(4S,5R,6S)-3-[[10-[[4-(2-amino-2-oxoethyl)-1,4-diazoniabicyclo[2.2.2]octan-1-yl]methyl]-2,2-dioxo-2lambda6-thia-3-azatricyclo[6.3.1.04,12]dodeca-1(12),4,6,8,10-pentaen-3-yl]methyl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;chloride

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4S,5R,6S)-3-[[10-[[4-(2-amino-2-oxoethyl)-1,4-diazoniabicyclo[2.2.2]octan-1-yl]methyl]-2,2-dioxo-2lambda6-thia-3-azatricyclo[6.3.1.04,12]dodeca-1(12),4,6,8,10-pentaen-3-yl]methyl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;chloride
• 英文别名: (4S,5R,6S)-3-[[10-[[4-(2-amino-2-oxoethyl)-1,4-diazoniabicyclo[2.2.2]octan-1-yl]methyl]-2,2-dioxo-2λ6-thia-3-azatricyclo[6.3.1.04,12]dodeca-1(12),4,6,8,10-pentaen-3-yl]methyl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;chloride
• 化学式: C₃₀H₃₆N₅O₇S*Cl
• 分子量: 646.164
• InChiKey: ASBPPMPRVANAEA-PTFJVRJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.14
• 重原子数：
  44
• 可旋转键数：
  7
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  170
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  在 四(三苯基膦)钯 、 5,5-二甲基-1,3-环己二酮 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到(4S,5R,6S)-3-[[10-[[4-(2-amino-2-oxoethyl)-1,4-diazoniabicyclo[2.2.2]octan-1-yl]methyl]-2,2-dioxo-2lambda6-thia-3-azatricyclo[6.3.1.04,12]dodeca-1(12),4,6,8,10-pentaen-3-yl]methyl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;chloride
  参考文献：
  名称：

  Synthesis and properties of 2-(naphthosultamyl)methyl-carbapenems with potent anti-MRSA activity: Discovery of L-786,392

  摘要：

  A series of 1 beta-methyl-2-(naphthosultamyl)methyl-carbapenems bearing dicationic groups on the naphthosultamyl moiety was prepared and evaluated for activity against resistant gram-positive bacteria. Based on a combination of excellent in vitro antibacterial activity, acceptable mouse acute toxicity, and a desirable fragmentation pattern on beta-lactam ring opening, the analog 2g (L-786,392) was selected for extended evaluation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00071-2

文献信息

• Synthesis and properties of 2-(naphthosultamyl)methyl-carbapenems with potent anti-MRSA activity: Discovery of L-786,392
  作者：R.W. Ratcliffe、R.R. Wilkening、K.J. Wildonger、S.T. Waddell、G.M. Santorelli、D.L. Parker、J.D. Morgan、T.A. Blizzard、M.L. Hammond、J.V. Heck、J. Huber、J. Kohler、K.L. Dorso、E. St. Rose、J.G. Sundelof、W.J. May、G.G. Hammond

  DOI：10.1016/s0960-894x(99)00071-2

  日期：1999.3

  A series of 1 beta-methyl-2-(naphthosultamyl)methyl-carbapenems bearing dicationic groups on the naphthosultamyl moiety was prepared and evaluated for activity against resistant gram-positive bacteria. Based on a combination of excellent in vitro antibacterial activity, acceptable mouse acute toxicity, and a desirable fragmentation pattern on beta-lactam ring opening, the analog 2g (L-786,392) was selected for extended evaluation. (C) 1999 Elsevier Science Ltd. All rights reserved.