and A549 cancer cell lines
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New acetamide (IV a-e) and 1,3-thiazolidinone derivatives (VII a-e) were designed, synthesized and assessed for their cytotoxic activity against MCF-7 and A549 cell lines along with their lead compounds (erlotinib and gefitinib). The newly designed compou
- Aziz, Marian W.,Kamal, Aliaa M.,Mohamed, Khaled O.,Elgendy, Adel A.
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- Design, synthesis, docking studies and biological evaluation of 2-phenyl-3-(Substituted benzo[d] thiazol-2-ylamino)-quinazoline-4(3H)-one derivatives as antimicrobial agents
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Objective: A new series 2-phenyl-3-(substituted benzo[d] thiazol-2-ylamino)-quinazoline-4(3H)-one was prepared by the fusion method by reacting 2-phenyl benzoxazine with 2-hydrazino benzothiazole and it was evaluated for their antimicrobial activity against gram positive, gram negative bacteria and fungi. Methods: Titled compounds were synthesized by fusion reactions. These compounds were evaluated by in vitro antibacterial and antifungal activity using the minimum inhibitory concentration and zone of inhibition methods. The synthesized compounds were characterized with the help of infrared, NMR and mass spectral studies. The benzothiazole moiety and the quinazoline ring have previously shown DNA gyrase inhibition and target related antibacterial activity. Thus, molecular docking studies of synthesized compounds were carried out (PDB: 3G75) to study the possible interaction of compounds with the target. The batch grid docking was performed to determine the probable. Results: These compounds showed significant activity against gram positive and gram negative bacteria as well against the fungi. The compound A5 was found to be active against B. subtilis, P aeruginosa and C. albican at 12.5 μg/ml MIC. The compound A3 was found to be active against all microbial strains selected at 25 and 12.5 μg/ml MIC. Conclusion: Though the relationship between the activities shown by these compounds in, the antimicrobial study is still to be established, the docking studies conducted found to be consistent with antimicrobial results. Thus the results indicate that the designed structure can be a potential lead as an antimicrobial agent.
- Pisal, Pooja,Deodhar, Meenakshi,Kale, Amol,Nigade, Ganesh,Pawar, Smita
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- Synthesis, characterization and antimicrobial activity of new 2-phenylquinoline-4(3H)-one derivatives
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Quinazolinones is an important chemical synthesis with different physiological significance and pharmacological utility. Reaction of anthranilic acid with benzoyl chloride in pyridine yielded 2-phenyl-4H-benzo[d][1,3]oxazin-4-one, which on condensation reaction with the tryptophan in glacial acetic acid afforded 3-(1H-indol-3-yl)-2-(4-oxo-2-phenylquinazolin-3(4H)-yl) propanoic acid (2). Treatment of compound (2) with thionyl chloride produced 3-(1H-indol-3-yl)-2-(4-oxo-2-phenylquinazolin-3(4H)-yl) propanoyl chloride (3).Condensation of compound (3) with hydrazine hydrate gave 3-(1H-indol-3-yl)-2-(4-oxo-2-phenylquinazolin-3(4H)-yl) propanehydrazide (4). Condensation of compound (4) with ethyl aceto acetate in glacial acetic acid yielded 3-(3-(1H-indol-3-yl)-1-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)-1-oxopropan-2-yl)-2-phenylquinazolin-4(3H)-one (5). The reaction of compound (4) with carbon disulfide and sodium hydroxide yielded3-(2-(1H-indol-3-yl)-1-(5-mercapto-1,3,4-oxadiazol-2-yl) ethyl)-2-phenylquinazolin-4(3H)-one (6).Condensation of compound (6) with hydrazine hydrate afforded 2-hydrazinyl-5- (2-(1H-indol-3-yl) ethyl)-2-phenylquinazolin-4(3H)-one(7). Compound (8) 2-(3-(1H-indol-3-yl)-2-(4-oxo-2-phenylquinazolin-3(4H)-yl)propanoyl)-2,3-dihydrophthalazine-1,4-dione was synthesized by condensing compound (4) with phthalic anhydride in glacial acetic acid. When compound (4) was reacted with different aromatic aldehydes in abs. ethanol afforded different substituted (9a-d).Moreover, N-(1,5-dioxo-3-substituted-1,5-dihydrobenzo[e][1,3] oxazepin-4(3H)-yl)-3-(1H-indol-3-yl)-2-(4-oxo-2-phenylquinazolin-3(4H)-yl) propanamide (10a,b) were prepared from the cyclic condensation of Schiff bases compounds with phthalic anhydride. The structures of newly synthesized compounds were characterized by m.p., TLC, FTIR and 1H, 13C-NMR spectral analysis. The antimicrobial activity of the synthesized phenylquinazoline on two kinds of bacteria namely, staphylococcus aureous and Escherichia coli was investigated.
- Samir, Ali Hammadi
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- Design, molecular docking, in vitro, and in vivo studies of new quinazolin-4(3H)-ones as VEGFR-2 inhibitors with potential activity against hepatocellular carcinoma
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A series of new VEGFR-2 inhibitors were designed, synthesized and evaluated for their anti-proliferative activities against hepatocellular carcinoma (HepG-2 cell line). Compound 29b (IC50 = 4.33 ± 0.2 μg/ml) was found to be the most potent derivative as it has showed to be more active than doxorubicin (IC50 = 4.50 ± 0.2 μg/ml) and 78% of sorafenib activity (IC50 = 3.40 ± 0.25 μg/ml). The inhibitory profiles against VEGFR-2 were also assessed for the most promising candidates (16b, 20c, 22b, 24a, 24b, 28c, 28e, 29a, 29b and 29c). Compounds 29b, 29c and 29a exhibited potent inhibitory activities towards VEGFR-2 at IC50 values of 3.1 ± 0.04, 3.4 ± 0.05 and 3.7 ± 0.06 μM, respectively, comparing sorafenib (IC50 = 2.4 ± 0.05 μM). Furthermorer, compound 29b induced apoptosis and arrested the cell cycle growth at G2/M phase. Additionally, in vivo antitumor experiments revealed that compounds 29b and 29c have significant tumor growth inhibition. The test of immuno-histochemical expression of activated caspase-3 revealed that there is a time-dependent increase in cleaved caspase-3 protein expression upon exposure of HepG-2 cells to compound 29b. Moreover, the fibroblastic proliferative index test revealed that compound 29b could attenuate liver fibrosis. Docking studies also supported the results concluded from the biological screening via prediction of the possible binding interactions of the target compounds with VEGFR-2 active sites using the crystal structure of VEGFR-2 downloaded from the Protein Data Bank, (PDB ID: 2OH4) using Discovery Studio 2.5 software. Further structural optimization of the most active candidates may serve as a useful strategy for getting new lead compounds in search for powerful and selective antineoplastic agents.
- Eissa, Ibrahim.H.,Ibrahim, Mohammed K.,Metwaly, Ahmed M.,Belal, Amany,Mehany, Ahmed B.M.,Abdelhady, Alsayed A.,Elhendawy, Mostafa A.,Radwan, Mohamed M.,ElSohly, Mahmoud A.,Mahdy, Hazem A.
