Intramolecular nonbonded S•••N interaction in rabeprazole

被引：22

作者：

Hayasi, Kazuhiko ^{[1
]}

Ogawa, Shiho ^{[2
]}

Sano, Shigeki ^{[2
]}

Shiro, Motoo ^{[3
]}

Yamaguchi, Kentaro ^{[4
]}

Sei, Yoshihisa ^{[4
]}

Nagao, Yoshimitsu ^{[2
]}

机构：

[1] Kinjo Gakin Univ, Coll Pharm, Moriyama Ku, Nagoya, Aichi 4638521, Japan

[2] Univ Tokushima, Grad Sch Pharmaceut Sci, Sho, Tokushima 7708505, Japan

[3] Rigaku Corp, Tokyo 1968666, Japan

[4] Tokushima Bunri Univ, Fac Pharmaceut Sci, Kagawa 7692193, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2008年 / 56卷 / 06期

关键词：

nonbonded interaction; rabeprazole; X-ray crystallographic analysis; proton pump inhibitor; close contact;

D O I：

10.1248/cpb.56.802

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Intramolecular nonbonded S center dot center dot center dot N interactions in the crystal structures of the derivatives (7a-d) of sodium rabeprazole (1) and an intermolecular nonbonded S center dot center dot center dot N interaction between ethylmethylsulfoxide and pyridine in a solution were recognized. These results made us estimate that the intramolecular nonbonded S center dot center dot center dot N interaction existed in 1 and its derivatives in a solution, and formed the 4-membered quasi-ring in 2 (Fig. 1) followed by the increase of the reactivity of 2 to give the putative spiro sulfoxide 3, which is the key intermediate in the reaction cascade of 1 (Chart 1).

引用

页码：802 / 806

页数：5

共 32 条

[1] SIR97:: a new tool for crystal structure determination and refinement [J].

Altomare, A ;

Burla, MC ;

Camalli, M ;

Cascarano, GL ;

Giacovazzo, C ;

Guagliardi, A ;

Moliterni, AGG ;

Polidori, G ;

Spagna, R .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1999, 32 :115-119

[2]

[Anonymous], 1975, METOODILINE JUHEND, P1

[3]

[Anonymous], 1985, TEXSAN CRYST STRUCT

[4] LANSOPRAZOLE - A REVIEW OF ITS PHARMACODYNAMIC AND PHARMACOKINETIC PROPERTIES AND ITS THERAPEUTIC EFFICACY IN ACID-RELATED DISORDERS [J].

BARRADELL, LB ;

FAULDS, D ;

MCTAVISH, D .

DRUGS, 1992, 44 (02) :225-250

[5]

BEURSKENS PT, 1994, DIRDIF94 PROGRAM SYS

[6] VAN DER WAALS VOLUMES + RADII [J].

BONDI, A .

JOURNAL OF PHYSICAL CHEMISTRY, 1964, 68 (03) :441-+

[7] 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

[8] OMEPRAZOLE - A PRELIMINARY REVIEW OF ITS PHARMACODYNAMIC AND PHARMACOKINETIC PROPERTIES, AND THERAPEUTIC POTENTIAL IN PEPTIC-ULCER DISEASE AND ZOLLINGER-ELLISON SYNDROME [J].

CLISSOLD, SP ;

CAMPOLIRICHARDS, DM .

DRUGS, 1986, 32 (01) :15-47

[9]

Creagh D. C., 1992, INT TABLES CRYSTALLO, VC, P200

[10]

CROMER DT, 1974, INT TABLES XRAY CRYS, V4, P72

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