| 1428445-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• CAS: 1428445-26-4
• 化学式: C₁₀H₇BrClN₃O
• 分子量: 300.542
• InChiKey: BVHBHNIUWNFEHM-UHFFFAOYSA-N

物化性质

• 沸点：
  493.6±55.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.68
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(R)-aminopiperidine dihydrochloride 、 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 以81.8%的产率得到2-[(3R)-3-aminopiperidin-1-yl]-7-bromo-3-but-2-ynyl-5H-pyrrolo[3,2-d]pyrimidin-4-one
  参考文献：
  名称：

  Discovery of potent dipeptidyl peptidase IV inhibitors through pharmacophore hybridization and hit-to-lead optimization

  摘要：

  A novel dipeptidyl peptidase IV inhibitor hit (5, IC50 = 0.86 mu M) was structurally derived from our recently disclosed preclinical candidate 4 by replacing the cyanobenzyl with a butynyl based on pharmacophore hybridization. A hit-to-lead optimization effort was then initiated to improve its potency. Most N-substituted analogs exhibited good in vitro activity, and compound 180 (IC50 = 1.55 nM) was identified to be a potent dipeptidyl peptidase IV inhibitor with a significantly improved pharmacokinetic properties (bioavailablity: 41% vs 82.9%; T-1/2: 2 h vs 4.9 h). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.062
• 作为产物：
  描述：

  6-甲基尿嘧啶 在 盐酸 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 硝酸 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 、 sodium hydroxide 、 锌 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Discovery of potent dipeptidyl peptidase IV inhibitors through pharmacophore hybridization and hit-to-lead optimization

  摘要：

  A novel dipeptidyl peptidase IV inhibitor hit (5, IC50 = 0.86 mu M) was structurally derived from our recently disclosed preclinical candidate 4 by replacing the cyanobenzyl with a butynyl based on pharmacophore hybridization. A hit-to-lead optimization effort was then initiated to improve its potency. Most N-substituted analogs exhibited good in vitro activity, and compound 180 (IC50 = 1.55 nM) was identified to be a potent dipeptidyl peptidase IV inhibitor with a significantly improved pharmacokinetic properties (bioavailablity: 41% vs 82.9%; T-1/2: 2 h vs 4.9 h). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.062