Novel 3-O-carbamoyl erythromycin A derivatives (carbamolides) with activity against resistant staphylococcal and streptococcal isolates

被引：19
|
作者：
Magee, Thomas V. [1 ]
Han, Seungil [2 ]
McCurdy, Sandra P. [3 ]
Thuy-Trinh Nguyen [6 ]
Granskog, Karl [6 ]
Marr, Eric S. [2 ]
Maguire, Bruce A. [4 ]
Huband, Michael D. [5 ]
Chen, Jinshan Michael [6 ]
Subashi, Timothy A. [4 ]
Shanmugasundaram, Veerabahu [7 ]
机构：
[1] Pfizer, Cardiovasc Metab & Endocrine Dis CVMED Chem, Cambridge, MA 02139 USA
[2] Pfizer Inc, Struct Biol & Biophys, Groton, CT 06340 USA
[3] Cubist Pharmaceut, Lexington, MA 02421 USA
[4] Pfizer Inc, Primary Pharmacol Grp, Groton, CT 06340 USA
[5] Astra Zeneca, Waltham, MA 02451 USA
[6] Pfizer Inc, Exploratory Discovery Chem, Groton, CT 06340 USA
[7] Pfizer Inc, Computat Chem, Groton, CT 06340 USA
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2013年 / 23卷 / 06期
关键词：
Bacterial resistance; cfr; erm; MLSb; MRSA; Macrolide; Carbamolide; Clarithromycin; Oxazolidinone; Linezolid; Ribosome X-ray; Deinococcus radiodurans; PEPTIDYL TRANSFERASE CENTER; ANTIBACTERIAL ACTIVITY; MACROLIDE RESISTANCE; ANTIBIOTICS; RIBOSOME; CLARITHROMYCIN; TELITHROMYCIN; PNEUMONIAE; INCREASES; DESIGN;
D O I：
10.1016/j.bmcl.2013.01.067
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A novel series of 3-O-carbamoyl erythromycin A derived analogs, labeled carbamolides, with activity versus resistant bacterial isolates of staphylococci (including macrolide and oxazolidinone resistant strains) and streptococci are reported. An (R)-2-aryl substituent on a pyrrolidine carbamate appeared to be critical for achieving potency against resistant strains. Crystal structures showed a distinct aromatic interaction between the (R)-2-aryl (3-pyridyl for 4d) substituent on the pyrrolidine and G2484 (G2505, Escherichia coli) of the Deinococcus radiodurans 50S ribosome (3.2 angstrom resolution). (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1727 / 1731
页数：5
相关论文
共 50 条
  • [1] Synthesis and antibacterial activity of 3-O-carbamoyl derivatives of 6,11-di-O-methylerythromycin A: A novel class of acylides
    Wu, Zhongyuan
    Lu, Yong
    Luo, Ming
    He, Xianran
    Xiao, Yuling
    Yang, Jin
    Pan, Yuanhu
    Qiu, Guofu
    Guo, Hao
    Hu, Hao
    Zhou, Dingshan
    Hu, Xianming
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (09) : 3636 - 3644
  • [2] Synthesis and antibacterial activity of novel 3-O-carbamoyl derivatives of clarithromycin and 11,12-cyclic carbonate azithromycin
    Zhang, Ling
    Song, Linchen
    Liu, Zhaopeng
    Li, Hui
    Lu, Yingdong
    Li, Zerong
    Ma, Shutao
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (03) : 915 - 922
  • [3] Synthesis and Antibacterial Activity of Novel 4"-O-Carbamoyl Erythromycin-A Derivatives
    Qi, Yunkun
    Jiao, Bo
    Ma, Xiaodong
    Cui, Wenping
    Ma, Shutao
    ARCHIV DER PHARMAZIE, 2010, 343 (08) : 458 - 464
  • [4] Synthesis and antibacterial activity of 3-O-acyl-6-O-carbamoyl erythromycin A derivatives
    Zhu, B
    Marinelli, BA
    Abbanat, D
    Foleno, BD
    Henninger, TC
    Bush, K
    Macielag, MJ
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (04) : 1054 - 1059
  • [5] Synthesis and antibacterial activity of 3-O-acyl-6-O-carbamoyl erythromycin A derivatives.
    Zhu, B
    Marinelli, B
    Abbanat, D
    Foleno, B
    Henninger, T
    Wira, E
    Bush, K
    Macielag, M
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U17 - U18
  • [6] Moxifloxacin activity against quinolone resistant Staphylococcal ocular isolates.
    Stroman, DT
    Clark, L
    Macke, L
    Mendoza, B
    Schlech, BA
    O'Brien, T
    INVESTIGATIVE OPHTHALMOLOGY & VISUAL SCIENCE, 2001, 42 (04) : S255 - S255
  • [7] Synthesis and antibacterial activity of 3-keto-6-O-carbamoyl-11,12-cyclic thiocarbamate erythromycin A derivatives
    Zhu, Bin
    Marinelli, Brett A.
    Abbanat, Darren
    Foleno, Barbara D.
    Bush, Karen
    Macielag, Mark J.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (14) : 3900 - 3904
  • [8] Antimicrobial activity and spectrum of sparfloxacin tested against erythromycin-resistant Streptococcus pneumoniae isolates
    Barrett, MS
    Jones, RN
    DIAGNOSTIC MICROBIOLOGY AND INFECTIOUS DISEASE, 1996, 24 (02) : 113 - 116
  • [9] Development of Novel Erythromycin Derivatives with Inhibitory Activity against Proliferation of Tumor Cells
    Wu, Lan
    Bao, Kai
    Song, Rui
    Wang, Defa
    Zhang, Lei
    Wang, Weiyun
    Zhang, Weige
    Bin, Wen
    PLOS ONE, 2016, 11 (07):
  • [10] Synthesis and antibacterial activity of novel 6-O-substituted erythromycin A derivatives
    Clark, RF
    Ma, ZK
    Wang, SY
    Griesgraber, G
    Tufano, M
    Yong, H
    Li, LP
    Zhang, XL
    Nilius, AM
    Chu, DTW
    Or, YS
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (08) : 815 - 819
12345