(5R,5aR,8aS,9S)-9-(5-benzoyl-1H-tetrazol-1-yl)-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: (5R,5aR,8aS,9S)-9-(5-benzoyl-1H-tetrazol-1-yl)-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one
• 英文别名: (5S,5aS,8aR,9R)-5-(5-benzoyltetrazol-1-yl)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
• 化学式: C₃₀H₂₆N₄O₈
• 分子量: 570.558
• InChiKey: IJJXFLVKFFZDHH-QNMIOERPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  5,8,8a,9-四氢-9-羟基-5-(3,4,5-三甲氧基苯基)-(5R,5aR,8aR,9S)-呋喃并[3',4':6,7]萘并[2,3-d]-1,3-二氧杂环戊烯-6(5aH)-酮 在 sodium azide 、 三氟乙酸 、 zinc dibromide 作用下， 以 氯仿 为溶剂， 反应 48.0h， 生成 (5R,5aR,8aS,9S)-9-(5-benzoyl-1H-tetrazol-1-yl)-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one
  参考文献：
  名称：

  Synthesis and Biological evaluation of novel 4β-[(5-substituted)-1,2,3,4-tetrazolyl] podophyllotoxins as anticancer compounds

  摘要：

  A series of novel 4 beta-[(5-substituted)-1,2,3,4-tetrazolyl] podophyllotoxin derivatives were synthesized by employing azide-nitrile click chemistry approach. All the derivatives were evaluated for their cytotoxicity against a panel of four human cancer cell lines and their IC50 values were found to be in the range of 2.4-29.06 mu M. The cytotoxicity exhibited by the majority of test compounds were found to comparable and often more effective than doxorubicin and all compounds exhibited higher cytotoxicity on A-549 cell lines. Cell cycle analysis showed that the novel 4 beta-[(5-substituted)-1,2,3,4-tetrazolyl] podophyllotoxins resulted in cell cycle arrest at G2/M phase and were also found to be the potent inhibitors of tubulin polymerization in vitro. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.053

文献信息

• Synthesis and Biological evaluation of novel 4β-[(5-substituted)-1,2,3,4-tetrazolyl] podophyllotoxins as anticancer compounds
  作者：Irfan Hyder、Deepthi Yedlapudi、Shasi V. Kalivendi、Jabeena Khazir、Tabasum Ismail、Naresh Nalla、Sreekanth Miryala、Halmuthur M. Sampath Kumar

  DOI：10.1016/j.bmcl.2015.04.053

  日期：2015.7

  A series of novel 4 beta-[(5-substituted)-1,2,3,4-tetrazolyl] podophyllotoxin derivatives were synthesized by employing azide-nitrile click chemistry approach. All the derivatives were evaluated for their cytotoxicity against a panel of four human cancer cell lines and their IC50 values were found to be in the range of 2.4-29.06 mu M. The cytotoxicity exhibited by the majority of test compounds were found to comparable and often more effective than doxorubicin and all compounds exhibited higher cytotoxicity on A-549 cell lines. Cell cycle analysis showed that the novel 4 beta-[(5-substituted)-1,2,3,4-tetrazolyl] podophyllotoxins resulted in cell cycle arrest at G2/M phase and were also found to be the potent inhibitors of tubulin polymerization in vitro. (C) 2015 Elsevier Ltd. All rights reserved.