Synthesis and Activity of a New Series of(Z)-3-Phenyl-2-benzoylpropenoic Acid Derivatives as Aldose Reductase Inhibitors

doi:10.3390/12040885

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Molecules 2007, 12(4), 885-895; doi:10.3390/12040885

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Synthesis and Activity of a New Series of(Z)-3-Phenyl-2-benzoylpropenoic Acid Derivatives as Aldose Reductase Inhibitors

Shao-Jie Wang^1,* , Ju-Fang Yan², Dong Hao¹, Xin-Wen Niu¹ and Mao-Sheng Cheng¹

¹ Key Laboratory of New Drugs Design and Discovery of Liaoning Province, Shenyang Pharmaceutical University, Shenyang 110016, P.R. China ² Drug Screening Center, Di Ao Pharmaceutical Group, Chengdu 123388, P.R. China

* Author to whom correspondence should be addressed.

Received: 21 March 2007; in revised form: 23 April 2007 / Accepted: 23 April 2007 / Published: 30 April 2007

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Abstract: During the course of studies directed towards the discovery of novel aldose reductase inhibitors for the treatment of diabetic complications, we synthesized a series of new (Z)-3-phenyl-2-benzoylpropenoic acid derivatives and tested their in vitro inhibitory activities on rat lens aldose reductase. Of these compounds, (Z)-3-(3,4-dihydroxyphenyl)-2-(4-methylbenzoyl)propenoicacid(3k) was identified as the most potent inhibitor, with an IC₅₀ of 0.49μM. The theoretical binding mode of 3k was obtained by simulation of its docking into the active site of the human aldose reductase crystal structure.

Keywords: (Z)-3-Phenyl-2-benzoylpropenoic acid; aldose reductase inhibitor; structure-activity relationships

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MDPI and ACS Style

Wang, S.-J.; Yan, J.-F.; Hao, D.; Niu, X.-W.; Cheng, M.-S. Synthesis and Activity of a New Series of(Z)-3-Phenyl-2-benzoylpropenoic Acid Derivatives as Aldose Reductase Inhibitors. Molecules 2007, 12, 885-895.

AMA Style

Wang S-J, Yan J-F, Hao D, Niu X-W, Cheng M-S. Synthesis and Activity of a New Series of(Z)-3-Phenyl-2-benzoylpropenoic Acid Derivatives as Aldose Reductase Inhibitors. Molecules. 2007; 12(4):885-895.

Chicago/Turabian Style

Wang, Shao-Jie; Yan, Ju-Fang; Hao, Dong; Niu, Xin-Wen; Cheng, Mao-Sheng. 2007. "Synthesis and Activity of a New Series of(Z)-3-Phenyl-2-benzoylpropenoic Acid Derivatives as Aldose Reductase Inhibitors." Molecules 12, no. 4: 885-895.

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