(1S,5R,6S)-2-(4-(2-(((carbamoylmethyl)-1,4-diazoniabicyclo[2.2.2]oct-1-yl))-ethyl)(1,8-napthosultam)methyl)-6-[1(R)-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate chloride | 198472-47-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S,5R,6S)-2-(4-(2-(((carbamoylmethyl)-1,4-diazoniabicyclo[2.2.2]oct-1-yl))-ethyl)(1,8-napthosultam)methyl)-6-[1(R)-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate chloride
• 英文别名: 1,4-Diazoniabicyclo(2.2.2)octane, 1-(2-amino-2-oxoethyl)-4-(2-(2-(((4S,5R,6S)-2-carboxy-6-((1R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-en-3-yl)methyl)-1,1-dioxido-2H-naphth(1,8-cd)isothiazol-6-yl)ethyl)-, inner salt, chloride；(4S,5R,6S)-3-[[9-[2-[4-(2-amino-2-oxoethyl)-1,4-diazoniabicyclo[2.2.2]octan-1-yl]ethyl]-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
• CAS: 198472-47-8
• 化学式: C₃₁H₃₈N₅O₇S*Cl
• 分子量: 660.191
• InChiKey: BRFWKOFAMCKDLC-OZBXVNDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  45
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  allyl (1S,5R,6S)-2-(4-(2-(hydroxy)-ethyl-1,8-naphthosultam)methyl)-6-[1(R)-(allyloxycarbonyl)oxyethyl]-1-methylcarbapen-2-em-3-carboxylate 在 2,6-二甲基吡啶 、 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 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (1S,5R,6S)-2-(4-(2-(((carbamoylmethyl)-1,4-diazoniabicyclo[2.2.2]oct-1-yl))-ethyl)(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

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
• Synthesis of an Anti-Methicillin-Resistant <i>Staphylococcus aureus </i>(MRSA) Carbapenem via Stannatrane-Mediated Stille Coupling
  作者：Mark S. Jensen、Chunhua Yang、Yi Hsiao、Nelo Rivera、Kenneth M. Wells、John Y. L. Chung、Nobuyoshi Yasuda、David L. Hughes、Paul J. Reider

  DOI：10.1021/ol005641d

  日期：2000.4.1

  A short synthesis of carbapenem 1 is described. The key step involves the cross-coupling of an enol triflate with an amino-substituted sp(3) carbon. This cross-couping, which allows the introduction of the complete side chain in one step, utilizes a stannatrane as the heteroalkyl transfer reagent.
• 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.