Synthesis, antitumor activity and molecular docking study of some novel 3-benzyl-4(3H)quinazolinone analogues

References

• Harris CC, Hollstein M. Clinical implications of the P53 tumor suppressor gene. N Engl J Med 1993;329:1318–27
   PubMed Web of Science ®Google Scholar
• Liott LA, Steeg PS, Steller-Stevenson WG. Cancer metastasis and angiogenesis: an imbalance of positive and negative regulation. Cell 1991;64:327–36
   PubMed Web of Science ®Google Scholar
• Mignatti P. Rifkin DB. Biology and biochemistry of proteinases in tumor invasion. Physiol Rev 1993;73:161–5
   PubMed Web of Science ®Google Scholar
• Auerbuch D. Alkylating agents. In: Chabner BA. Collins JM, eds. Cancer chemotherapy: principles and practice. Philadelphia: Lippincott; 1990:314–28
   Google Scholar
• (a) El-Azab AS, Kamal EH. Synthesis and anticonvulsant evaluation of some new 2,3,8-trisubstituted-4(3H)-quinazoline derivatives. Bioorg Med Chem Lett 2012;22:327–33. (b) Alanazi AM, Abdel-Aziz A-MA, Al-Suwaidan I, et al. Design, synthesis and biological evaluation of some novel substituted quinazolines as antitumor agents. Eur J Med Chem 2014;79:446–54. (c) Aziza MA, Nassar MW, Abdel-Hamide SG, et al. Synthesis and antimicrobial activities of some new 3-heteroaryl- quinazolin-4-ones. Indian J Heterocycl Chem 1996;6:25–30. (d) El-Azab AS. Synthesis of some new substituted 2-mercaptoquinazoline analogs as potential antimicrobial agents. Phosphorus Sulfur Silicon Relat Elem 2007;183:333–48
   Google Scholar
• (a) Habib NS, Ismail KA, El-Tombary AA, Abdel-Aziem T. Antilipidemic agents, Part. IV: synthesis and antilipidemic testing of some heterocyclic derivatives of hexadecyl and cyclohexyl hemisuccinate esters. Pharmazie 2000;55:495–9. (b) Al-Omar MA, El-Azab AS, El-Obeid HA, Abdel Hamide SG. Synthesis of some new 4(3H) quinazoline analogs as potential antioxidant agents. J Saudi Chem Soc 2006;10:113–28. (c) Alafeefy AM, Kadi AA, El-Azab AS, et al. Synthesis, analgesic and anti-inflammatory evaluation of some new 3H-quinazolin-4-one derivatives. Arch Pharm 2008;341:377–85. (d) Kumar A, Sharma S, Archana A, et al. Some new 2,3,6-trisubstituted quinazolinones as potent anti-inflammatory, analgesic and COX-II inhibitors. Bioorg Med Chem 2003;11:5293–9
   Google Scholar
• (a) Alagarsamy V, Solomon VR, Dhanabal K. Synthesis and pharmacological evaluation of some 3-phenyl-2-substituted-3Hquinazolin-4-one as analgesic, anti-inflammatory agents. Bioorg Med Chem 2007;15:235–41. (b) El-Azab AS, Kamal EH, Attia SM. Synthesis and anticonvulsant evaluation of some novel 4(3H)-quinazolinones. Monatsh Chem 2011;142:837–48
   Google Scholar
• (a) El-Azab AS, Kamal EH. Design and synthesis of novel 7-aminoquinazoline derivatives: antitumor and anticonvulsant activities. Bioorg Med Chem Lett 2012;22:1879–85. (b) Kashaw SK, Kashaw V, Mishra P, et al. Synthesis, anticonvulsant and CNS depressant activity of some new bioactive 1-(4-substituted-phenyl)-3-(4-oxo-2-phenyl/ethyl-4H-quinazolin-3-yl)-urea. Eur J Med Chem 2009;44:4335–43
   Google Scholar
• (a) Archana V, Srivastava K, Kumar A. Synthesis of some newer derivatives of substituted quinazolinonyl-2-oxo/thiobarbituric acid as potent anticonvulsant agents. Bioorg Med Chem 2004;12:1257–64. (b) Alafeefy A, El-Azab AS, Mohamed MA, et al. Synthesis of some new substituted iodoquinazolinederivatives and their antimicrobial screening. J Saudi Chem Soc 2011;15:319–25
