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Research Paper

Development of 3-methyl/3-(morpholinomethyl)benzofuran derivatives as novel antitumor agents towards non-small cell lung cancer cells

, , , , , , , , & show all
Pages 987-999 | Received 28 Feb 2021, Accepted 06 Apr 2021, Published online: 13 May 2021

References

  • Bray F, Ferlay J, Soerjomataram I, et al. Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer J Clin 2018;68:394–424.
  • Alonso R, Pineros M, Laversanne M, et al. Lung cancer incidence trends in Uruguay 1990–2014: an age-period-cohort analysis. Cancer Epidemiol 2018;55:17–22.
  • Lortet-Tieulent J, Renteria E, Sharp L, et al. Convergence of decreasing male and increasing female incidence rates in major tobacco-related cancers in Europe in 1988–2010. Eur J Cancer 2015;51:1144–63.
  • Bistrovic A, Krstulovic L, Harej A, et al. Design, synthesis and biological evaluation of novel benzimidazole amidines as potent multi-target inhibitors for the treatment of non-small cell lung cancer. Eur J Med Chem 2017;143:1616.
  • Almahli H, Hadchity E, Jaballah MY, et al. Development of novel synthesized phthalazinone-based PARP-1 inhibitors with apoptosis inducing mechanism in lung cancer. Bioorg Chem 2018;77:443–56.
  • Atal S, Asokan P, Jhaj R. Recent advances in targeted small‐molecule inhibitor therapy for non–small‐cell lung cancer—an update. J Clin Pharm Ther 2020;45:580–4.
  • Nevagi RJ, Dighe SN, Dighe SN. Biological and medicinal significance of benzofuran. Eur J Med Chem 2015;97:561–81.
  • Miao Y-h, Hu Y-h, Yang J, et al. Natural source, bioactivity and synthesis of benzofuran derivatives. RSC Adv 2019;9:27510–40.
  • Radadiya A, Shah A. Bioactive benzofuran derivatives: an insight on lead developments, radioligands and advances of the last decade. Eur J Med Chem 2015;97:356–76.
  • Shamsuzzaman HK. Bioactive Benzofuran derivatives: a review. Eur J Med Chem 2015;97:483–504.95.
  • Abdelrahman MA, Eldehna WM, Nocentini A, et al. Novel benzofuran-based sulphonamides as selective carbonic anhydrases IX and XII inhibitors: synthesis and in vitro biological evaluation. J Enzyme Inhib Med Chem 2020;35:298–305.
  • Shaldam M, Eldehna WM, Nocentini A, et al. Development of novel benzofuran-based SLC-0111 analogs as selective cancer-associated carbonic anhydrase isoform IX inhibitors. Eur J Med Chem 2021;216:113283.
  • Chand K, Rajeshwari, Hiremathad A, et al. A review on antioxidant potential of bioactive heterocycle benzofuran: natural and synthetic derivatives. Pharmacol Rep 2017;69:281–95.
  • Goyal D, Kaur A, Goyal B. Benzofuran and indole: promising scaffolds for drug development in Alzheimer’s disease. ChemMedChem 2018;13:1275–99.
  • Alizadeh M, Jalal M, Hamed K, et al. Recent updates on anti-inflammatory and antimicrobial effects of furan natural derivatives. J Inflamm Res 2020;13:451–63.
  • Hiremathad A, Patil MR, Chand K, et al. Benzofuran: an emerging scaffold for antimicrobial agents. RSC Adv 2015;5:96809.
  • Xu Z, Zhao S, Zaosheng L, et al. Benzofuran derivatives and their anti-tubercular, anti-bacterial activities. Eur J Med Chem 2019;162:266–76.
  • Kwiecień H, Goszczyńska A, Rokosz P. Benzofuran small molecules as potential inhibitors of human protein kinases. A review. Curr Pharm Des 2016;22:879–94.
  • Eldehna WM, Al-Rashood ST, Al-Warhi T, et al. Novel oxindole/benzofuran hybrids as potential dual CDK2/GSK-3β inhibitors targeting breast cancer: design, synthesis, biological evaluation, and in silico studies. J Enzyme Inhib Med Chem 2021;36:270–85.
  • Gao C, Sun X, Wu Z, et al. A novel benzofuran derivative Moracin N induces autophagy and apoptosis through ROS generation in lung cancer. Front Pharmacol 2020;11:391.
