3-acetyl-7-amino-1-phenyl-[1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-one | 499795-63-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-acetyl-7-amino-1-phenyl-[1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-one
• 英文别名: 3-Acetyl-7-amino-1-phenyl-[1,2,4]triazolo[4,3-a]pyrimidin-5-one
• CAS: 499795-63-0
• 化学式: C₁₃H₁₁N₅O₂
• 分子量: 269.263
• InChiKey: CVHVJUXQZCPAHB-UHFFFAOYSA-N

物化性质

• 沸点：
  413.9±48.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  91.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-acetyl-7-amino-1-phenyl-[1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-one 在 sodium ethanolate 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 生成 7-benzoylamino-3-acetyl-1-phenyl-pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5,6-(1H,8H)-dione
  参考文献：
  名称：

  A Convenient Synthesis of NovelDerivatives of Pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine-5,6-dione

  摘要：

  Reaction of 6-Amino-2-thiouracil with hydrazonoyl halides yielded regioselectively 7-amino-1,3-disubstituted-1,2,4-triazolo[4,3-a]pyrimidine derivatives. Upon treatment with methyl (Z)-2-benzoylamino-3-dimethylaminopropenoate, the corresponding methyl (Z)-2-benzoylamino-3-([1,2,4]triazolo[4,3-a]pyrimidin-7-yl)-amino propenoates were obtained which cyclized in the presence of sodium ethoxide to afford novel derivatives of pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine-5,6(1H,8H)-diones.

  DOI：

  10.1007/s00706-002-0469-8
• 作为产物：
  描述：

  6-氨基-2-硫脲嘧啶 、 1-氯-1-(2-苯基亚肼基)乙酮 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以65%的产率得到3-acetyl-7-amino-1-phenyl-[1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-one
  参考文献：
  名称：

  A Convenient Synthesis of NovelDerivatives of Pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine-5,6-dione

  摘要：

  Reaction of 6-Amino-2-thiouracil with hydrazonoyl halides yielded regioselectively 7-amino-1,3-disubstituted-1,2,4-triazolo[4,3-a]pyrimidine derivatives. Upon treatment with methyl (Z)-2-benzoylamino-3-dimethylaminopropenoate, the corresponding methyl (Z)-2-benzoylamino-3-([1,2,4]triazolo[4,3-a]pyrimidin-7-yl)-amino propenoates were obtained which cyclized in the presence of sodium ethoxide to afford novel derivatives of pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine-5,6(1H,8H)-diones.

  DOI：

  10.1007/s00706-002-0469-8

文献信息

• Synthesis of New 3-Heteroarylindoles as Potential Anticancer Agents
  作者：Abdou Abdelhamid、Sobhi Gomha、Nadia Abdelriheem、Saher Kandeel

  DOI：10.3390/molecules21070929

  日期：——

  3-d]pyrimidin-4(1H)-ones, respectively. Also, hydrazonoyl halides were reacted with N’-(1-(1H-indol-3-yl)ethylidene)-2-cyanoacetohydrazide to afford 1,3,4-thiadiazole derivatives. Structures of the new synthesis were elucidated on the basis of elemental analysis, spectral data, and alternative synthetic routes whenever possible. Fifteen of the new compounds have been evaluated for their antitumor activity

  2-(3-(1H-Indol-3-yl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-取代-5-(取代二氮烯基)噻唑和2-(1H-indol-3-yl)-9-取代-4,7-二取代吡啶并[3,2-e][1,2,4]三唑并[4,3-a]嘧啶-5(7H) -ones 通过腙酰卤化物与 3-(1H-indol-2-yl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide 和 7-(1H -indol-3-yl)-2-thioxo-5-取代的-2,3-二氢吡啶并[2,3-d]嘧啶-4(1H)-ones，分别。此外，腙酰卤与N'-(1-(1H-吲哚-3-基)亚乙基)-2-氰基乙酰肼反应得到1,3,4-噻二唑衍生物。新合成的结构是在元素分析、光谱数据和可能的替代合成路线的基础上阐明的。已经评估了 15 种新化合物对
• Clean Grinding Technique: A Facile Synthesis and In Silico Antiviral Activity of Hydrazones, Pyrazoles, and Pyrazines Bearing Thiazole Moiety against SARS-CoV-2 Main Protease (Mpro)
  作者：Sraa Abu-Melha、Mastoura M. Edrees、Sayed M. Riyadh、Mohamad R. Abdelaziz、Abdo A. Elfiky、Sobhi M. Gomha

