2-{[(1R,2S)-2-(3,5-Dibromo-2-ethoxybenzylamino)cyclopentylmethyl]amino}-1H-quinolin-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-{[(1R,2S)-2-(3,5-Dibromo-2-ethoxybenzylamino)cyclopentylmethyl]amino}-1H-quinolin-4-one
• 英文别名: 2-[[(1R,2S)-2-[(3,5-dibromo-2-ethoxyphenyl)methylamino]cyclopentyl]methylamino]-1H-quinolin-4-one
• 化学式: C₂₄H₂₇Br₂N₃O₂
• 分子量: 549.305
• InChiKey: AVRYAKFFWIGWDD-QRWLVFNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  {(1S,2S)-2-[Benzyl-((S)-1-phenyl-ethyl)-amino]-cyclopentyl}-methanol 在 盐酸 、 palladium on activated charcoal 、 三丁基膦 、 甲酸铵 、 sodium cyanoborohydride 、 溶剂黄146 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 甲醇 、 苯 为溶剂， 反应 4.0h， 生成 2-{[(1R,2S)-2-(3,5-Dibromo-2-ethoxybenzylamino)cyclopentylmethyl]amino}-1H-quinolin-4-one
  参考文献：
  名称：

  Conformational restriction of methionyl tRNA synthetase inhibitors leading to analogues with potent inhibition and excellent gram-Positive antibacterial activity

  摘要：

  Conformationally restricted analogues of the central linker unit of bacterial methionyl tRNA synthetase (MRS) inhibitors have been prepared. The (IS,2R)-cyclopentylmethyl moiety was identified as the preferred cyclic linker, with significant diastereo- and enantio selectivity of activity. Combination of this linker with an optimal substituted aryl right-hand side has resulted in a compound with exceptionally good antibacterial activity against staphylococci and enterococci, including antibiotic resistant strains. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00093-3

文献信息

• [EN] QUINOLONES USED AS MRS INHIBITORS AND BACTERICIDES<br/>[FR] QUINOLONES UTILISEES COMME INHIBITEURS DE MRS ET BACTERICIDES
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO1999055677A1

  公开（公告）日：1999-11-04

  (EN) Compounds of formula (I) are inhibitors of the bacterial enzyme $i(S aureus) methionyl tRNA synthetase and are of use in treating bacterial infections.(FR) L'invention concerne des composés de formule (I), qui sont des inhibiteurs de l'enzyme bactérienne méthionyl-ARNt synthétase de $i(S aureus) utilisés dans le traitement des infections bactériennes.

  化合物的公式（I）是细菌酶 $i(S aureus) 甲硫氨酰-tRNA 合成酶的抑制剂，并可用于治疗细菌感染。
• QUINOLONES USED AS MRS INHIBITORS AND BACTERICIDES
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1084110A1

  公开（公告）日：2001-03-21
• US6320051B1
  申请人：——

  公开号：US6320051B1

  公开（公告）日：2001-11-20
• Conformational restriction of methionyl tRNA synthetase inhibitors leading to analogues with potent inhibition and excellent gram-Positive antibacterial activity
  作者：Richard L. Jarvest、John M. Berge、Pamela Brown、Catherine S.V. Houge-Frydrych、Peter J. O'Hanlon、David J. McNair、Andrew J. Pope、Stephen Rittenhouse

  DOI：10.1016/s0960-894x(03)00093-3

  日期：2003.4

  Conformationally restricted analogues of the central linker unit of bacterial methionyl tRNA synthetase (MRS) inhibitors have been prepared. The (IS,2R)-cyclopentylmethyl moiety was identified as the preferred cyclic linker, with significant diastereo- and enantio selectivity of activity. Combination of this linker with an optimal substituted aryl right-hand side has resulted in a compound with exceptionally good antibacterial activity against staphylococci and enterococci, including antibiotic resistant strains. (C) 2003 Elsevier Science Ltd. All rights reserved.