2-((1H-benzo[d]imidazol-2-yl)methylthio)-1,6-dihydro-6-oxo-4-phenylpyrimidine-5-carbonitrile

• 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: 2-((1H-benzo[d]imidazol-2-yl)methylthio)-1,6-dihydro-6-oxo-4-phenylpyrimidine-5-carbonitrile
• 英文别名: 2-(1H-benzimidazol-2-ylmethylsulfanyl)-6-oxo-4-phenyl-1H-pyrimidine-5-carbonitrile
• 化学式: C₁₉H₁₃N₅OS
• 分子量: 359.411
• InChiKey: YBTNAGBPIWZPFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-((1H-benzo[d]imidazol-2-yl)methylthio)-1,6-dihydro-6-oxo-4-phenylpyrimidine-5-carbonitrile 在 三氯氧磷 作用下， 以97.61%的产率得到2-((1H-benzo[d]imidazol-2-yl)methylthio)-4-chloro-6-phenylpyrimidine-5-carbonitrile
  参考文献：
  名称：

  Novel benzimidazole–pyrimidine conjugates as potent antitumor agents

  摘要：

  As a continuation to our previous work in synthesizing antitumor benzimidazoles, a series of 2-((1H-benzo[d]imidazol-2-yl)methylthio)-4-(substituted)-6-phenylpyrimidine-5-carbonitriles was synthesized. Evaluation of the synthesized compounds for their in vitro cytotoxic activity against twelve cell lines namely, Cervical carcinoma (KB), Ovarial carcinoma (SK OV-3), CNS cancer (SF-268), Non small lung cancer (NCI H460), Colonadenocarcinoma (RKOP27), Leukaemia (HL60, U937, K562), Melanoma (G361, SK-MEL-28) and Neuroblastoma (GOTO, NB-1) revealed their marked potency when compared with known anticancer drugs.

  DOI：

  10.1016/j.ejmech.2010.02.011
• 作为产物：
  描述：

  邻苯二胺 在 盐酸 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 31.0h， 生成 2-((1H-benzo[d]imidazol-2-yl)methylthio)-1,6-dihydro-6-oxo-4-phenylpyrimidine-5-carbonitrile
  参考文献：
  名称：

  新型苯并咪唑衍生物作为丙型肝炎病毒RNA复制抑制剂的合成，分子建模和生物学评估。

  摘要：

  在这项研究中，进行了一系列新的苯并咪唑衍生物的合成和对接研究，这些衍生物通过亚甲基硫键或其生物等位亚甲基氨基桥与取代的嘧啶连接。评价所有合成的化合物的丙型肝炎病毒（HCV）RNA复制抑制活性。发现化合物4d，4f和4h比VX-950更有效（IC50 / 90为4d = 0.123 / 0.321、4f = 0.145 / 0.345、4h = 0.129 / 0.432，VX-950 = 0.20 / 0.45 µM ）和6d（IC50 / 90 = 0.116 / 0.452 µM）所显示的活性与标准品非常相似。化合物4d，4f，4h和6d是有效的HCV RNA复制抑制剂，是进一步研究的良好候选药物。

  DOI：

  10.1248/cpb.c13-01009

文献信息

• Synthesis and Fungicidal Activity of New Imidazoles from 2-(Chloromethyl)-1<i>H</i>-benzimidazole
  作者：H. M. F. Madkour、A. A. Farag、S. Sh. Ramses、N. A. A. Ibrahiem

  DOI：10.1080/104265090970241

  日期：2006.2

  A series of substituted 2-thiomethylbenzimidazoles 2–4, 2-phenoxy-methylbenzimidazoles 5 and 2-aminomethylbenzimidazoles 6 and 7 were synthesized by reactions of 2-chloromethylbenzimidazole 1 with dithiocarbamate, pyrimidine-2-thiones, phenol derivatives, as well as primary aromatic and heterocyclic amines, respectively. Most of the synthesized compounds were screened for their antifungal activity

  通过 2-氯甲基苯并咪唑 1 与二硫代氨基甲酸酯、嘧啶-2-硫酮、苯酚衍生物以及主要芳香族化合物的反应，合成了一系列取代的 2-硫甲基苯并咪唑 2-4、2-苯氧基-甲基苯并咪唑 5 和 2-氨基甲基苯并咪唑 6 和 7。和杂环胺，分别。筛选了大多数合成的化合物对 B. sinerea、F. solani、R. solani 和真菌的抗真菌活性。一些测试化合物在 200-1000 ppm 的浓度范围内显示出对真菌生长的 100% 抑制。
• Novel benzimidazole–pyrimidine conjugates as potent antitumor agents
  作者：Heba T. Abdel-Mohsen、Fatma A.F. Ragab、Mostafa M. Ramla、Hoda I. El Diwani

  DOI：10.1016/j.ejmech.2010.02.011

  日期：2010.6

  As a continuation to our previous work in synthesizing antitumor benzimidazoles, a series of 2-((1H-benzo[d]imidazol-2-yl)methylthio)-4-(substituted)-6-phenylpyrimidine-5-carbonitriles was synthesized. Evaluation of the synthesized compounds for their in vitro cytotoxic activity against twelve cell lines namely, Cervical carcinoma (KB), Ovarial carcinoma (SK OV-3), CNS cancer (SF-268), Non small lung cancer (NCI H460), Colonadenocarcinoma (RKOP27), Leukaemia (HL60, U937, K562), Melanoma (G361, SK-MEL-28) and Neuroblastoma (GOTO, NB-1) revealed their marked potency when compared with known anticancer drugs.
• Synthesis, Molecular Modeling, and Biological Evaluation of Novel Benzimidazole Derivatives as Inhibitors of Hepatitis C Virus RNA Replication
  作者：Hoda Ibrahim El Diwani、Heba Tawfik Abdel-Mohsen、Ismail Salama、Fatma Abdel-Fattah Ragab、Mostafa Mahmoud Ramla、Shadia Ahmed Galal、Mohamed Mostafa Abdalla、Abeer Abdel-Wahab、Maha Adel El Demellawy

  DOI：10.1248/cpb.c13-01009

  日期：——

  In this study, synthesis and docking studies of a series of new benzimidazole derivatives linked to substituted pyrimidines either through the methylenethio linkage or its bioisosteric methylene amino bridge were carried out. All the synthesized compounds were evaluated for their hepatitis C virus (HCV) RNA replication-inhibitory activity. Compounds 4d, 4f, and 4h were found to be more potent than

  在这项研究中，进行了一系列新的苯并咪唑衍生物的合成和对接研究，这些衍生物通过亚甲基硫键或其生物等位亚甲基氨基桥与取代的嘧啶连接。评价所有合成的化合物的丙型肝炎病毒（HCV）RNA复制抑制活性。发现化合物4d，4f和4h比VX-950更有效（IC50 / 90为4d = 0.123 / 0.321、4f = 0.145 / 0.345、4h = 0.129 / 0.432，VX-950 = 0.20 / 0.45 µM ）和6d（IC50 / 90 = 0.116 / 0.452 µM）所显示的活性与标准品非常相似。化合物4d，4f，4h和6d是有效的HCV RNA复制抑制剂，是进一步研究的良好候选药物。