ethyl N-(3,4-dihydro-2-methyl-4-oxoquinazolin-3-yl)glycinate | 518292-59-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl N-(3,4-dihydro-2-methyl-4-oxoquinazolin-3-yl)glycinate
• 英文别名: ethyl 2-(2-methyl-4-oxoquinazolin-3(4H)-ylamino)acetate；ethyl [(2-methyl-4-oxoquinazolin-3(4H)-yl)amino]acetate；Ethyl 2-(2-methyl-4-oxoquinazolin-3(4h)-ylamino) acetate；ethyl 2-[(2-methyl-4-oxoquinazolin-3-yl)amino]acetate
• CAS: 518292-59-6
• 化学式: C₁₃H₁₅N₃O₃
• 分子量: 261.28
• InChiKey: SDFJCXMZEDHFMR-UHFFFAOYSA-N

物化性质

• 熔点：
  122 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  407.0±47.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl N-(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]-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：

  邻乙酰胺苯甲酸內酯 在 potassium carbonate 、 一水合肼 作用下， 以 丙酮 为溶剂， 反应 15.0h， 生成 ethyl N-(3,4-dihydro-2-methyl-4-oxoquinazolin-3-yl)glycinate
  参考文献：
  名称：

  2-{2"-carbomyl-5"-[3'-amino-2'-methylmono/Dihalosubstituted Quinazolin-4'(3’h)-onome thylene]-1",3",4"-oxadiazol-2"-yl}-4,5-dihydroimidazolines as Potential Antihypertensive Agents

  摘要：

  制备并评价了12种新的2-{2"-羧基-5"-[3'-氨基-2'-甲基单/二卤代喹唉-4'(3'H)-亚甲基]-",3",4"-噁二唑-2"-基}-4,5-二氢咪唑啉的心血管活性。其中最活性的化合物为2-{2"-羧基-5"-[3'-氨基-2'-甲基-6-溴喹唑啉-4'(3'H)-亚甲基]-",3",4"-噁二唑-2"-基}-4,5-二氢咪唑啉，即化合物VIc。

  DOI：

  10.13005/ojc/300243

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％）。
• Antitumor and antileishmanial evaluation of novel heterocycles derived from quinazoline scaffold: a molecular modeling approach
  作者：Daisy H. Fleita、Rafat M. Mohareb、Ola K. Sakka

  DOI：10.1007/s00044-012-0213-9

  日期：2013.5

  Novel thiazole, pyrimidine and benzylidene derivatives derived from quinazoline scaffold have been synthesized. The antitumor evaluation of the newly synthesized products against three cancer cell lines namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460), and CNS cancer (SF-268) showed that the benzylidene-quinazoline derivative 12a showed remarkable activity against all three cell lines. The thiazolo-quinazoline derivative 10 showed greater activity than the control against breast adenocarcinoma (MCF-7) with a concentration of 0.01 mu M. Moreover, the antileishmanial activity of the newly synthesized products tested on Leishmania donovani amastigotes showed that compounds 4, 14, and 18 had very promising activity.
• 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：——