5,6,7,8-四氢-8-甲基-2-(三氟甲基)-[1,2,4]噻唑并[1,5-a]吡嗪 | 781614-02-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 5,6,7,8-四氢-8-甲基-2-(三氟甲基)-[1,2,4]噻唑并[1,5-a]吡嗪
• 英文名称: 8-Methyl-2-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine
• CAS: 781614-02-6
• 化学式: C₇H₉F₃N₄
• 分子量: 206.17
• InChiKey: QLEVXYXJLSXVMY-UHFFFAOYSA-N

物化性质

• 沸点：
  269.6±50.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  42.7
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5,6,7,8-四氢-8-甲基-2-(三氟甲基)-[1,2,4]噻唑并[1,5-a]吡嗪 、 Boc-(R)-3-氨基-4-(2,4,5-三氟苯基)丁酸 在 N-羟基-7-氮杂苯并三氮唑 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 tert-butyl ((R)-4-((S)-8-methyl-2-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl)-4-oxo-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate 、 tert-butyl ((R)-4-((R)-8-methyl-2-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl)-4-oxo-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of triazolopiperazine-based β-amino amides as potent, orally active dipeptidyl peptidase IV (DPP-4) inhibitors

  摘要：

  Various P-amino amides containing triazolopiperazine heterocycles have been prepared and evaluated as potent, selective, orally active dipeptidyl peptidase IV (DPP-4) inhibitors. These compounds display excellent oral bioavailability and good overall pharmacokinetic profiles in preclinical species. Moreover, in vivo efficacy in an oral glucose tolerance test in lean mice is demonstrated. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.100
• 作为产物：
  描述：

  7-N-(tert-Butoxycarbonyl)-8-methyl-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazine 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 5,6,7,8-四氢-8-甲基-2-(三氟甲基)-[1,2,4]噻唑并[1,5-a]吡嗪
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of triazolopiperazine-based β-amino amides as potent, orally active dipeptidyl peptidase IV (DPP-4) inhibitors

  摘要：

  Various P-amino amides containing triazolopiperazine heterocycles have been prepared and evaluated as potent, selective, orally active dipeptidyl peptidase IV (DPP-4) inhibitors. These compounds display excellent oral bioavailability and good overall pharmacokinetic profiles in preclinical species. Moreover, in vivo efficacy in an oral glucose tolerance test in lean mice is demonstrated. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.100

文献信息

• ANTIDIABETIC BETA-AMINO HETEROCYCLIC DIPEPTIDYL PEPTIDASE INHIBITORS
  申请人：Merck & Co., Inc.

  公开号：EP1554280B1

  公开（公告）日：2007-08-15
• Design, synthesis, and biological evaluation of triazolopiperazine-based β-amino amides as potent, orally active dipeptidyl peptidase IV (DPP-4) inhibitors
  作者：Jennifer E. Kowalchick、Barbara Leiting、KellyAnn D. Pryor、Frank Marsilio、Joseph K. Wu、Huaibing He、Kathryn A. Lyons、George J. Eiermann、Aleksandr Petrov、Giovanna Scapin、Reshma A. Patel、Nancy A. Thornberry、Ann E. Weber、Dooseop Kim

  DOI：10.1016/j.bmcl.2007.07.100

  日期：2007.11

  Various P-amino amides containing triazolopiperazine heterocycles have been prepared and evaluated as potent, selective, orally active dipeptidyl peptidase IV (DPP-4) inhibitors. These compounds display excellent oral bioavailability and good overall pharmacokinetic profiles in preclinical species. Moreover, in vivo efficacy in an oral glucose tolerance test in lean mice is demonstrated. (c) 2007 Elsevier Ltd. All rights reserved.