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- A general palladium-catalyzed carbonylative synthesis of 2-alkylbenzoxazinones from 2-bromoanilines and acid anhydrides
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(C), its (O)K! An efficient palladium-catalyzed carbonylative synthesis of 2-alkylbenzoxazinones has been developed (see scheme). By starting from 2-bromoanilines and acid anhydrides, the corresponding products were isolated in good yields. Copyright
- Wu, Xiao-Feng,Neumann, Helfried,Beller, Matthias
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- Synthesis, Characterization, and Screening for Analgesic and Anti-Inflammatory Activities of Schiff Bases of 1,3,4-Oxadiazoles Linked With Quinazolin-4-One
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Sixteen Schiff bases of quinazolin-4-one-linked 1,3,4-oxadiazoles were synthesized by reaction with different aromatic aldehydes. Purity of newly synthesized derivatives was confirmed through thin-layer chromatography, combustion analysis, and melting poi
- Dewangan, Dhansay,Nakhate, Kartik T.,Verma, Vinay Sagar,Nagori, Kushagra,Tripathi, Dulal Krishna
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- Silver and Palladium Cocatalyzed Carbonylative Activation of Benzotriazoles to Benzoxazinones under Neutral Conditions
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A novel and efficient method for the carbonylative activation of benzotriazoles to benzoxazinones has been developed. By using a silver and palladium bimetallic catalyst system, a broad range of benzotriazoles were transformed into the corresponding benzoxazinones in moderate to good yields with excellent functional group tolerance. Notably, this procedure proceeds under neutral conditions.
- Yin, Zhiping,Wang, Zechao,Wu, Xiao-Feng
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- Synthesis and antiviral bioactivities of 2-aryl- or 2-methyl-3- (substituted- benzalamino)-4(3H)-quinazolinone derivatives
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A simple and general method has been developed for the synthesis of various 4(3H)-quinazolinone derivatives by the treatment of the appropriate 3-amino-2-aryl-4(3H)-quinazolinone with a substituted benzaldehyde in ethanol. The structures of the compounds were characterized by elemental analysis, IR, 1H-NMR and 13C-NMR spectra. The title 2-aryl- or 2-methyl-3-(substituted-benzalamino)-4(3H)-quinazolinone compounds III-1-III-31 were found to possess moderate to good antiviral activity. Semi-quantitative PCR and Real Time PCR assays were used to ascertain the target of action of compound III-31 against TMV. The studies suggest that III-31 possesses antiviral activity due to induction of up-regulation of PR-1a and PR-5, thereby inhibiting virus proliferation and movement by enhancement of the activity of some defensive enzyme.
- Gao, Xingwen,Cai, Xuejian,Yan, Kai,Song, Baoan,Gao, Lili,Chen, Zhuo
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- RETRACTED ARTICLE: Palladium-Catalyzed Decarboxylative Selective Acylation of 4H-Benzo[d][1,3]oxazin-4-one Derivatives with α-Oxo Carboxylic acids via Preferential Cyclic Imine-N-Directed Aryl C-H Activation
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The benzoxazine scaffolds are of much interest as they are found in a large array of natural products and pharmaceutical drugs with diverse activities. We have developed a palladium-catalyzed decarboxylative selective mono- and bis-acylation of 4H-benzo[d
- Majhi, Biju,Kundu, Debasish,Ghosh, Tubai,Ranu, Brindaban C.
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- Recyclable keggin heteropolyacids as an environmentally benign catalyst for the synthesis of new 2-benzoylamino-n-phenyl-benzamide derivatives under microwave irradiations at solvent-free conditions and the evaluation of biological activity
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2-Benzoylamino-N-phenyl-benzamide derivatives (5a–h) were prepared from 2-phenyl-3,1-(4H)-benzoxazin-4-one 3 and substituted anilines 4a–h in the presence of a Keggin-type heteropolyacids series (H3PW12O40·13H2O
- Ighilahriz-Boubchir, Karima,Boutemeur-Kheddis, Baya,Rabia, Cherifa,Makhloufi-Chebli, Malika,Hamdi, Maamar,Silva, Artur M. S.
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- Synthesis and antimicrobial activity of 2-Aryl-4H-3,1-benzoxazin-4-ones
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Twenty derivatives of 2-aryl-4H-3,1-benzoxazin-4-one synthesized and their potential therapeutically significance tested against two strains of Gram positive bacteria (Staphylococcus aureus and Bacillus subtilis) and four strains of Gram negative bacteria (Shigella flexnari, Escherichia coli, Salmonella typhi and Pseudomonas aeruginsoa) by agar well diffusion method. The 2-(3-nitrophenyl)-4H-3,1-benzoxazin-4-one (3f) recorded significant antibacterial activity against Bacillus subtilis whereas 2-(4-bromophenyl)-4H-3, 1-benzoxazin-one (3o) exhibited weak antibacterial activity against Staphylococcus aureus. Further 2-(2-methylphenyl)-4H-3,1-benzoxazin-4-one (3b) showed significant activity against Shigella Flexnari, Escherichia coli, Pseudomonas aeruginsoa and Salmonella typhi. The antibacterial activity of synthesized derivatives of 2-aryl-4H-3,1-benzoxazin-4-one was compared to reference standard antibiotics amoxycillin, streptomycin, kanamycin and ciprofloxacin. The present study revealed that 2-aryl-4H-3,1-benzoxazin-4-ones possess good bactericidal activity against a panel of bacteria causing common bacterial diseases and therefore opens the possibility of finding latest clinically useful antibacterial compounds. The synthesized compounds were characterized by 1H NMR, EI, FT-IR and elemental analysis.
- Khan, Zulfiqar Ali,Naqvi, Syed Ali Raza,Shahzad, Sohail Anjum,Mahmood, Nasir,Yar, Muhammad,Zahoor, Ameer Fawad
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- New-route to synthesis and QSAR study of 1,2,4-aryl substituted triazoles
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Several substituted 1,2,4-triazoles have been synthesized by a new route and characterized by IR, NMR, mass spectral, and x-ray diffraction studies. The computer programme PASS for the prediction of biological activities established that these compounds a
- Deshmukh,Suryawanshi,Mali,Desai, S.R. Dhongade
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- Silver- versus gold-catalyzed sequential oxidative cyclization of unprotected 2-alkynylanilines with oxone
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Unprecedented domino oxidative cyclization reactions of unprotected 2-alkynylanilines to give functionalized 4H-benzo[d][1,3]oxazin-4-one or benzisoxazole derivatives in moderate to good yields are achieved by silver vs. gold selective catalysis. The search for the optimal reaction conditions revealed the divergent catalytic activity of NaAuCl4·H2O and AgNO3.
