(20S,20aR)-9,10-(1,3-dioxolane)-20a-hydroxyhomocamptothecin | 1393646-21-3

• 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)-9,10-(1,3-dioxolane)-20a-hydroxyhomocamptothecin
• 英文别名: (5S,6R)-5-ethyl-5,6-dihydroxy-8,19,21-trioxa-12,25-diazahexacyclo[12.11.0.02,12.04,10.016,24.018,22]pentacosa-1(14),2,4(10),15,17,22,24-heptaene-7,11-dione
• CAS: 1393646-21-3
• 化学式: C₂₂H₁₈N₂O₇
• 分子量: 422.394
• InChiKey: VJYPWBHSWIWXCY-UGKGYDQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  31
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (20S,20aR)-9,10-(1,3-dioxolane)-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)-9,10-(1,3-dioxolane)-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

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.