20-chlorocamptothecin | 7691-05-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 英文名称: 20-chlorocamptothecin
• 英文别名: (S)-4-Chloro-4-ethyl-1H-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione；19-chloro-19-ethyl-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
• CAS: 7691-05-6
• 化学式: C₂₀H₁₅ClN₂O₃
• 分子量: 366.804
• InChiKey: YFCMUKGFTGDDDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  59.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  20-chlorocamptothecin 在 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到4-Ethyl-1-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione
  参考文献：
  名称：

  从喜树碱制备马比汀酮的方法：喜树碱E环的化学反应

  摘要：

  将喜树碱及其类似物在150–200°C下加热，通过从α-羟基内酯中损失掉二氧化碳来产生马比汀酮衍生物。

  DOI：

  10.1016/s0040-4039(00)78177-9
• 作为产物：
  描述：

  喜树碱 在 吡啶 、 氯化亚砜 作用下， 以 苯 为溶剂， 反应 2.0h， 以66%的产率得到20-chlorocamptothecin
  参考文献：
  名称：

  On the role of E-ring oxygen atoms in the binding of camptothecin to the topoisomerase I–DNA covalent binary complex

  摘要：

  A recent X-ray crystallographic analysis of the binding of a water soluble camptothecin analogue to the human topoisomerase I-DNA covalent binary complex has suggested the existence of some novel features in the way that camptothecin is bound to the binary complex. Four additional models based on chemical and biochemical data have also been proposed. Presently we describe S-containing analogues of camptothecin prepared on the basis of these models, and report their ability to form stable ternary complexes with human topoisomerase 1, and to mediate cytotoxicity at the locus of topoisomerase 1. The results indicate that replacement of the 20-OH group of CPT with a SH functionality results in diminution of the potency of CPT as a topoisomerase I poison, while replacement of the O atoms at positions 20 and 21 with S atoms results in essentially complete loss of topoisomerase I inhibitory activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.011