AG-690/13704140 | 335215-61-7

• 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: AG-690/13704140
• 英文别名: 3-Amino-6-phenyl-4-(p-tolyl)thieno[2,3-b]pyridine-2-carboxamide；3-amino-4-(4-methylphenyl)-6-phenylthieno[2,3-b]pyridine-2-carboxamide
• CAS: 335215-61-7
• 化学式: C₂₁H₁₇N₃OS
• 分子量: 359.451
• InChiKey: RUBRDGDLVPOYIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  AG-690/13704140 在 tetraphosphorus decasulfide 、 zinc(II) chloride 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 7'-phenyl-9'-(p-tolyl)-1'H-spiro[cyclopentane-1,2'-pyrido[3',2':4,5]thieno[3,2-d]pyrimidine]-4'(3'H)-thione
  参考文献：
  名称：

  新型吡啶并噻吩并嘧啶衍生物：作为抗菌剂和抗癌剂的设计、合成和生物学评价

  摘要：

  除了癌症患者数量的持续增加之外，抗菌药物耐药性的风险日益增加，对全球健康构成了巨大威胁，这需要加紧努力发现新的生物活性化合物作为抗菌剂和抗癌剂。因此，通过3-氨基-噻吩并[2,3-b]吡啶-2-甲酰胺1a,b与不同试剂的环化反应合成了一组新的吡啶并噻吩并嘧啶衍生物2a,b–9a,b。所有新化合物均针对五种细菌和五种真菌菌株进行了评估。许多目标化合物表现出显着的抗菌活性。此外，新衍生物还进一步针对HepG-2和MCF-7癌细胞系进行了细胞毒性评估。最有效的细胞毒性候选药物（3a、4a、5a、6b、8b 和 9b）作为 EGFR 激酶抑制剂进行了检查。还进行了分子对接研究来探索这些衍生物在EGFR-PK活性位点的结合模式。化合物 3a、5a 和 9b 显示出广谱抗菌活性，MIC 范围为 4–16 µg/mL，并且具有有效的细胞毒活性，IC50 范围为 1.17–2.79 µM。此外，它们还具有针对

  DOI：

  10.3390/molecules27030803
• 作为产物：
  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

文献信息

• Novel Pyridothienopyrimidine Derivatives: Design, Synthesis and Biological Evaluation as Antimicrobial and Anticancer Agents
  作者：Eman M. Mohi El-Deen、Manal M. Anwar、Amina A. Abd El-Gwaad、Eman A. Karam、Mohamed K. El-Ashrey、Rafika R. Kassab

  DOI：10.3390/molecules27030803

  日期：——

  3-b]pyridine-2-carboxamides 1a,b with different reagents. All new compounds were evaluated against five bacterial and five fungal strains. Many of the target compounds showed significant antimicrobial activity. In addition, the new derivatives were further subjected to cytotoxicity evaluation against HepG-2 and MCF-7 cancer cell lines. The most potent cytotoxic candidates (3a, 4a, 5a, 6b, 8b and 9b)

  除了癌症患者数量的持续增加之外，抗菌药物耐药性的风险日益增加，对全球健康构成了巨大威胁，这需要加紧努力发现新的生物活性化合物作为抗菌剂和抗癌剂。因此，通过3-氨基-噻吩并[2,3-b]吡啶-2-甲酰胺1a,b与不同试剂的环化反应合成了一组新的吡啶并噻吩并嘧啶衍生物2a,b–9a,b。所有新化合物均针对五种细菌和五种真菌菌株进行了评估。许多目标化合物表现出显着的抗菌活性。此外，新衍生物还进一步针对HepG-2和MCF-7癌细胞系进行了细胞毒性评估。最有效的细胞毒性候选药物（3a、4a、5a、6b、8b 和 9b）作为 EGFR 激酶抑制剂进行了检查。还进行了分子对接研究来探索这些衍生物在EGFR-PK活性位点的结合模式。化合物 3a、5a 和 9b 显示出广谱抗菌活性，MIC 范围为 4–16 µg/mL，并且具有有效的细胞毒活性，IC50 范围为 1.17–2.79 µM。此外，它们还具有针对
• 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.