(5,5-diphenyloxolan-2-yl)methyl 4-methylbenzene-1-sulfonate | 1353573-44-0

• 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: (5,5-diphenyloxolan-2-yl)methyl 4-methylbenzene-1-sulfonate
• 英文别名: (5,5-Diphenyloxolan-2-yl)methyl 4-methylbenzenesulfonate
• CAS: 1353573-44-0
• 化学式: C₂₄H₂₄O₄S
• 分子量: 408.518
• InChiKey: FYSWTXOGBYYKGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5,5-diphenyloxolan-2-yl)methyl 4-methylbenzene-1-sulfonate 以 乙醚 、 N,N-二甲基甲酰胺 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：

  对甲苯磺酰氯 、 2,2-diphenyl-5-hydroxymethyltetrahydrofuran 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 24.5h， 以62%的产率得到(5,5-diphenyloxolan-2-yl)methyl 4-methylbenzene-1-sulfonate
  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

• Scouting new sigma receptor ligands: Synthesis, pharmacological evaluation and molecular modeling of 1,3-dioxolane-based structures and derivatives
  作者：Silvia Franchini、Umberto Maria Battisti、Adolfo Prandi、Annalisa Tait、Chiara Borsari、Elena Cichero、Paola Fossa、Antonio Cilia、Orazio Prezzavento、Simone Ronsisvalle、Giuseppina Aricò、Carmela Parenti、Livio Brasili

  DOI：10.1016/j.ejmech.2016.01.059

  日期：2016.4

  Herein we report the synthesis and biological activity of new sigma receptor (σR) ligands obtained by combining different substituted five-membered heterocyclic rings with appropriate σR pharmacophoric amines. Radioligand binding assay, performed on guinea pig brain membranes, identified 25b (1-(1,4-dioxaspiro[4.5]decan-2-ylmethyl)-4-benzylpiperazine) as the most interesting compound of the series

  本文中，我们报告了通过将不同的取代五元杂环与适当的σR药效学胺结合而获得的新sigma受体（σR）配体的合成和生物学活性。在豚鼠脑膜上进行的放射性配体结合测定法确定了25b（1-（1,4-dioxaspiro [4.5] decan-2-ylmethyl）-4-苄基哌嗪）是该系列中最有趣的化合物，显示出高亲和力和选择性为σ 1个R（的pK我σ 1  = 9.13;σ 1 /σ 2  = 47）。在体内评估了25b调节κ激动剂（-）-U-50,488H和μ激动剂吗啡的镇痛作用的能力通过辐射热甩尾测试。它显示出在两个κ和μ受体介导的镇痛的抗阿片作用，这表明在σ激动行为1 R.对接研究的理论σ进行1 - [R同源模型。目前的工作表示用于更有效和选择性σ的设计一个新的起点1 - [R配体。