- Arcadi,Chiarini,Vecchio, L. Del,Marinelli,Michelet
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- One-pot approach to 2-arylbenzoxazinone derivatives from 2-alkynylanilines using copper-mediated tandem reactions
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In this study, we describe a one-pot method to obtain a variety of 2-arylbenzoxazinones and N-benzoyl anthranilic acid by using a copper catalyst and molecular oxygen as oxidants. This protocol involves tandem cyclization and oxidative processes of 2-alkynylanilines to afford significant motifs in synthetic and medicinal chemistry with moderate yields. We also demonstrated that combining the Sonogashira coupling and the developed method realized the synthesis of 2-arylbenzoxazinones derivatives from commercially available 2-iodoanilines and terminal acetylenes.
- Yamashita, Mitsuaki,Iida, Akira
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- A synthetic approach and molecular docking study of hybrids of quinazolin-4-ones and thiazolidin-4-ones as anticancer agents
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A series of 3-(4-(2-(aryl)-4-oxothiazolidin-3-yl)phenyl-2-phenylquinazolin-4(3H)-one derivatives were synthesized in appreciable yield by using anthranilic acid as a starting material. The structures of synthesized compounds (QT1–QT10) were confirmed on t
- Thakral, Samridhi,Saini, Deepika,Kumar, Ashwani,Jain, Neelam,Jain, Sandeep
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- Synthesis of 2-Aryl-4H-3,1-Benzoxazin-4-ones: A Class of α-Chymotrypsin Inhibitors
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Twenty one derivatives of 2-aryl-4H-3,1-benzoxazin-4-one were synthesized and their potential therapeutically significance and structureactivity relationship were tested against α-chymotrypsin. Majority of synthesized compounds showed significant in vitro α-chymotrypsin inhibitory properties having IC50values in the range of 5.42 ± 1.66 - 41.27 ± 1.33 μM, whereas standard inhibitor chymostatin have IC50 value 7.13 ± 1.06 μM. In the present series compounds 2-(2-fluorophenyl)-4H-3,1-benzoxazin-4-one (3h), 2-(2-bromophenyl)-4H-3,1- benzoxazin-4-one (3n) and 2-(1-naphthyl)-4H-3, 1-benzoxazin-4-one (3t) with IC50values 7.22 ± 0.75, 6.99 ± 0.29 and 5.42 ± 1.66 μM, respectively were found to be most active members of series, even better than standard inhibitor a-chymostatin.
- Khan, Zulfiqar Ali,Afzal, Noshaba,Hussain, Zaib,Naqvi, Syed Ali Raza,Bari, Ayesha,Shahzad, Sohail Anjum,Yar, Muhammad,Mahmood, Nasir,Bukhari, Shazia Anwer,Mansha, Asim,Zahoor, Ameer Fawad,Khan, Abdur Rahman,Ahmad, Matloob
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- Copper-mediated oxidative tandem reactions with molecular oxygen: Synthesis of 2-arylbenzoxazinone derivatives from indoles
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We developed an efficient method for the transformation of indoles by utilizing a copper catalyst and molecular oxygen as the oxidant. The transformation involves a tandem oxidative process of 2-arylindoles. Our reaction afforded a variety of N-benzoyl an
- Yamashita, Mitsuaki,Iida, Akira
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- Synthesis, biological evaluation of 2,3-disubstituted-imidazolyl/benzimidazolyl-quinazolin-4(3H)-one derivatives
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A series of disubstituted-quinazolin-4(3H)-ones derivatives have been synthesized and confirmed through IR, 1H- and 13C-NMR, MS spectroscopy and elemental analysis. Synthesized compounds were screened for in vitro and in vivo anti-inflammatory using human red blood cell membrane stabilization method and carrageenan-induced rat paw edema. The antimicrobial potency was measured by disk diffusion method. The compounds with imidazole (3g) and benzimidazole nucleus (4b and 4f) displayed a significant anti-inflammatory activity by in vitro method. Moreover, the compounds 3d and 4a exhibited a significant anti-inflammatory activity in vivo. The compounds 3d, 3f and 4g were found to be active antimicrobial agents, when compared with reference drug ciprofloxacin and amphotericin B. Thus, these compounds can serve as promising leads for further biological studies.
- Patil, Dilip A.,Surana, Sanjay J.
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- Oxidative Cleavage of Indoles Mediated by Urea Hydrogen Peroxide or H2O2 in Polar Solvents
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The oxidative cleavage of indoles (Witkop oxidation) involving the use of H2O2 or urea hydrogen peroxide in combination with a polar solvent has been described. Among these solvents, 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) stands out as the one affording the corresponding 2-ketoacetanilides generally in higher yields The protocol described has also enabled the oxidation of different pyrroles and furans derivatives. Furthermore, the procedure was implemented in a larger-scale and HFIP was distilled from the reaction mixture and reused (up to 4 cycles) without a significant detriment in the reaction outcome, which remarks its sustainability and applicability. (Figure presented.).
- Llopis, Natalia,Gisbert, Patricia,Baeza, Alejandro
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supporting information
p. 3245 - 3249
(2021/06/08)
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- Recyclable palladium-catalyzed carbonylative annulation of 2-iodoanilines with acid anhydrides: A practical synthesis of 2-alkylbenzoxazinones
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A highly efficient heterogeneous palladium-catalyzed carbonylative annulation of 2-iodoanilines and acid anhydrides has been developed. The reaction proceeds effectively in toluene using N,N-diisopropylethylamine (DiPEA) as the base at 100 °C under 2 bar of CO and provides a novel, general, and practical method for the assembly of a wide variety of 2-alkylbenzoxazinones with high functional group tolerance and good to excellent yields. This supported palladium complex can be readily separated from the product and recovered by a simple filtration of the reaction solution and reused up to seven times with almost consistent catalytic efficiency.
- Zhou, Zebiao,Huang, Bin,Cai, Mingzhong
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p. 3150 - 3163
(2021/08/30)
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- New amino acid schiff bases as anticancer agents via potential mitochondrial complex i-associated hexokinase inhibition and targeting amp-protein kinases/mtor signaling pathway
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Two series of novel amino acid Schiff base ligands containing heterocyclic moieties, such as quinazolinone 3–11 and indole 12–20 were successfully synthesized and confirmed by spectroscopic techniques and elemental analysis. Furthermore, all compounds wer
- Abdelmonsef, Aboubakr H.,El-Naggar, Mohamed,Noser, Ahmed A.,Salem, Maha M.
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- One pot synthesis of some new N-allyl and N-benzyl quinazolinones and their anti-inflammatory activity
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The simple and more reliable one-pot synthesis of some novel compounds of allyl/Benzyl quinazolinone (4aa-4bd) with good yields from readily available derivatives of anthranilic acid and benzoyl chloride was also reported. Interestingly, as compared to Di
- Sudula, Sudharshan Reddy,Jala, Ranjith,Siddoju, Kavitha,Ega, Jagadeesh Kumar
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- Pd-Catalyzed Carbonylative Synthesis of 4H-Benzo[d][1,3]Oxazin-4-Ones Using Benzene-1,3,5-Triyl Triformate as the CO Source
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A facile synthesis of 4H-benzo[d][1,3]oxazin-4-one derivatives by Pd-catalyzed carbonylative cross-coupling between N-(ortho-bromoaryl)amides and benzene-1,3,5-triyl triformate (TFBen) was developed. This procedure does not require the toxic and flammable gas CO as the carbonyl source and tolerates a wide scope of functional groups. Remarkably, 4H-benzo[d][1,3]oxazin-4-ones incorporated to natural products and drugs can be constructed by this method.
