(4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-7-oxo-3-(pyrrolidine-1-carbothioylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester | 177910-27-9

• 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)-4-methyl-7-oxo-3-(pyrrolidine-1-carbothioylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
• 英文别名: p-nitrobenzyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-2-[(1-pyrrolidinyl)thiocarbonylthio]-1-methyl-1-carbapen-2-em-3-carboxylate；(4-nitrophenyl)methyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-(pyrrolidine-1-carbothioylsulfanyl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 177910-27-9
• 化学式: C₂₂H₂₅N₃O₆S₂
• 分子量: 491.589
• InChiKey: XBZXUMVQVQCYAZ-BQGCOEIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  173
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-7-oxo-3-(pyrrolidine-1-carbothioylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 在 palladium on activated charcoal 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以51%的产率得到Sodium; (4R,5S,6S)-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-3-(pyrrolidine-1-carbothioylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate
  参考文献：
  名称：

  Novel dithiocarbamate carbapenems with anti-MRSA activity

  摘要：

  A new series of 1 beta-methyl carbapenems, in which a disubstituted-aminothiocarbonylthio moiety was attached to the C-2 position of the carbapenem nucleus, were prepared and evaluated for anti-MRSA activity. These derivatives showed good in vitro antibacterial activity against high-level MRSA, and the finding of good affinity for PBP-2' supported these results. Some of the compounds having favorable protein-binding affinity showed excellent in vivo anti-MRSA activity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00069-8
• 作为产物：
  描述：

  triethylammonium pyrrolidine-1-dithiocarboxylate 、 杂氮双环磷酸酯 在 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 生成 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-7-oxo-3-(pyrrolidine-1-carbothioylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
  参考文献：
  名称：

  Novel dithiocarbamate carbapenems1 with anti-MRSA activity

  摘要：

  A new series of carbapenems, in which disubstituted-aminothiocarbonylthio moiety, directly attached to the C-2 position, were prepared and evaluated for their antibacterial potency. These analogs showed potent activity against high-level MRSA, Among them, 9e and 9i were found to exhibit good in vivo efficacy comparable to that of vancomycin, for mouse septicemia model with high-level MRSA. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00272-2

文献信息

• Carbapenem derivatives
  申请人：Banyu Pharmaceutical Co., Ltd.

  公开号：US06251891B1

  公开（公告）日：2001-06-26

  A compound represented by the general formula wherein R1 either represents a hydrogen atom or a lower alkyl group, R2 represents a hydrogen atom, an ester residue, an alkali metal or negative charge, and R3 and R4 are the same or different, and each represent a hydrogen atom or a hydrocarbonic group optionally containing hetero atom(s) selected from the group consisting of oxygen atom(s), sulfur atom(s) and nitrogen atom(s), or they are combined together with the nitrogen atom to which they bound to form a heterocyclic group, and the use thereof as an antibacterial agent.

  一种化合物，其一般式为其中R1代表氢原子或低碳基，R2代表氢原子、酯基、碱金属或负电荷，R3和R4相同或不同，分别代表氢原子或含有氧原子、硫原子和氮原子等杂原子的烃基，或与它们结合在一起形成杂环基团，其作为抗菌剂的用途。