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
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