- Zheng, Yan,Dong, Mengke,Qu, Erdong,Bai, Jin,Wu, Xiao-Feng,Li, Wanfang
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supporting information
p. 16219 - 16224
(2021/10/06)
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- Photolysis of 3-Azido-3-phenyl-3H-isobenzofuran-1-one at Ambient and Cryogenic Temperatures?
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Although alkyl azides are known to typically form imines under direct irradiation, the product formation mechanism remains ambiguous as some alkyl azides also yield the corresponding triplet?alkylnitrenes at cryogenic temperatures. The photoreactivity of 3-azido-3-phenyl-3H-isobenzofuran-1-one (1) was investigated in solution and in cryogenic matrices. Irradiation (λ?=?254?nm) of azide 1 in acetonitrile yielded a mixture of imines 2 and 3. Monitoring of the reaction progress using UV-Vis absorption spectroscopy revealed an isosbestic point at 210?nm, indicating that the reaction proceeded cleanly. Similar results were observed for the photoreactivity of azide 1 in a frozen 2-methyltetrahydrofuran (mTHF) matrix. Irradiation of azide 1 in an argon matrix at 6?K resulted in the disappearance of its IR bands with the concurrent appearance of IR bands corresponding to imines 2 and 3. Thus, it was theorized that azide 1 forms imines 2 and 3 via a concerted mechanism from its singlet excited state or through singlet?alkylnitrene 11N, which does not intersystem cross to its triplet configuration. This proposal was supported by CASPT2 calculations on a model system, which suggested that the energy gap between the singlet and triplet configurations of alkylnitrene 1N is 33?kcal/mol, thus making intersystem crossing inefficient.
- Thenna-Hewa, Kosala,Sebastien, William,Lemen, Elaine M.,Karney, William L.,Abe, Manabu,Gudmundsdottir, Anna D.
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p. 1397 - 1406
(2021/08/25)
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- Direct synthesis of benzoxazinones via Cp*Co(III)-catalyzed C–H activation and annulation of sulfoxonium ylides with dioxazolones
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A highly novel and direct synthesis of benzoxazinones was developed via Cp*Co(III)-catalyzed C–H activation and [3 + 3] annulation between sulfoxonium ylides and dioxazolones. The reaction is conducted under base-free conditions and tolerates various functional groups. Starting from diverse readily available sulfoxonium ylides and dioxazolones, a variety of benzoxazinones could be synthesized in one step in 32%-75% yields.
- Yu, Yongqi,Xia, Zhen,Wu, Qianlong,Liu, Da,Yu, Lin,Xiao, Yuanjiu,Tan, Ze,Deng, Wei,Zhu, Gangguo
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p. 1263 - 1266
(2020/10/08)
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- Visible-Light-Mediated Dearomatisation of Indoles and Pyrroles to Pharmaceuticals and Pesticides
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Dearomatisation of indole derivatives to the corresponding isatin derivatives has been achieved with the aid of visible light and oxygen. It should be noted that isatin derivatives are highly important for the synthesis of pharmaceuticals and bioactive compounds. Notably, this chemistry works excellently with N-protected and protection-free indoles. Additionally, this methodology can also be applied to dearomatise pyrrole derivatives to generate cyclic imides in a single step. Later this methodology was applied for the synthesis of four pharmaceuticals and a pesticide called dianthalexin B. Detailed mechanistic studies revealed the actual role of oxygen and photocatalyst.
- Schilling, Waldemar,Zhang, Yu,Riemer, Daniel,Das, Shoubhik
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p. 390 - 395
(2019/12/15)
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- Design, synthesis, molecular modeling, in vivo studies and anticancer evaluation of quinazolin-4(3H)-one derivatives as potential VEGFR-2 inhibitors and apoptosis inducers
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Inhibiting VEGFR-2 has been set up as a therapeutic strategy for treatment of cancer. Accordingly, new quinazoline-based derivatives having the structural features of VEGFR-2 inhibitors were designed and synthesized. Anti-proliferative activities were evaluated against three human cancer cell lines (HepG-2, MCF-7 and HCT-116) using MTT assay method. Doxorubicin and sorafenib were used as positive controls. Compounds 26b, 29a, 29b and 30 showed excellent anti-cancer activities against all cell lines. Moreover, compound 31 was the most active with IC 50 values of 3.97 ± 0.2, 4.83 ± 0.2 and 4.58 ± 0.3 μM, respectively. The most active cytotoxic agents were further evaluated in vitro for their VEGFR-2 inhibitory activities, compound 31 showed a high activity against VEGFR-2 with an IC50 value of 2.5 ± 0.04 μM, almost equal to that of sorafenib (IC50 = 2.4 ± 0.05 μM). Further studies revealed the ability of this promising quinazoline derivative 31 to induce apoptosis and arrest cell cycle growth at G2/M phase. In vivo antitumor activities of the synthesized compounds revealed that compounds 30 and 31 possessed significant tumor growth inhibition effect. Molecular docking studies were also performed and finally we can say that VEGFR-2 inhibition confers the reported cytotoxic activities.
- Belal, Amany,Eissa, Ibrahim H.,El-Gamal, Kamal M. A.,El-Sharkawy, Abdou,Elhendawy, Mostafa A.,Elsohly, Mahmoud A.,Ibrahim, Mohammed K.,Mahdy, Hazem A.,Mehany, Ahmed B. M.,Metwaly, Ahmed M.,Radwan, Mohamed M.
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- Recyclable Heterogeneous Palladium-Catalyzed Cyclocarbonylation of 2-Iodoanilines with Acyl Chlorides in the Biomass-Derived Solvent 2-Methyltetrahydrofuran
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A highly efficient, green palladium-catalyzed cyclocarbonylation of 2-iodoanilines with acyl chlorides has been developed that proceeds smoothly in a biomass-derived solvent 2-methyltetrahydrofuran with N,N-diisopropylethylamine as base at 100 °C under 20 bar of carbon monoxide using an 2-aminoethylamino-modified MCM-41-anchored palladium acetate complex [2N-MCM-41-Pd(OAc)2] as a heterogeneous catalyst, yielding a wide variety of 2-substituted 4H-3,1-benzoxazin-4-one derivatives in good to excellent yields. This supported palladium catalyst could be facilely obtained by a two-step procedure from easily available starting materials and readily recovered via a simple filtration process and recycled at least 8 times without any apparent decrease in catalytic efficiency. The developed methodology not only avoids the use of toxic solvents such as tetrahydrofuran and dimethylformamide but also solves the basic problem of expensive palladium catalyst recovery and reuse and prevents effectively palladium contamination of the desired product.
