2-((2-chloro-4-oxo-5-(trifluoromethyl)thieno[2,3-d]pyrimidin-3(4H)-yl)methyl)benzonitrile | 1265593-76-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 2-((2-chloro-4-oxo-5-(trifluoromethyl)thieno[2,3-d]pyrimidin-3(4H)-yl)methyl)benzonitrile
• 英文别名: 2-[[2-Chloro-4-oxo-5-(trifluoromethyl)thieno[2,3-d]pyrimidin-3-yl]methyl]benzonitrile
• CAS: 1265593-76-7
• 化学式: C₁₅H₇ClF₃N₃OS
• 分子量: 369.754
• InChiKey: LSCUGAYUWIANLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(R)-aminopiperidine dihydrochloride 、 2-((2-chloro-4-oxo-5-(trifluoromethyl)thieno[2,3-d]pyrimidin-3(4H)-yl)methyl)benzonitrile 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以82%的产率得到(R)-2-((2-(3-aminopiperidin-1-yl)-4-oxo-5-(trifluoromethyl)thieno[2,3-d]pyrimidin-3(4H)-yl)methyl)benzonitrile
  参考文献：
  名称：

  The highly potent and selective dipeptidyl peptidase IV inhibitors bearing a thienopyrimidine scaffold effectively treat type 2 diabetes

  摘要：

  New dipeptidyl peptidase IV inhibitors were designed based on Alogliptin using a scaffold-hopping strategy. All of the compounds constructed on a thienopyrimidine scaffold demonstrated good inhibition and selectivity for DPP-IV. Compound 10d exhibited subnanomolar (IC50 = 0.33 nM) DPP-IV inhibitory activity, good in vivo efficacy and an acceptable pharmacokinetic profile. A pharmacokinetic-driven optimization of 10d may lead to a new class of clinical candidate DPP-IV inhibitors. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.10.016
• 作为产物：
  描述：

  2-chloro-5-(trifluoromethyl)thieno[2,3-d]pyrimidin-4(3H)-one 、 2-氰基溴苄 在 sodium hydride 、 lithium bromide 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.58h， 以70%的产率得到2-((2-chloro-4-oxo-5-(trifluoromethyl)thieno[2,3-d]pyrimidin-3(4H)-yl)methyl)benzonitrile
  参考文献：
  名称：

  The highly potent and selective dipeptidyl peptidase IV inhibitors bearing a thienopyrimidine scaffold effectively treat type 2 diabetes

  摘要：

  New dipeptidyl peptidase IV inhibitors were designed based on Alogliptin using a scaffold-hopping strategy. All of the compounds constructed on a thienopyrimidine scaffold demonstrated good inhibition and selectivity for DPP-IV. Compound 10d exhibited subnanomolar (IC50 = 0.33 nM) DPP-IV inhibitory activity, good in vivo efficacy and an acceptable pharmacokinetic profile. A pharmacokinetic-driven optimization of 10d may lead to a new class of clinical candidate DPP-IV inhibitors. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.10.016

文献信息

• The highly potent and selective dipeptidyl peptidase IV inhibitors bearing a thienopyrimidine scaffold effectively treat type 2 diabetes
  作者：Jifeng Deng、Li Peng、Guicheng Zhang、Xiaobing Lan、Chufang Li、Fuxin Chen、Yayao Zhou、Zuoxian Lin、Ling Chen、Renke Dai、Hongjiang Xu、Ling Yang、Xiquan Zhang、Wenhui Hu

  DOI：10.1016/j.ejmech.2010.10.016

  日期：2011.1

  New dipeptidyl peptidase IV inhibitors were designed based on Alogliptin using a scaffold-hopping strategy. All of the compounds constructed on a thienopyrimidine scaffold demonstrated good inhibition and selectivity for DPP-IV. Compound 10d exhibited subnanomolar (IC50 = 0.33 nM) DPP-IV inhibitory activity, good in vivo efficacy and an acceptable pharmacokinetic profile. A pharmacokinetic-driven optimization of 10d may lead to a new class of clinical candidate DPP-IV inhibitors. (C) 2010 Elsevier Masson SAS. All rights reserved.