Synthesis and structure-activity relationships of novel lincomycin derivatives. Part 1. Newly generated antibacterial activities against Gram-positive bacteria with erm gene by C-7 modification

被引：9

作者：

Wakiyama, Yoshinari ^{[1
]}

Kumura, Ko ^{[1
]}

Umemura, Eijiro ^{[1
]}

Ueda, Kazutaka ^{[1
]}

Masaki, Satomi ^{[1
]}

Kumura, Megumi ^{[1
]}

Fushimi, Hideki ^{[1
]}

Ajito, Keiichi ^{[1
]}

机构：

[1] Meiji Seika Pharma Co Ltd, Pharmaceut Res Ctr, Kohoku Ku, Yokohama, Kanagawa 2228567, Japan

来源：

JOURNAL OF ANTIBIOTICS | 2016年 / 69卷 / 05期

关键词：

23S RIBOSOMAL-RNA; PEPTIDYL TRANSFERASE CENTER; DOMAIN-II; RESISTANCE; TELITHROMYCIN; ANTIBIOTICS; PATHOGENS; POTENT;

D O I：

10.1038/ja.2015.119

中图分类号：

Q81 [生物工程学（生物技术）]; Q93 [微生物学];

学科分类号：

071005 ; 0836 ; 090102 ; 100705 ;

摘要：

We synthesized 7(S)-7-deoxy-7-arylthiolincomycin derivatives possessing a heterocyclic ring at the C-7 position via sulfur atom by either Mitsunobu reaction of 2,3,4-tris-O-(trimethylsiliyl)lincomycin or S(N)2 reaction of 7-O-methanesulfonyl-2,3,4-tri-O-trimethylsiliyllincomycin. As a result, 7(S)-7-deoxy-7-arylthiolincomycin derivatives 16, 21 and 27 exhibited antibacterial activities against respiratory infection-related Gram-positive bacteria with erm gene, although clindamycin did not have any activities against those pathogens. Furthermore, 7(S)-configuration of lincomycin derivatives was found to be necessary for enhancing antibacterial activities from the comparison results of configurations of 16 (S-configuration) and 30 (R-configuration) at the 7-position.

引用

页码：368 / 380

页数：13

共 15 条

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