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，
• (2<i>R</i>)-4-Oxo-4-[3-(Trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-<i>a</i>]pyrazin- 7(8<i>H</i>)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine:  A Potent, Orally Active Dipeptidyl Peptidase IV Inhibitor for the Treatment of Type 2 Diabetes
  作者：Dooseop Kim、Liping Wang、Maria Beconi、George J. Eiermann、Michael H. Fisher、Huaibing He、Gerard J. Hickey、Jennifer E. Kowalchick、Barbara Leiting、Kathryn Lyons、Frank Marsilio、Margaret E. McCann、Reshma A. Patel、Aleksandr Petrov、Giovanna Scapin、Sangita B. Patel、Ranabir Sinha Roy、Joseph K. Wu、Matthew J. Wyvratt、Bei B. Zhang、Lan Zhu、Nancy A. Thornberry、Ann E. Weber

  DOI：10.1021/jm0493156

  日期：2005.1.1

  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.