3-[(5-benzylideneamino-1,3,4-thiadiazol-2-yl)methylamino]-6-bromo-2-methylquinazolin-4(3H)-one | 518292-71-2

• 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: 3-[(5-benzylideneamino-1,3,4-thiadiazol-2-yl)methylamino]-6-bromo-2-methylquinazolin-4(3H)-one
• 英文别名: 3-[[5-(Benzylideneamino)-1,3,4-thiadiazol-2-yl]methylamino]-6-bromo-2-methylquinazolin-4-one
• CAS: 518292-71-2
• 化学式: C₁₉H₁₅BrN₆OS
• 分子量: 455.338
• InChiKey: BCMQGAVESRMZSC-UHFFFAOYSA-N

物化性质

• 熔点：
  64 °C(Solv: methanol (67-56-1))
• 沸点：
  640.4±65.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  85.06
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  巯基乙酸 、 3-[(5-benzylideneamino-1,3,4-thiadiazol-2-yl)methylamino]-6-bromo-2-methylquinazolin-4(3H)-one 在 zinc(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以62%的产率得到3-({4-[2-phenyl-4-oxo-1,3-thiazolidin-3-yl]-1,3,4-thiadiazol-2-yl}methylamino)-6-bromo-2-methylquinazolin-4(3H)-one
  参考文献：
  名称：

  Synthesis of newer thiadiazolyl and thiazolidinonyl quinazolin-4(3H)-ones as potential anticonvulsant agents

  摘要：

  A series of 3-{[5-(alkylbenzylideneamino)-1,3,4-thiadiazol-2-yl]methylamino}-2-methyl-6-monosubstitutedquinazolin-4(3 H)-one (4a-4l) have been synthesized via condensation of 3-[(5-amino-1,3,4-thiadiazol-2-yl)methylamino]-2-methyl-6-monosubstitutedquinazolin-4(3H)-one (3a-3b) with various aromatic aldehydes. Cycloaddition of thioglycolic acid with 4a-4l yielded 3-({4-[2(alkylphenyl)-4-oxo-1,3-thiazolidin-3-yl]-1,3,4-thiadiazol-2-yl}methylamino)-2-methyl-6-monosubstitutedquinazolin-4(3H)-one (5a-5l). The compounds were screened for their anticonvulsant activity and were compared with the standard drugs, phenytoin sodium, lamotrigine and sodium valproate. Out of the 30 compounds the most active compound was 3-({4-[2-(m-methoxy p-hydroxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]-1,3,4-thiadiazol-2-yl}methylamino)-2-methyl-6-bromo-quinazolin-4(3H)-one (5l). (C) 2002 Published by Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(02)01389-2
• 作为产物：
  描述：

  ethyl N-(6-bromo-3,4-dihydro-2-methyl-4-oxoquinazolin-3-yl)glycinate 在 硫酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 23.0h， 生成 3-[(5-benzylideneamino-1,3,4-thiadiazol-2-yl)methylamino]-6-bromo-2-methylquinazolin-4(3H)-one
  参考文献：
  名称：

  Synthesis of newer thiadiazolyl and thiazolidinonyl quinazolin-4(3H)-ones as potential anticonvulsant agents

  摘要：

  A series of 3-{[5-(alkylbenzylideneamino)-1,3,4-thiadiazol-2-yl]methylamino}-2-methyl-6-monosubstitutedquinazolin-4(3 H)-one (4a-4l) have been synthesized via condensation of 3-[(5-amino-1,3,4-thiadiazol-2-yl)methylamino]-2-methyl-6-monosubstitutedquinazolin-4(3H)-one (3a-3b) with various aromatic aldehydes. Cycloaddition of thioglycolic acid with 4a-4l yielded 3-({4-[2(alkylphenyl)-4-oxo-1,3-thiazolidin-3-yl]-1,3,4-thiadiazol-2-yl}methylamino)-2-methyl-6-monosubstitutedquinazolin-4(3H)-one (5a-5l). The compounds were screened for their anticonvulsant activity and were compared with the standard drugs, phenytoin sodium, lamotrigine and sodium valproate. Out of the 30 compounds the most active compound was 3-({4-[2-(m-methoxy p-hydroxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]-1,3,4-thiadiazol-2-yl}methylamino)-2-methyl-6-bromo-quinazolin-4(3H)-one (5l). (C) 2002 Published by Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(02)01389-2