Chlor-2 dihydro-3,4 methyl-5 oxo-4 thieno<2,3-d>pyrimidin | 56844-37-2

• 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: Chlor-2 dihydro-3,4 methyl-5 oxo-4 thieno<2,3-d>pyrimidin
• 英文别名: 2-chloro-5-methylthieno[2,3-d]pyrimidin-4(3H)-one；2-chloro-5-methyl-3H-thieno[2,3-d]pyrimidin-4-one；2-chloro-5-methyl-3H-thieno[2,3-d]pyrimidin-4-one
• CAS: 56844-37-2
• 化学式: C₇H₅ClN₂OS
• 分子量: 200.649
• InChiKey: CXTGAZPHAAPHJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氰基溴苄 、 Chlor-2 dihydro-3,4 methyl-5 oxo-4 thieno<2,3-d>pyrimidin 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68.7%的产率得到2-((2-chloro-5-methyl-4-oxothieno[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：

  2,4-二氯-5-甲基噻吩并[2,3-D]嘧啶 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以90.3%的产率得到Chlor-2 dihydro-3,4 methyl-5 oxo-4 thieno<2,3-d>pyrimidin
  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

• Robba,M. et al., Bulletin de la Societe Chimique de France, 1975, p. 592 - 597
  作者：Robba,M. et al.

  DOI：——

  日期：——
• ROBBA M.; LECOMTE J.-M.; CUGNON DE SEVRICOURT M., BULL. SOC. CHIM. FRANCE <BSCF-AS>, 1975, NO 3-4, PART. 2, 592-597
  作者：ROBBA M.、 LECOMTE J.-M.、 CUGNON DE SEVRICOURT M.

  DOI：——

  日期：——
• 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.