2-硝基-6,7-二氢-5H-咪唑并[2,1-b][1,3]噁嗪-6-醇 | 880345-50-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-硝基-6,7-二氢-5H-咪唑并[2,1-b][1,3]噁嗪-6-醇
• 中文别名: 2-硝基-6,7-二氢-5H-咪唑并[2,1-B][1,3]噁嗪-6-醇
• 英文名称: 2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol
• CAS: 880345-50-6
• 化学式: C₆H₇N₃O₄
• 分子量: 185.139
• InChiKey: HMFPMGBWSFUHEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-硝基-6,7-二氢-5H-咪唑并[2,1-b][1,3]噁嗪-6-醇 、 1,4-对二氯苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以37%的产率得到6-(4-chloromethyl-benzyloxy)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine
  参考文献：
  名称：

  WO2008/8480

  摘要：

  公开号：
• 作为产物：
  描述：

  1-{[叔丁基(二甲基)甲硅烷基]氧基}-3-(2,4-二硝基-1H-咪唑-1-基)-2-丙醇 在 4-二甲氨基吡啶 、 肉桂酸 、 N,N'-二环己基碳二亚胺 、 四丁基氟化铵 、 titanium(IV) isopropylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 34.0h， 以64%的产率得到2-硝基-6,7-二氢-5H-咪唑并[2,1-b][1,3]噁嗪-6-醇
  参考文献：
  名称：

  Process for preparing for imidazopyran derivatives

  摘要：

  一种制备咪唑吡喃衍生物的新工艺，公式如下：其中R1为卤素原子、氢原子、C1到C3烷基、芳基或被C1到C3烷基取代的芳基，该工艺使用二硝基咪唑和2,3-环氧-1-丙醇作为起始材料，经过五个步骤制备而成。

  公开号：

  US20060063929A1

文献信息

• Nitroimidazole Compounds
  申请人：Jiricek Jan

  公开号：US20080275035A1

  公开（公告）日：2008-11-06

  The present invention relates to certain nitroimidazole compounds, which have interesting pharmaceutical properties. In particular, the compounds are useful in the treatment and/or prevention of infections such as those caused by Mycobacterium tuberculosis, Trypanosoma cruzi or Leishmania donovani . The invention also relates to pharmaceutical compositions containing the compounds, as well as processes for their preparation.

  本发明涉及某些硝基咪唑化合物，具有有趣的药理特性。特别地，这些化合物在治疗和/或预防由结核分枝杆菌、克鲁兹锥虫或唇鞭毛虫等引起的感染方面是有用的。该发明还涉及含有这些化合物的药物组合物，以及它们的制备方法。
• Nitroheteroaryl-containing rifamycin derivatives
  申请人：Ding Charles Z.

  公开号：US20080139577A1

  公开（公告）日：2008-06-12

  Substituted rifamycin derivatives in which a nitroimidazole, nitrothiazole or nitrofuran pharmacophore is covalently bonded to a rifamycin, methods of using the rifamycin derivatives, and pharmaceutical compositions containing the rifamycin derivatives are disclosed. Methods of synthesizing these substituted rifamycin derivatives are also disclosed. The rifamycin derivatives possess antibacterial activity, and are effective against a number of human and veterinary pathogens in the treatment of bacterial diseases.

  本发明公开了替代利福霉素衍生物，其中硝基咪唑、硝基噻唑或硝基呋喃药效团与利福霉素共价键合，公开了使用该利福霉素衍生物的方法以及含有该利福霉素衍生物的制药组合物。还公开了合成这些替代利福霉素衍生物的方法。该利福霉素衍生物具有抗菌活性，并且在治疗细菌性疾病中对许多人类和兽医病原体有效。
• BICYCLIC NITROIMIDAZOLE-SUBSTITUTED PHENYL OXAZOLIDINONES
  申请人：Ding Charles Z.

  公开号：US20090281088A1

  公开（公告）日：2009-11-12

  The current invention provides a series of bicyclic nitroimidazole-substituted phenyl oxazolidinones in which a bicyclic nitroimidazole pharmacophore is covalently bonded to a phenyl oxazolidinone, their pharmaceutical compositions, and the method of use of the compositions for prevention and treatment of bacterial infections. The bicyclic nitroimidazole-substituted phenyl oxazolidinones possess surprising antibacterial activity against wild-type and resistant strains of pathogens, and are therefore useful for the prevention, control and treatment of a number of human and veterinary bacterial infections caused by these pathogens, such as Mycobacterium tuberculosis.

  本发明提供了一系列双环硝基咪唑取代的苯基噁唑烷酮，其中双环硝基咪唑药效团与苯基噁唑烷酮共价键合，它们的制药组合物以及用于预防和治疗细菌感染的组合物的使用方法。这些双环硝基咪唑取代的苯基噁唑烷酮对野生型和耐药菌株具有惊人的抗菌活性，因此对于预防、控制和治疗由这些病原体引起的许多人类和兽医细菌感染是有用的，如结核分枝杆菌。
• WO2007/75872
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.