3-(chloromethyl)pyrazin-2-amine | 1314953-24-6

• 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-(chloromethyl)pyrazin-2-amine
• 英文别名: 3-amino-2-chloromethylpyrazine
• CAS: 1314953-24-6
• 化学式: C₅H₆ClN₃
• mdl: MFCD19207688
• 分子量: 143.576
• InChiKey: BIIDOTDBYQCNGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(chloromethyl)pyrazin-2-amine 在 碳酸氢钠 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 methyl 2-(((3-aminopyrazin-2-yl)methyl)((benzyloxy)carbonyl)amino)acetate
  参考文献：
  名称：

  Design, Synthesis, and Pharmacological Evaluation of Fused β-Homophenylalanine Derivatives as Potent DPP-4 Inhibitors

  摘要：

  Dipeptidyl peptidase-4 (DPP-4) inhibitors are accepted as a favorable class of agents for the treatment of type 2 diabetes. Herein, a series of fused beta-homophenylalanine derivatives as novel DPP-4 inhibitors were designed, synthesized, and evaluated for their inhibitory activities against DPP-4. Most of them displayed excellent DPP-4 inhibitory activities and good selectivity. Among them, 9aa, 18a, and 18m also showed good efficacy in an oral glucose tolerance test (OGTT) in ICR mice. Moreover, when dosed 8 h prior to glucose challenge, 18m showed significantly greater potency than sitagliptin. It thus provides potential candidates for the further development into potent drugs targeting DPP-4.

  DOI：

  10.1021/acsmedchemlett.5b00074
• 作为产物：
  描述：

  3-氨基-2-吡嗪甲醇 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 生成 3-(chloromethyl)pyrazin-2-amine
  参考文献：
  名称：

  Design, Synthesis, and Pharmacological Evaluation of Fused β-Homophenylalanine Derivatives as Potent DPP-4 Inhibitors

  摘要：

  Dipeptidyl peptidase-4 (DPP-4) inhibitors are accepted as a favorable class of agents for the treatment of type 2 diabetes. Herein, a series of fused beta-homophenylalanine derivatives as novel DPP-4 inhibitors were designed, synthesized, and evaluated for their inhibitory activities against DPP-4. Most of them displayed excellent DPP-4 inhibitory activities and good selectivity. Among them, 9aa, 18a, and 18m also showed good efficacy in an oral glucose tolerance test (OGTT) in ICR mice. Moreover, when dosed 8 h prior to glucose challenge, 18m showed significantly greater potency than sitagliptin. It thus provides potential candidates for the further development into potent drugs targeting DPP-4.

  DOI：

  10.1021/acsmedchemlett.5b00074

文献信息

• US3950333A
  申请人：——

  公开号：US3950333A

  公开（公告）日：1976-04-13
• US3950353A
  申请人：——

  公开号：US3950353A

  公开（公告）日：1976-04-13
• US4024271A
  申请人：——

  公开号：US4024271A

  公开（公告）日：1977-05-17
• US4018931A
  申请人：——

  公开号：US4018931A

  公开（公告）日：1977-04-19
• US4022797A
  申请人：——

  公开号：US4022797A

  公开（公告）日：1977-05-10