[2-(4-Ethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-11-yl)-ethyl]-propyl-carbamic acid benzyl ester | 177611-44-8

• 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: [2-(4-Ethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-11-yl)-ethyl]-propyl-carbamic acid benzyl ester
• 英文别名: benzyl N-[2-(19-ethyl-19-hydroxy-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-10-yl)ethyl]-N-propylcarbamate
• CAS: 177611-44-8
• 化学式: C₃₃H₃₃N₃O₆
• 分子量: 567.642
• InChiKey: YAYJCWOTIVMBGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [2-(4-Ethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-11-yl)-ethyl]-propyl-carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 以53%的产率得到4-Ethyl-4-hydroxy-11-(2-propylamino-ethyl)-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione
  参考文献：
  名称：

  Synthesis and antitumor activity of 7-substituted 20(RS)-camptothecin analogues

  摘要：

  Novel water-soluble camptothecin analogues with excellent antitumor activity have been designed and synthesized by total synthesis. The analogues were evaluated for cytotoxic activity against five tumor cell lines. The most potent analogue 6c exhibited significant antitumor activity at wider range of doses as compared with camptothecin (T/C 243 % at 70mg/kg; T/C > 150% at 8.75-140mg/kg). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00131-x
• 作为产物：
  描述：

  [3-(2-Nitro-phenyl)-3-oxo-propyl]-propyl-carbamic acid benzyl ester 在 sodium dithionite 、 对甲苯磺酸 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 [2-(4-Ethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-11-yl)-ethyl]-propyl-carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis and antitumor activity of 7-substituted 20(RS)-camptothecin analogues

  摘要：

  Novel water-soluble camptothecin analogues with excellent antitumor activity have been designed and synthesized by total synthesis. The analogues were evaluated for cytotoxic activity against five tumor cell lines. The most potent analogue 6c exhibited significant antitumor activity at wider range of doses as compared with camptothecin (T/C 243 % at 70mg/kg; T/C > 150% at 8.75-140mg/kg). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00131-x

文献信息

• Synthesis and antitumor activity of 7-substituted 20(RS)-camptothecin analogues
  作者：Sang-sup Jew、Hee-Jin Kim、Myoung Goo Kim、Eun-Young Roh、Youn-sang Cho、Joon-Kyum Kim、Kyung-Hoe Cha、Kang-Keun Lee、Hyun-Jung Han、Jae-Young Choi、Heesoon Lee

  DOI：10.1016/0960-894x(96)00131-x

  日期：1996.4

  Novel water-soluble camptothecin analogues with excellent antitumor activity have been designed and synthesized by total synthesis. The analogues were evaluated for cytotoxic activity against five tumor cell lines. The most potent analogue 6c exhibited significant antitumor activity at wider range of doses as compared with camptothecin (T/C 243 % at 70mg/kg; T/C > 150% at 8.75-140mg/kg). Copyright (C) 1996 Elsevier Science Ltd