  • Abbas HS, Abd El-Karim SS. Design, synthesis and anticervical cancer activity of new benzofuran–pyrazol-hydrazono-thiazolidin-4-one hybrids as potential EGFR inhibitors and apoptosis inducing agents. Bioorg Chem 2019;89:103035.
  • Mphahlele MJ, Maluleka MM, Aro A, et al. Benzofuran–appended 4-aminoquinazoline hybrids as epidermal growth factor receptor tyrosine kinase inhibitors: synthesis, biological evaluation and molecular docking studies. J Enzyme Inhib Med Chem 2018;33:1516–28.
  • Eldehna WM, Nocentini A, Elsayed ZM, et al. Benzofuran-based carboxylic acids as carbonic anhydrase inhibitors and antiproliferative agents against breast cancer. ACS Med Chem Lett 2020;11:1022–7.
  • Zou Y. Benzofuran‐isatin conjugates as potent VEGFR‐2 and cancer cell growth inhibitors. J Heterocycl Chem 2020;57:510–6.
  • Abdelhafez OM, Amin KM, Ali HI, et al. Design, synthesis and anticancer activity of benzofuran derivatives targeting VEGFR-2 tyrosine kinase. RSC Adv 2014;4:11569–79.
  • Abdelhafez OM, Ali HI, Amin KM, Abdalla MM. Design, synthesis and anticancer activity of furochromone and benzofuran derivatives targeting VEGFR-2 tyrosine kinase. RSC Adv 2015;5:25312–24.
  • Modi SJ, Kulkarni VM. Vascular endothelial growth factor receptor (VEGFR-2)/KDR inhibitors: medicinal chemistry perspective. Med Drug Discov 2019;2:100009.
  • Eldehna WM, El Kerdawy AM, Al-Ansary GH, et al. Type IIA–Type IIB protein tyrosine kinase inhibitors hybridization as an efficient approach for potent multikinase inhibitor development: design, synthesis, anti-proliferative activity, multikinase inhibitory activity and molecular modeling of novel indolinone-based ureides and amides. Eur J Med Chem 2019;163:37–53.
  • Sun Q, Zhou J, Zhang Z, et al. Discovery of fruquintinib, a potent and highly selective small molecule inhibitor of VEGFR 1, 2, 3 tyrosine kinases for cancer therapy. Cancer Biol Ther 2014;15:1635–45.
  • Shirley M. Fruquintinib: first global approval. Drugs 2018;78:1757–61.
  • Lu S, Chen G, Sun Y, et al. A Phase III, randomized, double-blind, placebo-controlled, multicenter study of fruquintinib in Chinese patients with advanced nonsquamous non-small-cell lung cancer–The FALUCA study. Lung Cancer 2020;146:252–62.
  • Bruce JY, LoRusso PM, Goncalves PH, et al. A pharmacodynamically guided dose selection of PF-00337210 in a phase I study in patients with advanced solid tumors. Cancer Chemother Pharmacol 2016;77:527–38.
  • Ho T-L. Hard soft acids bases (HSAB) principle and organic chemistry. Chem Rev 1975;75:1–20.
  • Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55–63.
  • Engels EA. Inflammation in the development of lung cancer: epidemiological evidence. Expert Rev Anticancer Ther 2008;8:605–15.
  • Franzblau SG, Witzig RS, McLaughlin JC, et al. Rapid, low-technology MIC determination with clinical Mycobacterium tuberculosis isolates by using the microplate Alamar Blue assay. J Clin Microbiol 1998;36:362–6.
  • McTigue M, Murray BW, Chen JH, et al. Molecular conformations, interactions, and properties associated with drug efficiency and clinical performance among VEGFR TK inhibitors. Proc Natl Acad Sci 2012;109:18281–9.
  • Grubenmann W, Erlenmeyer H. Über bromierte Cumaronderivate und über eine neue Darstellung von Cumaronyl‐3‐essigsäure. Helv Chim Acta 1948;31:78–83.
  • Trott O, Olson AJ. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization and multithreading. J Comput Chem 2010;31:455–61.
  • Morris GM, Huey R, Lindstrom W, et al. Autodock4 and AutoDockTools4: automated docking with selective receptor flexibility. J Comput Chem 2009;30:2785–91.