5-oxo-7-phenyl-4,5,6,7-tetrahydro-1,2,4-triazolo[1,5-a]pyrimidine | 223647-73-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: 5-oxo-7-phenyl-4,5,6,7-tetrahydro-1,2,4-triazolo[1,5-a]pyrimidine
• 英文别名: 7-phenyl-4,5,6,7-tetrahydro-1,2,4-triazolo[1,5-a]pyrimidin-5-one；7-phenyl-6,7-dihydro-1,2,4-triazolo[1,5-a]-pyrimidin-5(4H)-one；7-phenyl-6,7-dihydro-1H-[1,2,4]triazolo[1,5-a]pyrimidin-5-one
• CAS: 223647-73-2
• 化学式: C₁₁H₁₀N₄O
• mdl: MFCD00720465
• 分子量: 214.227
• InChiKey: FZUNCZJIZJBBHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  59.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-oxo-7-phenyl-4,5,6,7-tetrahydro-1,2,4-triazolo[1,5-a]pyrimidine 在 一水合肼 作用下， 以 异丙醇 为溶剂， 反应 0.33h， 以77%的产率得到3-(5-amino-1,2,4-triazol-1-yl)-3-phenylpropionic acid hydrazide
  参考文献：
  名称：

  3-氨基-1,2,4-三唑与取代的肉桂酸和芳族不饱和酮的酯缩合

  摘要：

  DOI：

  10.1023/a:1017531803879
• 作为产物：
  描述：

  亚苯甲基丙二酸二乙酯 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 5-oxo-7-phenyl-4,5,6,7-tetrahydro-1,2,4-triazolo[1,5-a]pyrimidine
  参考文献：
  名称：

  Reactions of α-aminoazoles with diethyl benzylidenemalonate

  摘要：

  Cyclocondensations of diethyl benzylidenemalonate with 3-amino-5-methylpyrazole, 3,5-diamino-1,2,4-triazole, 3,4,5-triamino-1,2,4-triazole, and 2-amino-benzimidazole in alcohols take a single route and lead to the formation of functionally substituted partially hydrogenated pyrazolo-, triazolo[1,5-a]-pyrimidin-5-ones and pyrimido[1,2-a]benzimidazol-2-one respectively. From reaction mixtures involving 3-amino-1,2,4-triazole and its 5-methylsulfanyl analog in methanol the intermediate products of heterocyclization were isolated forming as a result of alkylation with the beta-carbon of the unsaturated ester the endocyclic nucleophilic sites of aminoazoles. The structure of one among the products obtained, diethyl (3-amino-5-methylsulfanyl-1,2,4-triazol-2-yl)benzylmalonate was proved by X-ray crystallography. In DMF the same reagents yielded mixtures of partially hydrogenated triazolo[1,5-a]pyrimidin-5-ones.

  DOI：

  10.1134/s1070428007020169

文献信息

• Synthesis and anticonvulsant activity of 7-phenyl-6,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-ones and their derivatives
  作者：Xian-Qing Deng、Li-Na Quan、Ming-Xia Song、Cheng-Xi Wei、Zhe-Shan Quan

  DOI：10.1016/j.ejmech.2011.04.020

  日期：2011.7

  Herein, we described the syntheses and anticonvulsant activities of 7-(substituted-phenyl)-6,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-ones (1a–1o) and their derivatives. Most of the synthesized compounds exhibited potent anticonvulsant activities in the maximal electroshock test (MES). The most promising compound 1i showed significant anticonvulsant activity in MES test with ED50 value of 19

  在这里，我们描述了7-（取代的苯基）-6,7-二氢-[1,2,4]三唑[1,5 - a ]嘧啶-5（4 H）-ones（1a – 1o）及其派生词。大多数合成的化合物在最大电击试验（MES）中均显示出强大的抗惊厥活性。最有希望的化合物1i在MES测试中显示出显着的抗惊厥活性，ED 50值为19.7 mg / kg。它显示出很大的安全性，保护指数远高于标准药物。此外，化合物1i的效力在化学诱导的癫痫发作试验中，针对由戊四唑，异烟肼，硫代氨基脲，3-巯基丙酸和Bi​​cuculline引起的癫痫发作表明，化合物1i在几种模型中均具有广谱活性，并且可能具有多种作用机制，包括抑制电压-门控离子通道和调节GABA能活性。
• Cyclecondensation of 3-amino-1,2,4-triazole with substituted methyl cinnamates
  作者：Sergey M. Desenko、Victoria V. Lipson、Oleg V. Shishkin、Sergey A. Komykhov、Valery D. Orlov、Evgeny E. Lakin、Valery P. Kuznetsov、Herbert Meier

  DOI：10.1002/jhet.5570360131

  日期：1999.1

  The reaction of 3-amino-1,2,4-triazole (1) with substituted methyl cinnamates 2a-h leads selectively to the formation of 7-aryl-6,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-ones 3a-h. The structure eluci dation of the products is based on ir, 1H and 13C nmr measurements and X-ray diffraction.

  3-氨基-1,2,4-三唑（1）与取代的肉桂酸酯2a-h的反应选择性地导致7-芳基-6,7-二氢[1,2,4]三唑[1， 5 - a ]嘧啶-5（4 H）-酮3a-h。产品的结构阐明是基于ir，1 H和13 C nmr测量以及X射线衍射。
• Reaction of arylidene derivatives of Meldrum's acid with 3-amino-1,2,4-triazole
  作者：V. V. Lipson、V. D. Orlov、S. M. Desenko、T. M. Karnozhitskaya、M. G. Shirobokova

  DOI：10.1007/bf02324645

  日期：1999.5
• Reactions of α-aminoazoles with diethyl benzylidenemalonate
  作者：V. V. Lipson、T. M. Karnozhitskaya、S. M. Desenko、S. V. Shishkina、O. E. Shishkin、V. I. Musatov

  DOI：10.1134/s1070428007020169

  日期：2007.2

  Cyclocondensations of diethyl benzylidenemalonate with 3-amino-5-methylpyrazole, 3,5-diamino-1,2,4-triazole, 3,4,5-triamino-1,2,4-triazole, and 2-amino-benzimidazole in alcohols take a single route and lead to the formation of functionally substituted partially hydrogenated pyrazolo-, triazolo[1,5-a]-pyrimidin-5-ones and pyrimido[1,2-a]benzimidazol-2-one respectively. From reaction mixtures involving 3-amino-1,2,4-triazole and its 5-methylsulfanyl analog in methanol the intermediate products of heterocyclization were isolated forming as a result of alkylation with the beta-carbon of the unsaturated ester the endocyclic nucleophilic sites of aminoazoles. The structure of one among the products obtained, diethyl (3-amino-5-methylsulfanyl-1,2,4-triazol-2-yl)benzylmalonate was proved by X-ray crystallography. In DMF the same reagents yielded mixtures of partially hydrogenated triazolo[1,5-a]pyrimidin-5-ones.
• ——
  作者：V. V. Lipson、S. M. Desenko、V. D. Orlov、O. V. Shishkin、M. G. Shirobokova、V. N. Chernenko、L. I. Zinov'eva

  DOI：10.1023/a:1017531803879

  日期：——