(4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-{(3S,5S)-5-[(E)-2-(3-hydroxymethyl-isoxazol-5-yl)-vinyl]-pyrrolidin-3-ylsulfanyl}-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid | 326605-56-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-{(3S,5S)-5-[(E)-2-(3-hydroxymethyl-isoxazol-5-yl)-vinyl]-pyrrolidin-3-ylsulfanyl}-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• 英文别名: (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[(3S,5S)-5-[(E)-2-[3-(hydroxymethyl)-1,2-oxazol-5-yl]ethenyl]pyrrolidin-3-yl]sulfanyl-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• CAS: 326605-56-5
• 化学式: C₂₀H₂₅N₃O₆S
• 分子量: 435.501
• InChiKey: JUTMCDBWBVJWOH-UZBSKJLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  161
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  allyl (1R,5R,6S)-2-(diphenoxyphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-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 乙腈 为溶剂， 反应 2.0h， 生成 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-{(3S,5S)-5-[(E)-2-(3-hydroxymethyl-isoxazol-5-yl)-vinyl]-pyrrolidin-3-ylsulfanyl}-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological activity of 1β-methyl-2-[5′-isoxazoloethenylpyrrolidin-3′-ylthio]carbapenems

  摘要：

  A new series of 1 beta -methylcarbapenems 1a-i bearing isoxazoloethenyl groups on the pyrrolidine ring has been prepared and evaluated for in vitro antibacterial activity and stability to DHP-I. Most compounds showed excellent antibacterial activity and high stability to DHP-I superior to that of meropenem. Of these new carbapenems, 1a,b,h exhibited the best combination of antibacterial activity and DHP-I stability. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00575-8

文献信息

• Synthesis and biological activity of 1β-methyl-2-[5′-isoxazoloethenylpyrrolidin-3′-ylthio]carbapenems
  作者：Dong Jin Kim、Kyung Jae Seo、Kyung Seok Lee、Kye Jung Shin、Kyung Ho Yoo、Dong Chan Kim、Sang Woo Park

  DOI：10.1016/s0960-894x(00)00575-8

  日期：2000.12

  A new series of 1 beta -methylcarbapenems 1a-i bearing isoxazoloethenyl groups on the pyrrolidine ring has been prepared and evaluated for in vitro antibacterial activity and stability to DHP-I. Most compounds showed excellent antibacterial activity and high stability to DHP-I superior to that of meropenem. Of these new carbapenems, 1a,b,h exhibited the best combination of antibacterial activity and DHP-I stability. (C) 2000 Elsevier Science Ltd. All rights reserved.