4-(6,8-dibromo-2-methyl-4-oxoquinazolin-3(4H)-yl)benzoic acid | 24295-52-1

• 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: 4-(6,8-dibromo-2-methyl-4-oxoquinazolin-3(4H)-yl)benzoic acid
• 英文别名: 2-Methyl-3-(p-carboxyphenyl)-6,8-dibrom-3H-4-chinazolon；4-(6,8-dibromo-2-methyl-4-oxo-4H-quinazolin-3-yl)-benzoic acid；4-(6,8-Dibromo-2-methyl-4-oxoquinazolin-3-yl)benzoic acid
• CAS: 24295-52-1
• 化学式: C₁₆H₁₀Br₂N₂O₃
• 分子量: 438.075
• InChiKey: ILXHECQKBIFBNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(6,8-dibromo-2-methyl-4-oxoquinazolin-3(4H)-yl)benzoic acid 在 氯化亚砜 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 6,8-dibromo-2-methyl-3-(4-(3-phenyl-5-p-tolyl-4,5-dihydro-1H-pyrazole-1-carbonyl)phenyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of novel quinazolin-4(3H)-one derived pyrazole analogs

  摘要：

  Eighteen novel 6,8-(dibromo/unsubstituted)-2-(methyl/phenyl)-3-(4-(5-(substitutedphenyl)-3-phenyl-4,5-dihydro-1H-pyrazole-1-carbonyl)phenyl)-quinazolin-4(3H)-ones 4a-4r were designed and synthesized in good yield. Antiepileptic screening of the title compounds was performed using MES and scPTZ seizures tests while the neurotoxicity was determined by rotorod test. In the preliminary screening, compounds 4d, 4e, 4p, 4q, and 4r were found active in MES model, while 4a, 4d, 4f, 4m, and 4p showed significant antiepileptic activity in scPTZ model. Further, all these eight compounds were administered to rats and compounds 4e, 4p, and 4q showed better activity than Phenytoin in oral route. Among these compounds 4p revealed protection in MES after i.p. administration at a dose of 30 mg/kg (0.5 h) and 100 mg/kg (4 h). The compound 4p also provided protection in the scPTZ at a dose of 100 mg/kg (0.5 h) and 300 mg/kg (4 h).

  DOI：

  10.1007/s00044-012-0169-9
• 作为产物：
  描述：

  2-氨基-3,5-二溴苯甲酸 以 溶剂黄146 为溶剂， 反应 8.0h， 生成 4-(6,8-dibromo-2-methyl-4-oxoquinazolin-3(4H)-yl)benzoic acid
  参考文献：
  名称：

  Mishra, Pradeep; Paneerselvam, P.; Jain, Sandeep, Journal of the Indian Chemical Society, 1995, vol. 72, # 8, p. 559 - 560

  摘要：

  DOI：

文献信息

• Mishra, Pradeep; Paneerselvam, P.; Jain, Sandeep, Journal of the Indian Chemical Society, 1995, vol. 72, # 8, p. 559 - 560
  作者：Mishra, Pradeep、Paneerselvam, P.、Jain, Sandeep

  DOI：——

  日期：——
• Panda; Srinivas; Rao, M.E. Bhanoji, Journal of the Indian Chemical Society, 2002, vol. 79, # 9, p. 770 - 771
  作者：Panda、Srinivas、Rao, M.E. Bhanoji、Panda

  DOI：——

  日期：——
• Synthesis and anticonvulsant activity of novel quinazolin-4(3H)-one derived pyrazole analogs
  作者：Veerachamy Alagarsamy、Govindaraj Saravanan

  DOI：10.1007/s00044-012-0169-9

  日期：2013.4

  Eighteen novel 6,8-(dibromo/unsubstituted)-2-(methyl/phenyl)-3-(4-(5-(substitutedphenyl)-3-phenyl-4,5-dihydro-1H-pyrazole-1-carbonyl)phenyl)-quinazolin-4(3H)-ones 4a-4r were designed and synthesized in good yield. Antiepileptic screening of the title compounds was performed using MES and scPTZ seizures tests while the neurotoxicity was determined by rotorod test. In the preliminary screening, compounds 4d, 4e, 4p, 4q, and 4r were found active in MES model, while 4a, 4d, 4f, 4m, and 4p showed significant antiepileptic activity in scPTZ model. Further, all these eight compounds were administered to rats and compounds 4e, 4p, and 4q showed better activity than Phenytoin in oral route. Among these compounds 4p revealed protection in MES after i.p. administration at a dose of 30 mg/kg (0.5 h) and 100 mg/kg (4 h). The compound 4p also provided protection in the scPTZ at a dose of 100 mg/kg (0.5 h) and 300 mg/kg (4 h).