Design, synthesis and molecular modelling studies of some pyrazole derivatives as carbonic anhydrase inhibitors

References

• Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–81.
   PubMed Web of Science ®Google Scholar
• (a) Arslan T, Celik G, Celik H. Synthesis and biological evaluation of novel bischalcone derivatives as carbonic anhydrase inhibitors. Arch Pharm 2016;349:741–8;
   PubMed Web of Science ®Google Scholar
  (b) Vullo D, Del Prete S, Fisher GM. Sulfonamide inhibition studies of the η-class carbonic anhydrase from the malaria pathogen Plasmodium falciparum. Bioorg Med Chem 2015;23:526–31.
   PubMed Web of Science ®Google Scholar
• (a) Senturk M, Alici HA, Beydemir S. In vitro and in vivo effects of some benzodiazepine drugs on human and rabbit erythrocyte carbonic anhydrase enzymes. J Enzyme Inhib Med Chem 2012;27:680–4;
   PubMed Web of Science ®Google Scholar
  (b) De Simone G, Supuran CT. (In)organic anions as carbonic anhydrase inhibitors. J Inorg Biochem 2012;111:117–29;
   PubMed Web of Science ®Google Scholar
  (c) Akin Kazancioglu E, Guney M, Senturk M, et al. Simple methanesulfonates are hydrolyzed by the sulfatase carbonic anhydrase activity. J Enzyme Inhib Med Chem 2012;27:880–5.
   PubMed Web of Science ®Google Scholar
• Orhan F, Şentürk M, Supuran CT. Interaction of anions with a newly characterized alpha carbonic anhydrase from Halomonas sp. J Enzyme Inhib Med Chem 2016;31:1119–23.
   PubMed Web of Science ®Google Scholar
• (a) Abdel-Aziz AA-M, El-Azab AS, Ekinci D, et al. Investigation of arenesulfonyl-2-imidazolidinones as potent carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2015;30:81–4;
   PubMed Web of Science ®Google Scholar
  (b) Urcar H, Senturk E, Senturk M, et al. Investigation of effects of some catecholamines on the activity of carbonic anhydrase enzyme purified from bovine kidney tissue. Acta Physiol 2016;218:57;
   Web of Science ®Google Scholar
  (c) Tas M, Senturk E, Ekinci D, et al. Comparison of blood carbonic anhydrase activity of athletes performing interval and continuous running exercise at high altitude. J Enzyme Inhib Med Chem 2019;34:219–25.
   Web of Science ®Google Scholar
• Korkmaz N, Obaidi OA, Senturk M, et al. Synthesis and biological activity of novel thiourea derivatives as carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2015;30:75–80.
   PubMed Web of Science ®Google Scholar
• (a) Guney M, Cavdar H, Senturk M, et al. Synthesis and carbonic anhydrase inhibitory properties of novel uracil derivatives. Bioorg Med Chem Lett 2015;25:3261–3;
   PubMed Web of Science ®Google Scholar
  (b) Durdagi S, Senturk M, Guney M, et al. Design of novel uracil derivatives as inhibitors of carbonic anhydrase I & II, acetylcholinesterase, butyrylcholinesterase, and glutathione reductase using in silico, synthesis and in vitro studies. FEBS J 2016;283:106–106.
   Web of Science ®Google Scholar
• (a) Balaydin HT, Senturk M, Goksu S, et al. Synthesis and carbonic anhydrase inhibitory properties of novel bromophenols and their derivatives including natural products: Vidalol B. Eur J Med Chem 2012;54:423–8;
   PubMed Web of Science ®Google Scholar
  (b) Balaydin HT, Senturk M, Menzek A. Synthesis and carbonic anhydrase inhibitory properties of novel cyclohexanonyl bromophenol derivatives. Bioorg Med Chem Lett 2012;22:1352–7;
   PubMed Web of Science ®Google Scholar
  (c) Balaydin HT, Durdaği S, Ekinci D, et al. Inhibition of human carbonic anhydrase isozymes I, II and VI with a series of bisphenol, methoxy and bromophenol compounds. J Enzyme Inhib Med Chem 2012;27:467–75.
