tert-butyl 3-(2,4-dinitro-1H-imidazol-1-yl)-2-(tetrahydro-2H-pyran-2-yloxy)propylcarbamate | 1100750-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl 3-(2,4-dinitro-1H-imidazol-1-yl)-2-(tetrahydro-2H-pyran-2-yloxy)propylcarbamate
• 英文别名: tert-butyl N-[3-(2,4-dinitroimidazol-1-yl)-2-(oxan-2-yloxy)propyl]carbamate
• CAS: 1100750-19-3
• 化学式: C₁₆H₂₅N₅O₈
• 分子量: 415.403
• InChiKey: BGJBQYSLQPGDIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  166
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(2,4-dinitro-1H-imidazol-1-yl)-2-(tetrahydro-2H-pyran-2-yloxy)propylcarbamate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以55%的产率得到tert-butyl 2-nitro-6-(tetrahydro-2H-pyran-2-yloxy)-6,7-dihydroimidazo[1,2-a]pyrimidine-8(5H)-carboxylate
  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：

  3,4-二氢-2H-吡喃 、 tert-butyl 3-(2,4-dinitro-1H-imidazol-1-yl)-2-hydroxypropylcarbamate 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以76%的产率得到tert-butyl 3-(2,4-dinitro-1H-imidazol-1-yl)-2-(tetrahydro-2H-pyran-2-yloxy)propylcarbamate
  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