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Research Papers

Structure-guided approach on the role of substitution on amide-linked bipyrazoles and its effect on their anti-inflammatory activity

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Pages 2179-2190 | Received 24 May 2022, Accepted 28 Jul 2022, Published online: 11 Aug 2022

References

  • MA Ragab H, Bekhit AA, AF Rostom S, Bekhit E-DA. Compounds containing azole scaffolds as cyclooxygenase inhibitors: a review. Curr Topics Med Chem 2016;16:3569–81.
  • Faour WH, Mroueh M, Daher CF, et al. Synthesis of some new amide-linked bipyrazoles and their evaluation as anti-inflammatory and analgesic agents. J Enzyme Inhib Med Chem 2016;31:1079–94.
  • Mak TW, Saunders ME, Jett, BD. Primer to the immune response. Boston: Newnes; 2013.
  • Piomelli D. Arachidonic acid in cell signaling. Curr Opin Cell Biol 1993;5:274–80.
  • Marks AD, Lieberman M, Peet A. The molecular biology of cancer. In: Marks basic medical biochemistry a clinical approach. 5th ed. Philadelphia: Lippincott Williams & Wilkins; 2018:759–812.
  • Anwikar S, Bhitre M. Study of the synergistic anti-inflammatory activity of Solanum xanthocarpum Schrad and Wendl and Cassia fistula Linn. Int J Ayurveda Res 2010;1:167.
  • Sharma PK, Kumar S, Kumar P, et al. Synthesis and biological evaluation of some pyrazolylpyrazolines as anti-inflammatory–antimicrobial agents. Eur J Med Chem 2010;45:2650–5.
  • Zou H, Yuan C, Dong L, et al. Human cyclooxygenase-1 activity and its responses to COX inhibitors are allosterically regulated by nonsubstrate fatty acids. J Lipid Res 2012;53:1336–47.
  • AlFadly ED, Elzahhar PA, Tramarin A, et al. Tackling neuroinflammation and cholinergic deficit in Alzheimer's disease: multi-target inhibitors of cholinesterases, cyclooxygenase-2 and 15-lipoxygenase. Eur J Medi Chem 2019;167:161–86.
  • Qiu K-M, Yan R, Xing M, et al. Synthesis, biological evaluation and molecular modeling of dihydro-pyrazolyl-thiazolinone derivatives as potential COX-2 inhibitors. Bioorg Med Chem 2012;20:6648–54.
  • Yuan C, Sidhu RS, Kuklev DV, et al. Cyclooxygenase allosterism, fatty acid-mediated cross-talk between monomers of cyclooxygenase homodimers. J Biol Chem 2009;284:10046–55.
  • Hajjar ER, Cafiero AC, Hanlon JT. Polypharmacy in elderly patients. Am J Geriatric Pharmacother 2007;5:345–51.
  • Ragab FA, Gawad NMA, Georgey HH, Said MF. Synthesis of novel 1, 3, 4-trisubstituted pyrazoles as anti-inflammatory and analgesic agents. Eur J Med Chem 2013;63:645–54.
  • Guo B, Lager KM, Henningson JN, et al. Experimental infection of United States swine with a Chinese highly pathogenic strain of porcine reproductive and respiratory syndrome virus. Virology 2013;435:372–84.
  • Marza AD, Abdullah FFJ, Ahmed IM, et al. Involvement of nervous system in cattle and buffaloes due to Pasteurella multocida B: 2 infection: a review of clinicopathological and pathophysiological changes. J Adv Veter Anim Res 2015;2:252–62.
  • Moreland LW Rheumatology and immunology therapy: A to Z essentials. USA: Springer Science & Business Media, 2004.
  • Rubin E HM, Reisner Essentials of Rubin's pathology. USA: Lippincott Williams & Wilkins, 2009.
  • Mohy El‐Din MM, Senbel AM, Bistawroos AA, et al. A novel COX‐2 inhibitor pyrazole derivative proven effective as an anti‐inflammatory and analgesic drug. Basic Clin Pharmacol Toxicol 2011;108:263–73.
  • Abd El Razik HA, Mroueh M, Faour WH, et al. Synthesis of new pyrazolo [3, 4‐d] pyrimidine derivatives and evaluation of their anti‐inflammatory and anticancer activities. Chem Biol Drug Des 2017;90:83–96.
  • Khloya P, Kumar S, Kaushik P, et al. Synthesis and biological evaluation of pyrazolylthiazole carboxylic acids as potent anti-inflammatory–antimicrobial agents. Bioorg Med Chem Lett 2015;25:1177–81.
  • Keche AP, Hatnapure GD, Tale RH, et al. Synthesis, anti-inflammatory and antimicrobial evaluation of novel 1-acetyl-3,5-diaryl-4,5-dihydro (1H) pyrazole derivatives bearing urea, thiourea and sulfonamide moieties. Bioorg Med Chem Lett 2012;22:6611–5.
  • Fioravanti R, Bolasco A, Manna F, et al. Synthesis and biological evaluation of N-substituted-3, 5-diphenyl-2-pyrazoline derivatives as cyclooxygenase (COX-2) inhibitors. Eur J Med Chem 2010;45:6135–8.
  • Molecualr Operating Environment (MOE 2018), Chemical Computing Group Inc.: Montreal, http://www.chemcomp/com.
  • Shaaban MM, Ragab HM, Akaji K, et al. Design, synthesis, biological evaluation and in silico studies of certain aryl sulfonyl hydrazones conjugated with 1,3-diaryl pyrazoles as potent metallo-β-lactamase inhibitors. Bioorg Chem 2020;105:104386.
