Design, synthesis and anticancer activity of amide derivatives of substituted 3-methyl-benzofuran-2-carboxylic acid

References

• Khan, Z.; Bisen, P. S. Oncoapoptotic Signaling and Deregulated Target Genes in Cancers: Special Reference to Oral Cancer. Biochim. Biophys. Acta 2013, 1836, 123–145. DOI: 10.1016/j.bbcan.2013.04.002.
   PubMed Web of Science ®Google Scholar
• Soni, J. N.; Soman, S. S. Synthesis and Antimicrobial Evaluation of Amide Derivatives of Benzodifuran-2-Carboxylic Acid. Eur. J. Med. Chem. 2014, 75, 77–81. DOI: 10.1016/j.ejmech.2014.01.026.
   PubMed Web of Science ®Google Scholar
• Kawasaki, K. I.; Masubuchi, M.; Morikami, K.; Sogabe, S.; Aoyama, T.; Ebiike, H.; Niizuma, S.; Hayase, M.; Fujii, T.; Sakata, K.; et al. Design and Synthesis of Novel Benzofurans as a New Class of Antifungal Agents Targeting Fungal N-Myristoyltransferase. Part 3. Bioorganic Med. Chem. Lett. 2003, 13, 87–91. DOI: 10.1016/S0960-894X(02)00844-2.
   PubMed Web of Science ®Google Scholar
• Yadav, P.; Singh, P.; Tewari, A. K. Design, Synthesis, Docking and Anti-Inflammatory Evaluation of Novel Series of Benzofuran Based Prodrugs. Bioorg. Med. Chem. Lett. 2014, 24, 2251–2255. DOI: 10.1016/j.bmcl.2014.03.087.
   PubMed Web of Science ®Google Scholar
• Chand, K.; Hiremathad, A.; Singh, M.; Santos, M. A.; Keri.; R. S.; Rajeshwari. A Review on Antioxidant Potential of Bioactive Heterocycle Benzofuran: Natural and Synthetic Derivatives. Pharmacol. Rep. 2017, 69, 281–295. DOI: 10.1016/j.pharep.2016.11.007.
   PubMed Web of Science ®Google Scholar
• Khanam, H.; Shamsuzzaman. Bioactive Benzofuran Derivatives: A Review. Eur. J. Med. Chem. 2015, 97, 483–504. DOI: 10.1016/j.ejmech.2014.11.039.
   PubMed Web of Science ®Google Scholar
• Li, X. Y.; He, B. F.; Luo, H. J.; Huang, N. Y.; Deng, W. Q. 3-Acyl-5-Hydroxybenzofuran Derivatives as Potential Anti-Estrogen Breast Cancer Agents: A Combined Experimental and Theoretical Investigation. Bioorg. Med. Chem. Lett. 2013, 23, 4617–4621. DOI: 10.1016/j.bmcl.2013.06.022.
   PubMed Web of Science ®Google Scholar
• Choi, M.; Jo, H.; Park, H.-J.; Sateesh Kumar, A.; Lee, J.; Yun, J.; Kim, Y.; Han, S.-B.; Jung, J.-K.; Cho, J.; et al. Design, Synthesis, and Biological Evaluation of Benzofuran- and 2,3-Dihydrobenzofuran-2-Carboxylic Acid N-(Substituted)Phenylamide Derivatives as Anticancer Agents and Inhibitors of NF-ΚB. Bioorg. Med. Chem. Lett. 2015, 25, 2545–2549. DOI: 10.1016/j.bmcl.2015.04.050.
   PubMed Web of Science ®Google Scholar
• Hranjec, M.; Sović, I.; Ratkaj, I.; Pavlović, G.; Ilić, N.; Valjalo, L.; Pavelić, K.; Kraljević Pavelić, S.; Karminski-Zamola, G. Antiproliferative Potency of Novel Benzofuran-2-Carboxamides on Tumour Cell Lines: Cell Death Mechanisms and Determination of Crystal Structure. Eur. J. Med. Chem. 2013, 59, 111–119. DOI: 10.1016/j.ejmech.2012.11.009.
   PubMed Web of Science ®Google Scholar
• Xu, X. l.; Yang, Y. r.; Mo, X. f.; Wei, J. l.; Zhang, X. j.; You, Q. d Design, Synthesis, and Evaluation of Benzofuran Derivatives as Novel Anti-Pancreatic Carcinoma Agents via Interfering the Hypoxia Environment by Targeting HIF-1α Pathway. Eur. J. Med. Chem. 2017, 137, 45–62. DOI: 10.1016/j.ejmech.2017.05.042.
   PubMed Web of Science ®Google Scholar
• Al-Sanea, M. M.; Al-Ansary, G. H.; Elsayed, Z. M.; Maklad, R. M.; Elkaeed, E. B.; Abdelgawad, M. A.; Bukhari, S. N. A.; Abdel-Aziz, M. M.; Suliman, H.; Eldehna, W. M. Development of 3-Methyl/3-(Morpholinomethyl)Benzofuran Derivatives as Novel Antitumor Agents towards Non-Small Cell Lung Cancer Cells. J. Enzyme Inhib. Med. Chem. 2021, 36, 987–999. DOI: 10.1080/14756366.2021.1915302.
   PubMed Web of Science ®Google Scholar
• Karandikar, S.; Soni, R.; Soman, S. S.; Umar, S.; Suresh, B. 1,2-Benzisoxazole-3-Acetamide Derivatives as Dual Agents for DPP-IV Inhibition and Anticancer Activity. Synth. Commun. 2018, 48, 2877–2887. DOI: 10.1080/00397911.2018.1508723.
