2-Methyl-3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]quinazolin-4-one | 1048339-54-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-Methyl-3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]quinazolin-4-one
• 英文别名: 2-methyl-3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]quinazolin-4-one
• CAS: 1048339-54-3
• 化学式: C₁₈H₁₄N₄O₂
• 分子量: 318.335
• InChiKey: FTFFRJHSIOKJPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Methyl-3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]quinazolin-4-one 、 4-氯苯甲醛 以 溶剂黄146 为溶剂， 反应 18.0h， 以46.93%的产率得到2-[(E)-2-(4-chlorophenyl)ethenyl]-3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]quinazolin-4-one
  参考文献：
  名称：

  Synthesis and antimicrobial activity of some new 3–[5-(4-substituted) phenyl-1,3,4-oxadiazole-2yl]-2- styrylquinazoline-4(3H)-ones

  摘要：

  Several 3-[5-(4-substituted)phenyl-1,3,4-oxadiazole-2-yl]-2-styryl quinazoline-4(3H)-one were synthesized and screened for antibacterial activity against Staphylococcus aureus , Bacillus subtilis, Pseudomonas aeruginosa, and Escherichia coli and antifungal activity against Aspergillus niger and Fusariumoxysporum by the serial dilution technique. Compounds were prepared by reacting corresponding 2-methtyl quinazolinone and 4-subustituted benzaldehydes in glacial acetic acid. Physicochemical and spectral data were consistent with newly synthesized compounds. The prepared compounds were compared with previously synthesized 2-methyl-3-[5-(4-substituted)phenyl-1,3,4-oxadiazole-2-yl]-quinazoline-4(3H)-ones for antimicrobial activity. The present study revealed that styryl moiety at the second position of 4(3H) quinazolinone marginally increased the biological activity and exhibited better antibacterial than antifungal activities.

  DOI：

  10.1007/s00044-007-9054-3
• 作为产物：
  描述：

  邻乙酰胺苯甲酸內酯 、 5-(4-甲基苯基)-1,3,4-噁二唑-2-胺 以 溶剂黄146 为溶剂， 反应 4.0h， 生成 2-Methyl-3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]quinazolin-4-one
  参考文献：
  名称：

  Synthesis and antimicrobial activity of some new 3–[5-(4-substituted) phenyl-1,3,4-oxadiazole-2yl]-2- styrylquinazoline-4(3H)-ones

  摘要：

  Several 3-[5-(4-substituted)phenyl-1,3,4-oxadiazole-2-yl]-2-styryl quinazoline-4(3H)-one were synthesized and screened for antibacterial activity against Staphylococcus aureus , Bacillus subtilis, Pseudomonas aeruginosa, and Escherichia coli and antifungal activity against Aspergillus niger and Fusariumoxysporum by the serial dilution technique. Compounds were prepared by reacting corresponding 2-methtyl quinazolinone and 4-subustituted benzaldehydes in glacial acetic acid. Physicochemical and spectral data were consistent with newly synthesized compounds. The prepared compounds were compared with previously synthesized 2-methyl-3-[5-(4-substituted)phenyl-1,3,4-oxadiazole-2-yl]-quinazoline-4(3H)-ones for antimicrobial activity. The present study revealed that styryl moiety at the second position of 4(3H) quinazolinone marginally increased the biological activity and exhibited better antibacterial than antifungal activities.

  DOI：

  10.1007/s00044-007-9054-3

文献信息

• Synthesis and antimicrobial activity of some new 3–[5-(4-substituted) phenyl-1,3,4-oxadiazole-2yl]-2- styrylquinazoline-4(3H)-ones
  作者：Vivek Gupta、Sushil K. Kashaw、Varsha Jatav、Pradeep Mishra

  DOI：10.1007/s00044-007-9054-3

  日期：2008.6

  Several 3-[5-(4-substituted)phenyl-1,3,4-oxadiazole-2-yl]-2-styryl quinazoline-4(3H)-one were synthesized and screened for antibacterial activity against Staphylococcus aureus , Bacillus subtilis, Pseudomonas aeruginosa, and Escherichia coli and antifungal activity against Aspergillus niger and Fusariumoxysporum by the serial dilution technique. Compounds were prepared by reacting corresponding 2-methtyl quinazolinone and 4-subustituted benzaldehydes in glacial acetic acid. Physicochemical and spectral data were consistent with newly synthesized compounds. The prepared compounds were compared with previously synthesized 2-methyl-3-[5-(4-substituted)phenyl-1,3,4-oxadiazole-2-yl]-quinazoline-4(3H)-ones for antimicrobial activity. The present study revealed that styryl moiety at the second position of 4(3H) quinazolinone marginally increased the biological activity and exhibited better antibacterial than antifungal activities.
• Anticonvulsant and sedative-hypnotic activity of some novel 3-[5-(4-substituted) phenyl-1,3,4-oxadiazole-2yl]-2-styrylquinazoline-4(3H)-ones
  作者：Sushil K. Kashaw、Vivek Gupta、Varsha Kashaw、P. Mishra、J. P. Stables、N. K. Jain

  DOI：10.1007/s00044-009-9188-6

  日期：2010.4

  A few novel 3-[5-(4-substituted) phenyl-1,3,4-oxadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones were synthesized and evaluated for anticonvulsant, neurotoxicity, sedative-hypnotic, and phenobarbitone-induced hypnosis potentiation test. After i.p. injection to mice at doses of 30, 100, and 300 mg/kg body weight derivatives were examined in the maximal electroshock-induced seizures (MES) and subcutaneous pentylenetetrazole (scPTZ)-induced seizure models in mice. Spectroscopic data were consistence with the newly synthesized compounds. The neurotoxicity was assessed using the Rotorod method. Out of 15 compounds only 7e and 7o showed anticonvulsant activity at various doses in one or more test models. All except 7d, 7m, and 7n exhibited significant sedative-hypnotic activity via actophotometer screen. Central nervous system (CNS)-depressant activity screened with the help of the forced swim method resulted into some potent compounds. No percentage increase in the sleeping time was observed in any of the synthesized compounds evaluated by the phenobarbitone-induced hypnosis potentiation test. On the basis of experimental data, it can be concluded that synthesized compounds possessed relatively better sedative-hypnotic and CNS-depressant activities.