(4-nitrophenyl)methyl (4R,5S,6S)-3-[(3S,5S)-5-[2-(dimethylsulfamoyl)ethylcarbamoyl]-1-[(4-nitrophenyl)methoxycarbonyl]pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | 221659-35-4

• 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: (4-nitrophenyl)methyl (4R,5S,6S)-3-[(3S,5S)-5-[2-(dimethylsulfamoyl)ethylcarbamoyl]-1-[(4-nitrophenyl)methoxycarbonyl]pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 221659-35-4
• 化学式: C₃₄H₄₀N₆O₁₃S₂
• 分子量: 804.856
• InChiKey: NQPHUVMDQKHYCS-CCCPLFPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  55
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  288
• 氢给体数：
  2
• 氢受体数：
  15

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  杂氮双环磷酸酯	(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	90776-59-3	C29H27N2O10P	594.515
  ——	(4-nitrophenyl)methyl (2S,4S)-2-[2-(dimethylsulfamoyl)ethylcarbamoyl]-4-sulfanylpyrrolidine-1-carboxylate	212608-14-5	C17H24N4O7S2	460.532

反应信息

• 作为反应物：
  描述：

  (4-nitrophenyl)methyl (4R,5S,6S)-3-[(3S,5S)-5-[2-(dimethylsulfamoyl)ethylcarbamoyl]-1-[(4-nitrophenyl)methoxycarbonyl]pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (4R,5S,6S)-3-[(3S,5S)-5-(2-Dimethylsulfamoyl-ethylcarbamoyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-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 properties of new 1β-methylcarbapenems

  摘要：

  The synthesis and biological activity of the novel series of 1 beta-methylcarbapenems, 1 and 2 were described. Most compounds displayed high potent antibacterial activity. The best compound in this series, 2a (IH201; R-2=NH2) showed an excellent and a broad spectrum as well as high renal DHP-I stability. It also possessed good in vivo efficacy and high safety. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00270-4
• 作为产物：
  描述：

  (3S,5S)-3-acetylthio-5-carboxy-1-p-nitrobenzyloxycarbonylpyrrolidine 在 sodium hydroxide 、 TEA 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 生成 (4-nitrophenyl)methyl (4R,5S,6S)-3-[(3S,5S)-5-[2-(dimethylsulfamoyl)ethylcarbamoyl]-1-[(4-nitrophenyl)methoxycarbonyl]pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  参考文献：
  名称：

  Synthesis and biological properties of new 1β-methylcarbapenems

  摘要：

  The synthesis and biological activity of the novel series of 1 beta-methylcarbapenems, 1 and 2 were described. Most compounds displayed high potent antibacterial activity. The best compound in this series, 2a (IH201; R-2=NH2) showed an excellent and a broad spectrum as well as high renal DHP-I stability. It also possessed good in vivo efficacy and high safety. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00270-4

文献信息

• Synthesis and biological properties of new 1β-methylcarbapenems
  作者：Kye Jung Shin、Kyung Ho Yoo、Dong Jin Kim、Sang Woo Park、Bong Suck Ko、Sang Joo Lee、Jae Doo Huh、Seung Yong Park

  DOI：10.1016/s0960-894x(98)00270-4

  日期：1998.7

  The synthesis and biological activity of the novel series of 1 beta-methylcarbapenems, 1 and 2 were described. Most compounds displayed high potent antibacterial activity. The best compound in this series, 2a (IH201; R-2=NH2) showed an excellent and a broad spectrum as well as high renal DHP-I stability. It also possessed good in vivo efficacy and high safety. (C) 1998 Elsevier Science Ltd. All rights reserved.