10-benzyloxy-(20S, 21S)-diolcamptothecin | 1454574-94-7

• 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: 10-benzyloxy-(20S, 21S)-diolcamptothecin
• CAS: 1454574-94-7
• 化学式: C₂₇H₂₄N₂O₅
• 分子量: 456.498
• InChiKey: KMOQTLJPLJPDSC-GEVKEYJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  93.81
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  10-benzyloxy-(20S, 21S)-diolcamptothecin 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 以35%的产率得到10-benzyloxy-(20S, 21S)-fluorcamptothecin
  参考文献：
  名称：

  Synthesis and biological activities of fluorinated 10-hydroxycamptothecin and SN38

  摘要：

  It is an important strategy for fluorine substitution in drug design because of its small size and high electronegativity. Fluorinated 10-hydroxycamptothecin and SN 38 were prepared and screened for antiproliferative activities. Among them, fluorinated compound MF-6 showed higher antiproliferative activities against A549, HCT116 and MDA-MB-435 cancer cells than unfluorinated compound. The result of Topoisomerase I activity also confirmed that the C-21 carbonyl group of camptothecin structure is unnecessary to antitumor activity. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.10.016
• 作为产物：
  描述：

  (19S)-19-ethyl-19-hydroxy-7-phenylmethoxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione 在 钾硼氢 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 10-benzyloxy-(20S, 21S)-diolcamptothecin
  参考文献：
  名称：

  Synthesis and biological activities of fluorinated 10-hydroxycamptothecin and SN38

  摘要：

  It is an important strategy for fluorine substitution in drug design because of its small size and high electronegativity. Fluorinated 10-hydroxycamptothecin and SN 38 were prepared and screened for antiproliferative activities. Among them, fluorinated compound MF-6 showed higher antiproliferative activities against A549, HCT116 and MDA-MB-435 cancer cells than unfluorinated compound. The result of Topoisomerase I activity also confirmed that the C-21 carbonyl group of camptothecin structure is unnecessary to antitumor activity. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.10.016