   Google Scholar
• (a) Al-Omary FA, Abou-Zeid LA, Nagi MN, et al. Non-classical antifolates. Part 2: synthesis, biological evaluation, and molecular modeling study of some new 2,6-substituted-quinazolin-4-ones. Bioorg Med Chem 2010;18:2849–63. (b) Al-Obaid AM, Abdel-Hamide SG, El-Kashef HA, et al. Synthesis, in vitro antitumor activity and molecular modeling study of certain 2-thieno-4(3H)-quinazolinone analogs. Eur J Med Chem 2009;44:2379–91
   Google Scholar
• (a) El-Azab AS, Al-Omar MA, Abdel-Aziz AA, et al. Design, synthesis and biological evaluation of novel quinazoline derivatives as potential antitumor agents: molecular docking study. Eur J Med Chem 2010;45:4188–98. (b) El-Azab AS, Abdel-Hamide SG, Sayed-Ahmed MM, et al. Novel 4(3H)-quinazolinone analogs: synthesis and anticonvulsant activity. Med Chem Res 2013;22:2815–27. (c) Abdel Gawad NM, Georgey HH, Youssef RM, El-Sayed NA. 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
   Google Scholar
• (a) Fry DW, Kraker AJ, McMichael A, et al. A specific inhibitor of the epidermal growth factor receptor tyrosine kinase. Science 1994;265:1093–95. (b) Traxler PM, Furet P, Mett H, et al. 4-(Phenyl amino)pyrrolopyrimidines: potent and selective, ATP site directed inhibitors of the EGF-receptor protein tyrosine kinase. J Med Chem 1996;39:2285–92
   Google Scholar
• (a) Hynes JH, Tomazic A, Kumar A, et al. Inhibition of human dihydrofolate reductase by 2,4-diaminoquinazolines bearing simple substituents on the aromatic ring. J Heterocyclic Chem 1991;28:1981–6. (b) Harris NV, Smith C, Bowden K. Antifolate and antibacterial activities of 5-substituted 2,4-diaminoquinazolines. J Med Chem 1990;33:434–44. (c) Barlési F, Tchouhadjian C, Doddoli C, et al. Gefitinib (ZD1839, Iressa) in non-small-cell lung cancer: a review of clinical trials from a daily practice perspective. Fundam Clin Pharmacol 2005;3:385–93
   Google Scholar
• (a) Arteaga CL, Johnson DH. Tyrosine kinase inhibitors-ZD1839 (Iressa). Curr Opin Oncol 2001;13:491–8. (b) Barker AJ, Gibson KH, Grundy W, et al. Studies leading to the identification of ZD1839 (IRESSA): an orally active, selective epidermal growth factor receptor tyrosine kinase inhibitor targeted to the treatment of cancer. Bioorg Med Chem Lett 2001;11:1911–14
   Google Scholar
• (a) Ganjoo KN, Wakelee H. Review of erlotinib in the treatment of advanced non-small cell lung cancer. Biologics 2007;1:335–46. (b) Kopper L. Lapatinib: a sword with two edges. Pathol Oncol Res 2008;14:1–8
   Google Scholar
• (a) Dhillon S, Wagstaff AJ. Lapatinib. Drugs 2007;67:2101–8. (b) Burris HA, Hurwitz HI, Dees EC, et al. Phase I safety, pharmacokinetics, and clinical activity study of lapatinib (GW572016), a reversible dual inhibitor of epidermal growth factor receptor tyrosine kinases, in heavily pretreated patients with metastatic carcinomas. J Clin Oncol 2005;23:5305–13
   Google Scholar
• (a) Wood ER, Truesdale AT, McDonald OB, et al. A unique structure for epidermal growth factor receptor bound to GW572016 (Lapatinib): relationships among protein conformation, inhibitor off-rate, and receptor activity in tumor cells. Cancer Res 2004;64: 6652–59. (b) Hennequin LF, Stokes ES, Thomas AP, et al. Novel 4-anilinoquinazolines with C-7 basic side chains: design and structure activity relationship of a series of potent, orally active, VEGF receptor tyrosine kinase inhibitors. J Med Chem 2002;45:1300–12
