(2S)-2-amino-3-[4-[[(2S,5R)-7-oxo-6-sulfooxy-1,6-diazabicyclo[3.2.1]octane-2-carbonyl]amino]phenyl]propanoic acid | 1552306-80-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-2-amino-3-[4-[[(2S,5R)-7-oxo-6-sulfooxy-1,6-diazabicyclo[3.2.1]octane-2-carbonyl]amino]phenyl]propanoic acid
• CAS: 1552306-80-5
• 化学式: C₁₆H₂₀N₄O₈S
• 分子量: 428.423
• InChiKey: BXMHTFQRTLBDOP-AGIUHOORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  188
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (2S,5R)-6-(苄氧基)-7-氧代-1,6-二氮杂双环[3.2.1]辛烷-2-羧酸 在 吡啶 、 palladium 10% on activated carbon 、 2-氯-1-甲基吡啶碘化物 、 氢气 、 三氧化硫吡啶 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2S)-2-amino-3-[4-[[(2S,5R)-7-oxo-6-sulfooxy-1,6-diazabicyclo[3.2.1]octane-2-carbonyl]amino]phenyl]propanoic acid
  参考文献：
  名称：

  Discovery of MK-7655, a β-lactamase inhibitor for combination with Primaxin®

  摘要：

  beta-Lactamase inhibitors with a bicyclic urea core and a variety of heterocyclic side chains were prepared and evaluated as potential partners for combination with imipenem to overcome class A and C beta-lactamase mediated antibiotic resistance. The piperidine analog 3 (MK-7655) inhibited both class A and C beta-lactamases in vitro. It effectively restored imipenem's activity against imipenem-resistant Pseudomonas and Klebsiella strains at clinically achievable concentrations. A combination of MK-7655 and Primaxin (R) is currently in phase II clinical trials for the treatment of Gram-negative bacterial infections. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.101

文献信息

• Discovery of MK-7655, a β-lactamase inhibitor for combination with Primaxin®
  作者：Timothy A. Blizzard、Helen Chen、Seongkon Kim、Jane Wu、Rena Bodner、Candido Gude、Jason Imbriglio、Katherine Young、Young-Whan Park、Aimie Ogawa、Susan Raghoobar、Nichelle Hairston、Ronald E. Painter、Doug Wisniewski、Giovanna Scapin、Paula Fitzgerald、Nandini Sharma、Jun Lu、Sookhee Ha、Jeff Hermes、Milton L. Hammond

  DOI：10.1016/j.bmcl.2013.12.101

  日期：2014.2

  beta-Lactamase inhibitors with a bicyclic urea core and a variety of heterocyclic side chains were prepared and evaluated as potential partners for combination with imipenem to overcome class A and C beta-lactamase mediated antibiotic resistance. The piperidine analog 3 (MK-7655) inhibited both class A and C beta-lactamases in vitro. It effectively restored imipenem's activity against imipenem-resistant Pseudomonas and Klebsiella strains at clinically achievable concentrations. A combination of MK-7655 and Primaxin (R) is currently in phase II clinical trials for the treatment of Gram-negative bacterial infections. (C) 2014 Elsevier Ltd. All rights reserved.