Synthesis of diaryl ethers with acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase inhibitory actions

References

• Hennemann G, Docter R, Friesema EC, et al. Plasma membrane transport of thyroid hormones and its role in thyroid hormone metabolism and bioavailability. J Endocrine Rev 2001;22:451–76
   PubMed Web of Science ®Google Scholar
• Piehl S, Hoefig CS, Scanlan TS, Köhrle J. Thyronamines-past, present, and future. Endocr Rev 2011;32:64–80
   PubMed Web of Science ®Google Scholar
• Liu Y, Singh D, Nair MG. Pods of Khejri (Prosopis cineraria) consumed as a vegetable showed functional food properties. J Func Foods 2012;4:116–21
   Web of Science ®Google Scholar
• Choi MS, Lee SH, Cho HS, et al. Inhibitory effect of obovatol on nitric oxide production and activation of NF-kappaB/MAP kinases in lipopolysaccharide-treated RAW 264.7cells. Eur J Pharmacol 2007;556:181–9
   PubMed Web of Science ®Google Scholar
• Huang SH, Chen Y, Tung PY, et al. Mechanisms for the magnolol-induced cell death of CGTH W-2 thyroid carcinoma cells. J Cell Biochem 2007;101:1011–22
   PubMed Web of Science ®Google Scholar
• Gim HJ, Li H, Jeong JH, et al. Design, synthesis, and biological evaluation of a series of alkoxy-3-indolylacetic acids as peroxisome proliferator-activated receptor γ/δ agonists. Bioorg Med Chem 2015;23:3322–36
   PubMed Web of Science ®Google Scholar
• Oh KB, Jeon Heung B, Han YR, et al. Bromophenols as Candida albicans isocitrate lyase inhibitors. Bioorg Med Chem Lett 2010;20:6644–8
   PubMed Web of Science ®Google Scholar
• Xue F, Huang J, Ji H, et al. Structure-based design, synthesis, and biological evaluation of lipophilic-tailed monocationic inhibitors of neuronal nitric oxide synthase. Bioorg Med Chem 2010;18:6526–37
   PubMed Web of Science ®Google Scholar
• Bedos-Belval F, Rouch A, Vanucci-Bacque C, Baltas M. Diaryl ether derivatives as anticancer agents a review. Med Chem Commun 2012;3:1356–72
   Web of Science ®Google Scholar
• Barnish IT, Cross PE, Dickinson RP, et al. Inhibition of separated forms of cyclic nucleotide phosphodiesterase from pig coronary arteries by 1,3-disubstituted and 1,3,8-trisubstituted xanthines. J Med Chem 1981;24:959–64
   PubMed Web of Science ®Google Scholar
• Maresca A, Temperini C, Pochet L, et al. Deciphering the mechanism of carbonic anhydrase ınhibition with coumarins and thiocoumarins. J Med Chem 2010;53:335–44
   PubMed Web of Science ®Google Scholar
• Maresca A, Scozzafava A, Supuran CT. 7,8-Disubstituted- but not 6,7-disubstituted coumarins selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II in the low nanomolar/subnanomolar range. Bioorg Med Chem Lett 2010;20:7255–8
   PubMed Web of Science ®Google Scholar
• Durdagi S, Şentürk M, Ekinci D, et al. Kinetic and docking studies of phenol-based inhibitors of carbonic anhydrase isoforms I, II, IX and XII evidence a new binding mode within the enzyme active site. Bioorg Med Chem 2011;19:1381–9
   PubMed Web of Science ®Google Scholar
• Akbaba Y, Balaydın HT, Menzek A, et al. Synthesis and biological evaluation of novel bromophenol derivatives as carbonic anhydrase inhibitors. Arch Pharm (Weinheim) 2013;346:447–54
   PubMed Web of Science ®Google Scholar
• Göksu S, Naderi A, Akbaba Y, et al. Carbonic anhydrase inhibitory properties of novel benzylsulfamides using molecular modeling and experimental studies. Bioorg Chem 2014;56:75–82
   PubMed Web of Science ®Google Scholar
