2'-脱氧-L-呋喃岩藻糖基卡米诺霉素酮和-ε-吡咯霉素酮以及2'-脱氧-D-赤藓戊吡喃糖基柔红霉素酮、-卡米诺霉素酮和-ε-吡咯霉素酮的合成。

Synthesis of 2'-deoxy-L-fucopyranosylcarminomycinone and -epsilon-pyrromycinone as well as 2'-deoxy-D-erythro-pentopyranosyldaunomycinone, -carminomycinone, and -epsilon-pyrromycinone.

作者信息

El Khadem H S, Swartz D L

出版信息

J Med Chem. 1981 Jan;24(1):112-5. doi: 10.1021/jm00133a023.

PMID:7205866

Abstract

Treatment of di-O-acetyl-2-deoxy-L-fucopyranosyl bromide with carminomycinone and epsilon-pyrromycinone in the presence of mercuric bromide and mercuric cyanide afforded 3',4'-diO-acetyl-2'-deoxy-L-fucopyranosylcarminomycinone and -epsilon-pyrromycinone. Similarly, when di-O-acetyl-2-deoxy-D-erythrho-pentopyranosyl chloride was treated with daunomycinone, carminomycinone and epsilon-pyrromycinone, the di-O-acetyl derivatives of the anthracyclinone glycosides were obtained. Deacetylation of the previous acetates with sodium methoxide afforded 2'-deoxy-L-fucopyranosylcarminomycinone and -epsilon-pyrromycinone, as well as 2'-deoxy-D-erythro-pentopyranosyldaunomycinone, -carminomycinone, and -epsilon-pyrromycinone. 2'-Deoxy-L-fucopyranosylcarminomycinone was found to be more active than carminomycin at higher dosages on L1210.

摘要

在溴化汞和氰化汞存在的条件下，将二 - O - 乙酰基 - 2 - 脱氧 - L - 呋喃岩藻糖基溴与洋红霉素酮和ε - 吡咯霉素酮反应，得到3',4'-二 - O - 乙酰基 - 2'-脱氧 - L - 呋喃岩藻糖基洋红霉素酮和 - ε - 吡咯霉素酮。类似地，当用柔红霉素酮、洋红霉素酮和ε - 吡咯霉素酮处理二 - O - 乙酰基 - 2 - 脱氧 - D - 赤藓糖基戊吡喃糖基氯时，得到了蒽环酮糖苷的二 - O - 乙酰基衍生物。用甲醇钠对先前的乙酸酯进行脱乙酰化反应，得到2'-脱氧 - L - 呋喃岩藻糖基洋红霉素酮和 - ε - 吡咯霉素酮，以及2'-脱氧 - D - 赤藓糖基戊吡喃糖基柔红霉素酮、 - 洋红霉素酮和 - ε - 吡咯霉素酮。发现在较高剂量下，2'-脱氧 - L - 呋喃岩藻糖基洋红霉素酮对L1210细胞的活性比洋红霉素更强。