Intramolecular nonbonded S•••O interaction recognized in (acylimino)thiadiazoline derivatives as angiotensin II receptor antagonists and related compounds

被引：254

作者：

Nagao, Y ^{[1
]}

Hirata, T

Goto, S

Sano, S

Kakehi, A

Iizuka, K

Shiro, M

机构：

[1] Univ Tokushima, Fac Pharmaceut Sci, Sho, Tokushima 770, Japan

[2] Wakunaga Pharmaceut Co Ltd, Inst Med Res, Koda, Hiroshima 73911, Japan

[3] Shinshu Univ, Fac Engn, Nagano 380, Japan

[4] Kissei Pharmaceut Co Ltd, Hotaka, Nagano 39983, Japan

[5] Rigaku Corp, Tokyo 196, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1998年 / 120卷 / 13期

关键词：

D O I：

10.1021/ja973109o

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The intramolecular nonbonded 1,5-type S ... O interactions are recognized in the crystalline structures of the (acylimino)thiadiazoline derivatives (1-3) as angiotensin II receptor antagonists. The relative stability of the nonbonded 1,5-type S ... O interaction was investigated using the X-ray crystallographic analyses and the ab initio MO calculations (HF/3-21G*, 6-31G*, and 6-311+G**) of the simplified model compounds (6, 7, and 9). The concept of mimic-fused bicyclic heterocycles consisting of fairly stable nonbonded S ... O interaction seems to be an efficient approach toward the design and development of various drugs.

引用

页码：3104 / 3110

页数：7

共 31 条

[1] SIR92 - a program for automatic solution of crystal structures by direct methods [J].

ALTOMARE, A ;

CASCARANO, G ;

GIACOVAZZO, G ;

GUAGLIARDI, A ;

BURLA, MC ;

POLIDORI, G ;

CAMALLI, M .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 :435-435

[2] BONDING BETWEEN NONBONDED SULFUR AND OXYGEN-ATOMS IN SELECTED ORGANIC-MOLECULES (A QUANTUM CHEMICAL STUDY) [J].

ANGYAN, JG ;

POIRIER, RA ;

KUCSMAN, A ;

CSIZMADIA, IG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (08) :2237-2245

[3]

Barbieri G., 1989, J MOL STRUCT, V184, P269

[4]

BECKER P, 1986, APPLIED QUANTUM CHEM, P361

[5] SELF-CONSISTENT MOLECULAR-ORBITAL METHODS .21. SMALL SPLIT-VALENCE BASIS-SETS FOR 1ST-ROW ELEMENTS [J].

BINKLEY, JS ;

POPLE, JA ;

HEHRE, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (03) :939-947

[6] COMPUTATIONAL STUDIES OF NONBONDED SULFUR OXYGEN AND SELENIUM OXYGEN INTERACTIONS IN THE THIAZOLE AND SELENAZOLE NUCLEOSIDES [J].

BURLING, FT ;

GOLDSTEIN, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (07) :2313-2320

[7] NATURE OF S .... O INTERACTION IN SHORT X-S .... O CONTACTS - CHARGE-DENSITY EXPERIMENTAL STUDIES AND THEORETICAL INTERPRETATION [J].

COHENADDAD, C ;

LEHMANN, MS ;

BECKER, P ;

PARKANYI, L ;

KALMAN, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1984, (02) :191-196

[8] 2-(2-CHLOROBENZOYLIMINO)-1,3-THIAZOLIDINE - STRUCTURE REFINEMENT FROM NEUTRON-DIFFRACTION DATA AT 113-K AND CHARGE-DENSITY DEFORMATION MAPS [J].

COHENADDAD, C ;

SAVARIAULT, JM ;

LEHMANN, MS .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1981, 37 (SEP) :1703-1706

[9]

*DIV MED CHEM JAP, 1996, 5 ANN M DIV MED CHEM

[10] FURANFURIN AND THIOPHENFURIN - 2 NOVEL TIAZOFURIN ANALOGS - SYNTHESIS, STRUCTURE, ANTITUMOR-ACTIVITY, AND INTERACTIONS WITH INOSINE MONOPHOSPHATE DEHYDROGENASE [J].

FRANCHETTI, P ;

CAPPELLACCI, L ;

GRIFANTINI, M ;

BARZI, A ;

NOCENTINI, G ;

YANG, HY ;

OCONNOR, A ;

JAYARAM, HN ;

CARRELL, C ;

GOLDSTEIN, BM .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (19) :3829-3837

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