Quinazoline compounds for antitumor treatment
DOI:
https://doi.org/10.32471/exp-oncology.2312-8852.vol-41-no-1.12414Keywords:
antitumor action, antitumor treatment, quinazolines, targetsAbstract
Summary. Quinazolines are among the most useful heterocyclic compounds due to their diverse chemical reactivity and a wide range of biological activity. Despite a large number of publications devoted to quinazolines and their derivatives, information is presented predominantly regarding the features of the synthesis of these compounds and their structure. The studies of specific pharmacological activity and antitumor activity of these compounds are mainly limited to primary screening using enzyme systems and cell lines. In this mini review information concerning the potential targets for antitumor action of quinazoline compounds is summarized and discussed.
References
Long S, Resende DISP, Kijjoa A, et al. Antitumor activity of quinazolinone alkaloids inspired by marine natural products. Mar Drugs 2018; 16: e261.
Asif M. Chemical сharacteristics, synthetic methods, and biological potential of quinazoline and quinazolinone derivatives. Int J Med Chem 2014; 2014: 395637.
Srivastava S, Srivastava S. Biological activity of quinazoline: a review. Int J Pharma Sci Res 2015; 6: 1206–13.
Rakesh KP, Darshini N, Shubhavathi T, Mallesha N. Biological applications of quinazolinone analogues: A review. Org Med Chem IJ 2017; 2: 555585.
Abbott JR, Patel PA, Howes JE, et al. Discovery of quinazolines that activate SOS1-mediated nucleotide exchange on RAS. ACS Med Chem Lett 2018; 9: 941–6.
Chen J, Sang Z, Jiang Y, et al. Design, synthesis, and biological evaluation of quinazoline derivatives as dual HDAC1 and HDAC6 inhibitors for the treatment of cancer. Chem Biol Drug Des 2018. doi: 10.1111/cbdd.13405.
Hameed A, Al-Rashida M, Uroos M, et al. Quinazoline and quinazolinone as important medicinal scaffolds: a comparative patent review (2011–2016). Expert Opin Ther Pat 2018; 28: 281–97.
Conconi MT, Marzaro G, Urbani L, et al. Quinazoline-based multi-tyrosine kinase inhibitors: synthesis, modeling, antitumor and antiangiogenic properties. Eur J Med Chem 2013; 67: 373–83.
Alam MJ, Alam O, Naim MJ, et al. Recent investigations on quinazoline scaffold. Int J Advanced Res 2015; 3: 1656–64.
Abdel Gawad NM, Georgey HH, Youssef RM, et al. Synthesis and antitumor activity of some 2, 3-disubstituted quinazolin-4(3H)-ones and 4, 6-disubstituted-1, 2, 3, 4-tetrahydroquinazolin-2H-ones. Eur J Med Chem 2010; 45: 6058–67.
He J, Wang X, Zhao X, et al. Synthesis and antitumor activity of novel quinazoline derivatives containing thiosemicarbazide moiety. Eur J Med Chem 2012; 54: 925–30.
Marvania B, Lee PC, Chaniyara R, et al. Design, synthesis and antitumor evaluation of phenyl N-mustard-quinazoline conjugates. Bioorg Med Chem 2011; 19: 1987–98.
Alqasoumi SI, Al-Taweel AM, Alafeefy AM, et al. Discovering some novel tetrahydroquinoline derivatives bearing the biologically active sulfonamide moiety as a new class of antitumor agents. Eur J Med Chem 2010; 45: 1849–53.
Chinigo GM, Paige M, Grindrod S, et al. Asymmetric synthesis of 2,3-dihydro-2-arylquinazolin-4-ones: methodology and application to a potent fluorescent tubulin inhibitor with anticancer activity. J Med Chem 2008; 51: 4620–31.
Sirisoma N, Pervin A, Zhang H, et al. Discovery of N-methyl-4-(4-methoxyanilino)quinazolines as potent apoptosis inducers. Structure-activity relationship of the quinazoline ring. Bioorg Med Chem Lett 2010; 20: 2330–4.
Al-Obeed O, Vaali-Mohammed MA, Eldehna WM, et al. Novel quinazoline-based sulfonamide derivative (3D) induces apoptosis in colorectal cancer by inhibiting JAK2-STAT3 pathway. Onco Targets Ther 2018; 11: 3313–22.
Peng W, Tu ZC, Long ZJ, et al. Discovery of 2-(2-aminopyrimidin-5-yl)-4-morpholino-N-(pyridin-3-yl)quinazolin-7-amines as novel PI3K/mTOR inhibitors and anticancer agents. Eur J Med Chem 2016; 108: 644–54.
Krapf MK, Gallus J, Spindler A, et al. Synthesis and biological evaluation of quinazoline derivatives — A SAR study of novel inhibitors of ABCG2. Eur J Med Chem 2018; 161: 506–25.
Krapf MK, Gallus J, Wiese M. Synthesis and biological investigation of 2,4-substituted quinazolines as highly potent inhibitors of breast cancer resistance protein (ABCG2). Eur J Med Chem 2017; 139: 587–611.
Alafeefy AM, Kadi AA, Al-Deeb OA, et al. Synthesis, analgesic and anti-inflammatory evaluation of some novel quinazoline derivatives. Eur J Med Chem 2010; 45: 4947–52.