   Web of Science ®Google Scholar
• Durgapal, S. D.; Soman, S. S. Evaluation of Novel Coumarin-Proline Sulfonamide Hybrids as Anticancer and Antidiabetic Agents. Synth. Commun. 2019, 49, 2869-2883. DOI: 10.1080/00397911.2019.1647439.
   Web of Science ®Google Scholar
• Trachootham, D.; Zhou, Y.; Zhang, H.; Demizu, Y.; Chen, Z.; Pelicano, H.; Chiao, P. J.; Achanta, G.; Arlinghaus, R. B.; Liu, J.; Huang, P. Selective Killing of Oncogenically Transformed Cells through a ROS-Mediated Mechanism by β-Phenylethyl Isothiocyanate. Cancer Cell 2006, 10, 241–252. DOI: 10.1016/j.ccr.2006.08.009.
   PubMed Web of Science ®Google Scholar
• Reinehr, R.; Becker, S.; Eberle, A.; Grether-Beck, S.; Häussinger, D. Involvement of NADPH Oxidase Isoforms and Src Family Kinases in CD95-Dependent Hepatocyte Apoptosis. J. Biol. Chem. 2005, 280, 27179–27194. DOI: 10.1074/jbc.M414361200.
   PubMed Web of Science ®Google Scholar
• Ramsey, M. R.; Sharpless, N. E. ROS as a Tumour Suppressor? Nat. Cell. Biol. 2006, 8, 1213–1215. DOI: 10.1038/ncb1106-1213.
   PubMed Web of Science ®Google Scholar
• Sakkiah, S.; Lee, K. W. Pharmacophore-Based Virtual Screening and Density Functional Theory Approach to Identifying Novel Butyrylcholinesterase Inhibitors. Acta Pharmacol. Sin. 2012, 33, 964–978. DOI: 10.1038/aps.2012.21.
   PubMed Web of Science ®Google Scholar
• Drwal, M. N.; Banerjee, P.; Dunkel, M.; Wettig, M. R.; Preissner, R. ProTox: A Web Server for the In Silico Prediction of Rodent Oral Toxicity. Nucleic Acids Res. 2014, 42, 3–8. DOI: 10.1093/nar/gku401.
   PubMed Web of Science ®Google Scholar
• Hayakawa, I.; Shioya, R.; Agatsuma, T.; Furukawa, H.; Naruto, S.; Sugano, Y. 4-Hydroxy-3-Methyl-6-Phenylbenzofuran-2-Carboxylic Acid Ethyl Ester Derivatives as Potent Anti-Tumor Agents. Bioorg. Med. Chem. Lett. 2004, 14, 455–458. DOI: 10.1016/j.bmcl.2003.10.039.
   PubMed Web of Science ®Google Scholar
• He, J.; Tang, X. M.; Liu, T. T.; Peng, F.; Zhou, Q.; Liu, L. W.; He, M.; Xue, W. Synthesis and Antibacterial Activity of Novel Myricetin Derivatives Containing Sulfonylpiperazine. Chem. Pap. 2021, 75, 1021–1027. DOI: 10.1007/s11696-020-01363-3.
   Web of Science ®Google Scholar
• Mao, Z. W.; Zheng, X.; Lin, Y. P.; Hu, C. Y.; Wang, X. L.; Wan, C. P.; Rao, G. X. Design, Synthesis and Anticancer Activity of Novel Hybrid Compounds between Benzofuran and N-Aryl Piperazine. Bioorg. Med. Chem. Lett. 2016, 26, 3421–3424. DOI: 10.1016/j.bmcl.2016.06.055.
   PubMed Web of Science ®Google Scholar
• Durgapal, S. D.; Soni, R.; Umar, S.; Suresh, B.; Soman, S. S. Anticancer Activity and DNA Binding Studies of Novel 3,7-Disubstituted Benzopyrones. ChemistrySelect 2017, 2, 147–153. DOI: 10.1002/slct.201601361.
   Web of Science ®Google Scholar
• Elkady, A. I. Crude Alkaloid Extract of Rhazya Stricta Inhibits Cell Growth and Sensitizes Human Lung Cancer Cells to Cisplatin through Induction of Apoptosis. Genet. Mol. Biol. 2013, 36, 12–21. DOI: 10.1590/S1415-47572013005000009.
   PubMed Web of Science ®Google Scholar
• Umar, S.; Soni, R.; Durgapal, S. D.; Soman, S.; Balakrishnan, S. A Synthetic Coumarin Derivative (4-Flourophenylacetamide-Acetyl Coumarin) Impedes Cell Cycle at G0/G1 Stage, Induces Apoptosis, and Inhibits Metastasis via ROS-Mediated P53 and AKT Signaling Pathways in A549 Cells. J. Biochem. Mol. Toxicol. 2020, 34, e22553. DOI: 10.1002/jbt.22553.
   PubMed Web of Science ®Google Scholar
• Lipinski, C. A. Lead- and Drug-like Compounds: The Rule-of-Five Revolution. Drug Discov. Today Technol. 2004, 1, 337–341. DOI: 10.1016/j.ddtec.2004.11.007.
   PubMedGoogle Scholar
• Daina, A.; Blatter, M. C.; Baillie Gerritsen, V.; Palagi, P. M.; Marek, D.; Xenarios, I.; Schwede, T.; Michielin, O.; Zoete, V. Drug Design Workshop: A Web-Based Educational Tool to Introduce Computer-Aided Drug Design to the General Public. J. Chem. Educ. 2017, 94, 335–344. DOI: 10.1021/acs.jchemed.6b00596.
   Web of Science ®Google Scholar