Design, synthesis and biological evaluation of novel pyrazole-based compounds as potential chemotherapeutic agents

References

• Siegel RL, Miller KD, Wagle NS, Jemal A. Cancer statistics, 2023. CA Cancer J Clin. 2023;73(1):17–48. doi:10.3322/caac.21763
   PubMed Web of Science ®Google Scholar
• Petersen PE. Strengthening the prevention of oral cancer: the WHO perspective. Community Dent Oral Epidemiol. 2005;33(6):397–399. doi:10.1111/j.1600-0528.2005.00251.x
   PubMed Web of Science ®Google Scholar
• Miethke M, Pieroni M, Weber T, et al. Towards the sustainable discovery and development of new antibiotics. Nat Rev Chem. 2021;5(10):726–749. doi:10.1038/s41570-021-00313-1
   PubMed Web of Science ®Google Scholar
• Vitaku E, Smith DT, Njardarson JT. Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals. J Med Chem. 2014;57(24):10257–10274. doi:10.1021/jm501100b
   PubMed Web of Science ®Google Scholar
• Ugalde-Arbizu M, Aguilera-Correa JJ, García-Almodóvar V, et al. Dual anticancer and antibacterial properties of silica-based theranostic nanomaterials functionalized with coumarin343, folic acid and a cytotoxic organotin(IV) metallodrug. Pharmaceutics. 2023;15(2):560. doi:10.3390/pharmaceutics15020560
   PubMed Web of Science ®Google Scholar
• de Martel C, Georges D, Bray F, et al. Global burden of cancer attributable to infections in 2018: a worldwide incidence analysis. Lancet Glob Health. 2020;8(2):e180–e190. doi:10.1016/S2214-109X(19)30488-7
   PubMed Web of Science ®Google Scholar
• Frieri M, Kumar K, Boutin A. Antibiotic resistance. J Infect Public Health. 2017;10(4):369–378. doi:10.1016/j.jiph.2016.08.007
   PubMed Web of Science ®Google Scholar
• Rodrigues ME, Silva S, Azeredo J, et al. Novel strategies to fight Candida species infection. Crit Rev Microbiol. 2016;42(4):594–606. doi:10.3109/1040841X.2014.974500
   PubMed Web of Science ®Google Scholar
• Ebenezer O, Shapi M, Tuszynski JA. A Review of the Recent Development in the Synthesis and Biological Evaluations of Pyrazole Derivatives. Biomedicines. 2022;10(5):1124. doi:10.3390/biomedicines10051124
   PubMed Web of Science ®Google Scholar
• Verma R, Verma SK, Rakesh KP, et al. Pyrazole-based analogs as potential antibacterial agents against methicillin-resistance Staphylococcus aureus (MRSA) and its SAR elucidation. Eur J Med Chem. 2021;212:113134. doi:10.1016/j.ejmech.2020.113134
   PubMed Web of Science ®Google Scholar
• Karrouchi K, Radi S, Ramli Y, et al. Synthesis and pharmacological activities of pyrazole derivatives: a review. Molecules. 2018;23(1):134. doi:10.3390/molecules23010134
   PubMed Web of Science ®Google Scholar
• Ahmed AH, Mohamed MF, Allam RM, et al. Design, synthesis, and molecular docking of novel pyrazole-chalcone analogs of lonazolac as 5-LOX, iNOS and tubulin polymerization inhibitors with potential anticancer and anti-inflammatory activities. Bioorg Chem. 2022;129:106171. doi:10.1016/j.bioorg.2022.106171
   PubMed Web of Science ®Google Scholar
• Ouyang Y, Li J, Chen X, et al. Chalcone derivatives: role in anticancer therapy. Biomolecules. 2021;11(6):894. doi:10.3390/biom11060894
   PubMed Web of Science ®Google Scholar
• Rajendran G, Bhanu D, Aruchamy B, et al. Chalcone: a promising bioactive scaffold in medicinal chemistry. Pharmaceuticals (Basel). 2022;15(10):1250. doi:10.3390/ph15101250
   PubMedGoogle Scholar
• Viegas-Junior C, Danuello A, da Silva Bolzani V, et al. Molecular hybridization: a useful tool in the design of new drug prototypes. Curr Med Chem. 2007;14(17):1829–1852. doi:10.2174/092986707781058805
   PubMed Web of Science ®Google Scholar
