methyl (1R,3S)-2-[(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carbonyl]-1-phenyl-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylate | 274677-78-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: methyl (1R,3S)-2-[(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carbonyl]-1-phenyl-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylate
• CAS: 274677-78-0
• 化学式: C₃₉H₃₅N₃O₅
• 分子量: 625.724
• InChiKey: MDCZVYAYROAOJR-IXQHYERASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  47
• 可旋转键数：
  7
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  91.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (1R,3S)-2-[(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carbonyl]-1-phenyl-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylate 在 哌啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以89%的产率得到(1S,12R,15S)-12-phenyl-10,13,19-triazapentacyclo[11.7.0.03,11.04,9.015,19]icosa-3(11),4,6,8-tetraene-14,20-dione
  参考文献：
  名称：

  Synthesis and Evaluation of Tryprostatin B and Demethoxyfumitremorgin C Analogues

  摘要：

  Tryprostatin B and demethoxyfumitremorgin C are fungal inhibitors of mammalian cell cycle progression at the G(2)/M transition. N-Alkyl derivatives of the L-TrP-L-Pro diketopiperazine were prepared as analogues of tryprostatin B, and two of these were more active than the natural product. A second series of cis- and trans-tetrahydro-beta-carbolines annulated to a diketopiperazine were prepared as analogues of demethoxyfumitremorgin C. The nature of the alkyl substituent, as well as its cis or trans relationship in the tetrahydro-beta-carboline ring, was found to have a significant effect on cytotoxic activity. Small cis-alkyl substituents fall into the demethoxyfumitremorgin C family, whereas bulky benzyl trans compounds appear to act via a different mechanism of action.

  DOI：

  10.1021/jm9905662
• 作为产物：
  描述：

  L-色氨酸甲酯 在 sodium carbonate 、 三氟乙酸 、 原甲酸三甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 26.5h， 生成 methyl (1R,3S)-2-[(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carbonyl]-1-phenyl-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Synthesis and Evaluation of Tryprostatin B and Demethoxyfumitremorgin C Analogues

  摘要：

  Tryprostatin B and demethoxyfumitremorgin C are fungal inhibitors of mammalian cell cycle progression at the G(2)/M transition. N-Alkyl derivatives of the L-TrP-L-Pro diketopiperazine were prepared as analogues of tryprostatin B, and two of these were more active than the natural product. A second series of cis- and trans-tetrahydro-beta-carbolines annulated to a diketopiperazine were prepared as analogues of demethoxyfumitremorgin C. The nature of the alkyl substituent, as well as its cis or trans relationship in the tetrahydro-beta-carboline ring, was found to have a significant effect on cytotoxic activity. Small cis-alkyl substituents fall into the demethoxyfumitremorgin C family, whereas bulky benzyl trans compounds appear to act via a different mechanism of action.

  DOI：

  10.1021/jm9905662

文献信息

• Synthesis and Evaluation of Tryprostatin B and Demethoxyfumitremorgin C Analogues
  作者：Haishan Wang、Takeo Usui、Hiroyuki Osada、A. Ganesan

  DOI：10.1021/jm9905662

  日期：2000.4.1

  Tryprostatin B and demethoxyfumitremorgin C are fungal inhibitors of mammalian cell cycle progression at the G(2)/M transition. N-Alkyl derivatives of the L-TrP-L-Pro diketopiperazine were prepared as analogues of tryprostatin B, and two of these were more active than the natural product. A second series of cis- and trans-tetrahydro-beta-carbolines annulated to a diketopiperazine were prepared as analogues of demethoxyfumitremorgin C. The nature of the alkyl substituent, as well as its cis or trans relationship in the tetrahydro-beta-carboline ring, was found to have a significant effect on cytotoxic activity. Small cis-alkyl substituents fall into the demethoxyfumitremorgin C family, whereas bulky benzyl trans compounds appear to act via a different mechanism of action.