Chiral resolution, determination of absolute configuration, and biological evaluation of (1,2-benzothiazin-4-yl)acetic acid enantiomers as aldose reductase inhibitors

Xin Hao, Xiangyu Qin, Saghir Hussain, Shagufta Parveen, Wei Zhang, Fengyan Fu, Bing Ma, Changjin Zhu*

*此作品的通讯作者

科研成果: 期刊稿件 › 文章 › 同行评审

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摘要

A novel series of (1,2-benzothiazin-4-yl)acetic acid enantiomers was prepared by chiral resolution, and their absolute configurations were determined using the PGME method. The biological evaluation of the racemate and single enantiomers has shown a remarkable difference for the aldose reductase inhibitory activity and selectivity. The (R)-(-)-enantiomer exhibited the strongest aldose reductase activity with an IC50 value of 0.120 μM, which was 35 times more active than the S-(+)-enantiomer. Thus, the stereocenter at the C4 position of this scaffold was shown to have a major impact on the activity and selectivity.

源语言英语
页（从-至）846-851
页数6
期刊Journal of Enzyme Inhibition and Medicinal Chemistry
卷30
期5
DOI
出版状态已出版 - 3 9月 2015

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引用此

Hao, X., Qin, X., Hussain, S., Parveen, S., Zhang, W., Fu, F., Ma, B., & Zhu, C. (2015). Chiral resolution, determination of absolute configuration, and biological evaluation of (1,2-benzothiazin-4-yl)acetic acid enantiomers as aldose reductase inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry, 30(5), 846-851. https://doi.org/10.3109/14756366.2014.961447