• Balaydın HT, Durdağı 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
• Aksu K, Topal F, Gulcin İ, et al. Acetylcholinesterase inhibitory and antioxidant activities of novel symmetric sulfamides derived from phenethylamines. Arch Pharm 2015;348:446–55
   PubMed Web of Science ®Google Scholar
• Akincioglu A, Göçer A, Gülçin İ, et al. Discovery of potent carbonic anhydrase and acetylcholine esterase inhibitors: Novel sulfamoylcarbamates and sulfamides derived from acetophenones. Bioorg Med Chem 2015;23:3592–602
   PubMed Web of Science ®Google Scholar
• Öztaşkın N, Çetinkaya Y, Taslimi P, et al. Antioxidant and acetylcholinesterase inhibition properties of novel bromophenol derivatives. Bioorg Chem 2015;60:49–57
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrase inhibitors: an editorial. Expert Opin Ther Pat 2013;23:677–9
   PubMed Web of Science ®Google Scholar
• Scozzafava A, Kalın P, Supuran CT, et al. The impact of hydroquinone on acetylcholine esterase and certain human carbonic anhydrase isoenzymes (hCA I, II, IX, and XII). J Enzyme Inhib Med Chem 2015;30:941–6
   PubMed Web of Science ®Google Scholar
• Yıldırım A, Atmaca U, Keskin A, et al. N-Acylsulfonamides strongly inhibit human carbonic anhydrase isoenzymes I and II. Bioorg Med Chem 2015;23:2598–605
   PubMed Web of Science ®Google Scholar
• 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
• Artunç T, Çetinkaya Y, Göçer H, et al. Synthesis of 4-[2-(3,4-dimethoxybenzyl)cyclopentyl]-1,2-dimethoxybenzene derivatives and evaluations of their carbonic anhydrase isoenzymes inhibitory effects. Chem Biol Drug Des 2016;87:594–607
   PubMed Web of Science ®Google Scholar
• Boztaş M, Çetinkaya Y, Topal M, et al. Synthesis and carbonic anhydrase isoenzymes I, II, IX, and XII inhibitory effects of dimethoxy-bromophenol derivatives incorporating cyclopropane moieties. J Med Chem 2015;58:640–50
   PubMed Web of Science ®Google Scholar
• Gocer H, Aslan A, Gülçin İ, Supuran CT. Spirobisnaphthalenes effectively inhibit carbonic anhydrase. J Enzyme Inhib Med Chem 2016;31:503–7
   PubMed Web of Science ®Google Scholar
• Gocer H, Topal F, Topal M, et al. Acetylcholinesterase and carbonic anhydrase isoenzymes I and II inhibition profiles of taxifolin. J Enzyme Inhib Med Chem 2016;31:441–7
   PubMed Web of Science ®Google Scholar
• Scozzafava A, Passaponti M, Supuran CT, Gülçin İ. Carbonic anhydrase inhibitors: Guaiacol and catechol derivatives effectively inhibit certain human carbonic anhydrase isoenzymes (hCA I, II, IX, and XII). J Enzyme Inhib Med Chem 2015;30:586–91
   PubMed Web of Science ®Google Scholar
• Arabaci B, Gülçin İ, Alwasel S. Capsaicin: a potent inhibitor of carbonic anhydrase isoenzymes. Molecules 2015;19:10103–14
   Web of Science ®Google Scholar
• Göçer H, Akıncıoğlu A, Göksu S, et al. Carbonic anhydrase and acetylcholinesterase inhibitory effects of carbamates and sulfamoylcarbamates. J Enzyme Inhib Med Chem 2015;30:316–20
   PubMed Web of Science ®Google Scholar
• Taslimi P, Gulcin İ, Ozgeris B, et al. The human carbonic anhydrase isoenzymes I and II (hCA I and II) inhibition effects of trimethoxyindane derivatives. J Enzyme Inhib Med Chem 2016;31:152–7
   PubMed Web of Science ®Google Scholar
• Turan B, Sendil K, Sengul E, et al. The synthesis of some β-lactams and investigation of their metal chelating activity, carbonic anhydrase and achetylcholinesterase inhibition profiles. J Enzyme Inhib Med Chem 2016. [Epub ahead of print]. http://dx.doi.org/10.3109/14756366.2016.1170014
