9H-fluoren-9-ylmethyl (2S)-2-[[(2R)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl]-(3-methylbut-2-enyl)carbamoyl]pyrrolidine-1-carboxylate | 274677-91-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9H-fluoren-9-ylmethyl (2S)-2-[[(2R)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl]-(3-methylbut-2-enyl)carbamoyl]pyrrolidine-1-carboxylate
• CAS: 274677-91-7
• 化学式: C₃₇H₃₉N₃O₅
• 分子量: 605.734
• InChiKey: DJYOAFQUYWTCRN-SZAHLOSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  9H-fluoren-9-ylmethyl (2S)-2-[[(2R)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl]-(3-methylbut-2-enyl)carbamoyl]pyrrolidine-1-carboxylate 在 哌啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以58%的产率得到(3R,8aS)-3-(1H-indol-3-ylmethyl)-2-(3-methylbut-2-enyl)-6,7,8,8a-tetrahydro-3H-pyrrolo[1,2-a]pyrazine-1,4-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 三乙酰氧基硼氢化钠 、 sodium carbonate 、 原甲酸三甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 66.0h， 生成 9H-fluoren-9-ylmethyl (2S)-2-[[(2R)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl]-(3-methylbut-2-enyl)carbamoyl]pyrrolidine-1-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.