- Synthesis and evaluation of new phenyl acrylamide derivatives as potent non-nucleoside anti-HBV agents
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As a continuation of our previous work, a series of new phenyl acrylamide derivatives (4Aa-g, 4Ba-t, 5 and 6a-c) were designed and synthesized as non-nucleoside anti-HBV agents. Among them, compound 4Bs could potently inhibit HBV DNA replication in wild-type and lamivudine (3TC)/entecavir resistant HBV mutant strains with IC50 values of 0.19 and 0.18 μM, respectively. Notably, the selective index value of 4Bs was above 526, indicating the favorable safety profile. Interestingly, unlike nucleoside analogue 3TC, 4Bs could significantly inhibit 3.5 kb pgRNA expression. Molecular docking study revealed that 4Bs could fit well into the dimer-dimer interface of HBV core protein by hydrophobic, π–π and H-bond interactions. Considering the potent anti-HBV activity, low toxicity and diverse anti-HBV mechanism from that of nucleoside anti-HBV agent 3TC, compound 4Bs might be a promising lead to develop novel non-nucleoside anti-HBV therapeutic agents, and warranted further investigation.
- Gu, Xiaoke,Zhang, Yinpeng,Zou, Yueting,Li, Xin,Guan, Mingyu,Zhou, Qingqing,Qiu, Jingying
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- Base Induced Condensation of Malononitrile with Erlenmeyer Azlactones: An Unexpected Synthesis of Multi-Substituted Δ2-Pyrrolines and Their Cytotoxicity
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An efficient, metal free approach to synthesize multi-substituted Δ2-pyrroline derivatives by mild base catalyzed cyclocondensation of malononitrile with Erlenmeyer azlactones via 1,2 addition was developed. The modularity of this reaction was used to assemble a range of poly-substituted pyrrolines. Further, synthesized products were screened for cytotoxic properties on different cancer cell lines such as A549 (Human lung adenocarcinoma cells), HeLa (Human cervical adenocarcinoma cells), Jurkat (Human chronic myeloid leukemia cells) and K562 (Human leukemic T cell Lymphoblast cells). Among the synthesized library of compounds, 6f and 6q displayed potent cytotoxic activity.
- Anil, Seegehalli M.,Kiran, Kuppalli R.,Rajeev, Narasimhamurthy,Sadashiva, Maralinganadoddi P.,Shobith, Rangappa,Sudhanva, Muddenahalli S.,Swaroop, Toreshettahally R.,Vinayaka, Ajjampura C.
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- Synthesis, biological evaluation and in silico studies with 4-benzylidene-2-phenyl-5(4H)-imidazolone-based benzenesulfonamides as novel selective carbonic anhydrase IX inhibitors endowed with anticancer activity
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In the presented work, we report the synthesis of a series of 4-benzylidene-2-phenyl-5(4H)-imidazolone-based benzenesulfonamides 7a-f via the Erlenmeyer–Pl?chl reaction. All the prepared imidazolones 7a-f were evaluated as inhibitors of human (h) carbonic anhydrases (CA, EC 4.2.1.1) cytosolic isoforms hCA I and II, as well as transmembrane tumor-associated isoforms hCA IX and XII. All the tested hCA isoforms were inhibited by the prepared imidazolones 7a-f in variable degrees with the following KIs ranges: 673.2–8169 nM for hCA I, 61.2–592.1 nM for hCA II, 23–155.4 nM for hCA XI, and 21.8–179.6 nM for hCA XII. In particular, imidazolones 7a, 7e, and 7f exhibited good selectivity towards the tumor-associated isoforms (CAs IX and XII) over the off-target cytosolic (CAs I and II) with selectivity index (SI) in the range of 6.2–19.4 and 3.3–8, respectively. Moreover, imidazolones 7a-f were screened for their anticancer activity in one dose (10?5 M) assay against a panel of 60 cancer cell lines according to US-NCI protocol. Furthermore, 7a, 7e and 7f were evaluated for their anti-proliferative activity against colorectal cancer HCT-116 and breast cancer MCF-7 cell lines. Furthermore, 7e and 7f were screened for cell cycle disturbance and apoptosis induction in HCT-116 cells. Finally, a molecular docking study was carried out to rationalize the obtained results.
- Eldehna, Wagdy M.,Abdelrahman, Mohamed A.,Nocentini, Alessio,Bua, Silvia,Al-Rashood, Sara T.,Hassan, Ghada S.,Bonardi, Alessandro,Almehizia, Abdulrahman A.,Alkahtani, Hamad M.,Alharbi, Amal,Gratteri, Paola,Supuran, Claudiu T.
