SYNTHESIS OF TREHAZOLIN ANALOGS CONTAINING MODIFIED SUGAR MOIETIES

被引：21

作者：

UCHIDA, C ^{[1
]}

KITAHASHI, H ^{[1
]}

WATANABE, S ^{[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 | 1995年 / 13期

关键词：

D O I：

10.1039/p19950001707

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In order to elucidate the biological roles of the sugar moiety of the trehalase inhibitor trehazolin 1, the sugar portion was first replaced with hydrophobic aromatic functions, providing the N-phenyl 3 and N-benzyl derivatives 4 of trehazolin 1. Then the six analogues with the sugar moiety being replaced with D-mannopyranose 5, 3-deoxy-ribo-hexopyranose 6, D-galactopyranose 7, 6-deoxy-D-glucopyranose 8, 5a-carba-alpha-D-glucopyranose 9 and 5a-carba-alpha-D-xylo-hex-5(5a)-enopyranose residues 10 were synthesized. In the hope of improving the fungicidal activity of trehazolin 4, we prepared two disaccharide analogues, 11 and 12, containing maltose and cellobiose residues. A remarkable decrease in potency was observed in the analogues 5-8 and 10, but not for 5a'-carbatrehazolin 9, suggesting an essential role for the D-gluco configuration of the hexopyranose portion. The beta-D-glucosyl analogue 12 showed an increase in antifungal activity against Rhizoctonia solani, as compared with that of trehazolin 1. The analogues 3 and 4 were not trehalase inhibitors, but rather were moderate alpha-glucosidase inhibitors.

引用

页码：1707 / 1717

页数：11

共 24 条

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