  • Sanner MF. Python: a programming language for software integration and development. J Mol Graph Model 1999;17:57–61.
  • Elghoneimy LK, Ismail MI, Boeckler FM, et al. Facilitating SARS CoV-2 RNA-dependent RNA polymerase (RdRp) drug discovery by the aid of HCV NS5B palm subdomain binders: in silico approaches and benchmarking. Comput Biol Med 2021;134:104468.
  • Bekhit AA, Nasralla SN, El-Agroudy EJ, et al. Investigation of the anti-inflammatory and analgesic activities of promising pyrazole derivative. Eur J Pharm Sci 2022;168:106080.
  • Abraham MJ, Murtola T, Schulz R, et al. GROMACS: high performance molecular simulations through multi-level parallelism from laptops to supercomputers. SoftwareX 2015;1-2:19–25.
  • Huang J, MacKerell AD. Jr, CHARMM36 all-atom additive protein force field: validation based on comparison to NMR data. J Comput Chem 2013;34:2135–45.
  • Zoete V, Cuendet MA, Grosdidier A, Michielin O. SwissParam: a fast force field generation tool for small organic molecules. J Comput Chem 2011;32:2359–68.
  • P, Turner (2005) XMGRACE, Version 5.1. 19. Center for Coastal and Land-Margin Research, Oregon Graduate Institute of Science and Technology, Beaverton, OR.
  • Domiati S, Mehanna M, Ragab H, et al. Investigation of chronic efficacy and safety profile of two potential anti-inflammatory bipyrazole-based compounds in experimental animals. J Inflamm Res 2018;11:143–53.
  • Abouzeit-Har MS, Verimer T, Long JP. Effect of long term estrogen and lithium treatment on restraint induced gastric erosion in intact and ovariectomized rats. Die Pharmazie. 1982;37:593–5.
  • Tominaga Y, Honkawa Y, Hara M, Hosomi A. Synthesis of pyrazolo [3, 4‐d] pyrimidine derivatives using ketene dithioacetals. J Heterocyclic Chem 1990;27:775–83.
  • 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.
  • Ibrahim TM, Bauer MR, Boeckler FM. Applying DEKOIS 2.0 in structure-based virtual screening to probe the impact of preparation procedures and score normalization. J Cheminformatics 2015;7:1–16.
  • Bauer MR, Ibrahim TM, Vogel SM, Boeckler FM. Evaluation and optimization of virtual screening workflows with DEKOIS 2.0–a public library of challenging docking benchmark sets. J Chem Inform Model 2013;53:1447–62.
  • Wilcken R, Zimmermann MO, Lange A, et al. Principles and applications of halogen bonding in medicinal chemistry and chemical biology. J Med Chem 2013;56:1363–88.
  • Koebel MR, Schmadeke G, Posner RG, Sirimulla S. AutoDock VinaXB: implementation of XBSF, new empirical halogen bond scoring function, into AutoDock Vina. J Cheminform 2016;8:27.
  • Charlier C, Michaux C. Dual inhibition of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) as a new strategy to provide safer non-steroidal anti-inflammatory drugs. Eur J Med Chem 2003;38:645–59.
  • Dannhardt G, Kiefer W. Cyclooxygenase inhibitors–current status and future prospects. Eur J Med Chem 2001;36:109–26.
  • Kurumbail RG, Stevens AM, Gierse JK, et al. Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature 1996;384:644–8.
  • Arba M, Wahyudi ST, Brunt DJ, et al. Mechanistic insight on the remdesivir binding to RNA-Dependent RNA polymerase (RdRp) of SARS-cov-2. Comput Biol Med 2021;129:104156.
  • Ismail MI, Ragab HM, Bekhit AA, Ibrahim TM. Targeting multiple conformations of SARS-CoV2 papain-like protease for drug repositioning: an in-silico study. Comput Biol Med 2021;131:104295.
  • Morteau O. Prostaglandins and inflammation: the cyclooxygenase controversy. Arch Immunol Ther Exps 2000;48:473–80.
  • Robbins S Robbins and Cotran pathologic basis of disease. Philadelphia, PA: Saunders/Elsevier, 2010.
  • Ricciotti E, FitzGerald GA. Prostaglandins and inflammation. Arterioscler Thromb Vasc Biol 2011;31:986–1000.
  • Pitsillides AA (2004) Inflammation Protocols. Methods In Molecular Biology, Volume 225. Edited by P. G. Winyard and D. A. Willoughby. $99.50. Humana Press, Totowa, NJ, 2003. 380 pages. ISBN 0-86903-970-6. Rheumatology 43 814–814.
  • Ku EC, Lee W, Kothari HV, Scholer DW. Effect of diclofenac sodium on the arachidonic acid cascade. Am J Med 1986;80:18–23.
  • Sostres C, Gargallo CJ, Arroyo MT, Lanas A. Adverse effects of non-steroidal anti-inflammatory drugs (NSAIDs, aspirin and coxibs) on upper gastrointestinal tract. Best practice & research. Clin Gastroenterol 2010;24:121–32.
  • Laine L. The gastrointestinal effects of nonselective NSAIDs and COX-2-selective inhibitors. Sem Arthr Rheum 2002;32:25–32.