2,5-dibromo-1-(ethoxymethyl)-4-nitro-1H-imidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,5-dibromo-1-(ethoxymethyl)-4-nitro-1H-imidazole
• 英文别名: 1-ethoxymethyl-2,5-dibromo-4-nitroimidazole；2,5-dibromo-1-(ethoxymethyl)-4-nitroimidazole
• 化学式: C₆H₇Br₂N₃O₃
• 分子量: 328.948
• InChiKey: DFJNKJZKXKSDBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-dibromo-1-(ethoxymethyl)-4-nitro-1H-imidazole 在 sodium sulfite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 以88%的产率得到2-bromo-1-(ethoxymethyl)-4-nitro-1H-imidazole
  参考文献：
  名称：

  Synthesis, Reduction Potentials, and Antitubercular Activity of Ring A/B Analogues of the Bioreductive Drug (6S)-2-Nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824)

  摘要：

  The nitroimidazooxazine S-1 (PA-824) is a new class of bioreductive drug for tuberculosis. A series of related bicyclic nitroheterocycles was synthesized, designed to have a wide range of one-electron reduction potentials E(1) (from -570 to -338 mV, compared with -534 mV for S-1). The observed E(l) values closely correlated with the sigma(m) values of the heteroatom at the 4/8-position of the adjacent six-membered ring. Although the compounds spanned a range of E(1) values around that of S-1, only the nitroimidazothiazines showed significant antitubercular activity (at a similar level of potency), suggesting that E(1) is not the main driver of efficacy. Furthermore, there was a correlation between activity and the formation of imidazole ring-reduced products at the two-electron level, pointing to the potential importance of this reduction pathway, which is determined by the nature of the substituent at the 2-position of the 4-nitroimidazole ring.

  DOI：

  10.1021/jm801087e
• 作为产物：
  描述：

  二乙氧基甲烷 、 2,5-二溴-4-硝基咪唑 在 甲烷磺酸 作用下， 反应 1.5h， 以96.8%的产率得到2,5-dibromo-1-(ethoxymethyl)-4-nitro-1H-imidazole
  参考文献：
  名称：

  [EN] PROCESS FOR PRODUCTION OF 2-CHLORO-4-NITROIMIDAZOLE
  [FR] PROCEDE DE PRODUCTION DE 2-CHLORO-4-NITROIMIDAZOLE

  摘要：

  公开号：

  WO2006035960A3

文献信息

• PROCESS FOR PRODUCTION OF 2-CHLORO-4-NITROIMIDAZOLE
  申请人：Shinhama Koichi

  公开号：US20090082575A1

  公开（公告）日：2009-03-26

  The present invention provides a process for production of 2-chloro-4-nitroimidazole in a high yield and at a high purity by a simple operation in a safer manner involving a low risk of explosion or the like. The present invention provides a process for production of 2-chloro-4-nitroimidazole represented by the formula (1): comprising a reaction of a 1-alkoxyalkyl-2-bromo-4-nitroimidazole compound represented by the general formula (7): wherein R1 represents a lower alkyl group, and n represents an integer of 1 to 3, with hydrogen chloride.

  本发明提供了一种制备2-氯-4-硝基咪唑的方法，通过简单的操作以更安全的方式高产率高纯度地进行，具有低爆炸风险等优点。本发明提供了一种制备2-氯-4-硝基咪唑的方法，该方法包括将一种1-烷氧基烷基-2-溴-4-硝基咪唑化合物（通式（7））与氢氯酸反应，其中R1代表低碳基团，n为1至3的整数。
• Synthesis, Reduction Potentials, and Antitubercular Activity of Ring A/B Analogues of the Bioreductive Drug (6<i>S</i>)-2-Nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5<i>H</i>-imidazo[2,1-<i>b</i>][1,3]oxazine (PA-824)
  作者：Andrew M. Thompson、Adrian Blaser、Robert F. Anderson、Sujata S. Shinde、Scott G. Franzblau、Zhenkun Ma、William A. Denny、Brian D. Palmer

  DOI：10.1021/jm801087e

  日期：2009.2.12

  The nitroimidazooxazine S-1 (PA-824) is a new class of bioreductive drug for tuberculosis. A series of related bicyclic nitroheterocycles was synthesized, designed to have a wide range of one-electron reduction potentials E(1) (from -570 to -338 mV, compared with -534 mV for S-1). The observed E(l) values closely correlated with the sigma(m) values of the heteroatom at the 4/8-position of the adjacent six-membered ring. Although the compounds spanned a range of E(1) values around that of S-1, only the nitroimidazothiazines showed significant antitubercular activity (at a similar level of potency), suggesting that E(1) is not the main driver of efficacy. Furthermore, there was a correlation between activity and the formation of imidazole ring-reduced products at the two-electron level, pointing to the potential importance of this reduction pathway, which is determined by the nature of the substituent at the 2-position of the 4-nitroimidazole ring.
• [EN] PROCESS FOR PRODUCTION OF 2-CHLORO-4-NITROIMIDAZOLE<br/>[FR] PROCEDE DE PRODUCTION DE 2-CHLORO-4-NITROIMIDAZOLE
  申请人：OTSUKA PHARMA CO LTD

  公开号：WO2006035960A3

  公开（公告）日：2006-05-11