trans-[2-(3-methoxyphenyl)cyclopropyl]methylamine hydrochloride | 1142815-95-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: trans-[2-(3-methoxyphenyl)cyclopropyl]methylamine hydrochloride
• 英文别名: [(1R,2R)-2-(3-methoxyphenyl)cyclopropyl]methanamine hydrochloride；[(1R,2R)-2-(3-methoxyphenyl)cyclopropyl]methanamine;hydrochloride
• CAS: 1142815-95-9
• 化学式: C₁₁H₁₅NO*ClH
• 分子量: 213.707
• InChiKey: ABWWRNPKXWVLTE-ROLPUNSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  14
• 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：
  35.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-[2-(3-methoxyphenyl)cyclopropyl]methylamine hydrochloride 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 trans-[2-(3-hydroxyphenyl)cyclopropyl]methylamine
  参考文献：
  名称：

  Selective 5-Hydroxytryptamine 2C Receptor Agonists Derived from the Lead Compound Tranylcypromine: Identification of Drugs with Antidepressant-Like Action

  摘要：

  We report here the design, synthesis, and pharmacological properties of a series of compounds related to tranylcypromine (9), which itself was discovered as a lead compound in a high-throughput screening campaign. Starting from 9, which shows modest activity as a 5-HT2C agonist, a series of 1-aminomethyl-2-phenylcyclopropanes was investigated as 5-HT2C agonists through iterative structural modifications. Key pharmacophore feature of this new class of ligands is a 2-aminomethyl-trans-cyclopropyl side chain attached to a substituted benzene ring. Among the tested compounds, several were potent and efficacious 5-HT2C receptor agonists with selectivity over both 5-HT2A and 5-HT2B receptors in functional assays. The most promising compound is 37, with 120- and 14-fold selectivity over 5-HT2A and 5-HT2B, respectively (EC50 = 585, 65, and 4.8 nM at the 2A, 2B, and 2C subtypes, respectively). In animal studies, compound 37 (10-60 mg/kg) decreased immobility time in the mouse forced swim test.

  DOI：

  10.1021/jm801354e