Synthesis, cytotoxicity and carbonic anhydrase inhibitory activities of new pyrazolines

References

• Mahapatra DK, Bharti SK, Asati V. Anti-cancer chalcones: structural and molecular target perspectives. Eur J Med Chem 2015;98:69–114.
   PubMed Web of Science ®Google Scholar
• Qi L, Ding Y. Potential antitumor mechanisms of phenothiazine drugs. Sci China Life Sci 2013;56:1020–7.
   PubMed Web of Science ®Google Scholar
• Bisi A, Meli M, Gobbi S, et al. Multidrug resistance reverting activity and antitumor profile of new phenothiazine derivatives. Bioorg Med Chem 2008;16:6474–82.
   PubMed Web of Science ®Google Scholar
• Supuran CT. How many carbonic anhydrase inhibition mechanisms exist? J Enzyme Inhib Med Chem 2016;31:345–60.
   PubMed Web of Science ®Google Scholar
• Supuran CT, Scozzafava A. Carbonic anhydrases as targets for medicinal chemistry. Bioorg Med Chem 2007;15:4336–50.
   PubMed Web of Science ®Google Scholar
• Kucuk M, Gulcin I. Purification and characterization of the carbonic anhydrase enzyme from Black Sea trout (Salmo trutta Labrax Coruhensis) kidney and inhibition effects of some metal ions on enzyme activity. Environ Toxicol Pharmacol 2016;44:134–9.
   PubMed Web of Science ®Google Scholar
• Abbate F, Casini A, Owa T, et al. Carbonic anhydrase inhibitors: E7070, a sulfonamide anticancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumor-associated isozyme IX. Bioorg Med Chem Lett 2004;14:217–23.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Diuretics: from classical carbonic anhydrase inhibitors to novel applications of the sulfonamides. Curr Pharm Des 2008;14:641–8.
   PubMed Web of Science ®Google Scholar
• Fabrizi F, Mincione F, Somma T, et al. A new approach to antiglaucoma drugs: carbonic anhydrase inhibitors with or without NO donating moieties. Mechanism of action and preliminary pharmacology. J Enzyme Inhib Med Chem 2012;27:138–47.
   PubMed Web of Science ®Google Scholar
• Capasso C, Supuran CT. Anti-infective carbonic anhydrase inhibitors: a patent and literature review. Expert Opin Ther Pat 2013;23:693–704.
   PubMed Web of Science ®Google Scholar
• De Simone G, Supuran CT. Antiobesity carbonic anhydrase inhibitors. Curr Top Med Chem 2007;7:879–84.
   PubMed Web of Science ®Google Scholar
• Kumar V, Kaur K, Gupta GK, Sharma AK. Pyrazole containing natural products: synthetic preview and biological significance. Eur J Med Chem 2013;69:735–53.
   PubMed Web of Science ®Google Scholar
• Mojzych M, Bielawska A, Bielawski K, et al. 3-e][1,2,4]triazine sulfonamides as carbonic anhydrase inhibitors with antitumor activity. Bioorg Med Chem 2014;22:2643–7.
   PubMed Web of Science ®Google Scholar
• Raffa D, Maggio B, Raimondi MV, et al. Recent advanced in bioactive systems containing pyrazole fused with a five membered heterocycle. Eur J Med Chem 2015;97:732–46.
   PubMed Web of Science ®Google Scholar
• Kucukguzel SG, Senkardes S. Recent advances in bioactive pyrazoles. Eur J Med Chem 2015;97:786–815.
   PubMed Web of Science ®Google Scholar
• Li M, Zhao BX. Progress of the synthesis of condensed pyrazole derivatives (from 2010 to mid-2013). Eur J Med Chem 2014;85:311–40.
   PubMed Web of Science ®Google Scholar
• Maccioni E, Alcaro S, Orallo F, et al. Synthesis of new 3-aryl-4,5-dihydropyrazole-1-carbothioamide derivatives. An investigation on their ability to inhibit monoamine oxidase. Eur J Med Chem 2010;45:4490–8.
   PubMed Web of Science ®Google Scholar
• Gul HI, Tugrak M, Sakagami H, et al. Synthesis and bioactivity studies on new 4-(3-(4-substitutedphenyl)-3a,4-dihydro-3H-indeno[1,2-c]pyrazol-2-yl) benzenesulfonamides. J Enzyme Inhib Med Chem 2016. [Epub ahead of print]. doi: 10.3109/14756366.2016.1160077.
