3-[4-(2-methyl-1H-imidazol-1-yl)-2-butynyl]oxy-Δ²-isoxazoline | 675846-58-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-[4-(2-methyl-1H-imidazol-1-yl)-2-butynyl]oxy-Δ²-isoxazoline
• 英文别名: 3-[4-(2-Methyl-1H-imidazol-1-yl)-2-butynyl]oxy-delta2-isoxazoline sesquifumarate；3-[4-(2-methylimidazol-1-yl)but-2-ynoxy]-4,5-dihydro-1,2-oxazole
• CAS: 675846-58-9
• 化学式: C₁₁H₁₃N₃O₂
• 分子量: 219.243
• InChiKey: DCNMFOFKZLIEDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[4-(2-methyl-1H-imidazol-1-yl)-2-butynyl]oxy-Δ²-isoxazoline 、 碘甲烷 以 异丙醇 为溶剂， 生成 3-[4-(2,3-dimethyl-1H-imidazolium-1-yl)-2-butynyl]oxy-Δ²-isoxazoline iodide
  参考文献：
  名称：

  Synthesis and in vitro pharmacology of novel heterocyclic muscarinic ligands

  摘要：

  A set of novel heterocyclic ligands (7a-9a, 7b-9b, and 9c) structurally related to oxotremorine 2 was designed, synthesized, and tested at muscarinic receptor subtypes. In the binding experiments at cloned hm1-5, the presence of the 2-methylimidazole/2-methyl-3-alkylimidazolium moiety in place of the pyrrolidine ring revealed, in derivatives 8a, 8b, and 9c, a moderate selectivity for some receptor subtypes. The functional in vitro assays yielded results that correlated closely to binding data. In general, on passing from agonists bearing the pyrrolidine moiety to their analogues carrying the 2-methylimidazole function, the overall pharmacological efficacy profile is shifted from agonism toward partial agonism. The insertion of the 2-methyl-3-alkylimidazolium moiety advances the effect such that the compounds are pure antagonists. Quite similarly, chiral 3-oxo-Delta(2)-isoxazoline (+/-)-10 behaved as a weak antagonist unable to discriminate the different muscarinic receptor subtypes.

  DOI：

  10.1016/s0014-827x(03)00113-7
• 作为产物：
  描述：

  4-(4,5-二氢-1,2-恶唑-3-基氧基)-2-丁炔-1-醇 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 3-[4-(2-methyl-1H-imidazol-1-yl)-2-butynyl]oxy-Δ²-isoxazoline
  参考文献：
  名称：

  Synthesis and in vitro pharmacology of novel heterocyclic muscarinic ligands

  摘要：

  A set of novel heterocyclic ligands (7a-9a, 7b-9b, and 9c) structurally related to oxotremorine 2 was designed, synthesized, and tested at muscarinic receptor subtypes. In the binding experiments at cloned hm1-5, the presence of the 2-methylimidazole/2-methyl-3-alkylimidazolium moiety in place of the pyrrolidine ring revealed, in derivatives 8a, 8b, and 9c, a moderate selectivity for some receptor subtypes. The functional in vitro assays yielded results that correlated closely to binding data. In general, on passing from agonists bearing the pyrrolidine moiety to their analogues carrying the 2-methylimidazole function, the overall pharmacological efficacy profile is shifted from agonism toward partial agonism. The insertion of the 2-methyl-3-alkylimidazolium moiety advances the effect such that the compounds are pure antagonists. Quite similarly, chiral 3-oxo-Delta(2)-isoxazoline (+/-)-10 behaved as a weak antagonist unable to discriminate the different muscarinic receptor subtypes.

  DOI：

  10.1016/s0014-827x(03)00113-7

文献信息

• Synthesis and in vitro pharmacology of novel heterocyclic muscarinic ligands
  作者：Marco De Amici、Paola Conti、Ezio Fasoli、Elisabetta Barocelli、Vigilio Ballabeni、Simona Bertoni、Mariannina Impicciatore、Bryan L Roth、Paul Ernsberger、Carlo De Micheli

  DOI：10.1016/s0014-827x(03)00113-7

  日期：2003.9

  A set of novel heterocyclic ligands (7a-9a, 7b-9b, and 9c) structurally related to oxotremorine 2 was designed, synthesized, and tested at muscarinic receptor subtypes. In the binding experiments at cloned hm1-5, the presence of the 2-methylimidazole/2-methyl-3-alkylimidazolium moiety in place of the pyrrolidine ring revealed, in derivatives 8a, 8b, and 9c, a moderate selectivity for some receptor subtypes. The functional in vitro assays yielded results that correlated closely to binding data. In general, on passing from agonists bearing the pyrrolidine moiety to their analogues carrying the 2-methylimidazole function, the overall pharmacological efficacy profile is shifted from agonism toward partial agonism. The insertion of the 2-methyl-3-alkylimidazolium moiety advances the effect such that the compounds are pure antagonists. Quite similarly, chiral 3-oxo-Delta(2)-isoxazoline (+/-)-10 behaved as a weak antagonist unable to discriminate the different muscarinic receptor subtypes.