5-(4-fluorophenyl)-3-(4-(5-methoxy-1H-benzo[d]imidazol-2-yl)phenyl)-1,2,4-oxadiazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5-(4-fluorophenyl)-3-(4-(5-methoxy-1H-benzo[d]imidazol-2-yl)phenyl)-1,2,4-oxadiazole
• 英文别名: NSC 761136/1；5-(4-Fluorophenyl)-3-(4-(5-methoxy-1H-benzo[d]imidazol-2-yl)phenyl)-1,2,4-oxadiazole；5-(4-fluorophenyl)-3-[4-(6-methoxy-1H-benzimidazol-2-yl)phenyl]-1,2,4-oxadiazole
• 化学式: C₂₂H₁₅FN₄O₂
• 分子量: 386.385
• InChiKey: YDICDCLHLLRVRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 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：
  76.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-甲氧基邻苯二胺 在 sodium metabisulfite 、 盐酸羟胺 、 N,N'-羰基二咪唑 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.33h， 生成 5-(4-fluorophenyl)-3-(4-(5-methoxy-1H-benzo[d]imidazol-2-yl)phenyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Synthesis of 2-aryl-1,2,4-oxadiazolo-benzimidazoles: Tubulin polymerization inhibitors and apoptosis inducing agents

  摘要：

  A new series of 2-aryl 1,2,4-oxadiazolo-benzimidazole conjugates have been synthesized and evaluated for their antiproliferative activity in the sixty cancer cell line panel of the National Cancer Institute (NCI). Compounds 5l (NSC: 761109/1) and 5x (NSC: 761814/1) exhibited remarkable cytotoxic activity against most of the cancer cell lines in the one dose assay and were further screened at five dose concentrations (0.01, 0.1, 1, 10 and 100 mu M) which showed GI(50) values in the range of 0.79-28.2 mu M. Flow cytometric data of these compounds showed increased cells in G2/M phase, which is suggestive of G2/M cell cycle arrest. Further, compounds 5l and 5x showed inhibition of tubulin polymerization and disruption of the formation of microtubules. These compounds induce apoptosis byDNAfragmentation and chromatin condensation as well as by mitochondrial membrane depolarization. In addition, structure activity relationship studies within the series are also discussed. Molecular docking studies of compounds 5l and 5x into the colchicine-binding site of the tubulin, revealed the possible mode of interaction by these compounds. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.060

文献信息

• ANTICANCER AGENT AND PROCESS FOR THE PREPARATION THEREOF
  申请人：COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH

  公开号：US20160002214A1

  公开（公告）日：2016-01-07

  The present invention provides a compound of general formula A for use as a potential anticancer agent against human cancer cell lines and a process for the preparation thereof. wherein R is selected from the group consisting of H, F, Cl, Br, OMe, Me and CF 3 , R 1 is selected from the group consisting of H, 4-F, 4-Cl, 4-Br, 4-CF 3 , 4-OMe, 3,4-OMe, 3,5-OMe and 3,4,5-OMe, and n is an integer ranging from 1-3.

  本发明提供了一种通式A的化合物，用作潜在的抗癌剂，可用于人类癌细胞系，并提供其制备方法。其中，R选择自H、F、Cl、Br、OMe、Me和CF3组成的群体中的一种，R1选择自H、4-F、4-Cl、4-Br、4-CF3、4-OMe、3,4-OMe、3,5-OMe和3,4,5-OMe组成的群体中的一种，n为1-3之间的整数。
• DERIVATIVES OF 1-(BENZIMIDAZOL-2-YL)-4-(5-PHENYL-1,2,4-OXADIAZOL-3-YL)-BENZENE USEFUL AS ANTICANCER AGENTS AND PROCESS FOR THE PREPARATION THEREOF
  申请人：Council of Scientific & Industrial Research

  公开号：EP2966073A1

  公开（公告）日：2016-01-13

  The present invention provides a compound of general formula A for use as a potential anticancer agent against human cancer cell lines and a process for the preparation thereof. wherein R is selected from the group consisting of H, F, Cl, Br, OMe, Me and CF3, R1 is selected from the group consisting of H, 4-F, 4-Cl, 4-Br, 4-CF3, 4-OMe, 3,4-OMe, 3,5-OMe and 3,4,5-OMe, and n is an integer ranging from 1-3.

  本发明提供了一种通式 A 的化合物，可用作人类癌细胞株的潜在抗癌剂，并提供了其制备方法。 其中 R 选自由 H、F、Cl、Br、OMe、Me 和 CF3 组成的组、 R1 选自由 H、4-F、4-Cl、4-Br、4-CF3、4-OMe、3,4-OMe、3,5-OMe 和 3,4,5-OMe 组成的组，以及 n 是 1-3 之间的整数。
• US9522907B2
  申请人：——

  公开号：US9522907B2

  公开（公告）日：2016-12-20
• Synthesis of 2-aryl-1,2,4-oxadiazolo-benzimidazoles: Tubulin polymerization inhibitors and apoptosis inducing agents
  作者：Ahmed Kamal、T. Srinivasa Reddy、M.V.P.S. Vishnuvardhan、Vijaykumar D. Nimbarte、A.V. Subba Rao、Vunnam Srinivasulu、Nagula Shankaraiah

  DOI：10.1016/j.bmc.2015.05.060

  日期：2015.8

  A new series of 2-aryl 1,2,4-oxadiazolo-benzimidazole conjugates have been synthesized and evaluated for their antiproliferative activity in the sixty cancer cell line panel of the National Cancer Institute (NCI). Compounds 5l (NSC: 761109/1) and 5x (NSC: 761814/1) exhibited remarkable cytotoxic activity against most of the cancer cell lines in the one dose assay and were further screened at five dose concentrations (0.01, 0.1, 1, 10 and 100 mu M) which showed GI(50) values in the range of 0.79-28.2 mu M. Flow cytometric data of these compounds showed increased cells in G2/M phase, which is suggestive of G2/M cell cycle arrest. Further, compounds 5l and 5x showed inhibition of tubulin polymerization and disruption of the formation of microtubules. These compounds induce apoptosis byDNAfragmentation and chromatin condensation as well as by mitochondrial membrane depolarization. In addition, structure activity relationship studies within the series are also discussed. Molecular docking studies of compounds 5l and 5x into the colchicine-binding site of the tubulin, revealed the possible mode of interaction by these compounds. (C) 2015 Elsevier Ltd. All rights reserved.