   PubMed Web of Science ®Google Scholar
• (a) Arslan T, Türkoğlu EA, Şentürk M, et al. Novel chalcone substituted benzenesulfonamides as inhibitors for human carbonic anhydrases. Bioorg Med Chem Lett 2016;26:5867–70;
   PubMed Web of Science ®Google Scholar
  (b) Demirdag R, Comakli V, Senturk M, et al. Characterization of carbonic anhydrase from sheep kidney and effects of sulfonamides on enzyme activity. Bioorg Med Chem 2013;21:1522–5;
   PubMed Web of Science ®Google Scholar
  (c) Yaseen R, Ekinci D, Senturk M, et al. Pyridazinone substituted benzenesulfonamides as potent carbonic anhydrase inhibitors. Bioorg Med Chem Lett 2016;26:1337–41;
   PubMed Web of Science ®Google Scholar
  (d) Ekinci D, Senturk M, Senturk E. Purification and characterization of carbonic anhydrase enzyme from bovine heart tissue and investigation of inhibition effects of some sulphonamide derivative drugs. Acta Physiol 2015;215:99–99.
   Web of Science ®Google Scholar
• (a) Cavusoglu K, Celebi F, Celik M, et al. Investigation of the effect of Shiga-toxin on rat serum carbonic anhydrase enzyme. Acta Physiol 2017;221:125–125;
   Web of Science ®Google Scholar
  (b) Ekinci D, al-Rashida M, Abbas G, et al. Chromone containing sulfonamides as potent carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2012;27:744–7;
   PubMed Web of Science ®Google Scholar
  (c) Karagoz L, Arslan T, Ekinci D, et al. Purification of carbonic anhydrase enzyme from bovine liver tissue and investigation of the inhibitory effects of bischalcone derivatives. Acta Physiol 2016;218:57–57.
   Web of Science ®Google Scholar
• Reddy VG, Reddy TS, Nayak VL, et al. Design, synthesis and biological evaluation of N-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)-1,3-diphenyl-1H-pyrazole-4-carboxamides as CDK1/Cdc2 inhibitors. Eur J Med Chem 2016;122:164–77.
   PubMed Web of Science ®Google Scholar
• Alam R, Wahi D, Singh R, et al. Design, synthesis, cytotoxicity, HuTopoIIα inhibitory activity and molecular docking studies of pyrazole derivatives as potential anticancer agents. Bioorg Chem 2016;69:77–90.
   PubMed Web of Science ®Google Scholar
• Jiang D, Zheng X, Shao G, et al. Discovery of a novel series of phenyl pyrazole inner salts based on fipronil as potential dual-target insecticides. J Agric Food Chem 2014;62:3577–83.
   PubMed Web of Science ®Google Scholar
• Furuya T, Suwa A, Nakano M, et al. Synthesis and biological activity of a novel acaricide, pyflubumide. J Pestic Sci 2015;40:38–43.
   Web of Science ®Google Scholar
• Kaushik D, Khan SA, Chawla G, et al. N'-[(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene] 2/4-substituted hydrazides: synthesis and anticonvulsant activity. Eur J Med Chem 2010;45:3943–9.
   PubMed Web of Science ®Google Scholar
• Abdel-Aziz M, Abuo-Rahma GE-DA, Hassan AA. Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities. Eur J Med Chem 2009;44:3480–7.
   PubMed Web of Science ®Google Scholar
• Kumar S, Ceruso M, Tuccinardi T, et al. Pyrazolylbenzo[d]imidazoles as new potent and selective inhibitors of carbonic anhydrase isoforms hCA IX and XII. Bioorg Med Chem 2016;24:2907–13.
   PubMed Web of Science ®Google Scholar
• (a) Arslan T. Synthesis and characterisation of new sulfonamide chalcones containing an azo group. J Chem Res 2018;42:267–70;
   Web of Science ®Google Scholar
  (b) Arslan T. An efficient synthesis of novel type chalcones containing 8-hydroxyquinoline under green conditions. Erzincan University J Sci Technol 2018;11:321–7.
