allyl (2S,4S)-2-(3-(ethoxycarbonyl)-4-(hydroxyimino)pyrrolidine-1-carbonyl)-4-mercaptopyrrolidine-1-carboxylate | 654638-81-0

• 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: allyl (2S,4S)-2-(3-(ethoxycarbonyl)-4-(hydroxyimino)pyrrolidine-1-carbonyl)-4-mercaptopyrrolidine-1-carboxylate
• CAS: 654638-81-0
• 化学式: C₁₆H₂₃N₃O₆S
• 分子量: 385.441
• InChiKey: MWKBHBFZHYWRAU-BJEKPXQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  108.74
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  allyl (2S,4S)-2-(3-(ethoxycarbonyl)-4-(hydroxyimino)pyrrolidine-1-carbonyl)-4-mercaptopyrrolidine-1-carboxylate 在 四(三苯基膦)钯 、 三正丁基氢锡 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Synthesis and biological activity of novel 1β-Methylcarbapenems with oxyiminopyrrolidinylamide moiety

  摘要：

  The synthesis and antibacterial activity of novel 1beta-methylcarbapenems 1a-f bearing oxyiminopyrrolidinylamide moiety at C-5 position of pyrrolidine are described. Most compounds exhibited comparable antibacterial activity to meropenem against a wide range of Gram-positive and Gram-negative organisms including Pseudomonas aeruginosa isolates. Of these carbapenems, 1a showed potent and broad spectrum of antibacterial activity and similar stability to DHP-I to meropenem. Against clinical isolates of 40 Gram-negative bacterial species including MDR and ESBL-producing strains, the selected carbapenem 1a possessed excellent in vitro activity except for MDR P. aeruginosa, and was comparable in potency to meropenem. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.039
• 作为产物：
  描述：

  (3S,5S)-3-acetylthio-1-allyloxycarbonylpyrrolidin-5-carboxylic acid 在 sodium hydroxide 、 N,N'-羰基二咪唑 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 4.0h， 生成 allyl (2S,4S)-2-(3-(ethoxycarbonyl)-4-(hydroxyimino)pyrrolidine-1-carbonyl)-4-mercaptopyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis and biological activity of novel 1β-Methylcarbapenems with oxyiminopyrrolidinylamide moiety

  摘要：

  The synthesis and antibacterial activity of novel 1beta-methylcarbapenems 1a-f bearing oxyiminopyrrolidinylamide moiety at C-5 position of pyrrolidine are described. Most compounds exhibited comparable antibacterial activity to meropenem against a wide range of Gram-positive and Gram-negative organisms including Pseudomonas aeruginosa isolates. Of these carbapenems, 1a showed potent and broad spectrum of antibacterial activity and similar stability to DHP-I to meropenem. Against clinical isolates of 40 Gram-negative bacterial species including MDR and ESBL-producing strains, the selected carbapenem 1a possessed excellent in vitro activity except for MDR P. aeruginosa, and was comparable in potency to meropenem. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.039

文献信息

• Synthesis and in vitro activity of a series 1β-methylcarbapenem derivatives
  作者：H.C. Jeon、J.-W. Kim、J.H. Hong、J.-H. Cho、C.-H. Oh

  DOI：10.1016/j.ejmech.2006.05.003

  日期：2006.10

  The synthesis of a new series of 1beta-methylcarbapenems having pyrrolidine and piperidine moieties is described. Their in vitro antibacterial activities against both Gram-positive and Gram-negative bacteria were tested and the effect of substituent on the pyrrolidine ring was investigated. A particular compound (IIIb) having hydroxypyrrolidine moiety showed the most potent antibacterial activity.

  描述了具有吡咯烷和哌啶部分的一系列新的1β-甲基卡巴南的合成。测试了它们对革兰氏阳性和革兰氏阴性细菌的体外抗菌活性，并研究了取代基对吡咯烷环的影响。具有羟基吡咯烷部分的特定化合物（IIIb）显示出最有效的抗菌活性。