- Rapid synthesis of flavone-based monoamine oxidase (MAO) inhibitors targeting two active sites using click chemistry
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A new library of flavone derivatives targeting two active sites of monoamine oxidases (“aromatic cage” and substrate cavity) were designed and synthesized using click chemistry (CuAAC reaction) between 6-N3-2-phenyl chromones (Az1–Az2) and a series of alkynes (k1–k20). Their inhibitory activities against MAO isoforms (MAO-A and MAO-B) are evaluated. Compounds with fluorine, amide bonds, or amino bonds have shown better inhibition. The most potent flavone MAO inhibitor studied is Az2k19 (1.6?μm for MAO-A, 2.1?μm for MAO-B), while Az1k15 and Az2k15 displayed better selectivity toward MAO-B (SI?>?10). Docking studies are in accordance with our hypothesis that these inhibitors are most likely located at both the substrate cavity and the “aromatic cage”. Our results show that it is considerable to develop new MAO inhibitors from C6 substitution of flavone derivatives and that these compounds are also potential for the treatment of diseases associated with MAOs.
- Jia, Wei Zhen,Cheng, Feng,Zhang, Yin Jun,Ge, Jin Yan,Yao, Shao Q.,Zhu, Qing
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p. 141 - 151
(2016/12/16)
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- Pd(OAc)2/S=PPh3 accelerated activation of gem-dichloroalkenes for the construction of 3-arylchromones
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The Pd-catalyzed regioselective intramolecular nucleophilic substitution of gem-dichloroalkene derivatives with salicylaldehydes leading to the synthesis of 3-arylchromones has been developed. Pd(OAc)2/S=PPh3 could activate gem-dichloroalkenes and undergo nucleophilic substitution by salicylaldehydes with the aid of a base.
- Liu, Jianming,Song, Weiwei,Yue, Yuanyuan,Liu, Ren,Yi, Hong,Zhuo, Kelei,Lei, Aiwen
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supporting information
p. 17576 - 17579
(2015/12/08)
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- Synthesis and biological activities of some flavones
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Chalcones are synthesized by a base catalyzed Claisen Schmidt condensation reaction and then treated with dimethylsulphoxide in presence of iodine to get flavones. The synthesized compounds were evaluated for their antibacterial activity against Escherichia coilt P. aeruginosa, S. epidermidis and B. subtilis. All the flavones showed moderate to good activity. The structures of these compounds were confirmed by IR, UV, 1H NMR, Mass and elemental analysis.
- Sawant,Gill,Nirwan
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- Synthesis and biological activities of some flavones
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Chalcones are synthesized by a base catalyzed Claisen Schmidt condensation reaction and then treated with dimethylsulphoxide in presence of iodine to get flavones. The synthesized compounds were evaluated for their antibacterial activity against Escherichia coli, P. aeruginosa, S. epidermidis and B. subtilis. All the flavones showed moderate to good activity. The structures of these compounds were confirmed by IR, UV, 1H NMR, Mass and elemental analysis.
- Sawant,Gill,Nirwan
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p. 297 - 300
(2013/09/24)
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- Investigation on the substitution effects of the flavonoids as potent anticancer agents: A structure-activity relationships study
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Three series of flavonoid analogues substituted with different aminomethyl substitutions at C-6, C-7, and C-8 were designed and synthesized for the structure-activity relationship studies as potent anticancer agents. The prepared analogues were evaluated for their in vitro inhibitory activity against the growth of the hepatic cancer cell lines HepG2 and SMMC-7721. Structure-activity relationships indicated that not only the compounds with amino methyl groups were more active than those without the groups in the same series but also the compounds substituted by aminomethyl groups at position C-8 were more active than those at positions C-6 and C-7.
- Wang, Xiao-Bing,Yang, Lei,Kong, Ling-Yi,Liu, Wei,Guo, Qing-Long
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p. 1833 - 1849,17
(2020/07/30)
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- A new synthesis of flavones and pyranoflavone by intramolecular photochemical Wittig reaction in water
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A new synthetic approach toward the synthesis of flavones and pyranoflavone has been developed by light induced intramolecular photochemical Wittig reaction in water onto aryloxycarbonyl groups and suitably substituted phosphonium bromides sans any phase transfer catalyst or promoter.