• Ouyang Y, Li J, Chen X, et al. Chalcone derivatives: role in anticancer therapy. Biomolecules. 2021;11(6):894. doi:10.3390/biom11060894
   PubMed Web of Science ®Google Scholar
• Insuasty B, Tigreros A, Orozco F, et al. Synthesis of novel pyrazolic analogs of chalcones and their 3-aryl-4-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-1-phenyl-1H-pyrazole derivatives as potential antitumor agents. Bioorg Med Chem. 2010;18(14):4965–4974. doi:10.1016/j.bmc.2010.06.013
   PubMed Web of Science ®Google Scholar
• Nepali K, Lee HY, Liou JP. Nitro-group-containing drugs. J Med Chem. 2019;62(6):2851–2893. doi:10.1021/acs.jmedchem.8b00147
   PubMed Web of Science ®Google Scholar
• Dan W, Dai J. Recent developments of chalcones as potential antibacterial agents in medicinal chemistry. Eur J Med Chem. 2020;187:111980. doi:10.1016/j.ejmech.2019.111980
   PubMed Web of Science ®Google Scholar
• Shelke SN, Mhaske GR, Bonifácio VD, et al. Green synthesis and anti-infective activities of fluorinated pyrazoline derivatives. Bioorg Med Chem Lett. 2012;22(17):5727–5730. doi:10.1016/j.bmcl.2012.06.072
   PubMed Web of Science ®Google Scholar
• Siddiqui ZN, Musthafa TN, Ahmad A, et al. Thermal solvent-free synthesis of novel pyrazolyl chalcones and pyrazolines as potential antimicrobial agents. Bioorg Med Chem Lett. 2011;21(10):2860–2865. doi:10.1016/j.bmcl.2011.03.080
   PubMed Web of Science ®Google Scholar
• Bebernitz GR, Argentieri G, Battle B, et al. The effect of 1,3-diaryl-[1H]-pyrazole-4-acetamides on glucose utilization in ob/ob mice. J Med Chem. 2001;44(16):2601–2611. doi:10.1021/jm010032c
   PubMed Web of Science ®Google Scholar
• Wang Y, Xue S, Li R, et al. Synthesis and biological evaluation of novel synthetic chalcone derivatives as anti-tumor agents targeting Cat L and Cat K. Bioorg Med Chem. 2018;26(1):8–16. doi:10.1016/j.bmc.2017.09.019
   PubMed Web of Science ®Google Scholar
• Malla Reddy V, Ravinder Reddy K. Synthesis and antimicrobial activity of some novel 4-(1H-benz[d]imidazol-2yl)-1,3-thiazol-2-amines. Chem Pharm Bull (Tokyo). 2010;58(7):953–956. doi:10.1248/cpb.58.953
   PubMed Web of Science ®Google Scholar
• Skehan P, Storeng R, Scudiero D, et al. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst. 1990;82(13):1107–1112. doi:10.1093/jnci/82.13.1107
   PubMed Web of Science ®Google Scholar
• Balouiri M, Sadiki M, Ibnsouda SK. Methods for in vitro evaluating antimicrobial activity: a review. J Pharm Anal. 2016;6(2):71–79. doi:10.1016/j.jpha.2015.11.005
   PubMed Web of Science ®Google Scholar
• Wayne P. Performance standards for antimicrobial susceptibility testing: Twenty Fifth International Supplement M100-S25. Clinical and Laboratory Standards Institute. 2015;35(3):172–178.
   Google Scholar
• Tawari NR, Bairwa R, Ray MK, et al. Design, synthesis, and biological evaluation of 4-(5-nitrofuran-2-yl)prop-2-en-1-one derivatives as potent antitubercular agents. Bioorg Med Chem Lett. 2010;20(21):6175–6178. doi:10.1016/j.bmcl.2010.08.127
   PubMed Web of Science ®Google Scholar
• Hsu MH, Hsu SM, Kuo YC, et al. Treatment with low-dose sorafenib in combination with a novel benzimidazole derivative bearing a pyrolidine side chain provides synergistic anti-proliferative effects against human liver cancer. RSC Adv. 2017;7(26):16253–16263. doi:10.1039/C6RA28281D
   Web of Science ®Google Scholar
• Zhuang C, Zhang W, Sheng C, et al. Chalcone: a privileged structure in medicinal chemistry. Chem Rev. 2017;117(12):7762–7810. doi:10.1021/acs.chemrev.7b00020
   PubMed Web of Science ®Google Scholar
• Shoemaker RH. The NCI60 human tumour cell line anticancer drug screen. Nat Rev Cancer. 2006;6(10):813–823. doi:10.1038/nrc1951
   PubMed Web of Science ®Google Scholar