- Synthesis, structural characterization and biological evaluation of mononuclear transition metal complexes of zwitterionic dehydroacetic acid N-aroylhydrazone ligand
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Synthesis and characterization of mononuclear transition metal complexes viz., Co(II), Ni(II), Cu(II) and Zn(II) with a newly designed ligand, (E)-2-benzamido-N'-(1-(2-hydroxy-6-methyl-4-oxo-4H-pyran-3-yl) ethylidene) benzohydrazide (H2L) are r
- Kendur, Umashri,Chimmalagi, Geeta H.,Patil, Sunil M.,Gudasi, Kalagouda B.,Frampton, Christopher S.
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- Synthesis, characterization, biological evaluation and molecular docking studies of N-functionalized derivatives of 2-aminobenzohydrazide
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In this paper, N-functionalized derivatives of methyl anthranilate (1–3) were prepared by reacting it with various acid chlorides to give amide derivatives (1–3) which were further converted to benzohydrazide derivatives (4–6) by reacting them with hydraz
- Arshad, Muhammad Nadeem,Ashraf, Zaman,Asim, Mulazim Hussain,Asiri, Abdullah M.,Javid, Noman,Kausar, Naghmana,Murtaza, Shahzad,Rashid, Robina
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- Asymmetric Synthesis of N-N Axially Chiral Compounds by Phase-Transfer-Catalyzed Alkylations
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N-N axially chiral skeletons are significant structural motifs in natural products, pharmaceuticals, and functional materials. Herein we disclose a method for the asymmetric synthesis of N-N axially chiral compounds by phase-transfer catalysis. A wide range of N-N axially chiral quinazolinone derivatives were prepared in high yields with excellent stereoselectivities. Furthermore, the synthetic utility of the protocol was proved by large-scale reaction and transformation of the product. Density functional theory calculations provide insight into the mechanism.
- Pan, Ming,Shao, Ying-Bo,Zhao, Qun,Li, Xin
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supporting information
p. 374 - 378
(2022/01/04)
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- Novel O-acylated (E)-3-aryl-6,7-dihydrobenzisoxazol-4(5H)-one oximes targeting HSP90-HER2 axis in breast cancer cells
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Novel O-acylated (E)-3-aryl-6,7-dihydrobenzisoxazol-4(5H)-one oximes were designed as potential HSP90 inhibitors. A series of the compounds was synthesized by oximation of (E)-3-aryl-6,7-dihydrobenzisoxazol-4(5H)-ones followed by O-acylation with acylamid
- Piven, Yuri A.,Yastrebova, Margarita A.,Khamidullina, Alvina I.,Scherbakov, Alexander M.,Tatarskiy, Victor V.,Rusanova, Julia A.,Baranovsky, Alexander V.,Zinovich, Veronica G.,Khlebnicova, Tatyana S.,Lakhvich, Fedor A.
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supporting information
(2021/11/30)
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- Tunable Electrosynthesis of Anthranilic Acid Derivatives via a C-C Bond Cleavage of Isatins
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A facile and direct electrocatalytic C-C bond cleavage/functionalization reaction of isatins was developed. With isatins as the amino-attached C1 sources, a variety of aminobenzoates, and aminobenzamides were synthesized in moderate to good yields under mild conditions.
- Qian, Peng,Liu, Jiaojiao,Zhang, Yan,Wang, Zhiyong
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p. 16008 - 16015
(2021/07/31)
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- Design, synthesis, crystal structure, in vitro cytotoxicity evaluation, density functional theory calculations and docking studies of 2-(benzamido) benzohydrazide derivatives as potent AChE and BChE inhibitors
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A series of hydrazone derivatives of 2-(benzamido) benzohydrazide was designed, synthesized, and characterized utilizing FTIR, NMR and UV spectroscopic techniques along with mass spectrometry. Compound 10 was also characterized through X-ray crystallograp
- Altaf, Ataf Ali,Arshad, Muhammad Nadeem,Asiri, Abdullah M.,El-Bahy, Salah M.,Elnaggar, Ashraf Y.,Kausar, Naghmana,Kausar, Samia,Murtaza, Shahzad,Tatheer, Adina,Zaib Saleem, Rahman Shah
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p. 154 - 167
(2022/01/19)
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- Synthesis of 2-Amino-1,3-dienes from Propargyl Carbonates via Palladium-Catalyzed Carbon-Nitrogen Bond Formation
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A catalytic method to synthesize 1,3,-dienes from propargylic precursors is reported. This palladium-catalyzed carbon-nitrogen bond-forming reaction furnishes 2-amino-1,3-dienes in excellent yields (up to 98%) and shows a broad tolerance to functional group diversity. The reaction has been demonstrated for over 30 amine substrates, including anilines and indoles, and proceeds under mild neutral conditions. The resulting 1,3-dienes are of great synthetic interest because of their further reaction potential.
