(19S)-10-[[2-[(2-aminophenyl)disulfanyl]phenyl]iminomethyl]-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 喜树碱
• 英文名称: (19S)-10-[[2-[(2-aminophenyl)disulfanyl]phenyl]iminomethyl]-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione
• 化学式: C₃₃H₂₆N₄O₄S₂
• 分子量: 606.726
• InChiKey: NVYPVYUISOPBAA-XIFFEERXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  43
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  169
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (S)-11-formy-4-乙基-4-羟基-1,12-二氢-4H-2-噁-6,12a-二氮杂-二苯并b,h芴-3,13-二酮 、 双(2-氨基苯基)二硫 在 ytterbium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以45%的产率得到(19S)-10-[[2-[(2-aminophenyl)disulfanyl]phenyl]iminomethyl]-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione
  参考文献：
  名称：

  Synthesis and cytotoxic activity of substituted 7-aryliminomethyl derivatives of camptothecin

  摘要：

  A series of imines derived from camptothecin-7-aldehyde (CPT-CHO) and aromatic amines were synthesised and tested for their cytotoxicity against tumour cell line H460, that expresses a high level of topoisomerase I. In general ortho-substituted compounds showed higher cytotoxic potency than the corresponding para-substituted imines. This effect was dependent on the nature of the substituent. Structure-activity relationships were studied by calculation of docking energy with a model of the ternary complex camptothecin-DNA-topoisomerase I. The ability of selected compounds to stimulate the topoisomerase I-mediated DNA cleavage and the persistence of the cleavable complex were consistent with the cytotoxic activity. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.02.011

文献信息

• Synthesis and cytotoxic activity of substituted 7-aryliminomethyl derivatives of camptothecin
  作者：Sabrina Dallavalle、Lucio Merlini、Gabriella Morini、Loana Musso、Sergio Penco、Giovanni Luca Beretta、Stella Tinelli、Franco Zunino

  DOI：10.1016/j.ejmech.2004.02.011

  日期：2004.6

  A series of imines derived from camptothecin-7-aldehyde (CPT-CHO) and aromatic amines were synthesised and tested for their cytotoxicity against tumour cell line H460, that expresses a high level of topoisomerase I. In general ortho-substituted compounds showed higher cytotoxic potency than the corresponding para-substituted imines. This effect was dependent on the nature of the substituent. Structure-activity relationships were studied by calculation of docking energy with a model of the ternary complex camptothecin-DNA-topoisomerase I. The ability of selected compounds to stimulate the topoisomerase I-mediated DNA cleavage and the persistence of the cleavable complex were consistent with the cytotoxic activity. (C) 2004 Elsevier SAS. All rights reserved.