- Das, Jhantu,Ghosh, Somnath
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p. 7189 - 7194
(2012/01/05)
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- A facile synthesis of flavones catalysed by gallium(III) triflate
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Ga(OTf)3 was explored as a novel catalyst for the cyclisation of 1-(2-hydroxyphenyl)-3-aryl-1,3-propanediones in nitromethane to flavones with excellent yields.
- Jin, Can,He, Fei,Wu, Huayue,Chen, Jiuxi,Su, Weike
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experimental part
p. 27 - 29
(2009/09/25)
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- Manganese(III) acetate mediated oxidation of flavanones: A facile synthesis of flavones
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Oxidation of flavanones (1a-o) with manganese(III) acetate by heating in acetic acid in presence of perchloric acid afforded exclusively flavones (2a-o) by dehydrogenation in almost quantitative yields. Copyright Taylor & Francis, Inc.
- Singh, Om V.,Muthukrishnan,Raj, Gopan
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p. 2723 - 2728
(2007/10/03)
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- Hypervalent iodine oxidation of flavanones: A new synthesis of methyl 2-aryl-2,3-dihydrobenzofuran-3-carboxylates by 1,2-aryl shift
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Flavanones (1), on oxidation with (diacetoxyiodo)benzene-sulfuric acid (DIB-H2SO4) or (hydroxy(tosyloxy)iodo)benzene (HTIB) in trimethyl orthoformate, undergo facile ring contraction by 1,2-aryl shift, thereby yielding methyl 2-aryl-2,3-dihydrobenzofuran-3-carboxylates (4) as major products (40-80%). cis-3-Methoxyflavanones (5) and flavones (3) are the minor products formed in variable ratios.
- Prakash,Tanwar
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p. 1168 - 1171
(2007/10/02)
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- Hypervalent Iodine Oxidation of Flawanones: Convenient and Useful Syntheses of Flavones and IsoFlavones
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Hypervalent iodine oxidation of flavanones (1a-g) under a variety of conditions, offering convenient and valuable routes to the syntheses of flavones (2a-g) and isoflavones (3a-g), is described.The course of these oxidation reactions is greatly influenced by the reaction conditions and it is possible to select appropriate conditions for following a desired route (2/3).The mechanistic rationale for these transformations is also discussed.
- Prakash, Om,Tanwar, Madan P.
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p. 1429 - 1447
(2007/10/02)
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- Oxidation of Flavanones using Thallium(III) Salts: A New Route for the Synthesis of Flavones and Isoflavones
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When treated with thallium(III) acetate in acetic acid or acetonitrile, flavanones undergo facile dehydrogenation to afford flavones whereas, upon treatment with thallium(III) toluene-p-sulfonate or thallium(III) nitrate in propionitrile or acetonitrile, respectively, they undergo oxidative 2,3-aryl migration to give isoflavones in high yield.
- Khanna, Mahavir S.,Singh, Om V.,Garg, Chandra P.,Kapoor, Ram P.
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p. 2565 - 2568
(2007/10/02)
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- Epoxidation of Flavones by Dimethyldioxirane
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The synthesis of epoxides 2 by epoxidation of flavones 1 with isolated dimethyldioxirane (as acetone solution) at subambient temperatures is reported.These labile epoxides were isolated and completely characterized by UV, IR, 1H and 13C NMR, MS, and C,H analyses.Warming to room temperature led to rearrangement to afford quantitatively the 3-hydroxyflavones 3b,h,i,n.Treatment of the epoxides 2b,f with methanol led to the 3-hydroxy-2-methoxyflavanones 4b,f, as a mixture of cis and trans isomers.
- Adam, Waldemar,Golsch, Dieter,Hadjiarapoglou, Lazaros
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p. 7292 - 7297
(2007/10/02)
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- 6',2-(2'-Arylchromonyl) propionic acids, and analgesic and anti-inflammatory derivatives thereof
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Propionic acids and their functional derivatives having anti-inflammatory and analgesic properties correspond to the formula STR1 in which X is selected from phenyl, halophenyl, polyhalophenyl, lower alkylphenyl, trihalomethylphenyl, aryloxyphenyl, furyl and thienyl and R is selected from hydrogen, lower alkyl, lower omega-hydroxyalkyl, morpholinoethyl and lower dialkylaminoalkyl.
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