3-(pentafluoroethyl)-1,2,4-triazolo[4,3-a]pyrazine | 837430-17-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-(pentafluoroethyl)-1,2,4-triazolo[4,3-a]pyrazine
• 英文别名: 3-(1,1,2,2,2-pentafluoroethyl)-[1,2,4]triazolo[4,3-a]pyrazine
• CAS: 837430-17-8
• 化学式: C₇H₃F₅N₄
• 分子量: 238.12
• InChiKey: GSXOXRKMJZQWSO-UHFFFAOYSA-N

物化性质

• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(pentafluoroethyl)-1,2,4-triazolo[4,3-a]pyrazine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以73%的产率得到3-(pentafluoroethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazine
  参考文献：
  名称：

  (2R)-4-Oxo-4-[3-(Trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin- 7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine:  A Potent, Orally Active Dipeptidyl Peptidase IV Inhibitor for the Treatment of Type 2 Diabetes

  摘要：

  A novel series of beta-amino amides incorporating fused heterocycles, i.e., triazolopiperazines, were synthesized and evaluated as inhibitors of dipeptidyl peptidase IV (DPP-IV) for the treatment of type 2 diabetes. (2R)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine (1) is a potent, orally active DPP-IV inhibitor (IC(50) = 18 nM) with excellent selectivity over other proline-selective peptidases, oral bioavailability in preclinical species, and in vivo efficacy in animal models. MK-0431, the phosphate salt of compound 1, was selected for development as a potential new treatment for type 2 diabetes.

  DOI：

  10.1021/jm0493156
• 作为产物：
  描述：

  五氟丙酸 、 吡嗪-2-肼 在 PPA 作用下， 反应 8.0h， 以9%的产率得到3-(pentafluoroethyl)-1,2,4-triazolo[4,3-a]pyrazine
  参考文献：
  名称：

  (2R)-4-Oxo-4-[3-(Trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin- 7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine:  A Potent, Orally Active Dipeptidyl Peptidase IV Inhibitor for the Treatment of Type 2 Diabetes

  摘要：

  A novel series of beta-amino amides incorporating fused heterocycles, i.e., triazolopiperazines, were synthesized and evaluated as inhibitors of dipeptidyl peptidase IV (DPP-IV) for the treatment of type 2 diabetes. (2R)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine (1) is a potent, orally active DPP-IV inhibitor (IC(50) = 18 nM) with excellent selectivity over other proline-selective peptidases, oral bioavailability in preclinical species, and in vivo efficacy in animal models. MK-0431, the phosphate salt of compound 1, was selected for development as a potential new treatment for type 2 diabetes.

  DOI：

  10.1021/jm0493156

文献信息

• [EN] PHTHALAZINONE DERIVATIVE, AND PREPARATION METHOD AND USE THEREOF<br/>[FR] DÉRIVÉ DE PHTALAZINONE, ET PROCÉDÉ DE PRÉPARATION ET UTILISATION ASSOCIÉS<br/>[ZH] 酞嗪酮衍生物、其制备方法及用途
  申请人：SICHUAN KELUN-BIOTECH BIOPHARMACEUTICA CO LTD

  公开号：WO2017101796A1

  公开（公告）日：2017-06-22

  本申请涉及酞嗪酮衍生物、其制备方法及用途；具体涉及一种式I化合物、其前体药物、代谢物形式、药学上可接受的盐或酯、或前述的异构体、水合物、溶剂合物或晶型，其制备方法及用途，本申请的化合物可以明显提高对肿瘤细胞的增殖抑制作用；可以增加分子体内稳定性以及降低产生毒性代谢物的可能性；或者，可通过降低对酞嗪酮类化合物的结构修饰，降低化合物在体内P450细胞色素酶系作用下的氧化代谢能力，并提高了生物利用率，