   Google Scholar
• Fu D-J, Zhang S-Y, Liu Y-C, et al. Design, synthesis and antiproliferative activity studies of novel dithiocarbamate-chalcone derivates. Bioorg Med Chem Lett 2016;26:3918–22.
   PubMed Web of Science ®Google Scholar
• (a) Isik S, Vullo D, Durdagi S, et al. Interaction of carbonic anhydrase isozymes I, II, and IX with some pyridine and phenol hydrazinecarbothioamide derivatives. Bioorg Med Chem Lett 2015;25:5636–41;
   PubMed Web of Science ®Google Scholar
  (b) Fidan I, Salmas RE, Arslan M, et al. Carbonic anhydrase inhibitors: design, synthesis, kinetic, docking and molecular dynamics analysis of novel glycine and phenylalanine sulphonamide derivatives. Bioorg Med Chem 2015;23:7353–8;
   PubMed Web of Science ®Google Scholar
  (c) Ekinci D, Cavdar H, Durdagi S, et al. Structure-activity relationships for the interaction of 5,10-dihydroindeno[1,2-b]indole derivatives with human and bovine carbonic anhydrase isoforms I, II, III, IV and VI. Eur J Med Chem 2012;49:68–73.
   PubMed Web of Science ®Google Scholar
• (a) Ozdemir ZO, Senturk M, Ekinci D. Carbonic anhydrase inhibitors: Inhibition of mammalian isoforms I, II and VI with thiamine and thiamine-like molecules. J Enzyme Inhib Med Chem 2013;28:316–9;
   PubMed Web of Science ®Google Scholar
  (b) Yerlikaya E, Erdogan O, Demirdag R, et al. Expression of hCA IX isoenzyme by using sumo fusion partner and examining the effects of antitumor drugs. Turk J Biochem 2015;40:334–42;
   Web of Science ®Google Scholar
  (c) Arslan T, Biyiklioglu Z, Şentürk M. The synthesis of axially disubstituted silicon phthalocyanines, their quaternized derivatives and firstly inhibitor effect on human cytosolic carbonic anhydrase isozymes hCAI and II. RSC Advances 2018;8:10172–8.
   PubMed Web of Science ®Google Scholar
• Verpoorte JA, Mehta S, Edsall JT. Esterase activities of human carbonic anhydrases B and C. J Biol Chem 1967;242:4221–9.
   PubMed Web of Science ®Google Scholar
• (a) Tomar V, Bhattacharjee G, Kamaluddin S, et al. Synthesis of new chalcone derivatives containing acridinyl moiety with potential antimalarial activity. Eur J Med Chem 2010;45:745–51;
   PubMed Web of Science ®Google Scholar
  (b) Nepali K, Singh G, Turan A, et al. A rational approach for the design and synthesis of 1-acetyl-3,5-diaryl-4,5-dihydro(1H)pyrazoles as a new class of potential non-purine xanthine oxidase inhibitors. Bioorg Med Chem 2011;19:1950–8.
   PubMed Web of Science ®Google Scholar
• Turkoglu EA, Senturk M, Supuran CT, et al. Carbonic anhydrase inhibitory properties of some uracil derivatives. J Enzyme Inhib Med Chem 2017;32:74–7.
   PubMed Web of Science ®Google Scholar
• Lineweaver H, Burk D. The determination of enzyme dissociation constants. J Am Chem Soc 1934;56:658–66.
   Web of Science ®Google Scholar
• Schrödinger Release 2017-3: Schrödinger Suite 2017-3 Protein Preparation Wizard; Epik, Schrödinger, LLC, New York, NY, 2017; Impact, Schrödinger, LLC, New York, NY, 2017; LigPrep, Schrödinger, LLC, New York, NY, 2017; Prime, Schrödinger, LLC, New York, NY, 2017; QikProp, Schrödinger, LLC, New York, NY, 2017.
