[(4R,5S)-8-[(6-bromo-[1,3]dioxolo[4,5-g]quinolin-7-yl)methyl]-5-ethyl-5-hydroxy-3,9-dioxo-1,4-dihydrooxepino[3,4-c]pyridin-4-yl] acetate | 1393646-13-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: [(4R,5S)-8-[(6-bromo-[1,3]dioxolo[4,5-g]quinolin-7-yl)methyl]-5-ethyl-5-hydroxy-3,9-dioxo-1,4-dihydrooxepino[3,4-c]pyridin-4-yl] acetate
• CAS: 1393646-13-3
• 化学式: C₂₄H₂₁BrN₂O₈
• 分子量: 545.343
• InChiKey: BQHRLDFKBXRYFR-RDPSFJRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(4R,5S)-8-[(6-bromo-[1,3]dioxolo[4,5-g]quinolin-7-yl)methyl]-5-ethyl-5-hydroxy-3,9-dioxo-1,4-dihydrooxepino[3,4-c]pyridin-4-yl] acetate 在 四丁基氯化铵 、 potassium acetate 、 palladium diacetate 、 三(邻甲基苯基)磷 、 sodium hydroxide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 18.0h， 生成 (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
• 作为产物：
  描述：

  (5S,6R)-5-ethyl-5-hydroxy-1-methoxy-7-oxo-5,6,7,9-tetrahydro-8-oxa-2-azabenzocycloheptene-6-yl acetate 在 三甲基氯硅烷 、 potassium tert-butylate 、 sodium iodide 作用下， 以 乙二醇二甲醚 、 乙腈 为溶剂， 反应 10.5h， 生成 [(4R,5S)-8-[(6-bromo-[1,3]dioxolo[4,5-g]quinolin-7-yl)methyl]-5-ethyl-5-hydroxy-3,9-dioxo-1,4-dihydrooxepino[3,4-c]pyridin-4-yl] acetate
  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