5-(3-ethyl-1,2,4-oxadiazol-5-yl)-1,4,5,6-tetrahydropyrimidine trifluoroacetate | 146422-59-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-(3-ethyl-1,2,4-oxadiazol-5-yl)-1,4,5,6-tetrahydropyrimidine trifluoroacetate
• 英文别名: CDD-0102 trifluoroacetate；3-ethyl-5-(1,4,5,6-tetrahydropyrimidin-5-yl)-1,2,4-oxadiazole;2,2,2-trifluoroacetic acid
• CAS: 146422-59-5
• 化学式: C₂HF₃O₂*C₈H₁₂N₄O
• 分子量: 294.233
• InChiKey: DGWZWAJULKDIKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1-(triphenylmethyl)-5-(methoxycarbonyl)-1,4,5,6-tetrahydropyrimidine 在 sodium hydride 作用下， 反应 43.0h， 生成 5-(3-ethyl-1,2,4-oxadiazol-5-yl)-1,4,5,6-tetrahydropyrimidine trifluoroacetate
  参考文献：
  名称：

  Design, synthesis, and neurochemical evaluation of 5-(3-alkyl-1,2,4-oxadiazol-5-yl)-1,4,5,6-tetrahydropyrimidines as M1 muscarinic receptor agonists

  摘要：

  A series of 5-(3-alkyl-1,2,4-oxadiazol-5-yl)-1,4,5,6-tetrahydropyrimidines (7a-h) was synthesized for biological evaluation as selective agonists for M1 receptors coupled to phosphoinositide (PI) metabolism in the central nervous system. Each ligand bound with high affinity to muscarinic receptors from rat brain as measured by inhibition of [H-3]-(R)-quinuclidinyl benzilate ([H-3]-(R)-QNB)binding. 5-(3-Methyl-1,2,4-oxadiazol-5-yl)-1,4,5,6-tetrahydropyrimidine trifluoroacetate (CDD-0098-J; 7a) displayed high affinity (IC50 = 2.7 +/- 0.69 muM) and efficacy at muscarinic receptors coupled to PI metabolism in the rat cortex and hippocampus. Increasing the length of the alkyl substituent increased affinity for muscarinic receptors yet decreased activity in PI turnover assays. The hippocampal PI response of 7a was blocked by lower concentrations of pirenzepine (8) or by higher concentrations of either AF-DX 116 (9) or p-fluorohexahydrosiladifenidol (10), suggesting that at low concentrations 7a selectively stimulates PI turnover through M1 receptors.

  DOI：

  10.1021/jm00059a008

文献信息

• MUSCARINIC AGONISTS
  申请人：THE UNIVERSITY OF TOLEDO

  公开号：EP0630244A1

  公开（公告）日：1994-12-28
• EP0630244A4
  申请人：——

  公开号：EP0630244A4

  公开（公告）日：1994-04-07
• 4-ACYLAMINOPYRIDINE DERIVATIVE MEDIATED NEUROGENESIS
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：EP1986647A2

  公开（公告）日：2008-11-05
• EP1986647A4
  申请人：——

  公开号：EP1986647A4

  公开（公告）日：2009-09-02
• US5175166A
  申请人：——

  公开号：US5175166A

  公开（公告）日：1992-12-29