benzyl (2-((4S)-4-(2,5-dioxopyrrolidin-1-yloxycarbonylamino)azepan-1-yl)ethyl)carbamate | 1017575-64-2

• 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: benzyl (2-((4S)-4-(2,5-dioxopyrrolidin-1-yloxycarbonylamino)azepan-1-yl)ethyl)carbamate
• 英文别名: Benzyl {2-[(4s)-4-({[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}amino)azepan-1-yl]ethyl}carbamate；benzyl N-[2-[(4S)-4-[(2,5-dioxopyrrolidin-1-yl)oxycarbonylamino]azepan-1-yl]ethyl]carbamate
• CAS: 1017575-64-2
• 化学式: C₂₁H₂₈N₄O₆
• 分子量: 432.477
• InChiKey: LDVRUYBCQNEBCT-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl (2-((4S)-4-(2,5-dioxopyrrolidin-1-yloxycarbonylamino)azepan-1-yl)ethyl)carbamate 在 氢气 、 碳酸氢钠 、 钯 、 溶剂黄146 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 生成 (1S,5R)-2-((4S)-1-(2-aminoethyl)azepan-4-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). 2. N-Alkylated and open chain analogs of MK-8712

  摘要：

  The bridged monobactam beta-lactamase inhibitor MK-8712 (1) effectively inhibits class C beta-lactamases. Side chain N-alkylated and ring-opened analogs of 1 were prepared and evaluated for combination with imipenem to overcome class C beta-lactamase mediated resistance. Although some analogs were more potent inhibitors of AmpC, none exhibited better synergy with imipenem than 1. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.065
• 作为产物：
  描述：

  benzyl (2-((4S)-4-(tert-butoxycarbonylamino)azepan-1-yl)ethyl)carbamate 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 benzyl (2-((4S)-4-(2,5-dioxopyrrolidin-1-yloxycarbonylamino)azepan-1-yl)ethyl)carbamate
  参考文献：
  名称：

  Side chain SAR of bicyclic β-lactamase inhibitors (BLIs). 2. N-Alkylated and open chain analogs of MK-8712

  摘要：

  The bridged monobactam beta-lactamase inhibitor MK-8712 (1) effectively inhibits class C beta-lactamases. Side chain N-alkylated and ring-opened analogs of 1 were prepared and evaluated for combination with imipenem to overcome class C beta-lactamase mediated resistance. Although some analogs were more potent inhibitors of AmpC, none exhibited better synergy with imipenem than 1. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.065

文献信息

• NOVEL INHIBITORS OF BETA-LACTAMASE
  申请人：Blizzard Timothy A.

  公开号：US20100009957A1

  公开（公告）日：2010-01-14

  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 β-lactamase inhibitors. The compounds and their prodrugs and pharmaceutically acceptable salts are useful in the treatment of bacterial infections in combination with β-lactam antibiotics. In particular, the compounds are suitable for use with β-lactam antibiotics (e.g., imipenem and ceftazidime) against micro-organisms resistant to β-lactam antibiotics due to the presence of the β-lactamases.

  一类7-氧代-2,6-二氮杂双环[3.2.0]庚烷-6-磺酸化合物，在双环环上的2位取代了杂环氨基甲酰基团或碳环氨基甲酰基团，是β-内酰胺酶抑制剂。这些化合物及其前药和药学上可接受的盐在联合β-内酰胺类抗生素治疗细菌感染方面非常有用。特别是，这些化合物适用于与β-内酰胺类抗生素（例如亚胺培南和头孢他啶）一起使用，对于由于β-内酰胺酶的存在而对β-内酰胺类抗生素产生耐药性的微生物非常有效。
• WO2008/39420
  申请人：——

  公开号：——

  公开（公告）日：——
• [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). 2. N-Alkylated and open chain analogs of MK-8712
  作者：Helen Chen、Timothy A. Blizzard、Seongkon Kim、Jane Wu、Katherine Young、Young-Whan Park、Aimie M. Ogawa、Susan Raghoobar、Ronald E. Painter、Doug Wisniewski、Nichelle Hairston、Paula Fitzgerald、Nandini Sharma、Giovanna Scapin、Jun Lu、Jeff Hermes、Milton L. Hammond

  DOI：10.1016/j.bmcl.2011.05.065

  日期：2011.7

  The bridged monobactam beta-lactamase inhibitor MK-8712 (1) effectively inhibits class C beta-lactamases. Side chain N-alkylated and ring-opened analogs of 1 were prepared and evaluated for combination with imipenem to overcome class C beta-lactamase mediated resistance. Although some analogs were more potent inhibitors of AmpC, none exhibited better synergy with imipenem than 1. (C) 2011 Elsevier Ltd. All rights reserved.