2-(6-amino-1-phenyl-2-thioxo-1,2,3,4-tetra-hydropyrimidin-4-ylidene)-malononitrile | 1005764-38-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 2-(6-amino-1-phenyl-2-thioxo-1,2,3,4-tetra-hydropyrimidin-4-ylidene)-malononitrile
• 英文别名: 2-(6-amino-1-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-ylidene)malononitrile；6-amino-4-dicyanomethyliden-1-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine；2-Isopropoxymethyl-4-methylfuro[3,2-c]quino-line；2-(6-amino-1-phenyl-2-sulfanylidenepyrimidin-4-ylidene)propanedinitrile
• CAS: 1005764-38-4
• 化学式: C₁₃H₉N₅S
• 分子量: 267.314
• InChiKey: RAJXWGZNYPWYAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(6-amino-1-phenyl-2-thioxo-1,2,3,4-tetra-hydropyrimidin-4-ylidene)-malononitrile 在 水 、 sodium nitrite 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以84%的产率得到2-(6-amino-5-nitroso-1-phenyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-ylidene)malononitrile
  参考文献：
  名称：

  合成新的嘌呤，蝶啶和其他嘧啶衍生物

  摘要：

  The reaction of malononitrile dimer with phenyl isothiocyanate gave (6-amino-1-phenyl-2-thioxo1,2,3,4-tetrahydropyrimidin-4-ylidene)malononitrile which was then used as starting material in the synthesis of pharmacologically important fused pyrimidine derivatives, such as 4-dicyanomethylidene-1.5-diphenyl-2thioxo-1,2,3,4-tetrahydropyrrolo[2,3-d]pyrimidine, 6-cyano-4-dicyanomethylidene-7-methylsulfanyl-5-oxo-lphenyl-2-thioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine, 6-dicyanomethylidene-3-phenyl-2-thioxo1,2,3,6-tetrahydro-9H-purine, and 6-substituted 4-dicyanomethylidene-7-oxo-1-phenyl-2-thioxo-1,2,3,4,7,8-hexahydropteridines.

  DOI：

  10.1134/s1070428007030219
• 作为产物：
  描述：

  2-氨基-1-丙烯基-1,1,3-三甲腈 、 硫代异氰酸苯酯 在 吡啶 作用下， 反应 2.0h， 以72%的产率得到2-(6-amino-1-phenyl-2-thioxo-1,2,3,4-tetra-hydropyrimidin-4-ylidene)-malononitrile
  参考文献：
  名称：

  合成新的嘌呤，蝶啶和其他嘧啶衍生物

  摘要：

  The reaction of malononitrile dimer with phenyl isothiocyanate gave (6-amino-1-phenyl-2-thioxo1,2,3,4-tetrahydropyrimidin-4-ylidene)malononitrile which was then used as starting material in the synthesis of pharmacologically important fused pyrimidine derivatives, such as 4-dicyanomethylidene-1.5-diphenyl-2thioxo-1,2,3,4-tetrahydropyrrolo[2,3-d]pyrimidine, 6-cyano-4-dicyanomethylidene-7-methylsulfanyl-5-oxo-lphenyl-2-thioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine, 6-dicyanomethylidene-3-phenyl-2-thioxo1,2,3,6-tetrahydro-9H-purine, and 6-substituted 4-dicyanomethylidene-7-oxo-1-phenyl-2-thioxo-1,2,3,4,7,8-hexahydropteridines.

  DOI：

  10.1134/s1070428007030219

文献信息

• Utility of 6-Amino-2-thiouracils as a Core of Biologically Potent Polynitrogen-Sulfur Fused Heterocycles
  作者：Samira T. Rabie、Reham A. Abdel-Monem、Nadia R. Mohamed、Ahmed I. Hashem、Afaf A. Nada

  DOI：10.1002/jhet.1936

  日期：2014.8

  One pot three-component reaction was assisted to form some new pyridopyrimidine derivatives to be investigated as antimicrobial and antitumor agents. The newly synthesized compounds showed high significant antimicrobial activity against the applied strains of both Gram-positive and Gram-negative bacteria and fungi. The cytotoxic activity of some compounds was evaluated as inhibitor of growth in both

  一锅三组分反应有助于形成一些新的吡啶并嘧啶衍生物，以作为抗菌剂和抗肿瘤剂进行研究。新合成的化合物对革兰氏阳性和革兰氏阴性细菌和真菌的应用菌株均显示出很高的抗微生物活性。评价了某些化合物在人肝癌和乳腺癌细胞系中的生长抑制剂的细胞毒性活性。结果表明，某些化合物对人肝细胞系和乳腺癌细胞表现出非常高的细胞毒性。