3-{[(5-amino-1,3,4-thiadiazol-2-yl)methyl]amino}-2-methylquinazolin-4(3H)-one | 518292-63-2

• 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-amino-1,3,4-thiadiazol-2-yl)methyl]amino}-2-methylquinazolin-4(3H)-one
• 英文别名: 3-[(5-amino-1,3,4-thiadiazol-2-yl)methylamino]-2-methylquinazolin-4(3H)-one；3-[(5-Amino-1,3,4-thiadiazol-2-yl)methylamino]-2-methylquinazolin-4-one
• CAS: 518292-63-2
• 化学式: C₁₂H₁₂N₆OS
• 分子量: 288.333
• InChiKey: DLBIWSOIPLJWBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-{[(5-amino-1,3,4-thiadiazol-2-yl)methyl]amino}-2-methylquinazolin-4(3H)-one 在 溶剂黄146 、 zinc(II) chloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 3-({4-[2-(4-hydroxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]-1,3,4-thiadiazol-2-yl}methylamino)-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：

  2-{[(2-methyl-4-oxoquinazolin-3(4H)-yl)amino]acetyl}hydrazinecarbothioamide 在 硫酸 作用下， 以65%的产率得到3-{[(5-amino-1,3,4-thiadiazol-2-yl)methyl]amino}-2-methylquinazolin-4(3H)-one
  参考文献：
  名称：

  合成一些取代的喹唑啉酮基-2-氧代/硫代巴比妥酸衍生物作为有效的抗惊厥药。

  摘要：

  筛选了所有新合成的化合物在MES和PTZ模型中的抗惊厥活性，并与标准药物苯妥英钠和丙戊酸钠进行比较。有趣的是，发现这些化合物在测试时没有镇静和催眠活性。在所研究的化合物中，活性最高的化合物5h是5- [2'-氨基-5'-[3“-氨基亚甲基-2”-甲基-6“，8”-二溴喹唑啉-4“（3” H ）-芳基] -1'，3'，4'-噻二唑-2'-基] -2-硫代巴比妥酸显示出比标准药物更强的活性（90％）。

  DOI：

  10.1016/j.bmc.2003.08.035

文献信息

• Synthesis of some newer derivatives of substituted quinazolinonyl-2-oxo/thiobarbituric acid as potent anticonvulsant agents
  作者：Archana、V.K Srivastava、Ashok Kumar

  DOI：10.1016/j.bmc.2003.08.035

  日期：2004.3

  5-[1'-[3"-Aminoacetyl-2"-methyl-6",8"-dihalosubstitutedquinazolin-4"(3"H)-onyl]-t hiosemicarbazido]-2-oxo/thiobarbituric acids 3a-3h and 5-[2'-amino-5'-[3"-aminomethylene-2"-methyl-6",8"-dihalosubstitutedquinazolin-4"( 3"H)-onyl]-1',3',4'-thiadiazol-2'-yl]-2-oxo/thiobarbituric acid 5a-5h were prepared by incorporating 1-[3'-aminoacetyl-2'-methyl-6",8"-dihalosubstituted-quinazolin-4'(3'H)-onyl]-thio semicarbazides

  筛选了所有新合成的化合物在MES和PTZ模型中的抗惊厥活性，并与标准药物苯妥英钠和丙戊酸钠进行比较。有趣的是，发现这些化合物在测试时没有镇静和催眠活性。在所研究的化合物中，活性最高的化合物5h是5- [2'-氨基-5'-[3“-氨基亚甲基-2”-甲基-6“，8”-二溴喹唑啉-4“（3” H ）-芳基] -1'，3'，4'-噻二唑-2'-基] -2-硫代巴比妥酸显示出比标准药物更强的活性（90％）。
• Synthesis of newer thiadiazolyl and thiazolidinonyl quinazolin-4(3H)-ones as potential anticonvulsant agents
  作者：Archana、V.K Srivastava、Ashok Kumar

  DOI：10.1016/s0223-5234(02)01389-2

  日期：2002.11

  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.
• Rajak, Harish; Thakur, Bhupendra S.; Kumar, Pramod, Acta poloniae pharmaceutica, 2012, vol. 69, # 2, p. 253 - 261
  作者：Rajak, Harish、Thakur, Bhupendra S.、Kumar, Pramod、Parmar, Poonam、Sharma, Prabodh Chander、Veerasamy, Ravichandran、Kharya, Murli Dhar

  DOI：——

  日期：——