制霉菌素衍生物的合成与抗真菌活性。糖部分的修饰。

Synthesis and antifungal activity of pradimicin derivatives. Modifications of the sugar part.

作者信息

Aburaki S, Yamashita Y, Ohnuma T, Kamachi H, Moriyama T, Masuyoshi S, Kamei H, Konishi M, Oki T

机构信息

Bristol-Myers Squibb Research Institute, Bristol-Myers Squibb K.K., Tokyo, Japan.

出版信息

J Antibiot (Tokyo). 1993 Apr;46(4):631-40. doi: 10.7164/antibiotics.46.631.

DOI:10.7164/antibiotics.46.631

PMID:8501006

Abstract

Modifications at the sugar part of pradimicins were carried out by glycosidations of the aglycones or chemical transformations of natural pradimicins and their antifungal activity was evaluated. Among them, some of the D-xylose-modified derivatives (14, 17, 24) showed activity comparable to that of pradimicin A. The structure-activity relationships obtained through there studies clarified the role of the sugar part in the manifestation of antifungal activity: The 5-O-(6-deoxy-beta-D-sugar) is essential for activity and 2'-epi, 3'-oxo and 4'-deoxy sugar derivatives retain activity against yeasts.

摘要

通过对普拉地霉素苷元进行糖基化修饰或对天然普拉地霉素进行化学转化，对普拉地霉素的糖部分进行了修饰，并评估了它们的抗真菌活性。其中，一些D-木糖修饰的衍生物（14、17、24）表现出与普拉地霉素A相当的活性。通过这些研究获得的构效关系阐明了糖部分在抗真菌活性表现中的作用：5-O-(6-脱氧-β-D-糖)对活性至关重要，2'-表位、3'-氧代和4'-脱氧糖衍生物对酵母仍具有活性。