Literature DB >> 27118243

Synthesis and antibacterial activity of novel 11-[3-[(arylcarbamoyl)oxy]propylamino]-11-deoxy-6-O-methyl-3-oxoerythromycin A 11-N,12-O-cyclic carbamate derivatives.

Zhonghui Zheng1, Deping Du1, Lili Cao1, Jun Liu2, Xiaofang Chen2.   

Abstract

A series of novel 11-[3-[(arylcarbamoyl)oxy]propylamino]-11-deoxy-6-O-methyl-3-oxoerythromycin A 11-N,12-O-cyclic carbamate derivatives (6a-h) were designed, synthesized and evaluated for their antibacterial activities in vitro. Most of these compounds had significant antibacterial activity against two groups of pathogens of Methicillin-sensitive Staphylococcus aureus (MIC50=0.031-2 μg ml-1) except 6g and Methicillin-sensitive S. epidermidis (MIC50=0.031-0.5 μg ml-1). MIC90 of 6d against Methicillin-resistant S. epidermidis was at least 16-fold better than that of erythromycin (EMA), azithromycin (AZM) and ABT-773. 6d and 6e had more potent antibacterial activity against S. pneumoniae than EMA, AZM and ABT-773. In particular, compounds 6d and 6e also showed relatively potent activity against Haemophilus influenzae and Streptococcus hemolyticus.

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Year:  2016        PMID： 27118243     DOI： 10.1038/ja.2016.42

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


  23 in total

1.  Design, synthesis, and antimicrobial activity of 6-O-substituted ketolides active against resistant respiratory tract pathogens.

Authors:  Y S Or; R F Clark; S Wang; D T Chu; A M Nilius; R K Flamm; M Mitten; P Ewing; J Alder; Z Ma
Journal:  J Med Chem       Date:  2000-03-23       Impact factor: 7.446

2.  Resistance to macrolides and related antibiotics in Streptococcus pneumoniae.

Authors:  Roland Leclercq; Patrice Courvalin
Journal:  Antimicrob Agents Chemother       Date:  2002-09       Impact factor: 5.191

3.  Design, synthesis and structure-activity relationships of 6-O-arylpropargyl diazalides with potent activity against multidrug-resistant Streptococcus pneumoniae.

Authors:  Hong Yong; Yu Gui Gu; Richard F Clark; Thomas Marron; Zhenkun Ma; Niru Soni; Gregory G Stone; Angela M Nilius; Kennan Marsh; Stevan W Djuric
Journal:  Bioorg Med Chem Lett       Date:  2005-05-16       Impact factor: 2.823

4.  9-Oxime-3-ketolides: modification at the C-11,12-diol moiety and antibacterial activities against key respiratory pathogens.

Authors:  Takashi Nomura; Tatsuro Yasukata; Yukitoshi Narukawa; Kouichi Uotani
Journal:  Bioorg Med Chem       Date:  2005-11-01       Impact factor: 3.641

5.  Eight more ways to deal with antibiotic resistance.

Authors:  Matthew Metz; David M Shlaes
Journal:  Antimicrob Agents Chemother       Date:  2014-05-27       Impact factor: 5.191

6.  Anhydrolide macrolides. 1. Synthesis and antibacterial activity of 2,3-anhydro-6-O-methyl 11,12-carbamate erythromycin A analogues.

Authors:  R L Elliott; D Pireh; G Griesgraber; A M Nilius; P J Ewing; M H Bui; P M Raney; R K Flamm; K Kim; R F Henry; D T Chu; J J Plattner; Y S Or
Journal:  J Med Chem       Date:  1998-05-07       Impact factor: 7.446

7.  In vitro antibacterial activity of modithromycin, a novel 6,11-bridged bicyclolide, against respiratory pathogens, including macrolide-resistant Gram-positive cocci.

Authors:  Takafumi Sato; Kazuhiro Tateda; Soichiro Kimura; Morihiro Iwata; Yoshikazu Ishii; Keizo Yamaguchi
Journal:  Antimicrob Agents Chemother       Date:  2011-01-10       Impact factor: 5.191

8.  Synthesis and antibacterial activity of HMR 3647 a new ketolide highly potent against erythromycin-resistant and susceptible pathogens.

Authors:  A Denis; C Agouridas; J M Auger; Y Benedetti; A Bonnefoy; F Bretin; J F Chantot; A Dussarat; C Fromentin; S G D'Ambrières; S Lachaud; P Laurin; O Le Martret; V Loyau; N Tessot; J M Pejac; S Perron
Journal:  Bioorg Med Chem Lett       Date:  1999-11-01       Impact factor: 2.823

9.  Synthesis and antibacterial activity of 6-O-arylbutynyl ketolides with improved activity against some key erythromycin-resistant pathogens.

Authors:  Robert F Keyes; Justin J Carter; Erika E Englund; Melissa M Daly; Greg G Stone; Angela M Nilius; Zhenkun Ma
Journal:  J Med Chem       Date:  2003-05-08       Impact factor: 7.446

10.  Comparative Genotypes, Staphylococcal Cassette Chromosome mec (SCCmec) Genes and Antimicrobial Resistance amongst Staphylococcus epidermidis and Staphylococcus haemolyticus Isolates from Infections in Humans and Companion Animals.

Authors:  Brenda A McManus; David C Coleman; Emily C Deasy; Gráinne I Brennan; Brian O' Connell; Stefan Monecke; Ralf Ehricht; Bernadette Leggett; Nola Leonard; Anna C Shore
Journal:  PLoS One       Date:  2015-09-17       Impact factor: 3.240
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