6-amino-4-(4-hydroxyphenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile | 1435939-75-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-amino-4-(4-hydroxyphenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile
• CAS: 1435939-75-5
• 化学式: C₁₁H₁₀N₄OS
• 分子量: 246.293
• InChiKey: KBJBZZNXKXDMFS-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  6-amino-4-(4-hydroxyphenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile 在 双氧水 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 60.0h， 生成 4-amino-6-(4-hydroxyphenyl)-2-(methylsulfonyl)pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of novel substituted pyrimidine scaffold

  摘要：

  Synthesis and biological evaluation of substituted pyrimidine derivatives containing 4-amino and 5-cyano substituted derivatives are described. Biginelli typed three component reactions between an aldehyde, malononitrile, and a urea constituent give a rapid facile pyrimidine ring. The constitution of the products has been delineated by elemental analysis and spectral analysis. The products were assayed for their in vitro biological assay antibacterial activity against S. pyogenes MTCC-442, S. aureus MTCC-96, E. coli MTCC-443, and B. subtilis MTCC-441 bacterial strain and antifungal activity against Aspergillus niger MTCC-282 and Candida albicans MTCC-227 at different concentrations, which compared with Ampicillin, Chloramphenicol, Ciprofloxacin, Norfloxacin, and Griseofulvin as standard drug which are presented.

  DOI：

  10.1007/s00044-013-0596-2
• 作为产物：
  描述：

  对羟基苯甲醛 、 硫脲 、 丙二腈 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以37%的产率得到6-amino-4-(4-hydroxyphenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile
  参考文献：
  名称：

  6-amino-4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitriles 的合成及细胞毒性评价

  摘要：

  通过 Biginelli 型反应合成了 6-amino-4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitriles 的几种衍生物，并测试了它们对人乳腺癌 (MCF-7) 的抗增殖活性) 和人结肠癌 (HT29) 细胞系。恶性和非恶性细胞在 RPMI 培养基中培养，并与不同浓度的这些嘧啶一起培养。通过MTT测定评估细胞活力。使用 DAPI（4'-6-二脒基-2-苯基吲哚）和通过流式细胞术（亚 G1 峰）对 DNA 片段化的碘化丙啶染色确定凋亡细胞。6-氨基-4-(4-氯苯基)-2-硫代-1,2,3,4-四氢嘧啶-5-甲腈和6-氨基-4-[4-二甲氨基)苯基]-2-硫代-1，与 L929 细胞相比，2,3,4-四氢嘧啶-5-腈降低 MCF-7 和 HT29 细胞的活力。

  DOI：

  10.1134/s1068162016020047

文献信息

• An Efficient One-Pot Synthesis of New 2- Thioxo and 2-oxo-pyrimidine-5-carbonitriles in Ball-Milling Under Solvent-Free and Catalyst-Free Conditions
  作者：Mohamed Ould M’hamed、Omar K. Alduaij

  DOI：10.1080/10426507.2013.818995

  日期：2014.1.1

  Various 2-thioxo and 2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carbonitriles were synthesized in very high yields in 40min through a direct condensation of an equimolar amount of an aldehyde, malononitrile, and thiourea/urea under ball mill solvent-free and catalyst-free conditions.