3-{[(2-Hydroxyphenyl)methylidene]amino}-1-(pyridin-4-yl)urea

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-{[(2-Hydroxyphenyl)methylidene]amino}-1-(pyridin-4-yl)urea
• 英文别名: 1-[(2-hydroxyphenyl)methylideneamino]-3-pyridin-4-ylurea
• 化学式: C₁₃H₁₂N₄O₂
• 分子量: 256.264
• InChiKey: UCDUYUHBSRPAQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-{[(2-Hydroxyphenyl)methylidene]amino}-1-(pyridin-4-yl)urea 在 chloroamine-T 作用下， 以0.228 g的产率得到2-(5-(pyridin-4-ylamino)-1,3,4-oxadiazol-2-yl)phenol
  参考文献：
  名称：

  Design and development of 1,3,4-oxadiazole derivatives as potential inhibitors of acetylcholinesterase to ameliorate scopolamine-induced cognitive dysfunctions

  摘要：

  The novel hybrids bearing 4-aminopyridine (4-AP) tethered with substituted 1,3,4-oxadiazole nucleus were designed, synthesized, and evaluated for their potential AChE inhibitory property along with significant antioxidant potential. The inhibitory potential (IC50) of synthesized analogs was evaluated against human choli-nesterases (hAChE and hBChE) using Ellman's method. Among all the compounds, 9 with 4-hydroxyl substituent showed maximum hAChE inhibition with the non-competitive type of enzyme inhibition (IC50 = 1.098 mu M; Ki = 0.960 mu M). Further, parallel artificial membrane permeation assay (PAMPA-BBB) showed significant BBB permeability in most of the synthesized compounds. Meanwhile, compound 9 also inhibited AChE-induced A beta aggregation (38.2-65.9%) by thioflavin T assay. The in vivo behavioral studies showed dose-dependent improvement in learning and memory by compound 9. The ex vivo studies also affirmed the significant AChE inhibition and antioxidant potential of compound 9 in brain homogenates.

  DOI：

  10.1016/j.bioorg.2019.103025
• 作为产物：
  描述：

  吡啶-4-氨基甲酸苯酯 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 3-{[(2-Hydroxyphenyl)methylidene]amino}-1-(pyridin-4-yl)urea
  参考文献：
  名称：

  Design and development of 1,3,4-oxadiazole derivatives as potential inhibitors of acetylcholinesterase to ameliorate scopolamine-induced cognitive dysfunctions

  摘要：

  The novel hybrids bearing 4-aminopyridine (4-AP) tethered with substituted 1,3,4-oxadiazole nucleus were designed, synthesized, and evaluated for their potential AChE inhibitory property along with significant antioxidant potential. The inhibitory potential (IC50) of synthesized analogs was evaluated against human choli-nesterases (hAChE and hBChE) using Ellman's method. Among all the compounds, 9 with 4-hydroxyl substituent showed maximum hAChE inhibition with the non-competitive type of enzyme inhibition (IC50 = 1.098 mu M; Ki = 0.960 mu M). Further, parallel artificial membrane permeation assay (PAMPA-BBB) showed significant BBB permeability in most of the synthesized compounds. Meanwhile, compound 9 also inhibited AChE-induced A beta aggregation (38.2-65.9%) by thioflavin T assay. The in vivo behavioral studies showed dose-dependent improvement in learning and memory by compound 9. The ex vivo studies also affirmed the significant AChE inhibition and antioxidant potential of compound 9 in brain homogenates.

  DOI：

  10.1016/j.bioorg.2019.103025