- O'Broin, Calvin Q.,Guiry, Patrick J.
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supporting information
p. 879 - 883
(2020/02/04)
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- Para -Selective copper-catalyzed C(sp2)-H amidation/dimerization of anilides via a radical pathway
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Copper-catalyzed amidation/dimerization of anilides via regioselective C(sp2)-H functionalization is achieved. The para-selective amidation is accomplished on the anilide aromatic ring via a radical pathway leading to C-N bond formation in the presence of ammonium persulfate as a radical source/oxidant for the copper catalyst. The developed protocol tolerates a wide range of anilide substrates. The regioselectivity is confirmed by single-crystal X-ray studies.
- Viveki, Amol B.,Garad, Dnyaneshwar N.,Gonnade, Rajesh G.,Mhaske, Santosh B.
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supporting information
p. 1565 - 1568
(2020/02/13)
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- Latent Bronsted Base Solvent-Assisted Amide Formation from Amines and Acid Chlorides
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Weakly basic amines, including even neutral amines such as nitroaniline and aminocarboxylic acids, react with acid chlorides very efficiently in N, N -dimethylacetamide (DMAC), without addition of a base, to give the corresponding amides in high yields. The role of DMAC and related solvents as latent Bronsted bases was studied in these amidation reactions. Less basic amines, such as aromatic amines, reacted with benzoyl chloride faster than more basic aliphatic amines.
- Otsuka, Rikuto,Maruhashi, Kazuo,Ohwada, Tomohiko
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supporting information
p. 2041 - 2057
(2018/05/04)
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- Potassium Carbonate Promoted C-N Coupling Reaction between Benzamides and Aryl Iodides
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A practical and efficient method for N-arylation of benz-amides promoted by potassium carbonate in the presence of DMEDA was developed. The reaction was carried out without addition of any transition-metal catalyst to afford a variety of N-arylated products in moderate to good yields (up to 97%).
- Huang, Fei,Wu, San,Hu, Weiye,Zhang, Songlin
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supporting information
p. 1090 - 1096
(2017/11/29)
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- Synthetic studies and antibacterial activity of nucleobases and their N- and S-glucosides from 2-amino benzoic acid and its benzamido derivatives
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A series of S-glucosides 11a-14a and their benzamido derivatives 11b-14b have been synthesized by reacting D-glucose with thiol groups of 5-(2′-aminophenylene)-1,3,4-oxadiazole-2-thioles 7(a,b), 5-(2′-aminophenylene)-1,3,4-thiadiazole-2-thiols 8(a,b), 5-(2′-aminophenylene)-1,2,4-triazole-3-thiols 9(a,b) and 5-(2′-aminophenylene)-4-N-amino-1,2,4-triazole-3-thiols 10(a,b). The thiols 7(a,b)-10(a,b) have been synthesized from hydrazides 3(a,b) which already been synthesized from 2-aminobenzoic acid and its benzamido derivative. All synthesized compounds were characterized by IR, UV,1H- and13C- NMR. Nucleobases and a representative of S-glycoside were tested in vitro against the following microorganisms: two Gram-positive bacteria Staphylococcus aureus and Bacillus cereusand two Gram-negative bacteria Escherichia coli, Pseudomonas aeruginosa and they exhibited significant effects. Amykacine was used as positive standard.
- Benhammadi, Samia,Iraten, Salima,Othman, Adil A.
