1-[4-(4-iodophenoxy)butyl]-1H-imidazole | 415722-32-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-[4-(4-iodophenoxy)butyl]-1H-imidazole
• 英文别名: 1-(4-(4-Iodophenoxy)butyl)-1H-imidazole；1-[4-(4-iodophenoxy)butyl]imidazole
• CAS: 415722-32-6
• 化学式: C₁₃H₁₅IN₂O
• 分子量: 342.179
• InChiKey: OLXWUOZHYJJJSP-UHFFFAOYSA-N

物化性质

• 沸点：
  469.2±30.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-碘苯酚 在 四丁基溴化铵 、 potassium carbonate 、 三乙胺 作用下， 以 丙酮 、 乙腈 为溶剂， 90.0~100.0 ℃ 、1.03 MPa 条件下， 反应 45.5h， 生成 1-[4-(4-iodophenoxy)butyl]-1H-imidazole
  参考文献：
  名称：

  Evaluation of novel aryloxyalkyl derivatives of imidazole and 1,2,4-triazole as heme oxygenase-1 (HO-1) inhibitors and their antitumor properties

  摘要：

  A novel series of aryloxyalkyl derivatives of imidazole and 1,2,4-triazole, 17-31, was designed and synthesized as inhibitors of heme oxygenase-1 (HO-1) and heme oxygenase-2 (HO-2). Some of these compounds were found to be good inhibitors of HO-1, in particular those carrying an imidazole moiety as azolyl group and a 3-bromo or 4-iodophenyl as aryl moiety. The most potent compounds 6 and 30 were selected and studied for their antitumor properties in a model of LAMA-84 R cell line overexpressing HO-1 and resistant to imatinib mesylate (IM), a tyrosine-kinase inhibitor used in the treatment of multiple types of cancer, most notably Philadelphia Chromosome positive (Ph+) Chronic Myelogenous Leukemia (CML). Results show that both 6 and 30 sensitized LAMA-84 R cell line to antitumor properties of IM. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.040

文献信息

• [EN] ADMINISTRATION OF CARBOLINE DERIVATIVES USEFUL IN THE TREATMENT OF CANCER AND OTHER DISEASES<br/>[FR] ADMINISTRATION DE DÉRIVÉS DE CARBOLINE UTILISÉS DANS LE TRAITEMENT DU CANCER ET AUTRES MALADIES
  申请人：PTC THERAPEUTICS INC

  公开号：WO2008127714A1

  公开（公告）日：2008-10-23

  [EN] In accordance with the present invention, compounds are provided which are useful in a method or in the manufacture of a medicament for post-transcriptionally inhibiting the expression of VEGF in a subject in need thereof comprising inhibiting VEGF mRNA translation by orally administering said medicament once, twice or thrice daily to the subject.
  [FR] La présente invention concerne des composés utilisés dans un procédé ou dans la fabrication d'un médicament visant à inhiber de manière post-transcriptionnelle l'expression du facteur de croissance de l'endothélium vasculaire (VEGF) chez un sujet nécessitant un tel traitement, ledit procédé consistant à inhiber la traduction de l'ARNm du facteur de croissance VEGF en administrant ce médicament par voie orale audit sujet à raison d'une, deux ou trois fois par jour.
• Evaluation of novel aryloxyalkyl derivatives of imidazole and 1,2,4-triazole as heme oxygenase-1 (HO-1) inhibitors and their antitumor properties
  作者：Loredana Salerno、Valeria Pittalà、Giuseppe Romeo、Maria N. Modica、Maria A. Siracusa、Claudia Di Giacomo、Rosaria Acquaviva、Ignazio Barbagallo、Daniele Tibullo、Valeria Sorrenti

  DOI：10.1016/j.bmc.2013.06.040

  日期：2013.9

  A novel series of aryloxyalkyl derivatives of imidazole and 1,2,4-triazole, 17-31, was designed and synthesized as inhibitors of heme oxygenase-1 (HO-1) and heme oxygenase-2 (HO-2). Some of these compounds were found to be good inhibitors of HO-1, in particular those carrying an imidazole moiety as azolyl group and a 3-bromo or 4-iodophenyl as aryl moiety. The most potent compounds 6 and 30 were selected and studied for their antitumor properties in a model of LAMA-84 R cell line overexpressing HO-1 and resistant to imatinib mesylate (IM), a tyrosine-kinase inhibitor used in the treatment of multiple types of cancer, most notably Philadelphia Chromosome positive (Ph+) Chronic Myelogenous Leukemia (CML). Results show that both 6 and 30 sensitized LAMA-84 R cell line to antitumor properties of IM. (C) 2013 Elsevier Ltd. All rights reserved.