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- Synthesis and herbicidal activity of 4-benzylidene-2-phenyl oxazol-5(4H)-one derivatives using l-proline as catalyst
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A simple, efficient and environmentally benign method for the synthesis of 4-benzylidene-2-phenyl oxazol-5(4H)-one derivatives by the reaction of aromatic aldehydes and hippuric acid using acetic anhydride as dehydrating agent and L-proline as catalyst ha
- Bhandari,Kasana
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p. 1717 - 1722
(2018/07/10)
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- Stereoselective Intermolecular [2 + 2] Cycloadditions of Erlenmeyer-Pl?chl Azlactones Using Visible Light Photoredox Catalysis
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The first report of the preparation of symmetric and nonsymmetric diaminotruxinic derivatives through the photoredox [2 + 2] cycloadditions of Erlenmeyer azlactones is described, affording the desired compounds in high regio- and diastereocontrol (only head-to-head coupling). Mechanistic studies by DFT suggest that the reaction proceeds through a neutral photocatalytic pathway.
- Marra, Isabellar F. S.,De Almeida, Angelina M.,Silva, Larissa P.,De Castro, Pedro P.,Corrêa, Charlane C.,Amarante, Giovanni Wilson
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p. 15144 - 15154
(2018/12/14)
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- Synthesis and insecticidal evaluation of tetrahydroimidazo[1,2-a]pyridin-5(1H)-one derivatives
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A series of novel tetrahydroimidazo[1,2-a]pyridine-5(1H)-one derivatives containing a electronegative pharmacophore (=CNO2) were synthesized via practical aza-ene reaction and characterized by 1H NMR, 13C NMR, 19F NMR and HRMS. Preliminary bioassays showed that some of the target compounds exhibited good insecticidal activity against brown planthopper (Nilaparvata lugens) and cowpea aphids (Aphis craccivora) at 500 mg L-1. Among them, compound 11h was active against brown planthopper at 100 mg L-1. The insecticidal activities varied significantly depending on the types and patterns of the substituents, which provided guidance for further investigation on structure modifications.
- Liu, Xuan-Qi,Liu, Ya-Qin,Shao, Xu-Sheng,Xu, Zhi-Ping,Xu, Xiao-Yong,Li, Zhong
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- Nanocrystalline titanium dioxide catalyst for the synthesis of azlactones
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Titanium dioxide nanoparticles were prepared by a electrochemical reduction method using parameters such as current density, solvent polarity, distance between electrodes, and concentration of stabilizers to control the size of the nanoparticles. The nanoparticles were characterized by UV-Vis spectroscopy, X-ray diffraction, scanning electron microscopy and transmission electron microscopy, and their catalytic performance was tested for the synthesis of a series of 4-aryldiene-2-phenyl-5(4)-oxazolones from the cyclodehydration and condensation of the respective aldehyde, hippuric acid and acetic anhydride. Easy availability, reusability and eco-friendliness were some prominent features of the nanocrystalline titanium dioxide catalyst.
- Anandgaonker, Priyanka,Kulkarni, Ganesh,Gaikwad, Suresh,Rajbhoj, Anjali
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p. 196 - 200
(2014/03/21)
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- Ammonium metavanadate an efficient catalyst for Erlenmeyer synthesis
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An efficient method to synthesize azalactone derivatives using ammonium metavanadate (NH4VO3) as catalyst was performed in the absence of solvent. This method is environmentally friendly and affords the product azalactones in high yi
- Madje, Balaji,Ubale, Milind,Bharad, Jagdish,Shingare, Murlidhar
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p. 1295 - 1299
(2013/01/15)
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- Palladium-catalyzed diastereo- and enantioselective formal [3 + 2]-cycloadditions of substituted vinylcyclopropanes
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We describe a palladium-catalyzed diastereo- and enantioselective formal [3 + 2]-cycloaddition between substituted vinylcyclopropanes and electron-deficient olefins in the form of azlactone- and Meldrums acid alkylidenes to give highly substituted cyclopentane products. By modulation of the electronic properties of the vinylcyclopropane and the electron-deficient olefin, high levels of stereoselectivity were obtained. The remote stereoinduction afforded by the catalyst, distal from the chiral pocket generated by the ligand, is proposed to be the result of a new mechanism invoking the Curtin-Hammett principle.
- Trost, Barry M.,Morris, Patrick J.,Sprague, Simon J.
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supporting information
p. 17823 - 17831,9
(2012/12/12)
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- Palladium-catalyzed diastereo- and enantioselective formal [3 + 2]-cycloadditions of substituted vinylcyclopropanes
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We describe a palladium-catalyzed diastereo- and enantioselective formal [3 + 2]-cycloaddition between substituted vinylcyclopropanes and electron-deficient olefins in the form of azlactone- and Meldrums acid alkylidenes to give highly substituted cyclopentane products. By modulation of the electronic properties of the vinylcyclopropane and the electron-deficient olefin, high levels of stereoselectivity were obtained. The remote stereoinduction afforded by the catalyst, distal from the chiral pocket generated by the ligand, is proposed to be the result of a new mechanism invoking the Curtin-Hammett principle.
