2-(2-bromo-5-methyl-6,9-dioxo-5,6,7,9-tetrahydro-1H-imidazo[1,2-a]purin-1-yl)methyl-4-fluorobenzonitrile | 1417715-74-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2-(2-bromo-5-methyl-6,9-dioxo-5,6,7,9-tetrahydro-1H-imidazo[1,2-a]purin-1-yl)methyl-4-fluorobenzonitrile
• 英文别名: 2-[(2-bromo-5-methyl-6,9-dioxo-7H-imidazo[1,2-a]purin-3-yl)methyl]-4-fluorobenzonitrile
• CAS: 1417715-74-2
• 化学式: C₁₆H₁₀BrFN₆O₂
• 分子量: 417.197
• InChiKey: XZZAGVOSKMSSHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  94.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-[(4-methoxyphenyl)methyl]-5-methyl-6-methylimino-7H-imidazo[1,2-a]purin-9-one 在 盐酸 、 水 、 溴 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 31.0h， 生成 2-(2-bromo-5-methyl-6,9-dioxo-5,6,7,9-tetrahydro-1H-imidazo[1,2-a]purin-1-yl)methyl-4-fluorobenzonitrile
  参考文献：
  名称：

  [EN] TRICYCLIC HETEROCYCLES USEFUL AS DIPEPTIDYL PEPTIDASE-IV INHIBITORS
  [FR] HÉTÉROCYCLES TRICYCLIQUES UTILES COMME INHIBITEURS DE LA DIPEPTIDYL PEPTIDASE-IV

  摘要：

  公开号：

  WO2013006526A3

文献信息

• Discovery of Novel Tricyclic Heterocycles as Potent and Selective DPP-4 Inhibitors for the Treatment of Type 2 Diabetes
  作者：Wen-Lian Wu、Jinsong Hao、Martin Domalski、Duane A. Burnett、Dmitri Pissarnitski、Zhiqiang Zhao、Andrew Stamford、Giovanna Scapin、Ying-Duo Gao、Aileen Soriano、Terri M. Kelly、Zuliang Yao、Mary Ann Powles、Shiying Chen、Hong Mei、Joyce Hwa

  DOI：10.1021/acsmedchemlett.6b00027

  日期：2016.5.12

  generation DPP-4 inhibitors, we endeavored to identify distinct structures with long-acting (once weekly) potential. Taking advantage of X-ray cocrystal structures of sitagliptin and other DPP-4 inhibitors, such as alogliptin and linagliptin bound to DPP-4, and aided by molecular modeling, we designed several series of heterocyclic compounds as initial targets. During their synthesis, an unexpected chemical

  在开发第二代DPP-4抑制剂的过程中，我们努力确定具有长效作用（每周一次）的独特结构。利用西他列汀和其他DPP-4抑制剂（例如与DPP-4结合的阿格列汀和利拉列汀）的X射线共晶体结构，并借助分子建模，我们设计了一系列杂环化合物作为初始靶标。在其合成过程中，意外的化学转化提供了一种新颖的三环支架，这超出了我们的原始设计。利用这一偶然发现，我们将这种支架制成了非常有效和选择性的DPP-4抑制剂前导序列，如化合物17c所强调的那样。
• TRICYCLIC HETEROCYCLES USEFUL AS DIPEPTIDYL PEPTIDASE-IV INHIBITORS
  申请人：MERCK SHARP & DOHME CORP.

  公开号：US20140113920A1

  公开（公告）日：2014-04-24

  The present invention is directed to novel tricyclic heterocycles of structural formula (I) which are inhibitors of the dipeptidyl peptidase-IV enzyme and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly Type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.
• US9051329B2
  申请人：——

  公开号：US9051329B2

  公开（公告）日：2015-06-09