- Hao, Wenyan,Xu, Zhaotao,Zhou, Zebiao,Cai, Mingzhong
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p. 8522 - 8532
(2020/07/16)
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- Quinazolinone-schiff's base hybrids as phosphodiesterase 4b inhibitors with dual activity against COPD and lung cancer
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A series of thirty compounds of quinazolinone-Schiff's base hybrids were rationally designed, synthesized, and evaluated for their in vitro Phosphodiesterase 4B inhibition, anti-lung and anti-colon cancer activities. Compounds 9, 16, 23, 29, 30, 31, 32 an
- Mansour, Mostafa A.,El-Saadi, Mohamed T.,Amin, Noha H.,Canzoneri, Joshua C.,Keeton, Adam B.,Piazza, Gary A.,Abdel-Rahman, Hamdy M.
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p. 4851 - 4866
(2020/12/25)
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- Novel 3-{4-[2-amino-4-(Substitutedphenyl)-2H-[1, 3] oxazin/thiazin-6-Yl}-2-phenyl-3h-quinazolin-4-one derivatives as enhancer of GABA mediated inhibition: Synthesis, molecular modeling and pharmacological studies
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Background: According to WHO, the 50 million people worldwide are suffering from epilepsy, making it one of the most common neurological diseases globally. Epilepsy is often characterized by neurobiological, cognitive, psychological and behavioral changes
- Jain, Nimisha,Singour, Pradeep Kumar
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p. 199 - 213
(2020/02/29)
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- C2-substituted quinazolinone derivatives exhibit A1 and/or A2A adenosine receptor affinities in the low micromolar range
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Antagonists of the adenosine receptors (A1 and A2A subtypes) are widely researched as potential drug candidates for their role in Parkinson's disease-related cognitive deficits (A1 subtype), motor dysfunction (A2A subtype) and to exhibit neuroprotective properties (A2A subtype). Previously the benzo-α-pyrone based derivative, 3-phenyl-1H-2-benzopyran-1-one, was found to display both A1 and A2A adenosine receptor affinity in the low micromolar range. Prompted by this, the α-pyrone core was structurally modified to explore related benzoxazinone and quinazolinone homologues previously unknown as adenosine receptor antagonists. Overall, the C2-substituted quinazolinone analogues displayed superior A1 and A2A adenosine receptor affinity over their C2-substituted benzoxazinone homologues. The benzoxazinones were devoid of A2A adenosine receptor binding, with only two compounds displaying A1 adenosine receptor affinity. In turn, the quinazolinones displayed varying degrees of affinity (low micromolar range) towards the A1 and A2A adenosine receptor subtypes. The highest A1 adenosine receptor affinity and selectivity were favoured by methyl para-substitution of phenyl ring B (A1Ki = 2.50 μM). On the other hand, 3,4-dimethoxy substitution of phenyl ring B afforded the best A2A adenosine receptor binding (A2AKi = 2.81 μM) among the quinazolinones investigated. In conclusion, the quinazolinones are ideal lead compounds for further structural optimization to gain improved adenosine receptor affinity, which may find therapeutic relevance in Parkinson's disease-associated cognitive deficits and motor dysfunctions as well as exerting neuroprotective properties.
- Pieterse, Lianie,Terre'Blanche, Gisella,van der Walt, Mietha M.
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supporting information
(2020/06/08)
-
- Domino synthesis of pyrimido and imidazoquinazolinones
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A simple method for the synthesis of N-alkyl-2-arylquinazolin-4-amines, methyl 4-((2-arylquinazolin-4-yl)amino) butanoates, 6-aryl-2,3-dihydro-4H-pyrimido[1,2-c]quinazolin-4-ones, and 5-arylimidazo[1,2-c]quinazolin-3(2H)-ones has been described. It involves a simple reaction of N-(2-cyanophenyl)-substitutedbenzimidoyl chlorides with alkylamine, γ-aminobutyric acid, β-alanine, l-alanine, and glycine methyl esters hydrochloride in acetonitrile to afford the desired compounds after a series of instantaneous reactions that include Dimroth rearrangement. The reaction involves reflux for 12 hours, simple addition of reagents to an in situ generated benzimidoyl chloride, and simple workup, to form 21 examples of pure compounds in high yields. The active intermediate N-(2-cyanophenyl)-substitutedbenzimidoyl chlorides were formed by the reaction of N-(2-cyanophenyl)-substitutedbenzamides with thionyl chloride in a one-pot strategy. The alternative method described for this preparation deals with an exhausting multistep reactions starting from anthranilic acid.
- Fathalla, Walid,Nofal, Eman Y.,El-Moneim, Mohamed Abd
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p. 1266 - 1274
(2020/01/21)
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- Recyclable Heterogeneous Palladium-Catalyzed Carbonylative Cyclization of 2-Iodoanilines with Aryl Iodides Leading to 2-Arylbenzoxazinones
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A highly efficient and practical heterogeneous palladium-catalyzed carbonylative coupling of 2-iodoanilines with aryl iodides has been developed. The reaction occurs smoothly in toluene at 110 °C with N, N -diisopropylethylamine as base under carbon monoxide (5 bar) and offers a general and powerful tool for the construction of various valuable 2-arylbenzoxazinones with excellent atom-economy, high functional group tolerance, good to high yields, and easy recyclability of the palladium catalyst. The reaction is the first example of heterogeneous palladium-catalyzed carbonylative coupling for the preparation of diverse 2-arylbenzoxazinones from commercially easily available 2-iodoanilines and aryl iodides.
- Cai, Mingzhong,Huang, Bin,Xu, Zhaotao,Zhou, Zebiao
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p. 581 - 590
(2020/02/13)
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- Acyl Cyanides as Bifunctional Reagent: Application in Copper-Catalyzed Cyanoamidation and Cyanoesterification Reaction
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Cu-catalyzed domino decyanation and cyanation reaction of acyl cyanides with amines or alcohols have been developed. The cyano sources were generated in situ via C-CN cleavage yielding the corresponding cyano substituted amides or esters in moderate to excellent yields. This approach features a cheap copper catalyst, domino decyanation and cyanation reaction, readily available starting materials, broad substrate scope, operational simplicity, and the potential for further transformation of the cyano group.
