Design, synthesis and antitumor evaluation of novel pyrazolo[3,4-d]pyrimidines incorporating different amino acid conjugates as potential DHFR inhibitors

References

• Berman EM, Werbel LM. The renewed potential for folate antagonists in contemporary cancer chemotherapy. J Med Chem. 1991;34(2):479–485.
   PubMed Web of Science ®Google Scholar
• Visentin M, Zhao R, Goldman ID. The antifolates. Hematol Oncol Clin North Am. 2012;26(3):629–648, ix.
   PubMed Web of Science ®Google Scholar
• Wińska P, Widło Ł, Skierka K, Krzyśko A, Koronkiewicz M, Cieśla JM, Cieśla J, Bretner M. Simultaneous inhibition of protein kinase CK2 and dihydrofolate reductase results in synergistic effect on acute lymphoblastic leukemia cells. Anticancer Res. 2019;39(7):3531–3542.
   PubMed Web of Science ®Google Scholar
• Ng C, Xiao Y, Lum BL, Han Y. Quantitative structure activity relationships of methotrexate and methotrexate analogues transported by the rat multispecific resistance-associated protein 2 (rMrp2). Eur J Pharm Sci. 2005;26(5):405–413.
   PubMed Web of Science ®Google Scholar
• Walling J. From methotrexate to pemetrexed and beyond. A review of the pharmacodynamic and clinical properties of antifolates. Invest New Drugs. 2006;24(1):37–77.
   PubMed Web of Science ®Google Scholar
• Gangjee A, Devraj R, McGuire JJ, Kisliuk RL. Effect of bridge region variation on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidin. J Med Chem. 1995;38(19):3798–3805.
   PubMed Web of Science ®Google Scholar
• Santos IF, Guedes GP, Mercante LA, Bernardino AMR, Vaz MGF. Synthesis, crystal structure and magnetism of three novel copper (II) complexes with pyrazole-based ligands. J Mol Struct. 2012;1011:99–104.
   Web of Science ®Google Scholar
• Wang H-Q, Liu Z-J, Ding M-W. Versatile synthesis and fungicidal activity of 6-amino-3-alkylthio-1,5-dihydro-1-phenyl-pyrazolo[3,4-d]pyrimidin-4-one derivatives. Phosphorus Sulfur Silicon Relat Elem. 2004;179(10):2039–2050.
   Web of Science ®Google Scholar
• Sugimoto O, Sudo M, Tanji K. Lithiation of 1H-pyrazolo[3,4-d]pyrimidine derivative using lithium alkanetellurolate. Tetrahedron Lett. 1999;40(11):2139–2140.
   Web of Science ®Google Scholar
• Somakala K, Tariq S, Amir M. Synthesis, evaluation and docking of novel pyrazolo pyrimidines as potent p38α MAP kinase inhibitors with improved anti-inflammatory, ulcerogenic and TNF-α inhibitory properties. Bioorg Chem. 2019;87:550–559.
   PubMed Web of Science ®Google Scholar
• Youns M, Askoura M, Abbas HA, Attia GH, Khayyat AN, Goda RM, Almalki AJ, Khafagy E-S, Hegazy WAH. Celastrol modulates multiple signaling pathways to inhibit proliferation of pancreatic cancer via DDIT3 and ATF3 up-regulation and RRM2 and MCM4 down-regulation. Onco Targets Ther. 2021;14:3849–3860.
   PubMed Web of Science ®Google Scholar
• Askoura M, Abbas HA, Al Sadoun H, Abdulaal WH, Abu Lila AS, Almansour K, Alshammari F, Khafagy E-S, Ibrahim TS, Hegazy WAH. Elevated levels of IL-33, IL-17 and IL-25 indicate the progression from chronicity to hepatocellular carcinoma in hepatitis C virus patients. Pathogens. 2022;11(1):57.
   PubMed Web of Science ®Google Scholar
• Abbas HA, Hegazy WAH. Targeting the virulence factors of Serratia marcescens by ambroxol. Rouman Arch Microbiol Immunol. 2017;76:27–32.
   Google Scholar
• Youns M, Abdel Halim Hegazy W. The natural flavonoid fisetin inhibits cellular proliferation of hepatic, colorectal, and pancreatic cancer cells through modulation of multiple signaling pathways. PLoS One. 2017;12(1):e0169335.
   PubMed Web of Science ®Google Scholar
• Abdelaziz OA, El Husseiny WM, Selim KB, Eisa HM. Dihydrofolate reductase inhibition effect of 5-substituted pyrido[2,3-d]pyrimidines: synthesis, antitumor activity and molecular modeling study. Bioorg Chem. 2019;90:103076.
   PubMed Web of Science ®Google Scholar
• Aldawsari MF, Alalaiwe A, Khafagy ES, Al Saqr A, Alshahrani SM, Alsulays BB, Alshehri S, Lila ASA, Rizvi SMD, Hegazy WAH. Efficacy of SPG-ODN 1826 nanovehicles in inducing M1 phenotype through TLR-9 activation in murine alveolar J774A.1 cells: plausible nano-immunotherapy for lung carcinoma. IJMS. 2021;22(13):6833.
   Google Scholar
• Ibrahim TS, Malebari AM, Mohamed MFA. Design, synthesis, in vitro anticancer evaluation and molecular modelling studies of 3,4,5-trimethoxyphenyl-based derivatives as Dual EGFR/HDAC hybrid inhibitors. Pharmaceuticals. 2021;14(11):1177.
   Web of Science ®Google Scholar
• Moroy G, Sperandio O, Rielland S, Khemka S, Druart K, Goyal D, Perahia D, Miteva M. Sampling of conformational ensemble for virtual screening using molecular dynamics simulations and normal mode analysis. Future Med Chem. 2015;7(17):2317–2331.
   PubMed Web of Science ®Google Scholar
• Fotoohi AK, Albertioni F. Mechanisms of antifolate resistance and methotrexate efficacy in leukemia cells. Anticancer Res. 2008;3:410–426.
   Google Scholar
• Askoura M, Almalki AJ, Lila ASA, Almansour K, Alshammari F, Khafagy E, Ibrahim TS, Hegazy WAH. Alteration of Salmonella enterica virulence and host pathogenesis through targeting sdiA by using the CRISPR-Cas9 system. Microorganisms. 2021;9(12):2564.
   PubMed Web of Science ®Google Scholar
• Askoura M, Hegazy WAH. Ciprofloxacin interferes with Salmonella typhimurium intracellular survival and host virulence through repression of Salmonella pathogenicity island-2 (SPI-2) genes expression. Pathog Dis. 2020;78:1–12.
   Web of Science ®Google Scholar
• Hegazy WAH, Abbas HA. Evaluation of the role of SsaV Salmonella pathogenicity island-2 dependent type III secretion system components on the virulence behavior of Salmonella enterica serovar Typhimurium. African Journal of Biotechnology. 2017;16:718–726.
   Google Scholar