   Google Scholar
• (a) Fricker J. Tyrosine kinase inhibitors: the next generation. Lancet Oncol 2006;7:621. (b) Garofalo S, Rosa R, Bianco R, Tortora G. EGFR-targeting agents in oncology. Expert Opin Therap Patents 2008;18:889–901
   Google Scholar
• (a) Madhusudan S, Ganesan TS. Tyrosine kinase inhibitors in cancer therapy. Clin Biochem 2004;37:618–35. (b) Cockerill GS, Lackey KE. Small molecule inhibitors of the class 1 receptor tyrosine kinase family. Curr Top Med Chem 2002;2:1001–10
   Google Scholar
• (a) Harris PA. Cancer drug design and discovery. 2nd ed. New York: Academic Press; 2014. (b) Liechti C, Séquin U, Bold G, et al. Salicylanilides as inhibitors of the protein tyrosine kinase epidermal growth factor receptor. Eur J Med Chem 2004;39:11–26
   Google Scholar
• (a) Sheldrick GM. A short history of SHELX. Acta Crystallogr Sect A 2008;64:112–22. (b) El-Azab AS, Abdel-Aziz AA, Al-Swaidan IA, et al. 2-Methyl-sulfanyl-9H-1,3,4-thia-diazolo[2,3-b]quinazolin-9-one. Acta Crystallogr Sect E Struct Rep Online 2012;68:o2134
   Google Scholar
• Grever MR, Schepartz SA, Chabner BA. The National Cancer Institute: cancer drug discovery and development program. Semin Oncol 1992;19:622–38
   PubMed Web of Science ®Google Scholar
• Monks A, Scudiero D, Skehan P, et al. Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J Natl Cancer Inst 1991;83:757–66
   PubMed Web of Science ®Google Scholar
• Boyd MR, Paull K. Some practical considerations and applications of the national cancer institute in vitro anticancer drug discovery screen. Drug Dev Res 1995;34:91–109
   Web of Science ®Google Scholar
• Shoemaker RH. The NCI60 human tumour cell line anticancer drug screen. Nat Rev Cancer 2006;6:813−23
   PubMed Web of Science ®Google Scholar
• Alley MC, Scudiero DA, Monks PA, et al. Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay. Cancer Res 1988;48:589–601
   Google Scholar
• MOE 2008.10 of Chemical Computing Group. Inc. Available from: https://doi.org/http://www.chemcomp.com/press_releases/2008-11-04.htm
   Google Scholar
• Brose MS, Volpe P, Feldman M, et al. BRAF and RAS mutations in human lung cancer and melanoma. Cancer Res 2002;62:6997–7000
   PubMed Web of Science ®Google Scholar
• Stamos J, Sliwkowski MX, Eigenbrot C. Structure of the epidermal growth factor receptor kinase domain alone and in complex with a 4-anilinoquinazoline inhibitor. J Biol Chem 2002;277:46265–72
   Google Scholar
• Bridges AJ. The rationale and strategy used to develop a series of highly potent, irreversible, inhibitors of the epidermal growth factor receptor family of tyrosine kinases. Curr Med Chem 1999;6:825–43
   PubMed Web of Science ®Google Scholar
• Lv PC, Wang KR, Li QS, et al. Design, synthesis and biological evaluation of chrysin long-chain derivatives as potential anticancer agents. Bioorg Med Chem 2010;18:1117–23
   PubMed Web of Science ®Google Scholar
• Bollag G, Hirth P, Tsai J, et al. Clinical efficacy of a RAF inhibitor needs broad target blockade in BRAF-mutant melanoma. Nature 2010;467:596–9
   Google Scholar
• Choi WK, El-Gamal MI, Choi HS, et al. New diarylureas and diarylamides containing 1,3,4-triarylpyrazole scaffold: synthesis, antiproliferative evaluation against melanoma cell lines, ERK kinase inhibition, and molecular docking studies. Eur J Med Chem 2011;46:5754–62
   PubMed Web of Science ®Google Scholar