(1S,5R)-2-(1-benzyloxycarbonylazocan-5-ylaminocarbonyl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-6-sulfonic acid | 1017575-66-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,5R)-2-(1-benzyloxycarbonylazocan-5-ylaminocarbonyl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-6-sulfonic acid
• 英文别名: (1S,5R)-7-oxo-2-[(1-phenylmethoxycarbonylazocan-5-yl)carbamoyl]-2,6-diazabicyclo[3.2.0]heptane-6-sulfonic acid
• CAS: 1017575-66-4
• 化学式: C₂₁H₂₈N₄O₇S
• 分子量: 480.542
• InChiKey: UHNLVZWLQPSABO-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  145
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,5R)-2-(1-benzyloxycarbonylazocan-5-ylaminocarbonyl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-6-sulfonic acid 在 水 、 氢气 、 palladium(II) hydroxide 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 (1S,5R)-2-(azocan-5-ylaminocarbonyl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-6-sulfonic acid
  参考文献：
  名称：

  Side chain SAR of bicyclic β-lactamase inhibitors (BLIs). 1. Discovery of a class C BLI for combination with imipinem

  摘要：

  Bridged monobactam beta-lactamase inhibitors were prepared and evaluated as potential partners for combination with imipenem to overcome class C beta-lactamase mediated resistance. The (S)-azepine analog 2 was found to be effective in both in vitro and in vivo assays and was selected for preclinical development.

  DOI：

  10.1016/j.bmcl.2009.12.069
• 作为产物：
  描述：

  benzyl 5-(2,5-dioxopyrrolidin-1-yloxycarbonylamino)azocane-1-carboxylate 、 (1S,5R)-7-oxo-2,6-diazabicyclo<3.2.0>heptane-6-sulfonic acid 在 水 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 生成 (1S,5R)-2-(1-benzyloxycarbonylazocan-5-ylaminocarbonyl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-6-sulfonic acid
  参考文献：
  名称：

  Side chain SAR of bicyclic β-lactamase inhibitors (BLIs). 1. Discovery of a class C BLI for combination with imipinem

  摘要：

  Bridged monobactam beta-lactamase inhibitors were prepared and evaluated as potential partners for combination with imipenem to overcome class C beta-lactamase mediated resistance. The (S)-azepine analog 2 was found to be effective in both in vitro and in vivo assays and was selected for preclinical development.

  DOI：

  10.1016/j.bmcl.2009.12.069

文献信息

• [EN] NOVEL INHIBITORS OF BETA-LACTAMASE<br/>[FR] NOUVEAUX INHIBITEURS DE BÊTA-LACTAMASE
  申请人：MERCK & CO INC

  公开号：WO2008039420A2

  公开（公告）日：2008-04-03

  [EN] A class of 7-oxo-2,6-diazabicyclo-[3.2.0]-heptane-6-sulfonic acid compounds substituted at the two position of the bicyclic ring with a heterocyclylaminocarbonyl group or a carbocyclylaminocarbonyl group are ß-lactamase inhibitors. The compounds and their prodrugs and pharmaceutically acceptable salts are useful in the treatment of bacterial infections in combination with ß-lactam antibiotics. In particular, the compounds are suitable for use with ß-lactam antibiotics (e.g., imipenem and ceftazidime) against micro-organisms resistant to ß-lactam antibiotics due to the presence of the ß-lactamases.
  [FR] L'invention concerne une classe de composés d'acide 7-oxo-2,6-diazabicyclo-[3.2.0]-heptane-6-sulfonique, substitués à la position 2 du noyau bicyclique par un groupe hétérocyclylaminocarbonyle ou un groupe carbocyclylaminocarbonyle, qui sont des inhibiteurs de bêta-lactamase. Ces composés, ainsi que leurs promédicaments et leurs sels pharmaceutiquement acceptables, sont utiles dans le traitement d'infections bactériennes lorsqu'ils sont associés à des antibiotiques bêta-lactame (p. ex. imipenem and ceftazidime) pour lutter contre des micro-organismes résistants aux antibiotiques bêta-lactame, du fait de la présence des bêta-lactamases.
• Side chain SAR of bicyclic β-lactamase inhibitors (BLIs). 1. Discovery of a class C BLI for combination with imipinem
  作者：Timothy A. Blizzard、Helen Chen、Seongkon Kim、Jane Wu、Katherine Young、Young-Whan Park、Amy Ogawa、Susan Raghoobar、Ronald E. Painter、Nichelle Hairston、Sang Ho Lee、Andrew Misura、Tom Felcetto、Paula Fitzgerald、Nandini Sharma、Jun Lu、Sookhee Ha、Emily Hickey、Jeff Hermes、Milton L. Hammond

  DOI：10.1016/j.bmcl.2009.12.069

  日期：2010.2

  Bridged monobactam beta-lactamase inhibitors were prepared and evaluated as potential partners for combination with imipenem to overcome class C beta-lactamase mediated resistance. The (S)-azepine analog 2 was found to be effective in both in vitro and in vivo assays and was selected for preclinical development.