- Chen, Zhengwang,Wen, Xiaowei,Zheng, Weiping,He, Ruolan,Chen, Dou,Cao, Dingsheng,Long, Lipeng,Ye, Min
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p. 5691 - 5701
(2020/04/10)
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- Cp*Co(III)-Catalyzed o-Amidation of Benzaldehydes with Dioxazolones Using Transient Directing Group Strategy
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Transition metal-catalyzed ortho-selective C(sp2)?H amidation of weakly coordinating aldehydes remains limited to precious metals such as Ir, Rh, Ru, etc. Herein, we put forward a novel report on ortho-amidation of benzaldehydes employing user-
- Dwivedi, Vikas,Khan, Bhuttu,Sundararaju, Basker
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- Anti-HIV, Antitubercular and Antibacterial Activities of Novel 3-(Substituted Quinazolinylamino)-2-phenyl quinazolin-4(3H)ones
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In the present study, we have synthesized a series of novel 2-phenyl-3-(substituted quinazolinylamino)quinazolin-4(3H)-ones by the reaction of 3-(substituted)-2-hydrazinoquinazoline-4(3H)-ones with 2-phenyl-3,1-benzoxazin-4-one. The starting material 3-(substituted)-2-hydrazino-quinazolin-4(3H)-ones were synthesized from various primary amines. All the synthesized compounds were screened for their antitubercular, anti-HIV and antibacterial activity against different Gram-positive and Gram-negative strains by agar dilution method. Among the test compounds, 3-(4-nitrophenyl)-2-(4-oxo-2-phenylquinazolin-3(4H)-ylamino)quinazolin-4(3H)-one (BQZ6) and 3-(4-chlorophenyl)-2-(4-oxo-2-phenylquinazolin-3(4H)-ylamino)quinazolin-4(3H)-one (BQZ7) shown most potent antibacterial activity against E. coli, P. aeruginosa and S. aureus with the MIC of 3 μg/mL. The compound BQZ7 exhibited the antitubercular activity with the MIC of 25 μg/mL and anti-HIV activity with the MIC of 35.4 μg/mL against HIV1 and HIV2 and offers potential lead for further optimization and development to new antitubercular and anti-HIV agents. The results from this study confirm that the synthesized and biologically evaluated quinazolines showed promising antimicrobial, antitubercular and anti-HIV activities and are new scaffolds for antimicrobial activity.
- Sulthana,Chitra,Alagarsamy
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p. 281 - 286
(2020/01/08)
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- Oxidative NHC catalysis for base-free synthesis of benzoxazinones and benzoazoles by thermal activated NHCs precursor ionic liquid catalyst using air as oxidant
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A reusable thermal activated NHC precursor ionic liquid catalyst ([BMIm]2[WO4]) has been prepared and developed for the synthesis of nitrogen-containing heterocycles such as benzoxazinones and benzoazoles through imines activation. [BMIm]2[WO4] exhibited the good activity for the base-free condensation and oxidative NHC catalysis tandem under air atmosphere. The catalyst can be recovered and reused for at least five runs in gram scale synthesis without any decrease in catalytic activity. Furthermore, the control experiments demonstrated that the reaction involved formation of aromatic aldimines, NHC-catalyzed oxidative formation of imidoyl azoliums and intramolecular cyclization to generate the product.
- Guan, Jiali,Liu, Wei,Liu, Yuchen,Song, Zhibin,Tao, Duan-Jian,Yan, Jieying,Yuan, Jian-Jun,Zhou, Youkang
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- A straightforward TBHP-mediated synthesis of 2-amidobenzoic acids from 2-arylindoles and their antimicrobial activity
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A simple and highly efficient strategy has been developed for the synthesis of 2-amidobenzoic acids through the tert-butyl hydroperoxide (TBHP)-mediated oxygenation and sequential ring opening of 2-arylindoles in a one-pot fashion under metal-free aerobic conditions. The developed synthetic protocol is operationally simple, tolerates a wide range of functional groups, and is amenable to the gram-scale. Radical trapping experiments revealed that the reaction involves a radical pathway. The synthesized compounds (2a-s) were tested for in vitro antimicrobial activity. Among all screened compounds, 2d showed the maximum antibacterial activity against P. aerugunosa (ZOI = 17 mm, MIC = 32 μg mL-1) and compounds 2d and 2p showed the maximum (32 μg mL-1) antifungal activity against A. flavus and C. albicans.
- Patel, Om P.S.,Dhiman, Shiv,Khan, Shahid,Shinde, Vikki N.,Jaspal, Sonam,Srivathsa, Manu R.,Jha, Prabhat N.,Kumar, Anil
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p. 5962 - 5970
(2019/06/24)
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- Weakly Coordinating, Ketone-Directed (η5-Pentamethylcyclopentadienyl)cobalt(III)- and (η5-Pentamethylcyclopentadienyl)rhodium(III)-Catalyzed C?H Amidation of Arenes: A Route to Acridone Alkaloids
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The weakly coordinating, ketone-directed, regioselective monoamidation of aromatic ketones, chalcone, carbazole, and benzophenones was achieved by employing high-valent cobalt and rhodium catalysis to access numerous biologically important molecular building blocks. This amidation proceeded smoothly with a variety of ketones and several amidating partners. The application of the products in the synthesis of various heterocycles, including acridones, indoles, quinoline, quinolones, quinolinones, and quinazolines, was also explored. The total synthesis of acridone-based alkaloids, namely, toddaliopsin A, toddaliopsin D, and arborinine, and the formal synthesis of acronycine and noracronycin were also accomplished by applying this method. A mechanistic study revealed this amidation reaction follows a base-assisted intermolecular electrophilic substitution pathway.
- Bera, Sourav Sekhar,Sk, Md Raja,Maji, Modhu Sudan
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supporting information
p. 1806 - 1811
(2019/01/14)
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- Synthesis, characterisation, and reactivity of novel pseudocyclic hypervalent iodine reagents with heteroaryl carbonyl substituents
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Two new hypervalent iodine reagents containing furan and thiophene moieties in addition to a carbonyl group in the vicinity of the iodine atom were synthesised and characterised. The X-ray analysis of both compounds revealed a strong intramolecular contact between the carbonyl oxygen and the hypervalent iodine atom with tosylate as a counter ion. The two reagents showed a broad range of synthetic applications and proved to be versatile oxidizing agents.
- Qurban, Jihan,Elsherbini, Mohamed,Alharbi, Haifa,Wirth, Thomas
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supporting information
p. 7998 - 8000
(2019/07/12)
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- Palladium-Catalyzed Olefination of 4H-Benzo[d][1,3]oxazin-4-one Derivatives with Activated Alkenes via Preferential Cyclic Imine-N-Directed Aryl C-H Activation
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A palladium-catalyzed chelation-assisted selective ortho C-H bond olefination of biologically active 4H-benzo[d][1,3] oxazin-4-one derivatives with activated olefins has been achieved. The products are obtained in good yields with high regio- and stereose
- Panja, Subir,Maity, Srabani,Majhi, Biju,Ranu, Brindaban C.
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p. 5777 - 5786
(2019/08/30)
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- One-step synthesis of 4H-3,1-benzoxazin-4-ones from Weinreb amides and 1,4,2-dioxazol-5-ones via cobalt-catalyzed C-H bond activation
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A one-step synthesis of 4H-3,1-benzoxazin-4-ones from readily available Weinreb amides and 1,4,2-dioxazol-5-ones under Cp*Co(III) catalysis is described. The reactions proceeded in moderate to good yields with high functional group compatibility.
