benzyl (4S)-4-((tert-butyl-(R)-sulfinyl)amino)azepane-1-carboxylate | 1017575-21-1

• 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-butyl-(R)-sulfinyl)amino)azepane-1-carboxylate
• 英文别名: benzyl (4S)-4-[(tert-butyl (R)-sulfinyl)amino]azepane-1-carboxylate；benzyl (4S)-4-[[(R)-tert-butylsulfinyl]amino]azepane-1-carboxylate
• CAS: 1017575-21-1
• 化学式: C₁₈H₂₈N₂O₃S
• 分子量: 352.498
• InChiKey: KGNSETKTRNMUEZ-UPCLLVRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl (4S)-4-((tert-butyl-(R)-sulfinyl)amino)azepane-1-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 benzyl (4S)-4-aminoazepane-1-carboxylate
  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：

  在 chiral HPLC on OJ column 作用下， 以 乙醇 、 正庚烷 为溶剂， 以23%的产率得到benzyl (4R)-4-((tert-butyl-(R)-sulfinyl)amino)azepane-1-carboxylate
  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

• 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). 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.