N-[3-(p-anisyl)-1,2,4-oxadiazol-5-yl-methyl]phthalimide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-[3-(p-anisyl)-1,2,4-oxadiazol-5-yl-methyl]phthalimide
• 英文别名: 2-{[3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl]methyl}-1H-isoindole-1,3(2H)-dione；2-[[3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl]methyl]isoindole-1,3-dione
• 化学式: C₁₈H₁₃N₃O₄
• mdl: MFCD05853939
• 分子量: 335.319
• InChiKey: LEZMJMGYBFDCRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  85.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[3-(p-anisyl)-1,2,4-oxadiazol-5-yl-methyl]phthalimide 在 一水合肼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 4-chloro-N-{[3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl]methyl}benzenesulfonamide
  参考文献：
  名称：

  Synthesis, Molecular Docking, Analgesic, and Anti-Inflammatory Activities of New 1,2,4-Oxadiazolo-Sulfonamides

  摘要：

  In the present study novel 1,2,4-oxadiazolo sulfonamides 3a-3o are synthesized by an efficient method based on the reaction of 1,2,4-oxadiazole amines with aryl sulfonyl chlorides. Structures of the synthesized compounds are confirmed by IR, NMR and Mass spectra. Molecular interactions of the obtained compounds are studied by Discovery Studio v3.5, molecular docking with COX-2 enzyme. The compounds with high LibDock score are screened for their in vivo analgesic and anti inflammatory activities. The compound 3l demonstrates the highest activity.

  DOI：

  10.1134/s1070363218040278
• 作为产物：
  描述：

  邻苯二甲酰甘氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 乙二醇二甲醚 为溶剂， 生成 N-[3-(p-anisyl)-1,2,4-oxadiazol-5-yl-methyl]phthalimide
  参考文献：
  名称：

  具有有效止痛活性的新型邻苯二甲酰亚胺衍生物：II。

  摘要：

  由N-邻苯二甲酰基甘氨酸6和芳酰胺基肟7a-g合成了七个新的具有与氮相连的1,2,4-恶二唑-5-基甲基的邻苯二甲酰亚胺衍生物（9a-g）。所有这些都显示了乙酸引起的小鼠“扭体”试验的有效镇痛作用。发现更好的化合物之一（ID50 = 2.2 mg / Kg ip）为9a，它也显示出抗炎性疼痛的镇痛活性。

  DOI：

  10.1016/s0960-894x(98)00558-7

文献信息

• Synthesis, characterization and interaction mechanism of new oxadiazolo-phthalimides as peripheral analgesics. IV
  作者：Roberto Antunes、Hildson Batista、Rajendra M. Srivastava、George Thomas、Clidenor C. Araújo、Ricardo L. Longo、Hélio Magalhães、Marcelo B.C. Leão、Antônio C. Pavão

  DOI：10.1016/s0022-2860(03)00418-6

  日期：2003.11

  The synthesis, characterization and spectroscopic studies of compounds 6a-g with analgesic activity is described. A new model of interaction between the drug and the enzyme is suggested. Application of the Resonance Valence Bond theory led us to propose. for the first time, an entirely new mechanism involving an electron transfer from the amino acid residue of the enzyme to the drug. Theoretical studies of various transition states involved in the interaction mechanism employing the semi-empirical molecular orbital calculations (AMI method) have been carried out. This article also deals with an extensive study of the structure-activity relationships of seven oxadiazolo-phthalimides 6a-g. (C) 2003 Elsevier B.V. All rights reserved.