   Google Scholar
• Harder E, Damm W, Maple J, et al. OPLS3: A Force Field Providing Broad Coverage of Drug-like Small Molecules and Proteins. J Chem Theory Comput 2016;12:281–96.
   PubMed Web of Science ®Google Scholar
• Sastry GM, Adzhigirey M, Day T, et al. Protein and ligand preparation: parameters, protocols, and influence on virtual screening enrichments. J Comput Aided Mol Des 2013;27:221–34.
   PubMed Web of Science ®Google Scholar
• Friesner RA, Banks JL, Murphy RB, et al. Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. J Med Chem 2004;47:1739–49.
   PubMed Web of Science ®Google Scholar
• (a) Bashford D, Case DA. Generalized born models of macromolecular solvation effects. Annu Rev Phys Chem 2000;51:129–52;
   PubMed Web of Science ®Google Scholar
  (b) Li J, Abel R, Zhu K, et al. The VSGB 2.0 model: a next generation energy model for high resolution protein structure modeling. Proteins 2011;79:2794–812;
   PubMed Web of Science ®Google Scholar
  (c) Lipinski A, Lombardo F, Dominy BW, et al. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Delivery Rev 1997;23:3–26.
   Web of Science ®Google Scholar
• Singasane N, Kharkar PS, Ceruso M, et al. Inhibition of carbonic anhydrase isoforms I, II, IX and XII with Schiff’s bases incorporating iminoureido moieties. J Enzyme Inhib Med Chem 2015;30:901–7.
   PubMed Web of Science ®Google Scholar
• De Simone G, Alterio V, Supuran CT. Exploiting the hydrophobic and hydrophilic binding sites for designing carbonic anhydrase inhibitors. Expert Opin Drug Discov 2013;8:793–810.
   PubMed Web of Science ®Google Scholar
• (a) Ece A, Sevin F. The discovery of potential cyclin A/CDK2 inhibitors: a combination of 3D QSAR pharmacophore modeling, virtual screening, and molecular docking studies. Med Chem Res 2013;22:5832–43;
   Web of Science ®Google Scholar
  (b) Mascarenhas NM, Ghoshal N. An efficient tool for identifying inhibitors based on 3D-QSAR and docking using feature-shape pharmacophore of biologically active conformation—a case study with CDK2/cyclinA. Eur J Med Chem 2008;43:2807–18.
   PubMed Web of Science ®Google Scholar
• (a) Er M, Ergüven B, Tahtaci H, et al. Synthesis, characterization, preliminary SAR and molecular docking study of some novel substituted imidazo [2, 1-b][1, 3, 4] thiadiazole derivatives as antifungal agents. Med Chem Res 2017;26:615–30;
   Web of Science ®Google Scholar
  (b) Tahtaci H, Karacik H, Ece A, et al. Design, synthesis, SAR and molecular modeling studies of novel imidazo[2,1-b][1,3,4]thiadiazole derivatives as highly potent antimicrobial agents. Mol Inform 2018;37:83–92; (c) Türk S, Karakuş S, Ece A, et al. Synthesis, structure elucidation and biological activities of some novel 4 (3H)-quinazolinones as anti-biofilm agents. Lett Drug Des Disc 2019;16:313–321; (d) Ece A. Towards more effective acetylcholinesterase inhibitors: a comprehensive modelling study based on human acetylcholinesterase protein–drug complex. J Biomol Struct Dyn 2019;1–8; (e) Yamali C, Gul HI, Ece A, et al. Synthesis, biological evaluation and in silico modelling studies of 1, 3, 5-trisubstituted pyrazoles carrying benzenesulfonamide as potential anticancer agents and selective cancer-associated hCA IX isoenzyme inhibitors. Bioorg Chem 2019;92:103222.
   Web of Science ®Google Scholar
• Veber DF, Johnson SR, Cheng HY, et al. Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem 2002;45:2615–23.
   PubMed Web of Science ®Google Scholar