- Synthesis, structure-activity relationship analysis and kinetics study of reductive derivatives of flavonoids as Helicobacter pylori urease inhibitors
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In a continuing study for discovering urease inhibitors based on flavonoids, nineteen reductive derivatives of flavonoids were synthesized and evaluated against Helicobacter pylori urease. Analysis of structure-activity relationship disclosed that 4-deoxy analogues are more potent than other reductive products. Out of them, 4′,7,8-trihydroxyl-2-isoflavene (13) was found to be the most active with IC50 of 0.85 μM, being over 20-fold more potent than the commercial available urease inhibitor, acetohydroxamic acid (AHA). Kinetics study revealed that 13 is a competitive inhibitor of H. pylori urease with a Ki value of 0.641 μM, which is well matched with the results of molecular docking. Biological evaluation and mechanism study of 13 suggest that it is a good candidate for discovering novel anti-gastritis and anti-gastric ulcer agent.
- Xiao, Zhu-Ping,Peng, Zhi-Yun,Dong, Jing-Jun,He, Juan,Ouyang, Hui,Feng, Yu-Ting,Lu, Chun-Lei,Lin, Wan-Qiang,Wang, Jin-Xiang,Xiang, Yin-Ping,Zhu, Hai-Liang
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p. 685 - 695
(2013/07/25)
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- o-Quinone methide based approach to isoflavans: application to the total syntheses of equol, 3′-hydroxyequol and vestitol
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A concise strategy is developed for the synthesis of isoflavans employing a Diels-Alder reaction between o-quinone methides and aryl-substituted enol ethers followed by reductive cleavage of the acetal group. The method is extended towards the total syntheses of equol, 3′-hydroxyequol and vestitol.
- Gharpure, Santosh J.,Sathiyanarayanan,Jonnalagadda, Prasad
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p. 2974 - 2978
(2008/09/20)
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- The direct synthesis of isoflavans VIA α-alkylation of phenylacetates
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Deprotonation of oxygenated phenylacetates and quenching of the enolates with oxygenated benzylic electrophiles, afforded 2,3-diarylpropanoates which served as precursors to the isoflavans following consecutive reduction and cyclization steps.
- Versteeg, Marietjie,Bezuidenhoudt, Barend C. B.,Ferreira, Daneel
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p. 1373 - 1394
(2007/10/03)
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