benzyl 2-oxo-2,3-dihydro-1H-pyrido[3,2-e][1,4]diazepine-4(5H)-carboxylate | 1629195-06-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: benzyl 2-oxo-2,3-dihydro-1H-pyrido[3,2-e][1,4]diazepine-4(5H)-carboxylate
• 英文别名: 4H-Pyrido[3,2-e]-1,4-diazepine-4-carboxylic acid, 1,2,3,5-tetrahydro-2-oxo-, phenylmethyl ester；benzyl 2-oxo-3,5-dihydro-1H-pyrido[3,2-e][1,4]diazepine-4-carboxylate
• CAS: 1629195-06-7
• 化学式: C₁₆H₁₅N₃O₃
• 分子量: 297.313
• InChiKey: NIQHUNOXIRIUGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  71.53
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  benzyl 2-oxo-2,3-dihydro-1H-pyrido[3,2-e][1,4]diazepine-4(5H)-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 4,5-dihydro-1H-pyrido[3,2-e][1,4]diazepin-2(3H)-one
  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：

  2-(溴甲基)-3-硝基吡啶 在 铁粉 、 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.08h， 生成 benzyl 2-oxo-2,3-dihydro-1H-pyrido[3,2-e][1,4]diazepine-4(5H)-carboxylate
  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