2-(4-fluorophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine hydrochloride | 1575612-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-fluorophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine hydrochloride
• 英文别名: 2-(4-Fluorophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine;hydrochloride
• CAS: 1575612-05-3
• 化学式: C₁₂H₁₂FN₃*ClH
• 分子量: 253.707
• InChiKey: XGXRNSFBMRJKFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-fluorophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine hydrochloride 、 1-(((2R,3S),2-(2,4-二氟苯基)-3-甲基环氧乙烷-2-基)甲基)-1H-1,2,4-三唑 以 乙腈 为溶剂， 反应 24.0h， 以41.2%的产率得到(2R,3R)-2-(2,4-difluorophenyl)-3-(2-(4-fluorophenyl)-5,6-dihydroimidazo[1,2-a]piperazine-7(8H)-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
  参考文献：
  名称：

  Design, Synthesis, and Structure–Activity Relationship Studies of Novel Fused Heterocycles-Linked Triazoles with Good Activity and Water Solubility

  摘要：

  Triazoles with fused-heterocycle nuclei were designed and evaluated for their in vitro activity on the basis of the binding mode of albaconazole using molecular docking, along with SAR of antifungal triazoles. Tetrahydro-[1,2,4]-triazolo[1,5-a]pyrazine and tetrahydro-thiazolo[5,4-c]pyridine nuclei were preferable to the other four fused-heterocycle nuclei investigated. Potent in vitro activity, broad spectrum and better water solubility were attained when triazoles containing nitrogen aromatic heterocycles were attached to these two nuclei. The most potent compounds 27aa and 45x, with low hERG inhibition and hepatocyte toxicity, both exhibited excellent activity against Candida, Cryptococcus, and Aspergillus spp., as well as selected fluconazole-resistant strains. A high water-soluble compound 58 (the disulfate salt of 45x) displayed unsatisfactory in vivo activity because of its poor PK profiles. Mice infected with C.alb. SC5314 and C.alb. 103 (fluconazole-resistant strain) and administered with 27aa displayed significantly improved survival rates. 27aa also showed favorable pharmacokinetic (PK) profiles.

  DOI：

  10.1021/jm4016284
• 作为产物：
  描述：

  4-氟苯乙酮 在 palladium on activated charcoal 、 氢气 、 溴 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 15.0~50.0 ℃ 、344.75 kPa 条件下， 反应 36.33h， 生成 2-(4-fluorophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine hydrochloride
  参考文献：
  名称：

  EP3252059

  摘要：

  公开号：

文献信息

• ANTI-PULMONARY TUBERCULOSIS NITROIMIDAZOLE DERIVATIVE
  申请人：Medshine Discovery Inc.

  公开号：EP3252059A1

  公开（公告）日：2017-12-06

  Disclosed is a substituted nitroimidazole derivative, which is mainly used for treating related diseases caused by mycobacterial infections, such as Mycobacterium tuberculosis, especially being suitable for diseases caused by resistant Mycobacterium tuberculosis.

  本发明公开了一种取代的硝基咪唑衍生物，主要用于治疗结核分枝杆菌等分枝杆菌感染引起的相关疾病，尤其适用于耐药结核分枝杆菌引起的疾病。
• Anti-pulmonary tuberculosis nitroimidazole derivative
  申请人：MEDSHINE DISCOVERY INC.

  公开号：US10227362B2

  公开（公告）日：2019-03-12

  Disclosed is a substituted nitroimidazole derivative, which is mainly used for treating related diseases caused by mycobacterial infections, such as Mycobacterium tuberculosis, especially being suitable for diseases caused by resistant Mycobacterium tuberculosis.

  本发明公开了一种取代的硝基咪唑衍生物，主要用于治疗结核分枝杆菌等分枝杆菌感染引起的相关疾病，尤其适用于耐药结核分枝杆菌引起的疾病。