[(19S)-19-ethyl-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl] N-[2-(4,6-dioxo-1,2,5-dithiazepan-5-yl)ethyl]carbamate | 1261145-99-6

• 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)-19-ethyl-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl] N-[2-(4,6-dioxo-1,2,5-dithiazepan-5-yl)ethyl]carbamate
• CAS: 1261145-99-6
• 化学式: C₂₇H₂₄N₄O₇S₂
• 分子量: 580.642
• InChiKey: QSFLGZMNSGDWTE-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  186
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  [(19S)-19-ethyl-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl] N-(2-aminoethyl)carbamate 、 二硫醇二羟基乙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 [(19S)-19-ethyl-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl] N-[2-(4,6-dioxo-1,2,5-dithiazepan-5-yl)ethyl]carbamate 、 [(19S)-19-ethyl-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl] N-[2-[[2-[[2-[2-[[(19S)-19-ethyl-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl]oxycarbonylamino]ethylamino]-2-oxoethyl]disulfanyl]acetyl]amino]ethyl]carbamate
  参考文献：
  名称：

  Synthesis and biological evaluation of new camptothecin derivatives obtained by modification of position 20

  摘要：

  The preparation and biological evaluation of a novel series of dimeric camptothecin derivatives are described. All the new compounds showed a significant ability to inhibit human tumor cell growth with IC50 values ranging from 0.03 to 12.2 mu M. The interference with the activity of the nuclear enzymes topoisomerases has been demonstrated, highlighting the poison effect of one of the obtained byproducts toward topoisomerase I. A moderate antiangiogenic activity has been demonstrated for one of the obtained compounds. Moreover, the effects of four new compounds on caspases activity and ROS generation have been studied on transgenic mouse cell. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.069

文献信息

• Synthesis and biological evaluation of new camptothecin derivatives obtained by modification of position 20
  作者：Elena Riva、Daniela Comi、Stella Borrelli、Francesco Colombo、Bruno Danieli、Jurgen Borlak、Lasse Evensen、James B. Lorens、Gabriele Fontana、Ornella Maria Gia、Lisa Dalla Via、Daniele Passarella

  DOI：10.1016/j.bmc.2010.09.069

  日期：2010.12

  The preparation and biological evaluation of a novel series of dimeric camptothecin derivatives are described. All the new compounds showed a significant ability to inhibit human tumor cell growth with IC50 values ranging from 0.03 to 12.2 mu M. The interference with the activity of the nuclear enzymes topoisomerases has been demonstrated, highlighting the poison effect of one of the obtained byproducts toward topoisomerase I. A moderate antiangiogenic activity has been demonstrated for one of the obtained compounds. Moreover, the effects of four new compounds on caspases activity and ROS generation have been studied on transgenic mouse cell. (C) 2010 Elsevier Ltd. All rights reserved.