(20S,20aR)-10-methoxy-20a-acetoxyhomocamptothecin | 1393646-16-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (20S,20aR)-10-methoxy-20a-acetoxyhomocamptothecin
• 英文别名: [(19R,20S)-20-ethyl-20-hydroxy-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.9.0.02,11.04,9.015,21]docosa-1(22),2(11),3,5,7,9,15(21)-heptaen-19-yl] acetate
• CAS: 1393646-16-6
• 化学式: C₂₄H₂₂N₂O₇
• 分子量: 450.448
• InChiKey: HOCXVLPCEYHGKN-URXFXBBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (20S,20aR)-10-methoxy-20a-acetoxyhomocamptothecin 在 sodium hydroxide 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以60%的产率得到(20S,20aR)-10-methoxy-20a-hydroxyhomocamptothecin
  参考文献：
  名称：

  Synthesis and biological evaluation of new homocamptothecin analogs

  摘要：

  In order to increase the stability of E-ring of homocamptothecins, the electron-withdrawing group -OH or -OAc was induced to alpha position of ring-E lactone. Ten new homocamptothecin analogs were synthesized. Most compounds showed potent in vitro anticancer activity and potent Topo I inhibition, which was equal or superior to that of CPT, SN-38 and 10-HCPT. The stability studies of this series also displayed significant improvement of the stability. (c) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.002
• 作为产物：
  描述：

  (5S,6R)-5-ethyl-5-hydroxy-1,7-dioxo-1,2,5,6,7,9-hexahydro-8-oxa-2-aza-benzocyclohepten-6-yl acetate 在 potassium tert-butylate 、 四丁基氯化铵 、 potassium acetate 、 palladium diacetate 、 三(邻甲基苯基)磷 作用下， 以 乙二醇二甲醚 、 乙腈 为溶剂， 反应 21.5h， 生成 (20S,20aR)-10-methoxy-20a-acetoxyhomocamptothecin
  参考文献：
  名称：

  Synthesis and biological evaluation of new homocamptothecin analogs

  摘要：

  In order to increase the stability of E-ring of homocamptothecins, the electron-withdrawing group -OH or -OAc was induced to alpha position of ring-E lactone. Ten new homocamptothecin analogs were synthesized. Most compounds showed potent in vitro anticancer activity and potent Topo I inhibition, which was equal or superior to that of CPT, SN-38 and 10-HCPT. The stability studies of this series also displayed significant improvement of the stability. (c) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.002

文献信息

• CAMPTOTHECIN COMPOUND CONTAINING STABLE 7-MEMBERED LACTONE RING, PREPARATION METHOD AND USE
  申请人：Lv Wei

  公开号：US20140128421A1

  公开（公告）日：2014-05-08

  Provided are a camptothecin compound containing 7-membered lactone ring, as shown in general formula I, and pharmaceutically acceptable salt thereof, as well as the preparation method and use thereof. In general formula I, R 1 is H, a C1˜C3 alkyl, acetyl or propionyl; R 2 is H, a C1˜C6 alkyl, a C3˜C6 cycloalkyl, piperidyl; or a C1˜C6 alkyl substituted by an amino; R 3 is H, a C1˜C3 alkyl, or a C1˜C6 alkyl substituted by an amino; R 4 is H, a hydroxyl, or a C1˜C6 alkoxy; R 5 is H, or a C1˜C6 alkoxyl; or R 4 and R 5 are linked to each other to form —OCH 2 O— or —OCH 2 CH 2 O—. The compound has good anti-tumor activity, and can be clinically used via oral administration, intravenous injection, and intramuscular injection, among others.
• US9115150B2
  申请人：——

  公开号：US9115150B2

  公开（公告）日：2015-08-25
• Synthesis and biological evaluation of new homocamptothecin analogs
  作者：Yu Luo、Shanbao Yu、Linjiang Tong、Qingqing Huang、Wei Lu、Yi Chen

  DOI：10.1016/j.ejmech.2012.05.002

  日期：2012.8

  In order to increase the stability of E-ring of homocamptothecins, the electron-withdrawing group -OH or -OAc was induced to alpha position of ring-E lactone. Ten new homocamptothecin analogs were synthesized. Most compounds showed potent in vitro anticancer activity and potent Topo I inhibition, which was equal or superior to that of CPT, SN-38 and 10-HCPT. The stability studies of this series also displayed significant improvement of the stability. (c) 2012 Elsevier Masson SAS. All rights reserved.