3-[5-[(E)-(3-hydroxyphenyl)methyleneamino]-1,3,4-oxadiazol-2-yl]chromen-2-one | 1182345-17-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-[5-[(E)-(3-hydroxyphenyl)methyleneamino]-1,3,4-oxadiazol-2-yl]chromen-2-one
• 英文别名: 3-[5-[(E)-(3-hydroxyphenyl)methylideneamino]-1,3,4-oxadiazol-2-yl]chromen-2-one
• CAS: 1182345-17-0
• 化学式: C₁₈H₁₁N₃O₄
• 分子量: 333.303
• InChiKey: LWVZVMBNNAGZMD-VXLYETTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  香豆素-3-羧酸乙酯 在 一水合肼 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 19.5h， 生成 3-[5-[(E)-(3-hydroxyphenyl)methyleneamino]-1,3,4-oxadiazol-2-yl]chromen-2-one
  参考文献：
  名称：

  Antimicrobial activity of Schiff bases of coumarin-incorporated 1,3,4-oxadiazole derivatives: an in vitro evaluation

  摘要：

  A series of 3-{5-[(E)-(substituted benzylidene) amino]-1,3,4-oxadiazol-2-yl}-2H-chromen-2-ones (4a-r) were synthesized by the reaction of 3-(5-amino]-1,3,4-oxadiazol-2-yl}-2H-chromen-2-one with different substituted benzaldehydes to form Schiff bases of coumarin-incorporated 1,3,4-oxadiazole derivatives. The structures of the compounds were confirmed on the basis of their elemental analysis and spectral data. The compounds were screened against bacterial strains Staphylococcus aureus NCTC (10418), Escherichia coli NCTC (6571), and fungal strain Candida albicans ATCC (10231). Ciprofloxacin and Ketoconazole were used as standards. The test compounds and standards were evaluated at 100 mu g/ml concentration. DMF (N,N-dimethylformamide) was used as solvent and control. Most of the synthesized compounds possess significant antimicrobial activity. Compound (4m) without any substitution of the phenyl ring which is attached to 1,3,4-oxadiazole moiety showed highly significant in vitro growth inhibition against S. aureus and E. coli, while as compound (4g) with para N(CH3)(2) showed highly significant in vitro growth inhibition against C. albicans.

  DOI：

  10.1007/s00044-012-0452-9

文献信息

• Synthesis and<i>In Vivo</i>Anticonvulsant Screening of Coumarin Incorporated Schiff Bases of 1,3,4-Oxadiazoles
  作者：Nadeem Siddiqui、Mashooq A. Bhat、Suroor A. Khan、Waquar Ahsan、M. Shamsher Alam

  DOI：10.1002/jccs.200800199

  日期：2008.12

  A series of coumarin incorporated Schiff bases of 1,3,4-oxadiazoles (1-18) was synthesized. The structures of the synthesized compounds were confirmed on the basis of spectral data and elemental analysis. The anticonvulsant and neurotoxicity was studied by maximal electroshock seizure (MES) and rotorod method, respectively. A majority of the compounds were active in MES test. All the compounds were

  合成了一系列含有香豆素的 1,3,4-恶二唑 (1-18) 席夫碱。基于光谱数据和元素分析确认了合成化合物的结构。分别通过最大电休克发作（MES）和转子法研究抗惊厥药和神经毒性。大多数化合物在MES测试中具有活性。所有化合物的神经毒性均低于标准药物苯妥英。
• Antimicrobial activity of Schiff bases of coumarin-incorporated 1,3,4-oxadiazole derivatives: an in vitro evaluation
  作者：Mashooq Ahmad Bhat、Mohamed A. Al-Omar、Nadeem Siddiqui

  DOI：10.1007/s00044-012-0452-9

  日期：2013.9

  A series of 3-5-[(E)-(substituted benzylidene) amino]-1,3,4-oxadiazol-2-yl}-2H-chromen-2-ones (4a-r) were synthesized by the reaction of 3-(5-amino]-1,3,4-oxadiazol-2-yl}-2H-chromen-2-one with different substituted benzaldehydes to form Schiff bases of coumarin-incorporated 1,3,4-oxadiazole derivatives. The structures of the compounds were confirmed on the basis of their elemental analysis and spectral data. The compounds were screened against bacterial strains Staphylococcus aureus NCTC (10418), Escherichia coli NCTC (6571), and fungal strain Candida albicans ATCC (10231). Ciprofloxacin and Ketoconazole were used as standards. The test compounds and standards were evaluated at 100 mu g/ml concentration. DMF (N,N-dimethylformamide) was used as solvent and control. Most of the synthesized compounds possess significant antimicrobial activity. Compound (4m) without any substitution of the phenyl ring which is attached to 1,3,4-oxadiazole moiety showed highly significant in vitro growth inhibition against S. aureus and E. coli, while as compound (4g) with para N(CH3)(2) showed highly significant in vitro growth inhibition against C. albicans.