Intramolecular nonbonded S•••O interaction in acetazolamide and thiadiazolinethione molecules in their dimeric crystalline structures and complex crystalline structures with enzymes

被引：36

作者：

Nagao, Y ^{[1
]}

Honjo, T

Iimori, H

Goto, S

Sano, S

Shiro, M

Yamaguchi, K

Sei, Y

机构：

[1] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan

[2] Rigaku Corp, Akishima, Tokyo 1968666, Japan

[3] Tokushima Bunri Univ, Fac Pharmaceut Sci, Sanuki City, Kagawa 7692193, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 47期

基金：

日本学术振兴会;

关键词：

cold-spray ionization mass spectrometry; conformation analysis; density functional theory; enzyme inhibitor; X-ray crystallographic analysis;

D O I：

10.1016/j.tetlet.2004.09.103

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The dimeric crystalline structure of acetazolamide 1 and thiadiazolinethione 2 bearing intramolecular nonbonded (SO)-O-. . . interactions, in each different hydrogen-bonding manner was clarified by their X-ray crystallographic analysis. Existence of the dimeric structure of 1 and 2 in a MeOH solution could be suggested on the basis of their cold-spray ionization mass spectrometry. The intramolecular nonbonded (SO)-O-. . . interaction was precisely recognized in the complex crystalline structures of carbonic anhydrase I inhibitor 1 and stromelysin inhibitors 2-4 with each specific enzyme. The computational evaluation of the possible monomeric seven conformers of 1 and two model compounds 5 and 6 of 2-4 based on DFT calculations defined that the conformer bearing the intramolecular nonbonded (SO)-O-. . . interaction is most stable. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8757 / 8761

页数：5

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