5-(chloromethyl)-2,2-diphenyloxolane | 1353573-40-6

• 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-(chloromethyl)-2,2-diphenyloxolane
• CAS: 1353573-40-6
• 化学式: C₁₇H₁₇ClO
• 分子量: 272.774
• InChiKey: ROZPSHUMGCNMMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  5-(chloromethyl)-2,2-diphenyloxolane 以 乙醚 、 甲乙醚 为溶剂， 生成 1-[(5,5-diphenyloxolan-2-yl)methyl]-4-(2-methoxyphenyl)piperazine 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
• 作为产物：
  描述：

  2,2-diphenyl-5-hydroxymethyltetrahydrofuran 在 吡啶 、 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 1.25h， 以50%的产率得到5-(chloromethyl)-2,2-diphenyloxolane
  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