2-((3-cyano-6-phenyl-4-(p-tolyl)pyridin-2-yl)thio)acetamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-((3-cyano-6-phenyl-4-(p-tolyl)pyridin-2-yl)thio)acetamide
• 英文别名: 2-[3-Cyano-4-(4-methylphenyl)-6-phenylpyridin-2-yl]sulfanylacetamide
• 化学式: C₂₁H₁₇N₃OS
• 分子量: 359.451
• InChiKey: ZWRBYSCDVQOSFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((3-cyano-6-phenyl-4-(p-tolyl)pyridin-2-yl)thio)acetamide 在 甲醇 、 sodium methylate 作用下， 生成 AG-690/13704140
  参考文献：
  名称：

  一些新型噻吩并[2,3-b]吡啶类抗菌和抗癌化合物的合成和生物学评价

  摘要：

  AbstractThe risk elicited by the evolution of antimicrobial resistance, in addition to the annual increase in cancer rates, constitute the greatest threat to global health, which led to an urgent need to discover new molecules having potent antimicrobial and anticancer properties. Therefore, the present study involved with the synthesis of some new thieno[2,3-b]pyridine-based compounds 3a-c–6a,b via treatment of the starting 3-aminothienopyridine derivatives 2a,b with aryl isothiocyanates, maleic anhydride and cyclopentanone to afford the target 3-substituted-thienopyridine compounds 3a-c–5a,b. Also, the synthetic target cyclopentapyrido-thienopyridine-9-amines 6a,b were obtained upon treatment of the new 3-cyclopentylideneamino derivatives with phosphorous oxychloride. All the target compounds were evaluated for their in vitro antimicrobial activity against a panel of five bacterial and five fungal strains. Also, the cytotoxic potency of the target compounds was evaluated against two human cancer cell lines; hepatocellular carcinoma (HepG-2) and breast cancer cells (MCF-7). The new compounds showed promising antimicrobial and anticancer activities compared with the reference drugs. The most potent antimicrobial activity was revealed by 3c with MIC values range 4-16 μg/mL. While, the most potent cytotoxicity against both HepG-2 and MCF-7 cells was showed by 4b with IC50 values 3.12 µM and 20.55 µM, respectively.

  DOI：

  10.21608/ejchem.2022.136967.6042
• 作为产物：
  描述：

  苯乙酮 在 sodium 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 2-((3-cyano-6-phenyl-4-(p-tolyl)pyridin-2-yl)thio)acetamide
  参考文献：
  名称：

  作为流感病毒PA-PB1相互作用抑制剂的杂化衍生物文库的合成和生物学评价

  摘要：

  针对流感病毒的有限治疗选择以及对耐药性病毒不断出现的日益增长的公共健康问题，使得具有新型作用机制的新型抗流感药的开发至关重要。最吸引人的靶标之一是RNA依赖性RNA聚合酶PA和PB1的两个亚基之间的相互作用。在本文中，我们报告了从最近被鉴定为PA-PB1相互作用破坏者的3-氰基-4,6-二苯基吡啶骨架开始的杂合化合物的合理设计。在先前报道的SAR数据的指导下，合成了氨基酸衍生物库。生物学评估导致鉴定出新的PA-PB1抑制剂，这些抑制剂没有明显的毒性。分子模型进一步阐明了这些化合物的抑制机理。

  DOI：

  10.1016/j.ejmech.2018.08.032

文献信息

• Synthesis and biological evaluation of a library of hybrid derivatives as inhibitors of influenza virus PA-PB1 interaction
  作者：Ilaria D'Agostino、Ilaria Giacchello、Giulio Nannetti、Anna Lucia Fallacara、Davide Deodato、Francesca Musumeci、Giancarlo Grossi、Giorgio Palù、Ylenia Cau、Iuni Margaret Trist、Arianna Loregian、Silvia Schenone、Maurizio Botta

  DOI：10.1016/j.ejmech.2018.08.032

  日期：2018.9

  emergence of drug-resistant viruses make essential the development of new anti-flu agents with novel mechanisms of action. One of the most attractive targets is the interaction between two subunits of the RNA-dependent RNA polymerase, PA and PB1. Herein we report the rational design of hybrid compounds starting from a 3-cyano-4,6-diphenylpyridine scaffold recently identified as disruptor of PA-PB1 interactions

  针对流感病毒的有限治疗选择以及对耐药性病毒不断出现的日益增长的公共健康问题，使得具有新型作用机制的新型抗流感药的开发至关重要。最吸引人的靶标之一是RNA依赖性RNA聚合酶PA和PB1的两个亚基之间的相互作用。在本文中，我们报告了从最近被鉴定为PA-PB1相互作用破坏者的3-氰基-4,6-二苯基吡啶骨架开始的杂合化合物的合理设计。在先前报道的SAR数据的指导下，合成了氨基酸衍生物库。生物学评估导致鉴定出新的PA-PB1抑制剂，这些抑制剂没有明显的毒性。分子模型进一步阐明了这些化合物的抑制机理。
• Synthesis and Biological Evaluation of Some New Thieno[2,3-b]pyridine-based Compounds As Antimicrobial and Anticancer Agents
  作者：Eman Mohi El-Deen、Amina Abd El-Gwaad、Manal Anwar

  DOI：10.21608/ejchem.2022.136967.6042

  日期：2022.5.31

  AbstractThe risk elicited by the evolution of antimicrobial resistance, in addition to the annual increase in cancer rates, constitute the greatest threat to global health, which led to an urgent need to discover new molecules having potent antimicrobial and anticancer properties. Therefore, the present study involved with the synthesis of some new thieno[2,3-b]pyridine-based compounds 3a-c–6a,b via treatment of the starting 3-aminothienopyridine derivatives 2a,b with aryl isothiocyanates, maleic anhydride and cyclopentanone to afford the target 3-substituted-thienopyridine compounds 3a-c–5a,b. Also, the synthetic target cyclopentapyrido-thienopyridine-9-amines 6a,b were obtained upon treatment of the new 3-cyclopentylideneamino derivatives with phosphorous oxychloride. All the target compounds were evaluated for their in vitro antimicrobial activity against a panel of five bacterial and five fungal strains. Also, the cytotoxic potency of the target compounds was evaluated against two human cancer cell lines; hepatocellular carcinoma (HepG-2) and breast cancer cells (MCF-7). The new compounds showed promising antimicrobial and anticancer activities compared with the reference drugs. The most potent antimicrobial activity was revealed by 3c with MIC values range 4-16 μg/mL. While, the most potent cytotoxicity against both HepG-2 and MCF-7 cells was showed by 4b with IC50 values 3.12 µM and 20.55 µM, respectively.