5-({[2-(2-methoxyphenoxy)ethyl]amino}methyl)-2,2-diphenylcyclopentan-1-one oxalate | 1353573-85-9

• 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: 5-({[2-(2-methoxyphenoxy)ethyl]amino}methyl)-2,2-diphenylcyclopentan-1-one oxalate
• 英文别名: 5-[[2-(2-Methoxyphenoxy)ethylamino]methyl]-2,2-diphenylcyclopentan-1-one;oxalic acid
• CAS: 1353573-85-9
• 化学式: C₂H₂O₄*C₂₇H₂₉NO₃
• 分子量: 505.568
• InChiKey: FBIXRCIDRBFTIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,2-二苯基己烷-1,6-二腈 在 硫酸 、 sodium amide 作用下， 以 乙醚 、 乙醇 、 水 、 甲苯 为溶剂， 反应 36.0h， 生成 5-({[2-(2-methoxyphenoxy)ethyl]amino}methyl)-2,2-diphenylcyclopentan-1-one oxalate
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Docking Studies of Tetrahydrofuran- Cyclopentanone- and Cyclopentanol-Based Ligands Acting at Adrenergic α₁- and Serotonine 5-HT_1A Receptors

  摘要：

  A series of aralkylphenoxyethylamine and aralkylmethoxyphenylpiperazine compounds was synthesized and their in vitro pharmacological profile at both 5-HT1A receptors and alpha(1)-adrenoceptor subtypes was measured by binding assay and functional studies. The results showed that the replacement of the 1,3-dioxolane ring by a tetrahydrofuran, cyclopentanone, or cyclopentanol moiety leads to an overall reduction of in vitro affinity at the alpha(1)-adrenoceptor while both potency and efficacy were increased at the 5-HT1A receptor. A significant improvement of 5-HT1A/alpha 1 selectivity was observed in some of the cyclopentanol derivatives synthesized (4a cis, 4c cis and trans). Compounds 2a and 4c cis emerged as novel and interesting 5-HT1A receptor antagonist (pK(i) = 8.70) and a 5-HT1A receptor partial agonist (pK(i) = 9.25, pD(2) = 9.03, E-max = 47%, 5-HT1A/alpha 1a = 69), respectively. Docking studies were performed at support of the biological data and to elucidate the molecular basis for 5-HT1A agonism/antagonism activity.

  DOI：

  10.1021/jm200421e

文献信息

• Synthesis, Biological Evaluation, and Docking Studies of Tetrahydrofuran- Cyclopentanone- and Cyclopentanol-Based Ligands Acting at Adrenergic α₁- and Serotonine 5-HT_1A Receptors
  作者：Adolfo Prandi、Silvia Franchini、Leda Ivanova Manasieva、Paola Fossa、Elena Cichero、Gabriella Marucci、Michela Buccioni、Antonio Cilia、Lorenza Pirona、Livio Brasili

  DOI：10.1021/jm200421e

  日期：2012.1.12

  A series of aralkylphenoxyethylamine and aralkylmethoxyphenylpiperazine compounds was synthesized and their in vitro pharmacological profile at both 5-HT1A receptors and alpha(1)-adrenoceptor subtypes was measured by binding assay and functional studies. The results showed that the replacement of the 1,3-dioxolane ring by a tetrahydrofuran, cyclopentanone, or cyclopentanol moiety leads to an overall reduction of in vitro affinity at the alpha(1)-adrenoceptor while both potency and efficacy were increased at the 5-HT1A receptor. A significant improvement of 5-HT1A/alpha 1 selectivity was observed in some of the cyclopentanol derivatives synthesized (4a cis, 4c cis and trans). Compounds 2a and 4c cis emerged as novel and interesting 5-HT1A receptor antagonist (pK(i) = 8.70) and a 5-HT1A receptor partial agonist (pK(i) = 9.25, pD(2) = 9.03, E-max = 47%, 5-HT1A/alpha 1a = 69), respectively. Docking studies were performed at support of the biological data and to elucidate the molecular basis for 5-HT1A agonism/antagonism activity.