(4S,5R,6S)-3-[6-(3-aminopropyl)-7-methylsulfanylimidazo[5,1-b][1,3]thiazol-6-ium-2-yl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;hydrochloride

• 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-[6-(3-aminopropyl)-7-methylsulfanylimidazo[5,1-b][1,3]thiazol-6-ium-2-yl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;hydrochloride
• 化学式: C₁₉H₂₄N₄O₄S₂*ClH
• 分子量: 473.017
• InChiKey: ZANTXIHODROTNE-GGCUUADZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  169
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4S,5R,6S)-3-[6-(3-aminopropyl)-7-methylsulfanylimidazo[5,1-b][1,3]thiazol-6-ium-2-yl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;hydrochloride 、 甲亚胺乙酯盐酸盐 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.5h， 生成 (4S,5R,6S)-3-[6-[3-(aminomethylideneamino)propyl]-7-methylsulfanylimidazo[5,1-b][1,3]thiazol-6-ium-2-yl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  参考文献：
  名称：

  CP5484, a novel quaternary carbapenem with potent anti-MRSA activity and reduced toxicity

  摘要：

  A new series of 1 beta-methyl carbapenems possessing a 6,7-disubstituted imidazo[5, 1-b]thiazol-2-yl group directly attached to the C-2 position of the carbapenem nucleus was prepared, and the activities of these compounds against methicillin-resistant Staphylococcus aureus (MRSA) were evaluated. To study the effect of basic moieties on anti-MRSA activity, we introduced an amino, or imino, or amidino group at the 6-position of imidazo[5,1-b]thiazole in place of the carbamoylmethyl moiety of CP5068. Anti-MRSA activities of almost all basic group-substituted carbapenems were improved, though some of the compounds showed stronger acute toxicity in mice than IPM. In order to decrease the toxicity without decreasing the activity, we introduced various additional functionalities around the basic moiety. Finally, we obtained CP5484, which has excellent anti-MRSA activity and low acute toxicity. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.057