N1-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-(((3-chloro-4-fluoroanilino)carbonyl)amino)benzamide | 1449741-65-4

• 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: N1-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-(((3-chloro-4-fluoroanilino)carbonyl)amino)benzamide
• 英文别名: N-[(5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl]-4-[(3-chloro-4-fluorophenyl)carbamoylamino]benzamide
• CAS: 1449741-65-4
• 化学式: C₃₆H₃₁ClFN₃O₉
• 分子量: 704.108
• InChiKey: POFHQNUNJZBNEI-FPMZXNSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  50
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  143
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  N1-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-nitrobenzamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 13.0h， 生成 N1-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-(((3-chloro-4-fluoroanilino)carbonyl)amino)benzamide
  参考文献：
  名称：

  4β-[4′-(1-(Aryl)ureido)benzamide]podophyllotoxins as DNA topoisomerase I and IIα inhibitors and apoptosis inducing agents

  摘要：

  A series of 4 beta-[4'-(1-(aryl)ureido)benzamide]podophyllotoxin congeners (11a-1) were synthesized and evaluated for their cytotoxic activity against six human cancer cell lines. Some of the compounds like 11a, 11h, 11k and 11I showed significant anti-proliferative activity in Colo-205 cells and were superior to etoposide. The flow-cytometric analysis studies indicated that these compounds show strong G1 cell cycle arrest, as well exhibited improved inhibitory activities on DNA topoisomerase I and Ha enzymes. These compounds induce apoptosis by up regulating caspase-3 protein as observed by ELISA and Western blotting analysis. In addition, a brief structure-activity relationship studies within the series along with docking results of representative compounds 11a, 11h, 11k, 11I were presented. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.033

文献信息

• 4β-[4′-(1-(Aryl)ureido)benzamide]podophyllotoxins as DNA topoisomerase I and IIα inhibitors and apoptosis inducing agents
  作者：Ahmed Kamal、Paidakula Suresh、M. Janaki Ramaiah、T. Srinivasa Reddy、Ravi Kumar Kapavarapu、Bolla Narasimha Rao、Syed Imthiajali、T. Lakshminarayan Reddy、S.N.C.V.L. Pushpavalli、Nagula Shankaraiah、Manika Pal-Bhadra

  DOI：10.1016/j.bmc.2013.06.033

  日期：2013.9

  A series of 4 beta-[4'-(1-(aryl)ureido)benzamide]podophyllotoxin congeners (11a-1) were synthesized and evaluated for their cytotoxic activity against six human cancer cell lines. Some of the compounds like 11a, 11h, 11k and 11I showed significant anti-proliferative activity in Colo-205 cells and were superior to etoposide. The flow-cytometric analysis studies indicated that these compounds show strong G1 cell cycle arrest, as well exhibited improved inhibitory activities on DNA topoisomerase I and Ha enzymes. These compounds induce apoptosis by up regulating caspase-3 protein as observed by ELISA and Western blotting analysis. In addition, a brief structure-activity relationship studies within the series along with docking results of representative compounds 11a, 11h, 11k, 11I were presented. (C) 2013 Elsevier Ltd. All rights reserved.