(2S)-N-{4-[6-[2-methoxy-4-((E)-3-oxo-3-[4-(3,4,5-trimethoxybenzoyl)piperazino]-1-propenyl)phenoxy]hexyloxy]-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl dithioacetal | 1246890-26-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (2S)-N-{4-[6-[2-methoxy-4-((E)-3-oxo-3-[4-(3,4,5-trimethoxybenzoyl)piperazino]-1-propenyl)phenoxy]hexyloxy]-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl dithioacetal
• 英文别名: (E)-3-[4-[6-[4-[(2S)-2-[bis(ethylsulfanyl)methyl]pyrrolidine-1-carbonyl]-2-methoxy-5-nitrophenoxy]hexoxy]-3-methoxyphenyl]-1-[4-(3,4,5-trimethoxybenzoyl)piperazin-1-yl]prop-2-en-1-one
• CAS: 1246890-26-5
• 化学式: C₄₇H₆₂N₄O₁₂S₂
• 分子量: 939.161
• InChiKey: KARZHQZCTMYEHE-GYRCUWIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  65
• 可旋转键数：
  23
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  222
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (2S)-N-{4-[6-[2-methoxy-4-((E)-3-oxo-3-[4-(3,4,5-trimethoxybenzoyl)piperazino]-1-propenyl)phenoxy]hexyloxy]-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl dithioacetal 在 tin(II) chloride dihdyrate 作用下， 以 甲醇 为溶剂， 生成 (E)-3-[4-[6-[5-amino-4-[(2S)-2-[bis(ethylsulfanyl)methyl]pyrrolidine-1-carbonyl]-2-methoxyphenoxy]hexoxy]-3-methoxyphenyl]-1-[4-(3,4,5-trimethoxybenzoyl)piperazin-1-yl]prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and biological evaluation of cinnamido linked pyrrolo[2,1-c][1,4]benzodiazepines as antimitotic agents

  摘要：

  A series of new cinnamido-pyrrolo[2,1-c][1,4)benzodiazepine conjugates (4a-d and 5a-d) and their dimers (6a-d) have been designed, synthesized and evaluated for their biological activity. The anticancer screening of compound 4a by the NCI exhibited significant GI50 values ranging from 68 to 732 nM against 53 of 59 human cancer cell lines tested. Compounds 5a-d and 6a-d have also shown remarkable cytotoxic activity with GI50 values <0.1 mu M concentrations in a large number of cell lines. Interestingly, compounds 5b and 6b have been identified as a new class of inhibitors of tubulin polymerization and their action has been rationalized by the cell cycle arrest in GO and G2/M phase. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.041
• 作为产物：
  描述：

  (2S)-N-[4-(6-bromohexyloxy)-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl dithioacetal 、 (E)-3-(4-hydroxy-3-methoxyphenyl)-1-[4-(3,4,5-trimethoxybenzoyl)piperazino]-2-propen-1-one 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以74%的产率得到(2S)-N-{4-[6-[2-methoxy-4-((E)-3-oxo-3-[4-(3,4,5-trimethoxybenzoyl)piperazino]-1-propenyl)phenoxy]hexyloxy]-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl dithioacetal
  参考文献：
  名称：

  Synthesis and biological evaluation of cinnamido linked pyrrolo[2,1-c][1,4]benzodiazepines as antimitotic agents

  摘要：

  A series of new cinnamido-pyrrolo[2,1-c][1,4)benzodiazepine conjugates (4a-d and 5a-d) and their dimers (6a-d) have been designed, synthesized and evaluated for their biological activity. The anticancer screening of compound 4a by the NCI exhibited significant GI50 values ranging from 68 to 732 nM against 53 of 59 human cancer cell lines tested. Compounds 5a-d and 6a-d have also shown remarkable cytotoxic activity with GI50 values <0.1 mu M concentrations in a large number of cell lines. Interestingly, compounds 5b and 6b have been identified as a new class of inhibitors of tubulin polymerization and their action has been rationalized by the cell cycle arrest in GO and G2/M phase. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.041