Copper-catalyzed asymmetric synthesis and comparative aldose reductase inhibition activity of (+)/(-)-1,2-benzothiazine-1,1-dioxide acetic acid derivatives.
A copper catalyst system for the asymmetric 1,4-hydrosilylation of the α,β-unsaturated carboxylate class was developed by which synthesis of (+)- and (-)-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-activity relationship study yielded the following order of aldose reductase inhibition activity: (-)-enantiomers > racemic > (+)-enantiomers. Further, a molecular docking study suggested that the (-)-enantiomer had significant binding affinity and thus increased inhibition activity.
Department of Applied Chemistry, Beijing Institute of Technology , No. 5, Zhongguancun South Street, 100081 Beijing, China.
Shagufta
S
Parveen
Saghir
S
Hussain
Xiangyu
X
Qin
Xin
X
Hao
Shaojuan
S
Zhu
Miao
M
Rui
Shuzhen
S
Zhang
Fengyan
F
Fu
Bing
B
Ma
Qun
Q
Yu
Changjin
C
Zhu
D000085:Acetates / Q000138:chemical synthesis* / Q000737:chemistry*; D019342:Acetic Acid / Q000737:chemistry*; D000449:Aldehyde Reductase / Q000037:antagonists & inhibitors* / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013843:Thiazines / Q000138:chemical synthesis* / Q000737:chemistry*
C000594668:1,2-benzothiazine-1,1-dioxide acetic acid; D000085:Acetates; D000447:Aldehydes; D004791:Enzyme Inhibitors; D013843:Thiazines; D003300:Copper; D000449:Aldehyde Reductase; D019342:Acetic Acid