4-[4-(Cyanomethyl)-12-phenyl-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]benzenesulfonamide | 1023886-02-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-[4-(Cyanomethyl)-12-phenyl-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]benzenesulfonamide
• CAS: 1023886-02-3
• 化学式: C₂₁H₁₅N₇O₂S
• 分子量: 429.462
• InChiKey: URLNOPYHCVNWOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-(3-amino-4-imino-5-phenyl-3,4-dihydropyrrolo[2,3-d]pyrimidin-7-yl)benzenesulfonamide 、 氰乙酸乙酯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以76%的产率得到4-[4-(Cyanomethyl)-12-phenyl-3,5,6,8,10-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]benzenesulfonamide
  参考文献：
  名称：

  Molecular modeling study and synthesis of novel pyrrolo[2,3-d]pyrimidines and pyrrolotriazolopyrimidines of expected antitumor and radioprotective activities

  摘要：

  Novel pyrrolo[2,3-d]pyrimidine derivatives 4a-e, 10, 14, 15, pyrazolopyrrolopyrimidine 13, pyrrolotriazolopyrimidine 5-9, 17 and pyrrolopyrimidotriazine 18 are reported herein. The design of these compounds was based upon the molecular modeling simulation of the fitting values and conformational energy values of the best-fitted conformers to VEGFRTK inhibitor hypothesis. This hypothesis was generated from its corresponding lead compounds using CATALYST software. The structures of these compounds were confirmed by microanalyses, IR, H-1 NMR, and mass spectral data. Compounds 6 and 15 showed interesting in vitro antitumor activity compared to doxorubicin as positive control. These results are nearly consistent with the molecular modeling studies. Docking studies were made on compound 15 to predict its binding mode. Moreover, compound 10 exhibited a significant radioprotective activity. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.072

文献信息

• Molecular modeling study and synthesis of novel pyrrolo[2,3-d]pyrimidines and pyrrolotriazolopyrimidines of expected antitumor and radioprotective activities
  作者：Dalal A. Abou El Ella、Mostafa M. Ghorab、Eman Noaman、Helmy I. Heiba、Amira I. Khalil

  DOI：10.1016/j.bmc.2007.11.072

  日期：2008.3

  Novel pyrrolo[2,3-d]pyrimidine derivatives 4a-e, 10, 14, 15, pyrazolopyrrolopyrimidine 13, pyrrolotriazolopyrimidine 5-9, 17 and pyrrolopyrimidotriazine 18 are reported herein. The design of these compounds was based upon the molecular modeling simulation of the fitting values and conformational energy values of the best-fitted conformers to VEGFRTK inhibitor hypothesis. This hypothesis was generated from its corresponding lead compounds using CATALYST software. The structures of these compounds were confirmed by microanalyses, IR, H-1 NMR, and mass spectral data. Compounds 6 and 15 showed interesting in vitro antitumor activity compared to doxorubicin as positive control. These results are nearly consistent with the molecular modeling studies. Docking studies were made on compound 15 to predict its binding mode. Moreover, compound 10 exhibited a significant radioprotective activity. (C) 2007 Elsevier Ltd. All rights reserved.