20-O-acetyl-7-(pyridin-3-yl)camptothecin | 1579279-78-9

• 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: 20-O-acetyl-7-(pyridin-3-yl)camptothecin
• CAS: 1579279-78-9
• 化学式: C₂₇H₂₁N₃O₅
• 分子量: 467.481
• InChiKey: ORJRDAATMPMPJB-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  35.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  100.38
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  20-O-acetyl-7-(pyridin-3-yl)camptothecin 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以90%的产率得到7-(pyridin-3-yl)camptothecin
  参考文献：
  名称：

  Suzuki coupling based synthesis and in vitro cytotoxic evaluation of 7-heteroaryl-substituted camptothecin analogs

  摘要：

  In an effort to discover potent antitumor agents, a series of novel C-7-heteroaryl-substituted camptothecin derivatives were designed and synthesized via microwave-promoted Suzuki coupling reaction. These analogs were then assessed for cytotoxicity against three human tumor cell lines, A549, HCT116, HT-29, and inhibitory effects on topoisomerase I. All of the new compounds showed potent inhibition of human tumor cell growth, among which compound 10a showed higher cytotoxic activity than that of SN-38. Furthermore, this series of compounds retained or enhanced Topo I inhibition. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.049
• 作为产物：
  描述：

  20-acetyl-7-chlorocamptothecin 、 3-吡啶硼酸 在 四(三苯基膦)钯 、 cesium fluoride 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以91%的产率得到20-O-acetyl-7-(pyridin-3-yl)camptothecin
  参考文献：
  名称：

  Suzuki coupling based synthesis and in vitro cytotoxic evaluation of 7-heteroaryl-substituted camptothecin analogs

  摘要：

  In an effort to discover potent antitumor agents, a series of novel C-7-heteroaryl-substituted camptothecin derivatives were designed and synthesized via microwave-promoted Suzuki coupling reaction. These analogs were then assessed for cytotoxicity against three human tumor cell lines, A549, HCT116, HT-29, and inhibitory effects on topoisomerase I. All of the new compounds showed potent inhibition of human tumor cell growth, among which compound 10a showed higher cytotoxic activity than that of SN-38. Furthermore, this series of compounds retained or enhanced Topo I inhibition. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.049