- Trost, Barry M.,Morris, Patrick J.,Sprague, Simon J.
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supporting information
p. 17823 - 17831
(2013/01/15)
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- Palladium-catalyzed diastereo- and enantioselective synthesis of substituted cyclopentanes through a dynamic kinetic asymmetric formal [3+2]-cycloaddition of vinyl cyclopropanes and alkylidene azlactones
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An enantioselective preparation of vinylcyclopentanes has been achieved through the title reaction (see scheme). A range of aryl, heterocyclic, alkenyl, and alkyl substituted azlactone alkylidenes have been utilized, giving the cyclopentane products in go
- Trost, Barry M.,Morris, Patrick J.
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supporting information; experimental part
p. 6167 - 6170
(2011/08/22)
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- Molecular iodine-catalyzed, mild, effective, ecofriendly, microwave-assisted, one-pot synthesis of 5-arylmethylidene-2-phenyloxazol-4-ones (Azalactones) under solvent-free conditions
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Fourteen azalactones have been synthesized in excellent yields under solvent-free conditions by heating an aldehyde, hippuric acid, and acetic anhydride in the presence of molecular iodine as a catalyst in a microwave oven. The short reaction time, cleaner reaction, and easy workup make this protocol practical and economically attractive. Copyright
- Reddy, M. B. Madhusudana,Pasha
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experimental part
p. 1895 - 1898
(2010/09/07)
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- Alum an efficient catalyst for erlenmeyer synthesis
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A new and efficient method to synthesize azlactone derivatives using alum ascatalyst was performed in the absence of additional solvent. This method is environmentally friendly and affords the product azlactones in high yields after simple workup.
- Madje, Balaji R.,Ubale, Milind B.,Bharad, Jagdish V.,Shingare, Murlidhar S.
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experimental part
p. 158 - 161
(2012/01/06)
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- Synthesis, characterization and biological activity of 5-arylidene-3-(6,7-dicloro-1,3-benzothiazol-2-yl)-phenyl-3,5-dihydro-4H-imidazol-4-ones
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Some novel 5-arylidene-3-(6,7-dichloro-1,3-benzothiazol-2-yl)-2-phenyl-3,5-dihydro-4H-imidazol-4-ones (6a-q) have been synthesized and characterized by elemental analyses, IR, NMR, and mass spectra. The products have been evaluated for antibacterial and a
- Baldaniya
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scheme or table
p. 81 - 84
(2011/01/03)
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- Synthesis and immunomodulatory properties of selected oxazolone derivatives
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Eleven oxazolone derivatives were synthesized and characterized by 1H NMR, EI, IR and UV spectroscopic and CHN analysis. Three compounds, 4-[(E)-(4-nitrophenyl)methylidene]-2-phenyl-1,3-oxazol-5(4H)-one (11), 4-[(E)-(4-methoxyphenyl)methylidene]-2-methyl-1,3-oxazol-5-one (12) and 4-[(E)-(4-nitrophenyl)methylidene]-2-methyl-1,3-oxazol-5(4H)-one (13) were screened for phagocyte chemiluminescence, neutrophil chemotaxis, T-cell proliferation, cytokine production from mononuclear cells and cytotoxicity. 4-[(E)-(4-Nitrophenyl)methylidene]-2-methyl-1,3-oxazol-5(4H)-one (13) was found to be the most potent immunomodulator in the series.
- Mesaik, Muhammad A.,Rahat, Shagufta,Khan, Khalid M.,Zia-Ullah,Choudhary, Muhammad I.,Murad, Shahnaz,Ismail, Zakiah,Atta-ur-Rahman,Ahmad, Aqeel
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p. 2049 - 2057
(2007/10/03)
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- Bismuth (III) acetate: A new catalyst for preparation of azlactones via the Erlenmeyer synthesis
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Bismuth(III) acetate catalyzes the synthesis of azlactones from aromatic aldehydes in moderate to good yields via the Erlenmeyer synthesis. The relatively low toxicity and low cost of bismuth(III) acetate make this procedure particularly attractive.
- Monk, Keith A.,Sarapa, Dusan,Mohan, Ram S.
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p. 3167 - 3170
(2007/10/03)
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- Kinetics and mechanism of aminolysis of (Z)-4-arylidene-2-phenyl-5(4H)oxazolones
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The kinetics of the reactions of a series of (Z)-4-arylidene-2-phenyl-5(4H)oxazolones 1 with n-butylamine and piperidine were studied spectrophotometrically in dioxane, ethanol, and cyclohexane under pseudo-first-order conditions and at different temperat
- Alkaabi, Sharifa S.,Shawali, Ahmad S.
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p. 2515 - 2519
(2007/10/02)
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