- Tanimoto, Iku,Kawai, Kentaro,Sato, Akane,Yoshino, Tatsuhiko,Matsunaga, Shigeki
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p. 118 - 125
(2019/07/31)
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- One-Pot Synthesis of 2-Arylbenzoxazinones from 2-Arylindoles with (Diacetoxyiodo)benzene as the Sole Oxidant
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A series of synthetically interesting 2-arylbenzoxazinones was prepared from 2-arylindoles by an efficient oxidative reaction mediated by (diacetoxyiodo)benzene [PhI(OAc) 2 ] and assisted by water. PhI(OAc) 2 was used as the sole oxi
- Shang, Xian-Xing,Vu, Huu-Manh,Li, Xu-Qin
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supporting information
p. 377 - 383
(2017/10/30)
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- Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C-C Bond Cleavage of 2-Arylindoles
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A variety of 2-aminobenzonitriles were prepared from 2-arylindoles in good to excellent yields through tert-butylnitrite (TBN)-mediated nitrosation and sequential iron(III)-catalyzed C-C Bond cleavage in a one-pot fashion. The 2-aminobenzonitriles can be used to rapidly synthesize benzoxazinones by intramolecular condensation. The present method features an inexpensive iron(III) catalyst, gram scalable preparations, and novel C-C bond cleavage of indoles.
- Chen, Wei-Li,Wu, Si-Yi,Mo, Xue-Ling,Wei, Liu-Xu,Liang, Cui,Mo, Dong-Liang
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p. 3527 - 3530
(2018/06/26)
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- Design, synthesis and pharmacological evaluation of 2-phenyl quinazolin-4-one derivatives as anticolorectal cancer and anti-inflammatory agent
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Quinazoline derivatives are heterocyclic compounds that acts as important structural lead for the discovery of effective therapeutic agents. The anti-inflammatory activity along with cytotoxicity helps to reduce the inflammation and pain associated with carcinoma. Derivatives of quinazoline-4-one were preliminary screened and in silico molecular modelling studies using Autodock were performed. In the docking study, ligands were docked against anticancer and anti-inflammatory targets. In silico analysis revealed that the compounds with aromatic substitution at 3rd and halogen substitution at 6th or 7th positions possess lesser side effects and have more potent antitumor activity. Based upon these results 12 compounds were selected, synthesized, characterized and screened for their in vitro, anti-inflammatory, antioxidant and anticancer activities. From the in vitro studies, compounds QA4, QA7 and QB1 showed good anticancer, anti-inflammatory and antioxidant activity when compared to the standard.
- Bosco, Deena,Balakrishnan, Ashitha,Mishra, Rohan,Aneesh
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p. 2677 - 2685
(2018/11/20)
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- Discovery and validation of 2-styryl substituted benzoxazin-4-ones as a novel scaffold for rhomboid protease inhibitors
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Rhomboids are intramembrane serine proteases with diverse physiological functions in organisms ranging from archaea to humans. Crystal structure analysis has provided a detailed understanding of the catalytic mechanism, and rhomboids have been implicated in various disease contexts. Unfortunately, the design of specific rhomboid inhibitors has lagged behind, and previously described small molecule inhibitors displayed insufficient potency and/or selectivity. Using a computer-aided approach, we focused on the discovery of novel scaffolds with reduced liabilities and the possibility for broad structural variations. Docking studies with the E. coli rhomboid GlpG indicated that 2-styryl substituted benzoxazinones might comprise novel rhomboid inhibitors. Protease in vitro assays confirmed activity of 2-styryl substituted benzoxazinones against GlpG but not against the soluble serine protease α-chymotrypsin. Furthermore, mass spectrometry analysis demonstrated covalent modification of the catalytic residue Ser201, corroborating the predicted mechanism of inhibition and the formation of an acyl enzyme intermediate. In conclusion, 2-styryl substituted benzoxazinones are a novel rhomboid inhibitor scaffold with ample opportunity for optimization.
- Goel, Parul,Jumpertz, Thorsten,Tichá, Ane?ka,Ogorek, Isabella,Mikles, David C.,Hubalek, Martin,Pietrzik, Claus U.,Strisovsky, Kvido,Schmidt, Boris,Weggen, Sascha
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supporting information
p. 1417 - 1422
(2018/02/21)
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- Synthesis and study of modified polyvinyl alcohol containing amino acid moieties as anticancer agent
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A series of new phthalimides compounds[3-7]a-i were synthesized from reaction of Malic anhydride, phthalic anhydride, nitro phthalic anhydride, 2-phenyl-4H-benzo[d][1,3]oxazin-4-one, 2-(4-nitrophenyl)-4H-benzo[d][1,3]oxazin-4-one with different amino acids as glycine, alanine, valine, leucine, isoleucine, serine, threonine, tyrosine and Phenyl alanine [1]a-i under fusion conditions. Compounds [3-7]a-i react with SOCl2 in the presence of benzene to produce compounds [8-12]a-i. Chemical modification of Poly(vinyl alcohol)were obtained by reaction of PVA with compounds [8-12]a-i using the dimethyl formamide to give compounds [13-17]a-i. The structure of the synthesized compounds was characterized by their analytical and spectral data as, IR spectra, 1H, 13C-NMR, Elemental analysis (CHN), UV-Vis Spectroscopy, Scanning electron microscopy (SEM), Antibacterial activity were screened via two kinds of bacteria. Also, anticancer activity were examined for most of the modified polyvinyl alcohol.
- Samir, Ali H.,Saeed, Ruwaidah S.,Matty, Fadhel S.
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p. 286 - 294
(2018/03/21)
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- Quinazolinone platinum metal complexes: In silico design, synthesis and evaluation of anticancer activity
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Dihydrofolate reductase (DHFR) has been explored as a target for the development of agents for wide variety of human diseases, including cancer, autoimmune and infectious diseases. Several metal complexes are being used in management of cancer. The square planar Pt(II) complex, cis PtCl2(NH3)2 turned out to be even more effective at forcing filamentous growth. Cisplatin is an inorganic heavy metal complex that has activity similar to cell-cycle-phase-nonspecific alkylating agents such as cyclophosphamide and some other Ni and Cu metal complexes. It produces intrastrand DNA cross-link and form DNA adducts, thus inhibiting the synthesis of DNA, RNA and proteins preferentially. in silico Screening of platinum metal complexes was performed by Vlife MDS 4.3 software. In this procedure, selection of molecule, selection of PDB, optimization of PDB and docking of molecules was carried out. Synthesis of metal complexes was done by multi component reaction method. Platinum metal complexes of quinazolinone Schiff bases prioritized by in silico studies were characterized by IR, TLC, NMR, XRD, FESEM and some physico-chemical parameters. Prioritized molecules were further evaluated by in vitro anticancer cell line assay on ten cell lines with adriamycin as standard. The results showed that the platinum metal complexes of qunazolinone Schiff bases can be potential anticancer agents through DHFR inhibitory mechanism.
- Sawant, Sanjay D.,Sahu, Megha,Nerkar, Amit G.
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p. 2164 - 2170
(2018/09/10)
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- Synthesis and Antimicrobial Activity of Methyl 2-(2-(2-Arylquinazolin-4-yl)oxy) Acetylamino Alkanoates
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A series of methyl 2-(2-(2-arylquinazolin-4-yl)oxy) acetylamino alkanoate have been developed via N,N′-dicyclohexylcarbodiimide coupling of (2-arylquinazolin-4-yloxy) acetic acids with amino acid ester hydrochlorides. The O-substituted carboxylic acids we
- Megahed,Fathalla,Alsheikh, Amer A.
