[(4R,5S)-8-[(7-bromo-2,3-dihydro-[1,4]dioxino[2,3-g]quinolin-8-yl)methyl]-5-ethyl-5-hydroxy-3,9-dioxo-1,4-dihydrooxepino[3,4-c]pyridin-4-yl] acetate | 1393646-14-4

• 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: [(4R,5S)-8-[(7-bromo-2,3-dihydro-[1,4]dioxino[2,3-g]quinolin-8-yl)methyl]-5-ethyl-5-hydroxy-3,9-dioxo-1,4-dihydrooxepino[3,4-c]pyridin-4-yl] acetate
• CAS: 1393646-14-4
• 化学式: C₂₅H₂₃BrN₂O₈
• 分子量: 559.37
• InChiKey: DJLMCGIFLJPCTM-OFVILXPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 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-[(7-bromo-2,3-dihydro-[1,4]dioxino[2,3-g]quinolin-8-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-(1,4-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：

  2,3-dihydroxy-3-(3-hydroxymethyl-2-methoxy-pyridin-4-yl)-pentanoic acid 在 4-二甲氨基吡啶 、 三甲基氯硅烷 、 potassium tert-butylate 、 三乙胺 、 三氟乙酸 、 sodium iodide 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 34.5h， 生成 [(4R,5S)-8-[(7-bromo-2,3-dihydro-[1,4]dioxino[2,3-g]quinolin-8-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