   Web of Science ®Google Scholar
• Gul HI, Kucukoglu K, Yamali C, et al. Synthesis of 4-(2-substituted hydrazinyl)benzenesulfonamides and their carbonic anhydrase inhibitory effects. J Enzyme Inhib Med Chem 2016;31:568–73.
   PubMedGoogle Scholar
• Barresi E, Salerno S, Marini AM, et al. Sulfonamides incorporating heteropolycyclic scaffolds show potent inhibitory action against carbonic anhydrase isoforms I, II, IX and XII. Bioorg Med Chem 2016;24:921–7.
   PubMed Web of Science ®Google Scholar
• Pingaew R, Prachayasittikul V, Worachartcheewan A, et al. Novel 1,4-naphthoquinone-based sulfonamides: Synthesis, QSAR, anticancer and antimalarial studies. Eur J Med Chem 2015;103:446–59.
   PubMed Web of Science ®Google Scholar
• Khloya P, Celik G, SitaRam, et al. 4-Functionalized 1,3-diarylpyrazoles bearing benzenesulfonamide moiety as selective potent inhibitors of the tumor associated carbonic anhydrase isoforms IX and XII. Eur J Med Chem 2014;76:284–90.
   PubMed Web of Science ®Google Scholar
• Bashir R, Ovais S, Yaseen S, et al. Synthesis of some new 1,3,5-trisubstituted pyrazolines bearing benzene sulfonamide as anticancer and anti-inflammatory agents. Bioorg Med Chem Lett 2011;21:4301–5.
   PubMed Web of Science ®Google Scholar
• Supuran CT, Innocenti A, Mastrolorenzo A, Scozzafava A. Antiviral sulfonamide derivatives. Mini Rev Med Chem 2004;4:189–200.
   PubMed Web of Science ®Google Scholar
• Mete E, Comez B, Gul HI, et al. Synthesis and carbonic anhydrase inhibitory activities of new thienyl substituted pyrazoline benzensulfonamides. J Enzyme Inhib Med Chem 2016. [Epub ahead of print]. doi: 10.1080/14756366.2016.1181627.
   PubMed Web of Science ®Google Scholar
• Rathish IG, Javed K, Ahmad S, et al. Synthesis and antiinflammatory activity of some new 1,3,5-trisubstituted pyrazolines bearing benzene sulfonamide. Bioorg Med Chem Lett 2009;19:255–8.
   PubMed Web of Science ®Google Scholar
• Akincioglu A, Topal M, Gulcin I, Goksu S. Novel sulphamides and sulfonamides incorporating the tetralin scaffold as carbonic anhydrase and acetylcholine esterase inhibitors. Arch Pharm (Weinheim) 2014;347:68–76.
   PubMed Web of Science ®Google Scholar
• Senturk M, Gulcin I, Dastan A, et al. Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols. Bioorg Med Chem 2009;17:3207–11.
   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
• Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 1976;72:248–54.
   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
• Sakagami H, Shimada C, Kanda Y, et al. Effects of 3-styrylchromones on metabolic profiles and cell death in oral squamous cell carcinoma cells. Toxicol Rep 2015;2:1281–90.
   PubMed Web of Science ®Google Scholar
• Tugrak M, Yamali C, Sakagami H, Gul HI. Synthesis of mono Mannich bases of 2-(4-hydroxybenzylidene)-2,3-dihydroinden-1-one and evaluation of their cytotoxicities. J Enzyme Inhib Med Chem 2015;31:818–23.
   PubMed Web of Science ®Google Scholar
• Yerdelen KO, Gul HI, Sakagami H, Umemura N. Synthesis and biological evaluation of 1,5-bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one and its aminomethyl derivatives. J Enzyme Inhib Med Chem 2015;30:383–8.
   PubMed Web of Science ®Google Scholar
• Bilginer S, Gul HI, Mete E, et al. 1-(3-Aminomethyl-4-hydroxyphenyl)-3-pyridinyl-2-propen-1-ones: a novel group of tumour-selective cytotoxins. J Enzyme Inhib Med Chem 2013;28:974–80.
   PubMed Web of Science ®Google Scholar
• Gul HI, Yamali C, Yasa T, et al. Carbonic anhydrase inhibition and cytotoxicity studies of Mannich base derivatives of thymol. J Enzyme Inhib Med Chem 2016. [Epub ahead of print]. doi: 10.3109/14756366.2016.1140755.
   Web of Science ®Google Scholar
• Gul HI, Tugrak M, Sakagami H. Synthesis of some acrylophenones with N-methylpiperazine and evaluation of their cytotoxicities. J Enzyme Inhib Med Chem 2016;31:147–51.
   PubMed Web of Science ®Google Scholar