1-benzhydryl-3-(3-methyl-5-isoxazolyl)methyleneazetidine | 750557-97-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzhydryl-3-(3-methyl-5-isoxazolyl)methyleneazetidine
• 英文别名: 5-[(1-Benzhydrylazetidin-3-ylidene)methyl]-3-methyl-1,2-oxazole
• CAS: 750557-97-2
• 化学式: C₂₁H₂₀N₂O
• 分子量: 316.403
• InChiKey: XBZRRPZCYIBCSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  29.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzhydryl-3-(3-methyl-5-isoxazolyl)methyleneazetidine 在 甲醇 作用下， 以 甲苯 为溶剂， 反应 1.33h， 生成 3-(3-methyl-5-isoxazolyl)methyleneazetidine
  参考文献：
  名称：

  Improving the Nicotinic Pharmacophore with a Series of (Isoxazole)methylene-1-azacyclic Compounds:  Synthesis, Structure−Activity Relationship, and Molecular Modeling

  摘要：

  A series of (isoxazole)methylene-1-azacyclic compounds was prepared. The compounds were tested for affinity to central nicotinic acetylcholine receptors (nAChRs) and central muscarinic receptors. The compounds covered a broad range of affinities for the nAChRs (IC50 = 0.32 to >1000 nM), with selectivities for the nAChRs over the muscarinic receptors in the range of 3-183. The high-affinity compound (Z)-26 (3-(4-methyl-5-isoxazolyl)methylene-1-azabicyclo-[2.2.2]octane, IC50 = 3.2 nM) having only one energy minimum was used as the reference structure in a computational study. This ligand has enabled definition of an important distance parameter, and the existence of this parameter was supported by showing that other potent nicotinic ligands (for example, nicotine and epibatidine) fit the model.

  DOI：

  10.1021/jm9910627
• 作为产物：
  描述：

  1-二苯甲基氮杂环丁烷-3-酮 、 3-methyl-5-(trimethylsilylmethyl)isoxazole 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 1-benzhydryl-3-(3-methyl-5-isoxazolyl)methyleneazetidine
  参考文献：
  名称：

  Improving the Nicotinic Pharmacophore with a Series of (Isoxazole)methylene-1-azacyclic Compounds:  Synthesis, Structure−Activity Relationship, and Molecular Modeling

  摘要：

  A series of (isoxazole)methylene-1-azacyclic compounds was prepared. The compounds were tested for affinity to central nicotinic acetylcholine receptors (nAChRs) and central muscarinic receptors. The compounds covered a broad range of affinities for the nAChRs (IC50 = 0.32 to >1000 nM), with selectivities for the nAChRs over the muscarinic receptors in the range of 3-183. The high-affinity compound (Z)-26 (3-(4-methyl-5-isoxazolyl)methylene-1-azabicyclo-[2.2.2]octane, IC50 = 3.2 nM) having only one energy minimum was used as the reference structure in a computational study. This ligand has enabled definition of an important distance parameter, and the existence of this parameter was supported by showing that other potent nicotinic ligands (for example, nicotine and epibatidine) fit the model.

  DOI：

  10.1021/jm9910627

文献信息

• Improving the Nicotinic Pharmacophore with a Series of (Isoxazole)methylene-1-azacyclic Compounds:  Synthesis, Structure−Activity Relationship, and Molecular Modeling
  作者：Janne E. Tønder、John Bondo Hansen、Mikael Begtrup、Ingrid Pettersson、Karin Rimvall、Birgitte Christensen、Ulrich Ehrbar、Preben H. Olesen

  DOI：10.1021/jm9910627

  日期：1999.12.2

  A series of (isoxazole)methylene-1-azacyclic compounds was prepared. The compounds were tested for affinity to central nicotinic acetylcholine receptors (nAChRs) and central muscarinic receptors. The compounds covered a broad range of affinities for the nAChRs (IC50 = 0.32 to >1000 nM), with selectivities for the nAChRs over the muscarinic receptors in the range of 3-183. The high-affinity compound (Z)-26 (3-(4-methyl-5-isoxazolyl)methylene-1-azabicyclo-[2.2.2]octane, IC50 = 3.2 nM) having only one energy minimum was used as the reference structure in a computational study. This ligand has enabled definition of an important distance parameter, and the existence of this parameter was supported by showing that other potent nicotinic ligands (for example, nicotine and epibatidine) fit the model.