N-(4-methoxyphenyl)-5-(4-methylphenyl)-1,3,4-oxadiazol-2-amine | 1257257-02-5

• 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: N-(4-methoxyphenyl)-5-(4-methylphenyl)-1,3,4-oxadiazol-2-amine
• 英文别名: N-(4-methoxyphenyl)-5-p-tolyl-1,3,4-oxadiazol-2-amine
• CAS: 1257257-02-5
• 化学式: C₁₆H₁₅N₃O₂
• 分子量: 281.314
• InChiKey: NYOLVUJVQAIMLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-methoxyphenyl isoselenocyanate 、 对甲苯甲酰肼 在 air 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以97%的产率得到N-(4-methoxyphenyl)-5-(4-methylphenyl)-1,3,4-oxadiazol-2-amine
  参考文献：
  名称：

  Synthesis of 2-amino-1,3,4-oxadiazoles from isoselenocyanates via cyclodeselenization

  摘要：

  An efficient one-pot method to access 2-amino-1,3,4-oxadiazoles from isoselenocyanates and hydrazides or dihydrazides was developed via cyclodeselenization. Without any harsh reagents, various 2-amino-1,3,4-oxadiazoles were obtained in considerably high yields (82%-97%) and purities (>99%) directly with simple crystallization in ethanol. And the formed precipitated Se powder during the reaction could be recycled for preparation of isoselenocyanates efficiently. A plausible mechanism is proposed for the formation of the target products. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.100

文献信息

• Discovery of Novel GSK-3β Inhibitors with Potent in Vitro and in Vivo Activities and Excellent Brain Permeability Using Combined Ligand- and Structure-Based Virtual Screening
  作者：Mohammad A. Khanfar、Ronald A. Hill、Amal Kaddoumi、Khalid A. El Sayed

  DOI：10.1021/jm100941j

  日期：2010.12.23

  Dysregulation of glycogen synthase kinase (GSK-3 beta) is implicated in the pathophysiology of many diseases, including type-2 diabetes, stroke, Alzheimer's, and others. A multistage virtual screening strategy designed so as to overcome known caveats arising from the considerable flexibility of GSK-3 beta yielded, from among compounds in our in-house database and two commercial databases, new GSK-3 beta inhibitors with novel scaffold structures. The two most potent and selective validated hits, a 2-anilino-5-phenyl-1,3,4-oxadiazole (24) and a phenylmethylene hydantoin (28), both exhibited nanomolar affinity and selectivity over CDK2 and were potent enough for direct in vivo validation. Both were able to cause significant increases in liver glycogen accumulation in dose-dependent fashion. One also exhibited excellent blood-brain barrier permeability, the other adequate for a lead compound. Analogues of the oxadiazole 24 were synthesized to experimentally corroborate or rule out ligand-bound structures arising from docking studies. SAR results supported one docking study among a number of alternatives.
• Synthesis of 2-amino-1,3,4-oxadiazoles from isoselenocyanates via cyclodeselenization
  作者：Yuanyuan Xie、Junli Liu、Ping Yang、Xiangjun Shi、Jianjun Li

  DOI：10.1016/j.tet.2011.05.100

  日期：2011.7

  An efficient one-pot method to access 2-amino-1,3,4-oxadiazoles from isoselenocyanates and hydrazides or dihydrazides was developed via cyclodeselenization. Without any harsh reagents, various 2-amino-1,3,4-oxadiazoles were obtained in considerably high yields (82%-97%) and purities (>99%) directly with simple crystallization in ethanol. And the formed precipitated Se powder during the reaction could be recycled for preparation of isoselenocyanates efficiently. A plausible mechanism is proposed for the formation of the target products. (C) 2011 Elsevier Ltd. All rights reserved.