Chemical modification of erythromycins. II. Synthesis and antibacterial activity of O-alkyl derivatives of erythromycin A.
Chemical modification of erythromycins. II. Synthesis and antibacterial activity of O-alkyl derivatives of erythromycin A.
复制标题
红霉素的化学修饰。
DOI：
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发表时间：
1990
期刊：
影响因子：
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通讯作者：
Sadafumi Omura
中科院分区：
文献类型：
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作者：
S. Morimoto;Y. Misawa;Takashi Adachi;Takatoshi Nagate;Yoshiaki Watanabe;Sadafumi Omura
合成了一系列O-烷基红霉素A衍生物，并与红霉素A(1)和6-O-甲基红霉素A(3)的抗菌活性进行了比较。红霉素A类似物的羟基甲基化通过两条主要途径逐步进行，分别从C-6和C-11位开始。O-烷基化，而不是甲基化，只发生在C-11羟基上。在O-烷基衍生物中，6，12-二O-甲基红霉素A(5)的体外抗菌活性与1和3相当，11-O-甲基红霉素A(8)的活性略低于1，C-4“位的O-甲基化导致抗菌活性下降。
A series of O-alkyl erythromycin A derivatives have been synthesized and their antibacterial activities compared with those of erythromycin A (1) and 6-O-methylerythromycin A (3). Methylation of the hydroxyl groups of erythromycin A analogue proceeded stepwise by the two main pathways beginning at the C-6 and C-11 positions, individually. O-Alkylation, other than methylation, took place at the C-11 hydroxyl group exclusively. Among O-alkyl derivatives, 6,12-di-O-methylerythromycin A (5) showed comparable in vitro antibacterial activity to those of 1 and 3. 11-O-Methylerythromycin A (8) was slightly less active than 1. O-Methylation at the C-4" position resulted in a decrease of antibacterial activity.