methyl (8S)-8-(bromomethyl)-2-methyl-4-(piperazine-1-carbonyloxy)-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate | 192509-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl (8S)-8-(bromomethyl)-2-methyl-4-(piperazine-1-carbonyloxy)-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate
• CAS: 192509-09-4
• 化学式: C₃₁H₃₄BrN₅O₈
• 分子量: 684.544
• InChiKey: KONOZAUPBOCYIZ-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  45
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  147
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (8S)-8-(bromomethyl)-2-methyl-4-(piperazine-1-carbonyloxy)-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate 在 1-氯乙基氯甲酸酯 、 1,8-双二甲氨基萘 、 碳酸氢钠 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 72.0h， 生成 methyl (8S)-8-(chloromethyl)-2-methyl-4-(piperazine-1-carbonyloxy)-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate
  参考文献：
  名称：

  The synthesis of [3H]KW-2189, a novel active antitumor antibiotic

  摘要：

  The synthesis of [H-3]KW-2189, 2, a novel active antitumor antibiotic, is described. The key intermediate 6 in the synthesis, was synthesized in four steps from duocarmycin B2 (I). Treatment of 6 with [H-3]methyl iodide in the presence of NaHCO3 in MeOH-Me2CO (1:1) afforded the [H-3]KW-2189 with highly specific activity of 86.4 Ci/mmol.

  DOI：

  10.1002/(sici)1099-1344(199706)39:6<471::aid-jlcr991>3.0.co;2-k
• 作为产物：
  描述：

  methyl (2S,8S)-8-(bromomethyl)-4-hydroxy-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-2-carboxylate 在 sodium tetrahydroborate 、 camphor-10-sulfonic acid 、 三乙胺 、 烯丙醇 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 6.5h， 生成 methyl (8S)-8-(bromomethyl)-2-methyl-4-(piperazine-1-carbonyloxy)-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate
  参考文献：
  名称：

  The synthesis of [3H]KW-2189, a novel active antitumor antibiotic

  摘要：

  The synthesis of [H-3]KW-2189, 2, a novel active antitumor antibiotic, is described. The key intermediate 6 in the synthesis, was synthesized in four steps from duocarmycin B2 (I). Treatment of 6 with [H-3]methyl iodide in the presence of NaHCO3 in MeOH-Me2CO (1:1) afforded the [H-3]KW-2189 with highly specific activity of 86.4 Ci/mmol.

  DOI：

  10.1002/(sici)1099-1344(199706)39:6<471::aid-jlcr991>3.0.co;2-k

文献信息

• The synthesis of [3H]KW-2189, a novel active antitumor antibiotic
  作者：Satoro Nagamura、Masahiko Kinugawa、Takehiro Ogasa、Hiromitsu Saito

  DOI：10.1002/(sici)1099-1344(199706)39:6<471::aid-jlcr991>3.0.co;2-k

  日期：1997.6

  The synthesis of [H-3]KW-2189, 2, a novel active antitumor antibiotic, is described. The key intermediate 6 in the synthesis, was synthesized in four steps from duocarmycin B2 (I). Treatment of 6 with [H-3]methyl iodide in the presence of NaHCO3 in MeOH-Me2CO (1:1) afforded the [H-3]KW-2189 with highly specific activity of 86.4 Ci/mmol.