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p. 2567 - 2576
(2016/11/22)
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- Synthesis, Antimicrobial and Anticancer Evaluation of 2-Azetidinones Clubbed with Quinazolinone
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A novel series of 2-azetidinones clubbed with quinazolinone was synthesized using anthranilic acid. All the synthesized compounds were evaluated for their antimicrobial activity against two Gram positive bacterial strains (Bacillus subtilis and Staphyloco
- Deep, Aakash,Kumar, Pradeep,Narasimhan, Balasubrmanian,Meng, Lim Siong,Ramasamy, Kalavathy,Mishra, Rakesh Kumar,Mani, Vasudevan
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- Structural elucidation of thermolysis products of methyl N-methyl-N-nitrosoanthranilate
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Although it is common knowledge that N-nitroso compounds are thermally (and otherwise chemically) labile, little or nothing is known about the specific reactions that occur during thermal treatment of a compound possessing this functionality. Methyl N-met
- Miltojevi?, Ana B.,Radulovi?, Niko S.
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p. 53569 - 53585
(2015/06/30)
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- Copper-catalyzed regioselective synthesis of N-aryl amides from aldoximes and aryl halides
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Ligand-assisted copper-catalyzed reaction of aldoximes with aryl halides is described for the regioselective synthesis of N-aryl amides. This protocol is simple and compatible with a wide range of functional groups attached to the aryl ring of the halides as well as aldoximes. Copyright
- Panda, Niranjan,Mothkuri, Raghavender,Nayak, Dinesh Kumar
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supporting information
p. 1602 - 1605
(2014/03/21)
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- Copper-Catalyzed Regioselective Synthesis of N-Aryl Amides from Aldoximes and Aryl Halides
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Ligand-assisted copper-catalyzed reaction of aldoximes with aryl halides is described for the regioselective synthesis of N-aryl amides. This protocol is simple and compatible with a wide range of functional groups attached to the aryl ring of the halides as well as aldoximes.
- Panda, Niranjan,Mothkuri, Raghavender,Nayak, Dinesh Kumar
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supporting information
p. 1602 - 1605
(2015/10/05)
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- Synthesis of some new glutamine linked 2,3-disubstituted quinazolinone derivatives as potent antimicrobial and antioxidant agents
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A series of novel glutamine linked 2,3-disubstituted quinazolinone conjugates was synthesized from methyl anthranilate and different substituted acids and acid chlorides. The compounds 5a-l were prepared in good yields. All compounds were screened for their antibacterial activity against Gram-positive and Gram-negative bacteria and for antifungal activity against Candida albicans and Aspergillus flavus using paper disk diffusion technique. The minimum inhibitory concentrations of the compounds were also determined by agar streak dilution method. The compound 5b was found to exhibit the most potent in vitro anti-microbial activity. When tested for their antioxidant activity, compounds 5i and 5l showed potent radical scavenging activity, while compound 5g had moderate effect against 2,2-diphenyl-1-picrylhydrazyl, hydroxyl, nitric oxide, and superoxide radical scavenging assays. These results suggest that, the three quinazolinone analogs (5g, 5i, and 5l) could be considered as useful templates for future development to obtain more potent antioxidant agents.
- Prashanth,Revanasiddappa
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p. 2665 - 2676
(2013/07/26)
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- Discovery of novel bacterial RNA polymerase inhibitors: Pharmacophore-based virtual screening and hit optimization
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The bacterial RNA polymerase (RNAP) is a validated target for broad spectrum antibiotics. However, the efficiency of drugs is reduced by resistance. To discover novel RNAP inhibitors, a pharmacophore based on the alignment of described inhibitors was used for virtual screening. In an optimization process of hit compounds, novel derivatives with improved in vitro potency were discovered. Investigations concerning the molecular mechanism of RNAP inhibition reveal that they prevent the protein-protein interaction (PPI) between σ70 and the RNAP core enzyme. Besides of reducing RNA formation, the inhibitors were shown to interfere with bacterial lipid biosynthesis. The compounds were active against Gram-positive pathogens and revealed significantly lower resistance frequencies compared to clinically used rifampicin.
- Hinsberger, Stefan,Hüsecken, Kristina,Groh, Matthias,Negri, Matthias,Haupenthal, J?rg,Hartmann, Rolf W.
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supporting information
p. 8332 - 8338
(2013/12/04)
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- Application of H/D exchange to hydrogen bonding in small molecules
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Do you recognize me? A series of simple amides has been used to demonstrate the application of hydrogen/deuterium exchange in small-molecule hydrogen bonding. By comparison with similar controls, the degree of protection from H/D exchange can provide insight into the degree of hydrogen bonding (see scheme).
- Schneider, Tanya L.,Halloran, Kevin T.,Hillner, Julie A.,Conry, Rebecca R.,Linton, Brian R.
