benzyl (4S)-4-tert-butoxycarbonylaminoazepane-1-carboxylate | 1017575-40-4

• 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: benzyl (4S)-4-tert-butoxycarbonylaminoazepane-1-carboxylate
• 英文别名: Benzyl (4S)-4-[(tert-butoxycarbonyl)amino]azepane-1-carboxylate；benzyl (4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]azepane-1-carboxylate
• CAS: 1017575-40-4
• 化学式: C₁₉H₂₈N₂O₄
• 分子量: 348.442
• InChiKey: YJKRYTHUCOGXFX-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl (4S)-4-tert-butoxycarbonylaminoazepane-1-carboxylate 在 20% palladium hydroxide on carbon 、 氢气 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 24.0h， 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
• 作为产物：
  描述：

  benzyl (4S)-4-aminoazepane-1-carboxylate 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到benzyl (4S)-4-tert-butoxycarbonylaminoazepane-1-carboxylate
  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：——
• 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.