Marzaro G, Guiotto A, Chilin A. Quinazoline derivatives as potential anticancer agents: a patent review (2007–2010). Expert Opin Ther Pat 2012; 22: 223–52.
Ravez S, Castillo-Aguilera O, Depreux P, et al. Quinazoline derivatives as anticancer drugs: a patent review (2011–present). Expert Opin Ther Pat 2015; 25: 789–804.
Glenney JR. Tyrosine-phosphorylated proteins: mediators of signal transduction from the tyrosine kinases. Biochim Biophys Acta 1992; 1134: 113–27.
Karin M, Hunter T. Transcriptional control by protein phosphorylation: signal transmission from the cell surface to the nucleus. Curr Biol 1995; 5: 747–57.
Schlaepfer DD, Hunter T. Signal transduction from the extracellular matrix — a role for the focal adhesion protein-tyrosine kinase FAK. Cell Struct Funct 1996; 21: 445–50.
Tonks NK, Neel BG. From form to function: signaling by protein tyrosine phosphatases. Cell 1996; 87: 365–8.
Cadena DL, Gill GN. Receptor tyrosine kinases. FASEB J 1992; 6: 2332–7.
Rosell R, Moran T, Queralt C, et al. Screening for epidermal growth factor receptor mutations in lung cancer. N Engl J Med 2009; 361: 958–67.
Lynch TJ, Bell DW, Sordella R, et al. Activating mutations in the epidermal growth factor receptor underlying responsiveness of non-small-cell lung cancer to gefitinib. N Engl J Med 2004; 350: 2129–39.
Song Z, Zhang Y. Efficacy of gefitinib or erlotinib in patients with squamous cell lung cancer. Arch Med Sci 2015; 1: 164–8.
Asami K, Atagi S. Comparing the efficacy of gefitinib, erlotinib, and afatinib in non-small cell lung cancer with activating epidermal growth factor receptor (EGFR) mutations. Austin J of Lung Cancer Res 2016; 1: 1–6.
Maemondo M, Inoue A, Kobayashi K, et al. Gefitinib or chemotherapy for non-small-cell lung cancer with mutated EGFR. N Engl J Med 2010; 362: 2380–8.
Zhou C, Wu YL, Chen G, et al. Erlotinib versus chemotherapy as first-line treatment for patients with advanced EGFR mutation-positive non-small-cell lung cancer (OPTIMAL, CTONG-0802): a multicentre, open-label, randomised, phase 3 study. Lancet Oncol 2011; 12: 735–42.
Faehling M, Achenbach J, Staib P, et al. Erlotinib in routine clinical practice for first-line maintenance therapy in patients with advanced non-small cell lung cancer (NSCLC). J Cancer Res Clin Oncol 2018; 144: 1375–83.
Zhang W, Wei Y, Yu D, et al. Gefitinib provides similar effectiveness and improved safety than erlotinib for advanced non-small cell lung cancer: A meta-analysis. Medicine (Baltimore) 2018; 97: e0460.
Marquez-Medina D, Popat S. Afatinib: a second-generation EGF receptor and ErbB tyrosine kinase inhibitor for the treatment of advanced non-small-cell lung cancer. Future Oncol 2015; 11: 2525–40.
Joshi M, Rizvi SM, Belani CP. Afatinib for the treatment of metastatic non-small cell lung cancer. Cancer Manag Res 2015; 7: 75–82.
Sharma N, Graziano S. Overview of the LUX-Lung clinical trial program of afatinib for non-small cell lung cancer. Cancer Treat Rev 2018; 69: 143–51.
Yoshimura A, Uchino J, Tanimura K, et al. An observational study of the epidermal growth factor receptor-tyrosine kinase inhibitor resistance mechanism in epidermal growth factor receptor gene mutation-positive non-small cell lung cancer. Medicine (Baltimore) 2018; 97: e12660.
Sequist LV, Soria J-C, Goldman JW, et al. Rociletinib in EGFR-Mutated Non–Small-Cell Lung Cancer. N Engl J Med 2015; 372: 1700–9.
Fallahi P, Ferrari SM, Baldini E, et al. The safety and efficacy of vandetanib in the treatment of progressive medullary thyroid cancer. Expert Rev Anticancer Ther 2016; 16: 1109–18.
Hou W, Ren Y, Zhang Z, et al. Novel quinazoline derivatives bearing various 6-benzamide moieties as highly selective and potent EGFR inhibitors. Bioorg Med Chem 2018; 26: 1740–50.
Zayed MF, Rateb HS, Ahmed S, et al. Quinazolinone-amino acid hybrids as dual inhibitors of EGFR kinase and tubulin polymerization. Molecules 2018; 23: e1699.
Ding HW, Deng CL, Li DD, et al. Design, synthesis and biological evaluation of novel 4-aminoquinazolines as dual target inhibitors of EGFR-PI3Kα. Eur J Med Chem 2018; 146: 460–70.
Li W, Yin Y, Shuai W, et al. Discovery of novel quinazolines as potential anti-tubulin agents occupying three zones of colchicine domain. Bioorg Chem 2018; 83: 380–90.
Nilius B, Droogmans G. A role for K+ channels in cell proliferation. News Physiol Sci 1994; 9: 105–10.
Fraser S, Grimes J, Djamgo M. Effects of voltage-gated ion channel modulators on rat prostatic cancer cell proliferation: Comparison of strongly and weakly metastatic cell lines. Prostate 2000; 44: 61–76.
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