allyl (1S,5R,6S)-2-(4-(iodomethyl-1,8-naphthosultam)methyl)-6-[1(R)-(allyloxycarbonyl)oxyethyl]-1-methylcarbapen-2-em-3-carboxylate | 198472-43-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: allyl (1S,5R,6S)-2-(4-(iodomethyl-1,8-naphthosultam)methyl)-6-[1(R)-(allyloxycarbonyl)oxyethyl]-1-methylcarbapen-2-em-3-carboxylate
• 英文别名: prop-2-enyl (4S,5R,6S)-3-[[9-(iodomethyl)-2,2-dioxo-2λ6-thia-3-azatricyclo[6.3.1.04,12]dodeca-1(12),4,6,8,10-pentaen-3-yl]methyl]-4-methyl-7-oxo-6-[(1R)-1-prop-2-enoxycarbonyloxyethyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 198472-43-4
• 化学式: C₂₉H₂₉IN₂O₈S
• 分子量: 692.528
• InChiKey: HHJICKXRGWBXQR-KDVGALNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  allyl (1S,5R,6S)-2-(4-(iodomethyl-1,8-naphthosultam)methyl)-6-[1(R)-(allyloxycarbonyl)oxyethyl]-1-methylcarbapen-2-em-3-carboxylate 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 、 乙腈 为溶剂， 生成 (1S,5R,6S)-2-(4-(((carbamoylmethyl)-1,4-diazoniabicyclo[2.2.2]oct-1-yl)methyl)(1,8-napthosultam)methyl)-6-[1(R)-hydroxyethyl]-1-methylcarbapen-2-em-3-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
• 作为产物：
  描述：

  (4S,5R,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-3-(6-methanesulfonyloxymethyl-1,1-dioxo-1H-1λ⁶-naphtho[1,8-cd]isothiazol-2-ylmethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester 在 sodium iodide 作用下， 以 丙酮 为溶剂， 生成 allyl (1S,5R,6S)-2-(4-(iodomethyl-1,8-naphthosultam)methyl)-6-[1(R)-(allyloxycarbonyl)oxyethyl]-1-methylcarbapen-2-em-3-carboxylate
  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

• CARBAPENEM ANTIBACTERIAL COMPOUNDS, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF TREATMENT
  申请人：MERCK & CO., INC.

  公开号：EP0906313B1

  公开（公告）日：2004-03-03