5-(3-Butyl-[1,2,4]oxadiazol-5-yl)-1-trityl-1,4,5,6-tetrahydro-pyrimidine | 146422-73-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5-(3-Butyl-[1,2,4]oxadiazol-5-yl)-1-trityl-1,4,5,6-tetrahydro-pyrimidine
• 英文别名: 3-butyl-5-(1-trityl-5,6-dihydro-4H-pyrimidin-5-yl)-1,2,4-oxadiazole
• CAS: 146422-73-3
• 化学式: C₂₉H₃₀N₄O
• 分子量: 450.583
• InChiKey: LAGAGAFZZJLDST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(3-Butyl-[1,2,4]oxadiazol-5-yl)-1-trityl-1,4,5,6-tetrahydro-pyrimidine 、 三氟乙酸 反应 24.0h， 以27%的产率得到5-(3-butyl-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
• 作为产物：
  描述：

  三苯基氯甲烷 在 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 5-(3-Butyl-[1,2,4]oxadiazol-5-yl)-1-trityl-1,4,5,6-tetrahydro-pyrimidine
  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
• US5175166A
  申请人：——

  公开号：US5175166A

  公开（公告）日：1992-12-29
• US5403845A
  申请人：——

  公开号：US5403845A

  公开（公告）日：1995-04-04
• [EN] MUSCARINIC AGONISTS
  申请人：——

  公开号：WO1993003726A1

  公开（公告）日：1993-03-04

  [FR] On décrit des compositions de 1,4,5,6-tétrahydropyrimidine substituées, des compositions de 1,2,3,6-tétrahydropyrimidine substituées ainsi que des compositions de 3,4,5,6-tétrahydropyrimidine substituées. Lesdites compositions sont destinées à être utilisées pour la stimulation des récepteurs muscariniques comprenant, par exemple, le traitement des symptômes des troubles cognitifs, notamment la mémoire défaillante, qui sont associées à la synthèse diminuée de l'acétylcholine et à la génération de cellules cholinergiques.
  [EN] Substituted 1,4,5,6-tetrahydropyrimidine compositions, substituted 1,2,3,6-tetrahydropyrimidine compositions and substituted 3,4,5,6-tetrahydropyrimidine compositions are disclosed. They are useful for stimulating muscarinic receptors including, for example, treating the symptoms of cognitive disorders, especially impaired memory, which are associated with decreased acetylcholine synthesis and cholinergic cell degeneration.