Structure activity relationships of synthetic antibiotic analogues of chryscandin

Abstract

Anti-yeast activity with a series of chryscandin derivatives showed that the 0-methyl-L-tyrosyl moiety is not always required for activity at the target site. On the other hand, the adenyl-3'-aminoribofuranuronic acid moiety seemsto be essential for biological activity. Therefore, the various acyl derivativeson the amino group of the sugar part of the nucleoside were synthesized. 1-(6-Amino-9Lt-purin-9-yl)-3-(5-benzyl-L-cysteinylamino)-l, 3-dideoxy-/S-D-ribofuranuronic acid (16) showed the highestefficacy among them against Candida albicans. It exhibited sixteen-fold enhanced activity in vitro comparedwith that of native chryscandin. The in vivo activity of 16 against experimental infection of C. albicans showed the almost same as that of5-fluorocytosine and a superior to that of ketoconazole. © 1985, JAPAN ANTIBIOTICS RESEARCH ASSOCIATION. All rights reserved.