1-methyl-5-(3-bromo-4,5-dimethoxyphenyl)-4-(3-fluoro-4-methoxyphenyl)imidazole | 1345017-02-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-5-(3-bromo-4,5-dimethoxyphenyl)-4-(3-fluoro-4-methoxyphenyl)imidazole
• 英文别名: 5-(3-Bromo-4,5-dimethoxyphenyl)-4-(3-fluoro-4-methoxyphenyl)-1-methylimidazole
• CAS: 1345017-02-8
• 化学式: C₁₉H₁₈BrFN₂O₃
• 分子量: 421.266
• InChiKey: VMZOPGFJGGQILV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-methyl-5-(3-bromo-4,5-dimethoxyphenyl)-4-(3-fluoro-4-methoxyphenyl)imidazole 在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 0.08h， 以60 mg的产率得到1-methyl-5-(3-bromo-4,5-dimethoxyphenyl)-4-(3-fluoro-4-methoxyphenyl)imidazole hydrochloride
  参考文献：
  名称：

  [EN] COMBRETASTATIN ANALOGS FOR USE IN THE TREATMENT OF CANCER
  [FR] ANALOGUES DE LA COMBRÉTASTATINE POUR UTILISATION DANS LE TRAITEMENT DU CANCER

  摘要：

  本发明涉及康柏替斯汀的特定类似物，特别是本文所描述和定义的式(I)化合物，以及包含这些化合物的药物组合物，以及它们的医疗用途，特别是在治疗或预防癌症，包括多药耐药癌症方面。

  公开号：

  WO2011138409A1
• 作为产物：
  描述：

  3-溴-4,5-二甲氧基苯甲醛 在 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 1-methyl-5-(3-bromo-4,5-dimethoxyphenyl)-4-(3-fluoro-4-methoxyphenyl)imidazole
  参考文献：
  名称：

  Cytotoxic and antivascular 1-methyl-4-(3-fluoro-4-methoxyphenyl)-5-(halophenyl)-imidazoles

  摘要：

  A series of 1-methyl-4,5-diphenylimidazoles 6 with various patterns of m-halogen substitution at the 5-phenyl ring were tested for cytotoxicity in cancer and nonmalignant cell lines and for their capacity to prevent tube formation in HUVEC cultures. Unlike the monofluoro and difluoro derivatives 6a and 6e, the monobromo and diiodo analogs 6c and 6h were strongly cytotoxic and inhibited the polymerization of tubulin and the tube formation by HUVEC. The dibromo derivative 6g displayed a unique selectivity for KB-3-1 cervix and PC-3 prostate cancer cells. It also inhibited the tube formation by HUVEC and the polymerization of tubulin which is indicative of its potential antiangiogenic activity in solid tumors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.005

文献信息

• [EN] COMBRETASTATIN ANALOGS FOR USE IN THE TREATMENT OF CANCER<br/>[FR] ANALOGUES DE LA COMBRÉTASTATINE POUR UTILISATION DANS LE TRAITEMENT DU CANCER
  申请人：UNIV BAYREUTH

  公开号：WO2011138409A1

  公开（公告）日：2011-11-10

  The present invention relates to specific analogs of combretastatin, in particular the compounds of formula (I) as described and defined herein, and pharmaceutical compositions comprising the compounds, as well as their medical use, in particular in the treatment or prevention of cancer, including multidrug-resistant cancer.

  本发明涉及康柏替斯汀的特定类似物，特别是本文所描述和定义的式(I)化合物，以及包含这些化合物的药物组合物，以及它们的医疗用途，特别是在治疗或预防癌症，包括多药耐药癌症方面。
• COMBRETASTATIN ANALOGS FOR USE IN THE TREATMENT OF CANCER
  申请人：Schobert Rainer

  公开号：US20130137740A1

  公开（公告）日：2013-05-30

  The present invention relates to specific analogs of combretastatin, in particular the compounds of formula (I) as described and defined herein, and pharmaceutical compositions comprising the compounds, as well as their medical use, in particular in the treatment or prevention of cancer, including multidrug-resistant cancer.

  本发明涉及康布雷塔斯汀的特定类似物，特别是公式（I）中所描述和定义的化合物，以及包含这些化合物的药物组成物，以及它们的医疗用途，特别是在治疗或预防癌症，包括多药耐药性癌症方面的应用。
• US8980933B2
  申请人：——

  公开号：US8980933B2

  公开（公告）日：2015-03-17
• Cytotoxic and antivascular 1-methyl-4-(3-fluoro-4-methoxyphenyl)-5-(halophenyl)-imidazoles
  作者：Bernhard Biersack、Yazh Muthukumar、Rainer Schobert、Florenz Sasse

  DOI：10.1016/j.bmcl.2011.09.005

  日期：2011.11

  A series of 1-methyl-4,5-diphenylimidazoles 6 with various patterns of m-halogen substitution at the 5-phenyl ring were tested for cytotoxicity in cancer and nonmalignant cell lines and for their capacity to prevent tube formation in HUVEC cultures. Unlike the monofluoro and difluoro derivatives 6a and 6e, the monobromo and diiodo analogs 6c and 6h were strongly cytotoxic and inhibited the polymerization of tubulin and the tube formation by HUVEC. The dibromo derivative 6g displayed a unique selectivity for KB-3-1 cervix and PC-3 prostate cancer cells. It also inhibited the tube formation by HUVEC and the polymerization of tubulin which is indicative of its potential antiangiogenic activity in solid tumors. (C) 2011 Elsevier Ltd. All rights reserved.