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supporting information
p. 15101 - 15104
(2013/11/06)
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- Bio-inspired flavonol and quinolone dioxygenation by a non-heme iron catalyst modeling the action of flavonol and 3-hydroxy-4(1H)-quinolone 2,4-dioxygenases
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The mononuclear complex, FeIII(O-bs)(salen) (salenH2 = 1,6-bis(2-hydroxyphenyl)-2,5-diaza-hexa-1,5-diene; O-bsH = O-benzoylsalicylic acid) was synthesized as synthetic enzyme-depside complex, and characterized by spectroscopic methods and X-ray crystal analysis. The dioxygenation of flavonol (flaH) and 3-hydroxy-4-quinolone (quinH2) derivatives in the presence of catalytic amounts of FeIII(O-bs)(salen) results in the oxidative cleavage of the heterocyclic ring to give the corresponding O-benzoylsalicylic and anthranilic acid derivatives with concomitant release of carbon monoxide. These reactions can be regarded as biomimetic functional models with relevance to the iron-containing flavonol and the cofactor-independent 3-hydroxy-4(1H)-quinolone 2,4-dioxygenases.
- Pap, József S.,Matuz, Andrea,Baráth, Gábor,Kripli, Balázs,Giorgi, Michel,Speier, Gábor,Kaizer, József
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experimental part
p. 15 - 21
(2012/06/15)
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- N-Benzoyl-N-methylsulfonylanthranilates: Unexpected cyclization reaction to 4-alkoxy-2,1-benzothiazines
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The synthesis of 4-alkoxy-1H-2,1-benzothiazine 2,2-dioxide derivatives was achieved through an unexpected base-mediated cyclization of N-benzoyl-N- methylsulfonylanthranilates. A reaction mechanism involving the sulfene species has been postulated. The ob
- Manfroni, Giuseppe,Meschini, Francesco,Costantino, Ferdinando,Tabarrini, Oriana,Cecchettia, Violetta
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p. 165 - 176
(2011/08/07)
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- Study of reaction between triphenylphosphine and activated acetylenic esters in the presence of benzanilide and some its derivatives
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Triphenylphosphine reacts with dialkyl acetylenedicarboxylates in the presence of NH-acids, such as benzanilide, 2-cyanobenzanilide, N-(2-acetylphenyl)benzamide, 3-nitrobenzanilide and methyl 2-benzamidobenzoate to generate stable phosphorus ylides. These stable ylides exist in solution as a mixture of two geometrical isomers as a result of restricted rotation around the carbon-carbon partial double bond resulting from conjugation of the ylide moiety with the adjacent carbonyl group.
- Hazeri, Nourollah,Maghsoodlou, Malek Taher,Khorassani, Sayyed Mostafa Habibi,Nassiri, Mahmoud,Afarini, Zahra
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experimental part
p. 97 - 100
(2009/07/18)
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- Palladium-catalyzed intermolecular coupling of aryl halides and amides
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The first general intermolecular C-N bond-forming reactions between aryl halides and amides were realized using a palladium catalyst with Xantphos as the ligand. Aryl triflates, carbamates, and sulfonamides are also viable substrates for the amidations, which proceed at 45-110 °C with 1-4 mol% of Pd catalyst in 66-99% yields and exhibit good functional group compatibility.
- Yin, Jingjun,Buchwald, Stephen L.
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p. 1101 - 1104
(2007/10/03)
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- Sodium 2-ethylhexanoate: A mild acid scavenger useful in acylation of amines
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A highly useful method for the acylation of amines with acid chlorides utilizing sodium 2-ethylhexanoate as the base is described. This procedure is superior to the Schotten-Baumann conditions whenever the product is water soluble.
- Fitt, John,Prasad, Kapa,Repic, Oljan,Blacklock, Thomas J.
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p. 6991 - 6992
(2007/10/03)
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- Use of halomethyl resins to immobilize amines: An efficient method for synthesis of sulfonamides and amides on a solid support
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Methods for the synthesis of chloromethyl and bromomethyl equivalents of Wang's resin are described. To explore the utility of this acid clearable resin, amines were immobilized through the nitrogen atom, further functionalized, and then cleaved under acid conditions.
- Raju,Kogan, Timothy P.
