Literature DB >> 17721001

Novel azalides derived from sixteen-membered macrolides.

Tomoaki Miura1, Satomi Natsume, Kenichi Kanemoto, Kunio Atsumi, Hideki Fushimi, Hiroaki Sasai, Takayoshi Arai, Takuji Yoshida, Keiichi Ajito.   

Abstract

The design and synthesis of novel 15-membered 11-azalides and 16-membered 11,12-diazalide starting from 16-membered macrolides are reported. A mobile linear dialdehyde was isolated via a cyclic tetraol which was prepared by osmium oxidation of a conjugated diene. One-pot macrocyclization of this dialdehyde with an amine or a diamine afforded corresponding 15-membered azalides or 11,12-diazalide. Fundamental SAR studies of 15-membered 11-azalides disclosed their potentiality as a lead molecule for further chemical modifications. For environmental preservation, sustainable chemistry for synthesis of these azalides is also discussed.

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Year:  2007        PMID： 17721001     DOI： 10.1038/ja.2007.55

Source DB:  PubMed          Journal:  J Antibiot (Tokyo)        ISSN： 0021-8820            Impact factor:   2.649


  4 in total

1.  Synthesis and SARs of novel lincomycin derivatives Part 5: optimization of lincomycin analogs exhibiting potent antibacterial activities by chemical modification at the 6- and 7-positions.

Authors:  Yoshinari Wakiyama; Ko Kumura; Eijiro Umemura; Satomi Masaki; Kazutaka Ueda; Yasuo Sato; Yoko Hirai; Yoshio Hayashi; Keiichi Ajito
Journal:  J Antibiot (Tokyo)       Date:  2017-11-01       Impact factor: 2.649

2.  Synthesis and structure-activity relationships of novel lincomycin derivatives part 3: discovery of the 4-(pyrimidin-5-yl)phenyl group in synthesis of 7(S)-thiolincomycin analogs.

Authors:  Yoshinari Wakiyama; Ko Kumura; Eijiro Umemura; Satomi Masaki; Kazutaka Ueda; Yasuo Sato; Takashi Watanabe; Yoko Hirai; Keiichi Ajito
Journal:  J Antibiot (Tokyo)       Date:  2016-10-05       Impact factor: 2.649

3.  Synthesis and structure-activity relationships of novel lincomycin derivatives. Part 4: synthesis of novel lincomycin analogs modified at the 6- and 7-positions and their potent antibacterial activities.

Authors:  Yoshinari Wakiyama; Ko Kumura; Eijiro Umemura; Kazutaka Ueda; Takashi Watanabe; Keiko Yamada; Takafumi Okutomi; Keiichi Ajito
Journal:  J Antibiot (Tokyo)       Date:  2017-05-31       Impact factor: 2.649

4.  Synthesis and antibacterial activity of novel lincomycin derivatives. IV. Optimization of an N-6 substituent.

Authors:  Ko Kumura; Yoshinari Wakiyama; Kazutaka Ueda; Eijiro Umemura; Yoko Hirai; Keiko Yamada; Keiichi Ajito
Journal:  J Antibiot (Tokyo)       Date:  2017-11-08       Impact factor: 2.649
  4 in total

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