Literature DB >> 26758495

Synthesis and antibacterial activity of novel lincomycin derivatives. I. Enhancement of antibacterial activities by introduction of substituted azetidines.

Ko Kumura1, Yoshinari Wakiyama1, Kazutaka Ueda1, Eijiro Umemura1, Takashi Watanabe1, Eiki Shitara1, Hideki Fushimi1, Takuji Yoshida1, Keiichi Ajito1.   

Abstract

The synthesis and antibacterial activity of (7S)-7-sulfur-azetidin-3-yl lincomycin derivatives are described. Modification was achieved by a simple reaction of (7R)-7-O-methanesulfonyllincomycin and the corresponding substituted azetidine-2-thiol. Several compounds first showed moderate antibacterial activity against Streptococcus pneumoniae and Streptococcus pyogenes with erm gene as lincomycin derivatives.

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Year:  2016        PMID： 26758495     DOI： 10.1038/ja.2015.134

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


  10 in total

1.  Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria.

Authors:  F Schlünzen; R Zarivach; J Harms; A Bashan; A Tocilj; R Albrecht; A Yonath; F Franceschi
Journal:  Nature       Date:  2001-10-25       Impact factor: 49.962

2.  Syntheses and pharmacokinetic studies of prodrug esters for the development of oral carbapenem, L-084.

Authors:  Takeshi Isoda; Hideki Ushirogochi; Koichi Satoh; Tsuyoshi Takasaki; Itsuki Yamamura; Chisato Sato; Ado Mihira; Takao Abe; Satoshi Tamai; Shigeki Yamamoto; Toshio Kumagai; Yoshimitsu Nagao
Journal:  J Antibiot (Tokyo)       Date:  2006-04       Impact factor: 2.649

3.  Semisynthetic modification of antibiotic lincomycin.

Authors:  F Sztaricskai; Z Dinya; M M Puskás; G Batta; R Masuma; S Omura
Journal:  J Antibiot (Tokyo)       Date:  1996-09       Impact factor: 2.649

4.  Synthesis of novel lincomycin derivatives and their in vitro antibacterial activities.

Authors:  Eijiro Umemura; Yoshinari Wakiyama; Ko Kumura; Kazutaka Ueda; Satomi Masaki; Takashi Watanabe; Mikio Yamamoto; Yoko Hirai; Hideki Fushimi; Takuji Yoshida; Keiichi Ajito
Journal:  J Antibiot (Tokyo)       Date:  2012-12-12       Impact factor: 2.649

Review 5.  Chemical modification of tobramycin.

Authors:  K Igarashi
Journal:  Jpn J Antibiot       Date:  1979-12

6.  Modifications of lincomycin involving the carbohydrate portion. I. The 2-O-methyl and 2-deoxy-analogues.

Authors:  B Bannister
Journal:  J Chem Soc Perkin 1       Date:  1972

Review 7.  Erythromycin resistance by ribosome modification.

Authors:  B Weisblum
Journal:  Antimicrob Agents Chemother       Date:  1995-03       Impact factor: 5.191

8.  Activity of delafloxacin against methicillin-resistant Staphylococcus aureus: resistance selection and characterization.

Authors:  Joan M Remy; Cheryl A Tow-Keogh; Timothy S McConnell; James M Dalton; Joseph A Devito
Journal:  J Antimicrob Chemother       Date:  2012-08-08       Impact factor: 5.790

9.  Structure activity relationships in lincosamide and streptogramin antibiotics.

Authors:  F Le Goffic
Journal:  J Antimicrob Chemother       Date:  1985-07       Impact factor: 5.790

10.  Synthesis and evaluation of hetero- and homodimers of ribosome-targeting antibiotics: antimicrobial activity, in vitro inhibition of translation, and drug resistance.

Authors:  Yifat Berkov-Zrihen; Keith D Green; Kristin J Labby; Mark Feldman; Sylvie Garneau-Tsodikova; Micha Fridman
Journal:  J Med Chem       Date:  2013-07-01       Impact factor: 7.446
  10 in total
  5 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

5.  Synthesis and antibacterial activity of novel lincomycin derivatives. III. Optimization of a phenyl thiadiazole moiety.

Authors:  Ko Kumura; Yoshinari Wakiyama; Kazutaka Ueda; Eijiro Umemura; Takashi Watanabe; Mikio Yamamoto; Takuji Yoshida; Keiichi Ajito
Journal:  J Antibiot (Tokyo)       Date:  2017-07-05       Impact factor: 2.649
  5 in total

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