N-benzyl-3-[(3S)-5,6-dichloro-2,3-dihydro-1H-pyrrolizin-3-yl]-6-(4,5-dichloro-1H-pyrrol-2-yl)-2,4-dihydroxybenzamide | 1422263-39-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-3-[(3S)-5,6-dichloro-2,3-dihydro-1H-pyrrolizin-3-yl]-6-(4,5-dichloro-1H-pyrrol-2-yl)-2,4-dihydroxybenzamide
• CAS: 1422263-39-5
• 化学式: C₂₅H₁₉Cl₄N₃O₃
• 分子量: 551.256
• InChiKey: WFFVZQNXRVLTMS-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  90.3
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyl-3-[(3S)-5,6-dichloro-2,3-dihydro-1H-pyrrolizin-3-yl]-6-(4,5-dichloro-1H-pyrrol-2-yl)-2,4-dihydroxybenzamide 、 乙酸酐 在 吡啶 作用下， 以3.4 mg的产率得到[5-(1-acetyl-4,5-dichloropyrrol-2-yl)-3-acetyloxy-4-(benzylcarbamoyl)-2-[(3S)-5,6-dichloro-2,3-dihydro-1H-pyrrolizin-3-yl]phenyl] acetate
  参考文献：
  名称：

  Chlorizidine, a Cytotoxic 5H-Pyrrolo[2,1-a]isoindol-5-one-Containing Alkaloid from a Marine Streptomyces sp.

  摘要：

  Cultivation of an obligate marine Streptomyces strain has provided the cytotoxic natural product chlorizidine A. X-ray crystallographic analysis revealed that the metabolite is composed of a chlorinated 2,3-dihydropyrrolizine ring attached to a chlorinated 5H-pyrrolo[2,1-a]isoindol-5-one. The carbon stereocenter in the dihydropyrrolizine is S-configured. Remarkably, the 5H-pyrrolo[2,1-a]isoindol-5-one moiety has no precedence in the field of natural products. The presence of this ring system, which was demonstrated to undergo facile nucleophilic substitution reactions at the activated carbonyl group, is essential to the molecule's cytotoxicity against HCT-116 human colon cancer cells.

  DOI：

  10.1021/ol303374e
• 作为产物：
  描述：

  (-)-(S)-chlorizidine A 、 苄胺 以 乙腈 为溶剂， 反应 3.0h， 以33%的产率得到N-benzyl-3-[(3S)-5,6-dichloro-2,3-dihydro-1H-pyrrolizin-3-yl]-6-(4,5-dichloro-1H-pyrrol-2-yl)-2,4-dihydroxybenzamide
  参考文献：
  名称：

  Chlorizidine, a Cytotoxic 5H-Pyrrolo[2,1-a]isoindol-5-one-Containing Alkaloid from a Marine Streptomyces sp.

  摘要：

  Cultivation of an obligate marine Streptomyces strain has provided the cytotoxic natural product chlorizidine A. X-ray crystallographic analysis revealed that the metabolite is composed of a chlorinated 2,3-dihydropyrrolizine ring attached to a chlorinated 5H-pyrrolo[2,1-a]isoindol-5-one. The carbon stereocenter in the dihydropyrrolizine is S-configured. Remarkably, the 5H-pyrrolo[2,1-a]isoindol-5-one moiety has no precedence in the field of natural products. The presence of this ring system, which was demonstrated to undergo facile nucleophilic substitution reactions at the activated carbonyl group, is essential to the molecule's cytotoxicity against HCT-116 human colon cancer cells.

  DOI：

  10.1021/ol303374e

文献信息

• Chlorizidine, a Cytotoxic 5<i>H</i>-Pyrrolo[2,1-<i>a</i>]isoindol-5-one-Containing Alkaloid from a Marine <i>Streptomyces</i> sp.
  作者：Xavier Alvarez-Mico、Paul R. Jensen、William Fenical、Chambers C. Hughes

  DOI：10.1021/ol303374e

  日期：2013.3.1

  Cultivation of an obligate marine Streptomyces strain has provided the cytotoxic natural product chlorizidine A. X-ray crystallographic analysis revealed that the metabolite is composed of a chlorinated 2,3-dihydropyrrolizine ring attached to a chlorinated 5H-pyrrolo[2,1-a]isoindol-5-one. The carbon stereocenter in the dihydropyrrolizine is S-configured. Remarkably, the 5H-pyrrolo[2,1-a]isoindol-5-one moiety has no precedence in the field of natural products. The presence of this ring system, which was demonstrated to undergo facile nucleophilic substitution reactions at the activated carbonyl group, is essential to the molecule's cytotoxicity against HCT-116 human colon cancer cells.