methyl (8S)-8-(bromomethyl)-4-hydroxy-6-[(E)-3-[4-methoxy-3-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]phenyl]prop-2-enoyl]-2-methyl-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate | 1026035-80-2

• 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)-4-hydroxy-6-[(E)-3-[4-methoxy-3-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]phenyl]prop-2-enoyl]-2-methyl-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate
• CAS: 1026035-80-2
• 化学式: C₃₀H₃₃BrN₂O₈
• 分子量: 629.505
• InChiKey: YMDRVRGHOHUCGA-XSFOEPMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (8S)-8-(bromomethyl)-4-hydroxy-6-[(E)-3-[4-methoxy-3-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]phenyl]prop-2-enoyl]-2-methyl-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 methyl (8S)-8-(bromomethyl)-4-(dimethylcarbamoyloxy)-6-[(E)-3-[4-methoxy-3-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]phenyl]prop-2-enoyl]-2-methyl-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Duocarmycin Derivatives:  A-Ring Pyrrole Compounds Bearing Cinnamoyl Groups

  摘要：

  A series of N-cinnamates of the A-ring pyrrole compound of duocarmycin were synthesized and evaluated for in vitro anticellular activity against HeLa S-3 cells and in vivo antitumor activity against murine sarcoma 180 in mice. The 4'-methoxy- and 4'-BocNH-cinnamates exhibited strong in vitro anticellular activity among the synthesized compounds. The ortho substitution of the 4'-methoxycinnamate did not affect the anticellular activity and contributed to an enhancement of water solubility. Most of the 8-O-(N,N-dialkylcarbamoyl) derivatives of the 4'-methoxycinnamates displayed remarkably superior in vivo antitumor activity to duocarmycin A or B2. Moreover, it is noteworthy that these 8-O-(N,N-dialkylcarbamoyl) derivatives exhibited significant antitumor activity at wider range of doses as compared with the A-ring pyrrole derivatives having the trimethoxyindole skeleton in segment B.

  DOI：

  10.1021/jm9606094
• 作为产物：
  描述：

  3-methoxycarbonyl-2-methylduocarmycin A 在 甲醇 、 氢溴酸 、 sodium methylate 、 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 methyl (8S)-8-(bromomethyl)-4-hydroxy-6-[(E)-3-[4-methoxy-3-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]phenyl]prop-2-enoyl]-2-methyl-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Duocarmycin Derivatives:  A-Ring Pyrrole Compounds Bearing Cinnamoyl Groups

  摘要：

  A series of N-cinnamates of the A-ring pyrrole compound of duocarmycin were synthesized and evaluated for in vitro anticellular activity against HeLa S-3 cells and in vivo antitumor activity against murine sarcoma 180 in mice. The 4'-methoxy- and 4'-BocNH-cinnamates exhibited strong in vitro anticellular activity among the synthesized compounds. The ortho substitution of the 4'-methoxycinnamate did not affect the anticellular activity and contributed to an enhancement of water solubility. Most of the 8-O-(N,N-dialkylcarbamoyl) derivatives of the 4'-methoxycinnamates displayed remarkably superior in vivo antitumor activity to duocarmycin A or B2. Moreover, it is noteworthy that these 8-O-(N,N-dialkylcarbamoyl) derivatives exhibited significant antitumor activity at wider range of doses as compared with the A-ring pyrrole derivatives having the trimethoxyindole skeleton in segment B.

  DOI：

  10.1021/jm9606094

文献信息

• Synthesis and Antitumor Activity of Duocarmycin Derivatives:  A-Ring Pyrrole Compounds Bearing Cinnamoyl Groups
  作者：Satoru Nagamura、Akira Asai、Nobuyoshi Amishiro、Eiji Kobayashi、Katsushige Gomi、Hiromitsu Saito

  DOI：10.1021/jm9606094

  日期：1997.3.1

  A series of N-cinnamates of the A-ring pyrrole compound of duocarmycin were synthesized and evaluated for in vitro anticellular activity against HeLa S-3 cells and in vivo antitumor activity against murine sarcoma 180 in mice. The 4'-methoxy- and 4'-BocNH-cinnamates exhibited strong in vitro anticellular activity among the synthesized compounds. The ortho substitution of the 4'-methoxycinnamate did not affect the anticellular activity and contributed to an enhancement of water solubility. Most of the 8-O-(N,N-dialkylcarbamoyl) derivatives of the 4'-methoxycinnamates displayed remarkably superior in vivo antitumor activity to duocarmycin A or B2. Moreover, it is noteworthy that these 8-O-(N,N-dialkylcarbamoyl) derivatives exhibited significant antitumor activity at wider range of doses as compared with the A-ring pyrrole derivatives having the trimethoxyindole skeleton in segment B.