7-cyclopropylcarbonylcamptothecin | 1103530-11-5

• 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: 7-cyclopropylcarbonylcamptothecin
• 英文别名: CPT-c3C；(19S)-10-(cyclopropanecarbonyl)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione
• CAS: 1103530-11-5
• 化学式: C₂₄H₂₀N₂O₅
• 分子量: 416.433
• InChiKey: XSRMEJQKUDKZRF-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  96.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-cyclopropylcarbonylcamptothecin 、 氨基乙醛缩二甲醇 生成
  参考文献：
  名称：

  喜树碱γ-内酯类似物的半合成和生物活性。

  摘要：

  通过三步多米诺反应通过半合成法合成了一系列E环γ-内酯喜树碱衍生物。用磺基罗丹明-B（SRB）方法评估了它们在两种类型的人类肿瘤细胞系A549和HT-29上的生物学活性。这些化合物的抗肿瘤活性低于SN-38，仅发现化合物12c接近托泊替康的活性。研究和讨论了这些类似物的结构-活性关系（SAR）。

  DOI：

  10.1016/j.bmcl.2008.10.074
• 作为产物：
  描述：

  喜树碱 、 环丙甲醛 在 硫酸 、 水 、 双氧水 、 溶剂黄146 作用下， 反应 3.0h， 以22%的产率得到7-cyclopropylcarbonylcamptothecin
  参考文献：
  名称：

  7-Cycloalkylcamptothecin derivatives: Preparation and biological evaluation

  摘要：

  A series of 7-cycloalkylcamptothecin derivatives were synthesized from camptothecin with two methods. Their biological activities in vitro were evaluated with sulforhodamine-B (SRB) method on four types of human tumor cell lines A549/ATCC, HT29, NCI-H460 and HL60. Most of these camptothecin analogues show higher antitumor activity than the reference compounds SN-38 and Topotecan, with the IC50 values low to nM level. Structure-activity relationship studies of these compounds mostly match the conclusion we achieved before from quantitative structure-activity relationship (QSAR) research. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.010

文献信息

• 7-Cycloalkylcamptothecin derivatives: Preparation and biological evaluation
  作者：Mingzong Li、Wei Jin、Chen Jiang、Chao Zheng、Weidong Tang、Tianpa You、Liguang Lou

  DOI：10.1016/j.bmcl.2009.06.010

  日期：2009.8

  A series of 7-cycloalkylcamptothecin derivatives were synthesized from camptothecin with two methods. Their biological activities in vitro were evaluated with sulforhodamine-B (SRB) method on four types of human tumor cell lines A549/ATCC, HT29, NCI-H460 and HL60. Most of these camptothecin analogues show higher antitumor activity than the reference compounds SN-38 and Topotecan, with the IC50 values low to nM level. Structure-activity relationship studies of these compounds mostly match the conclusion we achieved before from quantitative structure-activity relationship (QSAR) research. (C) 2009 Elsevier Ltd. All rights reserved.
• Semi-synthesis and biological activity of γ-lactones analogs of camptothecin
  作者：Mingzong Li、Weidong Tang、Fuxing Zeng、Liguang Lou、Tianpa You

  DOI：10.1016/j.bmcl.2008.10.074

  日期：2008.12

  A series of E-ring gamma-lactone camptothecin derivatives were synthesized by semi-synthesis via a three-step domino reaction. Their biological activity was evaluated on two types of human tumor cell lines A549 and HT-29 with sulforhodamine-B (SRB) method. The antitumor activity of these compounds was lower than SN-38, only compound 12c was found to be close to the activity of Topotecan. The structure-activity

  通过三步多米诺反应通过半合成法合成了一系列E环γ-内酯喜树碱衍生物。用磺基罗丹明-B（SRB）方法评估了它们在两种类型的人类肿瘤细胞系A549和HT-29上的生物学活性。这些化合物的抗肿瘤活性低于SN-38，仅发现化合物12c接近托泊替康的活性。研究和讨论了这些类似物的结构-活性关系（SAR）。