Copper-Catalyzed Asymmetric Synthesis and Comparative Aldose Reductase Inhibition Activity of (+)/(鈭?-1,2-Benzothiazine-1,1-dioxide Acetic Acid Derivatives

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• 作者：Shagufta Parveen ; Saghir Hussain ; Xiangyu Qin ; Xin Hao ; Shaojuan Zhu ; Miao Rui ; Shuzhen Zhang ; Fengyan Fu ; Bing Ma ; Qun Yu ; Changjin Zhu
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：June 6, 2014
• 年：2014
• 卷：79
• 期：11
• 页码：4963-4972
• 全文大小：496K
• 年卷期：v.79,no.11(June 6, 2014)
• ISSN：1520-6904

文摘

A copper catalyst system for the asymmetric 1,4-hydrosilylation of the 伪,尾-unsaturated carboxylate class was developed by which synthesis of (+)- and (鈭?-enantiomers of 1,2-benzothiazine-1,1-dioxide acetates has been achieved with a good yield and an excellent level of enantioselectivity. A comparative structure鈥揳ctivity relationship study yielded the following order of aldose reductase inhibition activity: (鈭?-enantiomers > racemic > (+)-enantiomers. Further, a molecular docking study suggested that the (鈭?-enantiomer had significant binding affinity and thus increased inhibition activity.