  DOI：10.3390/molecules25194565

  日期：——

  A novel series of some hydrazones bearing thiazole moiety were generated via solvent-drop grinding of thiazole carbohydrazide 2 with various carbonyl compounds. Also, dehydrative-cyclocondensation of 2 with active methylene compounds or anhydrides gave the respective pyarzole or pyrazine derivatives. The structures of the newly synthesized compounds were established based on spectroscopic evidences

  通过溶剂滴研磨噻唑碳酰肼 2 与各种羰基化合物，生成了一系列带有噻唑部分的新型腙。此外，2与活性亚甲基化合物或酸酐的脱水环缩合反应得到各自的吡唑或吡嗪衍生物。新合成化合物的结构是基于光谱证据及其替代合成确定的。此外，使用分子对接结合分子动力学模拟 (MDS) 测试了所有产品的抗 SARS-CoV-2 主蛋白酶 (Mpro) 的抗病毒活性。化合物3a、3b和3c的平均结合亲和力（分别为-8.1 ± 0.33 kcal/mol、-8.0 ± 0.35 kcal/mol和-8.2 ± 0.21 kcal/mol）优于阳性对照奈非那韦(-6.9 ± 0.51 kcal/mol)。
• Multicomponent Synthesis of Novel Penta-Heterocyclic Ring Systems Incorporating a Benzopyranopyridine Scaffold
  作者：Sayed Riyadh、Sobhi Gomha

  DOI：10.1055/s-0033-1340085

  日期：——

  simple one-pot method is reported for the synthesis of several novel series of chromeno[4′,3′:4,5]pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine-6,14-diones, chromeno[4′,3′:4,5]pyr­ido[2,3-d]thiazolo[3,2-a]pyrimidine-6,14-diones, and chrom-­eno[4′′,3′′:4′,5′]pyrido[2′,3′:4,5]pyrimido[2,1-b][1,3]thiazine-6,15-dione by a multicomponent reaction of salicylaldehyde, ethyl acetoacetate, and the appropriate fused

  摘要 报道了一种简单的一锅法，用于合成几个新系列的chromeno [4'，3'：4,5] pyrido [2,3- d ] [1,2,4] triazolo [4,3- a ] pyrimidine-6,14-diones，chromeno [4'，3'：4,5] pyrido [2,3- d ] thiazolo [3,2 - a ] pyrimidine-6,14-diones和chrom-eno [通过多组分反应4''，3''：4'，5'] pyrido [2'，3'：4,5] pyrimido [2,1- b ] [1,3]噻嗪-6,15-二酮回流冰醋酸中的水杨醛，乙酰乙酸乙酯和适当的稠合杂环胺 通过光谱和元素分析确定了新合成化合物的结构。阐明了单步反应的机理。 报道了一种简单的一锅法，用于合成几个新系列的chromeno [4'，3'：4,5] pyrido [2,3- d ]
• Farghaly, Thoraya A.; Riyadh, Sayed M.; Abdallah, Magda A., Acta Chimica Slovenica, 2011, vol. 58, # 1, p. 87 - 94
  作者：Farghaly, Thoraya A.、Riyadh, Sayed M.、Abdallah, Magda A.、Ramadan, Mohamed A.

  DOI：——

  日期：——
• Synthesis and Antimicrobial Evaluation of Some Novel Thiazole, 1,3,4-Thiadiazole and Pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine Derivatives Incorporating Pyrazole Moiety
  作者：Abdou O. Abdelhamid、Sobhi M. Gomha、Ahmad S. Shawali

  DOI：10.3987/com-15-13319

  日期：——

  New series of novel functionalized thiazoles, 1,3,4-thiadiazoles and pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidines containing pyrazole moiety were synthesized using 4-acetylpyrazole as a precursor. The structures of the compounds prepared were confirmed by both spectral and elemental analyses and by alternative synthetic routes. The mechanisms of the studied reactions were also discussed. Sixteen compounds were evaluated for their in vitro antimicrobial activity. The results proclaimed that some of the tested compounds exhibited moderate to significant antibacterial and antifungal activities. Compounds lie, 11a, and lid exhibited high antibacterial activity against Bacillus subtilis compared with reference drug (Ampicillin) while compounds 11a, 6g, 18e, 18a, 11d, 6a, 11c, lib and 6d exhibited higher antifungal activity against Syncephalastrum racemosum than reference drug (Amphotericin B).