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p. 2799 - 2808
(2018/11/23)
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- Iridium-Catalyzed Aryl C-H Sulfonamidation and Amide Formation Using a Bifunctional Nitrogen Source
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A new strategy for the sequential formation of aryl and amidyl C-N bonds is reported. Using trichloroethoxysulfonyl azide as a bifunctional nitrogen source, Ir-catalyzed aryl C-H sulfonamidation and subsequent desulfonative amide formation proceed effectively without any need of oxidants or coupling reagents. This protocol is suitable for readily available benzamides and stable carboxylates including primary, secondary, and tertiary alkyl, alkenyl, and phenyl carboxylates, thereby providing a direct and efficient method for the synthesis of biologically and chemically useful N-arylamides.
- Yu, Meng,Zhang, Tao,Jalani, Hitesh B.,Dong, Xunqing,Lu, Hongjian,Li, Guigen
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p. 4828 - 4832
(2018/08/24)
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- Multi-substituted pentavalent quaternary cyclic phosphorus derivatives without hetero atom substituents as well as synthesis method and application of derivatives
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The invention relates to multi-substituted pentavalent quaternary cyclic phosphorus derivatives without hetero atom substituents. The chemical structural formula of the compounds is described in the description. A preparation method of the derivatives com
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Paragraph 0055-0060
(2018/07/30)
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- Palladium-catalyzed tandem addition/cyclization in aqueous medium: Synthesis of 2-arylindoles
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An efficient protocol to construct 2-arylindoles was developed through palladium-catalyzed tandem addition/cyclization of potassium aryltrifluoroborates with aliphatic nitriles in aqueous medium. The use of water as the reaction medium makes the synthesis process environmentally benign. A plausible mechanism for the formation of 2-arylindoles involving sequential nucleophilic addition followed by an intramolecular cyclization is proposed. Moreover, the utility of this catalytic tandem transformation was also demonstrated in an efficient gram-scale synthesis. This method provides an alternative synthetic tool for accessing a more diverse array of 2-arylindoles.
- Yu, Shuling,Hu, Kun,Gong, Julin,Qi, Linjun,Zhu, Jianghe,Zhang, Yetong,Cheng, Tianxing,Chen, Jiuxi
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p. 4300 - 4307
(2017/07/10)
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- Mechanochemical Synthesis of Substituted 4H-3,1-Benzoxazin-4-ones, 2-Aminobenzoxazin-4-ones, and 2-Amino-4H-3,1-benzothiazin-4-ones Mediated by 2,4,6-Trichloro-1,3,5-triazine and Triphenylphosphine
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A mild and convenient approach for the synthesis of 2-substituted 4H-3,1-benzoxazin-4-ones, 2-aminobenzoxazin-4-ones, and 2-amino-4H-3,1-benzothiazin-4-ones under solvent-assisted grinding is reported. In the presence of 2,4,6-trichloro-1,3,5-triazine and
- Pattarawarapan, Mookda,Wet-Osot, Sirawit,Yamano, Dolnapa,Phakhodee, Wong
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p. 589 - 592
(2017/03/11)
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- Silver-Mediated Synthesis of 4H-Benzoxazin-4-ones by Intramolecular Decarboxylative O-Acylation Reactions with α-Oxocarboxylic Acid
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The first example of an intramolecular decarboxylative acylation reaction for the synthesis of 4H-benzoxazin-4-one derivatives has been described. The silver-mediated reaction has a broad substrate scope and provides a mild and rapid approach to the corre
- Bharathimohan, Kuppusamy,Ponpandian, Thanasekaran,Jafar, Ahamed A.
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p. 2806 - 2813
(2017/05/29)
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- Pd-Catalyzed regioselective C-H halogenation of quinazolinones and benzoxazinones
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A Pd-catalyzed ortho-selective halogenation of benzoxazinone and quinazolinone scaffolds has been described employing N-halosuccinimide as both a halogen source and an oxidant reagent via C-H bond activation. This transformation shows high chemo- and regioselectivities and demonstrates a broad range of benzoxazinone and quinazolinone substrates with different functional groups and has been scaled up to the gram level.
- Dabiri, Minoo,Farajinia Lehi, Noushin,Kazemi Movahed, Siyavash,Khavasi, Hamid Reza
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supporting information
p. 6264 - 6268
(2017/08/02)
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- Design, Synthesis, and Pharmacological Characterization of N-(4-(2 (6,7-Dimethoxy-3,4-dihydroisoquinolin-2(1H)yl)ethyl)phenyl)quinazolin-4-amine Derivatives: Novel Inhibitors Reversing P-Glycoprotein-Mediated Multidrug Resistance
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P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) is a principal obstacle for successful cancer chemotherapy. A novel P-gp inhibitor with a quinazoline scaffold, 12k, was considered to be the most promising for in-depth study. 12k possessed high potency (EC50 = 57.9 ± 3.5 nM), low cytotoxicity, and long duration of activity in reversing doxorubicin (DOX) resistance in K562/A02 cells. 12k also boosted the potency of other MDR-related cytotoxic agents with different structures, increased accumulation of DOX, blocked P-gp-mediated Rh123 efflux, and suppressed P-gp ATPase activity in K562/A02 MDR cells. However, 12k did not have any effects on CYP3A4 activity or P-gp expression. In particular, 12k had a good half-life and oral bioavailability and displayed no influence on DOX metabolism to obviate the side effects closely related to increased plasma concentrations of cytotoxic agents in vivo.
- Qiu, Qianqian,Liu, Baomin,Cui, Jian,Li, Zheng,Deng, Xin,Qiang, Hao,Li, Jieming,Liao, Chen,Zhang, Bo,Shi, Wei,Pan, Miaobo,Huang, Wenlong,Qian, Hai
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supporting information
p. 3289 - 3302
(2017/05/05)
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- Design and synthesis of quinazolinones as EGFR inhibitors to overcome EGFR resistance obstacle
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The epidermal growth factor receptor (EGFR) T790M mutant is found in about 50% of clinically acquired resistance to gefitinib among patients with non-small cell lung cancer (NSCLC). New derivatives of 4(3H)-quinazolinones were synthesized and evaluated for their inhibitory activity against NSCLC. The results of the study demonstrated that compound 79, 7-chloro-3-(5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl)-2-phenylquinazolin-4(3H)-one was found to be the most potent compounds of the series with IC50 value of 0.031?μM against mutant T790M/L858R EGFR. Compounds 15, 51, 73, 75, 78, 79 and 96 were less potent against A549 (WT EGFR and k-Ras mutation) and HT-29 (non-special gene type) cells, showing a high safety index. The obtained results showed that compounds 15, 51, 73, 75, 78, 79 and 96 could be the promising template to overcome drug resistance mediated by the EGFR T790 Mutant.
- Patel, Harun M.,Pawara, Rahul,Ansari, Azim,Noolvi, Malleshappa,Surana, Sanjay
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p. 2713 - 2723
(2017/04/17)
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