STUDIES ON STEROIDS .54. RELATIONSHIP BETWEEN CHEMICAL-STRUCTURE AND ANTI-TUMOR ACTIVITY OF WITHAFERIN A ANALOGS

被引:23
作者
YOSHIDA, M [1 ]
HOSHI, A [1 ]
KURETANI, K [1 ]
ISHIGURO, M [1 ]
IKEKAWA, N [1 ]
机构
[1] TOKYO INST TECHNOL,CHEM NAT PROD LAB,MIDORI KU,YOKOHAMA 227,JAPAN
来源
JOURNAL OF PHARMACOBIO-DYNAMICS | 1979年 / 2卷 / 02期
关键词
AB ring analogue of withaferin A; antitumor activity; leukemia L5178Y; ring opening of epoxide; withaferin A; withanolide;
D O I
10.1248/bpb1978.2.92
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
The relationship between chemical structure and antitumor activity of AB ring analogues of withaferin A was examined by cell growth inhibition in mouse leukemia L5178Y cells in vitro. The 5, 6β-epoxy-4β-ol (5) and 5, 6α-epoxy-4α-ol (6) with 1-keto-2-ene function and cholesterol side chain have antitumor activity. The 4, 5-epoxy-6-hydroxyl compounds (9-16) were found to be equally or more active than corresponding 5, 6-epoxy-4-hydroxyl analogues. The antitumor activities of the 4, 5-epoxides paralleled the reactivities in ring opening reaction with acid. For the antitumor activity of withanolides, the unsaturated lactone in the side chain is important, and 1-keto-2-ene and epoxide functions were essential to elicit the activity. © 1979, The Pharmaceutical Society of Japan. All rights reserved.
引用
收藏
页码:92 / 97
页数:6
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