SYNTHESIS OF TREHAZOLIN ANALOGS CONTAINING MODIFIED AMINOCYCLITOL MOIETIES

被引：25

作者：

UCHIDA, C ^{[1
]}

KITAHASHI, H ^{[1
]}

YAMAGISHI, T ^{[1
]}

IWAISAKI, Y ^{[1
]}

OGAWA, S ^{[1
]}

机构：

[1] KEIO UNIV,FAC SCI & TECHNOL,DEPT APPL CHEM,KOHOKU KU,YOKOHAMA,KANAGAWA 223,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 19期

关键词：

D O I：

10.1039/p19940002775

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In order to elucidate structure-activity relationships of the trehalase inhibitor trehazolin 1, three analogues: deoxytrehazolin D-2, and de(hydroxymethyl)trehazolin D-3 and its diastereoisomer L-3 were synthesized by coupling of the sugar isothiocyanate 18 with the newly prepared aminocyclopentanetrataols D-10, D-26 and L-26, followed by cyclisation to give the isourea, and deprotection. In addition, an attempt was made to synthesize the analogue 4, the aminocyclitol moiety being replaced with the 5a-carba sugar, validamine. A biological assay showed that enantiomers D-3 and L-3 are strong inhibitors of trehalase, and, interestingly, the latter isomer, having the unnatural-type structure, is similar to 50 times more potent.

引用

页码：2775 / 2785

页数：11

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