[4S-(4α,5β,6β(S*))]-1-(2-amino-2-oxoethyl)-4-({6-[2-carboxy-6-(1-hydroxyethyl)4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]-9-oxo-9H-fluoren-2-yl}methyl)-1,4-diazaniabicyclo[2.2.2]octane chloride | 169957-63-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: [4S-(4α,5β,6β(S*))]-1-(2-amino-2-oxoethyl)-4-({6-[2-carboxy-6-(1-hydroxyethyl)4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]-9-oxo-9H-fluoren-2-yl}methyl)-1,4-diazaniabicyclo[2.2.2]octane chloride
• 英文别名: 1-(2-Amino-2-oxoethyl)-4-((6-(2-carboxy-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-en-3-yl)-9-oxo-9H-fluoren-2-yl)methyl)-1,4-diazoniabicyclo(2.2.2)octane chloride,4S-(4a,5b,6b(S*))；(4S,5R,6S)-3-[7-[[4-(2-amino-2-oxoethyl)-1,4-diazoniabicyclo[2.2.2]octan-1-yl]methyl]-9-oxofluoren-3-yl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;chloride
• CAS: 169957-63-5
• 化学式: C₃₂H₃₅N₄O₆*Cl
• 分子量: 607.106
• InChiKey: LKKUUWNEQCXTNI-BLNZHTMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.13
• 重原子数：
  43
• 可旋转键数：
  6
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [4S-(4α,5β,6β(S*))]-1-(2-amino-2-oxoethyl)-4-({6-[2-carboxy-6-(1-hydroxyethyl)4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]-9-oxo-9H-fluoren-2-yl}methyl)-1,4-diazaniabicyclo[2.2.2]octane chloride 在 potassium sulfate 作用下， 以 水 为溶剂， 生成 [4S-(4α,5β,6β(S*))]-1-(2-amino-2-oxoethyl)-4-({6-[2-carboxy-6-(1-hydroxyethyl)4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]-9-oxo-9H-fluoren-2-yl}methyl)-1,4-diazaniabicyclo[2.2.2]octane hemisulfate
  参考文献：
  名称：

  Practical Synthesis of Anti-Methicillin-Resistant Staphylococcus Aureus (MRSA) Carbapenem L-742,728

  摘要：

  Ani-MRSA carbapenem, L-742,728, has been prepared in large quantity using, the Suzuki-Miyaura cross-coupling as the key reaction. Three approaches have been examined by varying the coupling reaction between carbapenem nucleus A and side chains B, BC, and BCD, wherein BCD represents the fully elaborated side chain. The coupling of A with BCD offers the advantage of convergence and requires fewer chemical steps after installation of the thermally unstable carbapenem skeleton. This key reaction highlights the versatility and efficiency of the Suzuki-Miyaura reaction. This approach offers a general method for the preparation of the 3-aryl carbapenems, which possess strong antibacterial activity against resistant strains.

  DOI：

  10.1021/jo980381n
• 作为产物：
  描述：

  三乙烯二胺 在 platinum(II) oxide 氢气 作用下， 以 异丙醇 、 乙腈 为溶剂， 5.0~45.0 ℃ 、689.48 kPa 条件下， 反应 5.75h， 生成 [4S-(4α,5β,6β(S*))]-1-(2-amino-2-oxoethyl)-4-({6-[2-carboxy-6-(1-hydroxyethyl)4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]-9-oxo-9H-fluoren-2-yl}methyl)-1,4-diazaniabicyclo[2.2.2]octane chloride
  参考文献：
  名称：

  Practical Synthesis of Anti-Methicillin-Resistant Staphylococcus Aureus (MRSA) Carbapenem L-742,728

  摘要：

  Ani-MRSA carbapenem, L-742,728, has been prepared in large quantity using, the Suzuki-Miyaura cross-coupling as the key reaction. Three approaches have been examined by varying the coupling reaction between carbapenem nucleus A and side chains B, BC, and BCD, wherein BCD represents the fully elaborated side chain. The coupling of A with BCD offers the advantage of convergence and requires fewer chemical steps after installation of the thermally unstable carbapenem skeleton. This key reaction highlights the versatility and efficiency of the Suzuki-Miyaura reaction. This approach offers a general method for the preparation of the 3-aryl carbapenems, which possess strong antibacterial activity against resistant strains.

  DOI：

  10.1021/jo980381n

文献信息

• Dicationic 2-fluorenonylcarbapenems: Potent anti-MRS agents with improved solubility and pharmacokinetic properties
  作者：Mark L. Greenlee、Joanne B. Laub、Gregory P. Rouen、Frank DiNinno、Milton L. Hammond、Joann L. Huber、Jon G. Sundelof、Gail G. Hammond

  DOI：10.1016/s0960-894x(99)00567-3

  日期：1999.11

  The synthesis and biological evaluation of a series of dicationic-substituted 2-fluorenonylcarbapenems is described. This class of compounds showed enhanced water solubility while maintaining potent activity against MRS. Introduction of a beta 1--methyl substituent was found to improve pharmacokinetics. (C) 1999 Elsevier Science Ltd. All rights reserved.