(1-methyl-4-nitro-2-(prop-1-ynyl)-1H-imidazol-5-yl)methyl mesylate | 1245555-91-2

• 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-4-nitro-2-(prop-1-ynyl)-1H-imidazol-5-yl)methyl mesylate
• 英文别名: 1-Methyl-4-nitro-2-(1-propyn-1-yl)-1h-imidazole-5-methanol 5-methanesulfonate；(3-methyl-5-nitro-2-prop-1-ynylimidazol-4-yl)methyl methanesulfonate
• CAS: 1245555-91-2
• 化学式: C₉H₁₁N₃O₅S
• 分子量: 273.269
• InChiKey: JWBICABHVVZOQY-UHFFFAOYSA-N

物化性质

• 沸点：
  528.0±60.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.18
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  104.33
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1-methyl-4-nitro-2-(prop-1-ynyl)-1H-imidazol-5-yl)methyl mesylate 在 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以69%的产率得到5-(bromomethyl)-1-methyl-4-nitro-2-(prop-1-ynyl)-1H-imidazole
  参考文献：
  名称：

  Synthesis of substituted 5-bromomethyl-4-nitroimidazoles and use for the preparation of the hypoxia-selective multikinase inhibitor SN29966

  摘要：

  5-Bromomethyl-4-nitroimidazoles have utility as bioreductive trigger precursors for the preparation of hypoxia-selective prodrugs. Here we describe an efficient two-step synthesis of 5-(bromomethyl)-1-methyl-4-nitro-1H-imidazole, a preferred precursor, employing an N-bromosuccinimide mediated radical bromination. Use of this precursor to prepare SN29966, a promising hypoxia-selective irreversible pan-ErbB inhibitor is reported along with the preparation of four other prodrug candidates. 5-Bromomethyl-4-nitroimidazole analogues bearing electron-donating and electron-withdrawing substituents at the N-1 and C-2 positions are also described. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.037
• 作为产物：
  描述：

  1,5-二甲基-4-硝基咪唑 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 溴 、 potassium carbonate 、 三乙胺 作用下， 以 N-甲基吡咯烷酮 、 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 20.33h， 生成 (1-methyl-4-nitro-2-(prop-1-ynyl)-1H-imidazol-5-yl)methyl mesylate
  参考文献：
  名称：

  Synthesis of substituted 5-bromomethyl-4-nitroimidazoles and use for the preparation of the hypoxia-selective multikinase inhibitor SN29966

  摘要：

  5-Bromomethyl-4-nitroimidazoles have utility as bioreductive trigger precursors for the preparation of hypoxia-selective prodrugs. Here we describe an efficient two-step synthesis of 5-(bromomethyl)-1-methyl-4-nitro-1H-imidazole, a preferred precursor, employing an N-bromosuccinimide mediated radical bromination. Use of this precursor to prepare SN29966, a promising hypoxia-selective irreversible pan-ErbB inhibitor is reported along with the preparation of four other prodrug candidates. 5-Bromomethyl-4-nitroimidazole analogues bearing electron-donating and electron-withdrawing substituents at the N-1 and C-2 positions are also described. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.037

文献信息

• [EN] PRODRUG FORMS OF KINASE INHIBITORS AND THEIR USE IN THERAPY<br/>[FR] FORMES PROMÉDICAMENTS D'INHIBITEURS DE KINASE ET LEUR UTILISATION EN THÉRAPIE
  申请人：AUCKLAND UNISERVICES LTD

  公开号：WO2010104406A8

  公开（公告）日：2011-10-06