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p. 4965 - 4968
(2007/10/03)
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- Solid-phase synthesis of diverse tetrahydro-1,4-benzodiazepine-2-ones
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A general method for the construction of tetrahydro-1,4-benzodiazepine- 2-ones on solid-support has been developed utilising a cleavage-conjugate addition protocol as the key step in the design. Using this novel, methodology the synthesis of a diverse one
- Bhalay, Gurdip,Blaney, Paul,Palmer, Vanessa H.,Baxter, Anthony D.
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p. 8375 - 8378
(2007/10/03)
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- Production of 3-Benzoyl-2,1-benzisoxazoles, 2-Phenyl-4H-3,1-benzoxazin-4-ones, and Novel Quinolinone Derivatives from 2-Phenylquinolin-4(1H)-ones and Sodium Dichloroisocyanurate
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A simple synthesis of certain 3-benzoyl-2,1-benzisoxazoles 6 is accomplished via treatment of the corresponding 2-phenylquinolin-4(1H)-one 1 with sodium dichloroisocyanurate 2 in methanolic aq. alkali; the isomeric 2-phenyl-4H-3,1-benzoxazin-4-one 7 is al
- Staskun, Benjamin,Es, Theodorus van
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p. 511 - 516
(2007/10/02)
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- Synthesis and structure-activity relationships of N-substituted 2-[(2-imidazolylsulfinyl)methyl]anilines as a new class of gastric H+/K+-ATPase inhibitors
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A series of N-substituted 2-[(2-imidazolylsulfinyl)methyl]anilines was synthesized and evaluated for its biological activity against H+/K+-ATPase prepared from rabbit stomach and gastric acid secretions in Heidenhain pouch dogs. Monoalkyl substituents on the nitrogen atom of the aniline moiety markedly inhibited the enzyme activity to the same degree as omeprazole, a representative H+/K+-ATPase inhibitor. Most of these compounds, administered at 3 mg/kg i.v. inhibited histamine-stimulated gastric acid secretion. The inhibitory activity of these derivatives on the enzymes at pH 6.0 was more potent than that at pH 7.4, and was distinctly correlated to stability in aqueous solution at pH 5.0.
- Yamakawa,Matsukura,Nomura,Yoshioka,Masaki,Igata,Okabe
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p. 1746 - 1752
(2007/10/02)
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- Modified Procedure for the Preparation of 5-Nitro-2-furylmethylene Diacetate and Its Use in the Synthesis of Some Novel (5-Nitro-2-furyl)azomethines via 5-Nitro-2-furaldehyde
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A modified two-step procedure for the preparation of 5-nitro-2-furylmethylene diacetate (3) by nitration of 2-furaldehyde (1) or 2-furylmethylene diacetate (4) with acetyl nitrate via 2-acetoxy-5-nitro-2,5-dihydro-2-furylmethylene diacetate (2), or 1,1,5-triacetoxy-2-hydroxy-5-nitro-3-penten (5) and 1,1,5-triacetoxy-2-hydroxy-5-nitro-2,4-pentadiene (6), has been developed.Acid hydrolysis of 3 yields 5-nitro-2-furaldehyde (7) which is used in the carbonylamine condensation with various hydrazines (9-11, 14, 17, 19, 21, 24, 25, 28, 29, 32, 34, 36, 38, 39, 41 and 44-54) prepared by known methods, in order to obtain some novel potentially pharmaceutically active (5-nitro-2-furyl)azomethines.
- Vlaovic, Djordje,Milic, Bozidar Lj.,Mackenzie, Kenneth
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p. 1201 - 1218
(2007/10/02)
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- Phosphoramides. XIII. Phosphorus Pentaoxide-Amine Hydrochloride Mixtures as Reagents in the Synthesis of 4(3H)-Quinazolinones and 4-Quinazolinamines
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4(3H)-Quinazolinones 3a-r have been prepared by heating methyl N-acylanthranilates 1a-c and the hydrochlorides of primary aliphatic and aromatic amines with phosphorus pentaoxide and N,N-dimethylcyclohexylamine at 180 deg C. 4-Quinazolinamines 4 and the amidine 7 were isolated as by-products.The carboxamides 5 and 6 were believed to be reaction intermediates.By raising the temperature to 250 deg C 4 was obtained in a preparative yield.
- Nielsen, Knud Erik,Pedersen, Erik B.
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p. 637 - 642
(2007/10/02)
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