2-Benzhydryl-N-(2-phenoxyethyl)aminoethyl ether

• 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: 2-Benzhydryl-N-(2-phenoxyethyl)aminoethyl ether
• 英文别名: 2-(benzhydryloxy)-N-(2-phenoxyethyl)ethan-1-amine；N-(2-benzhydryloxyethyl)-2-phenoxyethanamine
• 化学式: C₂₃H₂₅NO₂
• 分子量: 347.457
• InChiKey: IQXCFSVBYLKYNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  草酸 、 2-Benzhydryl-N-(2-phenoxyethyl)aminoethyl ether 以 乙醚 为溶剂， 反应 24.0h， 以55%的产率得到2-(benzhydryloxy)-N-(2-phenoxyethyl)ethan-1-ammonium hydrogen oxalate
  参考文献：
  名称：

  1,3-Dioxane as a scaffold for potent and selective 5-HT1AR agonist with in-vivo anxiolytic, anti-depressant and anti-nociceptive activity

  摘要：

  A series of compounds generated by ring expansion/opening and molecular elongation/simplification of the 1,3-dioxolane scaffold were prepared and tested for binding affinity at 5-HT1AR and alpha(1) adrenoceptors. The compounds with greater affinity were selected for further functional studies. N4(2,2-dipheny1-1,3-dioxan-5-yl)methyl)-2-(2-methoxyphenoxy)ethan-1-ammonium hydrogen oxalate (12) emerged as highly potent full agonist at the 5-HT1AR (pKi 5-HT1A = 8.8; pD(2) = 9.22, %E-max = 92). The pharmacokinetic data in rats showed that the orally administered 12 has a high biodistribution in the brain compartment. Thus, 12 was further investigated in-vivo, showing an anxiolytic and antidepressant effect. Moreover, in the formalin test, 12 was able to decrease the late response to the noxious stimulus, indicating a potent1Al use in the treatment of chronic pain. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.05.024
• 作为产物：
  描述：

  (2-溴乙氧基)(苯基)甲基]苯 在 氨 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 40.0h， 生成 2-Benzhydryl-N-(2-phenoxyethyl)aminoethyl ether
  参考文献：
  名称：

  部分二苯甲基衍生物的合成及Ca2+拮抗活性

  摘要：

  描述了一系列二苯甲基衍生物的制备。在豚鼠的大肠杆菌中评估了它们作为钙拮抗剂的活性。这些新化合物作为 Ca - 拮抗剂的活性低于 Cinnarizine。

  DOI：

  10.1002/ardp.19893221207

文献信息

• CORSANO, STEFANO;STRAPPAGHETTI, GIOVANNELLA;DOMENICO, ELSA DI;BRASILI, LI+, ARCH. PHARM., 322,(1989) N2, C. 873-878
  作者：CORSANO, STEFANO、STRAPPAGHETTI, GIOVANNELLA、DOMENICO, ELSA DI、BRASILI, LI+

  DOI：——

  日期：——
• 1,3-Dioxane as a scaffold for potent and selective 5-HT1AR agonist with in-vivo anxiolytic, anti-depressant and anti-nociceptive activity
  作者：Silvia Franchini、Claudia Sorbi、Pasquale Linciano、Gianluca Carnevale、Annalisa Tait、Simone Ronsisvalle、Michela Buccioni、Fabio Del Bello、Antonio Cilia、Lorenza Pirona、Nunzio Denora、Rosa Maria Iacobazzi、Livio Brasili

  DOI：10.1016/j.ejmech.2019.05.024

  日期：2019.8

  A series of compounds generated by ring expansion/opening and molecular elongation/simplification of the 1,3-dioxolane scaffold were prepared and tested for binding affinity at 5-HT1AR and alpha(1) adrenoceptors. The compounds with greater affinity were selected for further functional studies. N4(2,2-dipheny1-1,3-dioxan-5-yl)methyl)-2-(2-methoxyphenoxy)ethan-1-ammonium hydrogen oxalate (12) emerged as highly potent full agonist at the 5-HT1AR (pKi 5-HT1A = 8.8; pD(2) = 9.22, %E-max = 92). The pharmacokinetic data in rats showed that the orally administered 12 has a high biodistribution in the brain compartment. Thus, 12 was further investigated in-vivo, showing an anxiolytic and antidepressant effect. Moreover, in the formalin test, 12 was able to decrease the late response to the noxious stimulus, indicating a potent1Al use in the treatment of chronic pain. (C) 2019 Elsevier Masson SAS. All rights reserved.
• Synthesis and Ca-Antagonist Activity of Some Benzhydryl Derivatives
  作者：Stefano Corsano、Giovannella Strappaghetti、Elsa Di Domenico、Livio Brasili、Maria Teresa Picchio

  DOI：10.1002/ardp.19893221207

  日期：——

  The preparation of a series of benzhydryl derivatives is described. Their activities as Calcium‐antagonists were evaluated on the taenia coli of the guineapig. These new compunds show lower activities as Ca‐antagonists than Cinnarizine.

  描述了一系列二苯甲基衍生物的制备。在豚鼠的大肠杆菌中评估了它们作为钙拮抗剂的活性。这些新化合物作为 Ca - 拮抗剂的活性低于 Cinnarizine。