(4S,5R,6S)-3-Aminomethyl-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid | 119914-29-3

• 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: (4S,5R,6S)-3-Aminomethyl-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• 英文别名: (4S,5R,6S)-3-(aminomethyl)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• CAS: 119914-29-3
• 化学式: C₁₁H₁₆N₂O₄
• 分子量: 240.259
• InChiKey: FKYNPGNHHCMNCO-LRSZDJBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5R,6S)-3-Aminomethyl-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 、 2-萘甲酰氯 生成 (4S,5R,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-3-{[(naphthalene-2-carbonyl)-amino]-methyl}-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and antibacterial activity of lipophilic carbapenems with anti-MRSA activity

  摘要：

  A series of sulphur-linked and carbon-linked lipophilic carbapenems has been prepared and evaluated for antibacterial activity in vitro and in vivo and for affinity for PBP2' of Staphylococcus aureus. Potent activity in vitro against methicillin-resistant S. aureus and methicillin-resistant coagulase negative staphylococci was observed despite IC50 values for PBP2' being higher than the MIC. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0960-894x(96)00450-7
• 作为产物：
  描述：

  (4S,5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-hydroxymethyl-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester 在 四(三苯基膦)钯 、 5,5-二甲基-1,3-环己二酮 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.5h， 生成 (4S,5R,6S)-3-Aminomethyl-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：

  Mitsunobu反应在合成C-2 N-甲基碳青霉烯中的新应用

  摘要：

  N-酰基酰胺和N-酰基氨基杂环可以在Mitsunobu条件下与C-2羟甲基碳青霉烯发生区域选择性反应：酰胺的合成，氨基杂环的环外烷基化和转化为2-氨基甲基碳青霉烯的报道。

  DOI：

  10.1016/s0040-4039(00)60855-9

文献信息

• New applications of the mitsunobu reaction in the synthesis of C-2 N-methyl carbapenems
  作者：J.C. Arnould、F. Landier、M.J. Pasquet

  DOI：10.1016/s0040-4039(00)60855-9

  日期：1992.11

  N-acyl amides and N-acylamino heterocycles can be reacted regioselectively with C-2 hydroxymethyl carbapenems under Mitsunobu conditions:synthesis of amides, exocyclic alkylation of amino heterocycles and transformation into 2-aminomethyl carbapenems are reported.

  N-酰基酰胺和N-酰基氨基杂环可以在Mitsunobu条件下与C-2羟甲基碳青霉烯发生区域选择性反应：酰胺的合成，氨基杂环的环外烷基化和转化为2-氨基甲基碳青霉烯的报道。
• Synthesis and antibacterial activity of lipophilic carbapenems with anti-MRSA activity
  作者：Jean Claude Arnould、Ruth N Illingworth、Wright W Nichols、R. Geoffrey Wilson

  DOI：10.1016/0960-894x(96)00450-7

  日期：1996.10

  A series of sulphur-linked and carbon-linked lipophilic carbapenems has been prepared and evaluated for antibacterial activity in vitro and in vivo and for affinity for PBP2' of Staphylococcus aureus. Potent activity in vitro against methicillin-resistant S. aureus and methicillin-resistant coagulase negative staphylococci was observed despite IC50 values for PBP2' being higher than the MIC. Copyright (C) 1996 Elsevier Science Ltd.