   PubMedGoogle Scholar
• Akbaba Y, Bastem E, Topal F, et al. Synthesis and carbonic anhydrase inhibitory effects of novel sulfamides derived from 1-aminoindanes and anilines. Arch Pharm (Weinheim) 2014;347:950–7
   PubMed Web of Science ®Google Scholar
• Güney M, Coşkun A, Topal F, et al. Oxidation of cyanobenzocycloheptatrienes: synthesis, photooxygenation reaction and carbonic anhydrase isoenzymes inhibition properties of some new benzotropone derivatives. Bioorg Med Chem 2014;22:3537–43
   PubMed Web of Science ®Google Scholar
• Capasso C, Supuran CT. An overview of the alpha-, beta- and gamma-carbonic anhydrases from bacteria: can bacterial carbonic anhydrases shed new light on evolution of bacteria? J Enzyme Inhib Med Chem 2015;30:325–32
   PubMed Web of Science ®Google Scholar
• Topal M, Gülçin İ. Rosmarinic acid: a potent carbonic anhydrase isoenzymes inhibitor. Turk J Chem 2014;38:894–902
   Web of Science ®Google Scholar
• Aksu K, Nar M, Tanç M, et al. The synthesis of sulfamide analogues of dopamine related compounds and their carbonic anhydrase inhibitory properties. Bioorg Med Chem 2013;21:2925–31
   PubMed Web of Science ®Google Scholar
• Çetinkaya Y, Göçer H, Gülçin İ, Menzek A. Synthesis and carbonic anhydrase isoenzymes inhibitory effects of brominated diphenylmethanone and its derivatives. Arch Pharm (Weinheim) 2014;347:354–9
   PubMed Web of Science ®Google Scholar
• Akıncıoğlu A, Topal M, Gülçin İ, Göksu S. Novel sulfamides and sulfonamides incorporating tetralin scaffold as carbonic anhydrase and acetylcholine esterase inhibitors. Arch Pharm 2014;347:68–76
   PubMed Web of Science ®Google Scholar
• Çetinkaya Y, Göçer H, Göksu S, Gülçin İ. Synthesis and carbonic anhydrase isoenzymes inhibitory effects of novel benzylamine derivatives. J Enzyme Inhib Med Chem 2014;29:168–74
   PubMed Web of Science ®Google Scholar
• Akbaba Y, Akıncıoğlu A, Göçer H, et al. Carbonic anhydrase inhibitory properties of novel sulfonamide derivatives of aminoindanes and aminotetralins. J Enzyme Inhib Med Chem 2014;29:35–42
   PubMed Web of Science ®Google Scholar
• Akıncıoğlu A, Akbaba Y, Göçer H, et al. Novel sulfamides as potential carbonic anhydrase isoenzymes inhibitors. Bioorg Med Chem 2013;21:1379–85
   PubMed Web of Science ®Google Scholar
• Ferraroni M, Carta F, Scozzafava A, Supuran CT. Thioxocoumarins show an alternative carbonic anhydrase inhibition mechanism compared to coumarins. J Med Chem 2016;59:462–73
   PubMed Web of Science ®Google Scholar
• Göçer H, Akıncıoğlu A, Öztaşkın N, et al. Synthesis, antioxidant, and antiacetylcholinesterase activities of sulfonamide derivatives of dopamine-related compounds. Arch Pharm (Weinheim) 2013;346:783–92
   PubMed Web of Science ®Google Scholar
• Polat KL, Gülçin İ, Gören AC, et al. LC-MS/MS analysis, antioxidant and anticholinergic properties of galanga (Alpinia officinarum Hance) rhizomes. Ind Crops Prod 2015;74:712–21
   Web of Science ®Google Scholar
• Topal M, Gocer H, Topal F, et al. Antioxidant, antiradical and anticholinergic properties of cynarin purified from the illyrian thistle (Onopordum illyricum L.). J Enzyme Inhib Med Chem 2016;31:266–75
   PubMed Web of Science ®Google Scholar
• Blokland A. Acetylcholine: a neurotransmitter for learning and memory? Brain Res Brain Res Rev 1995;21:285–300
   PubMedGoogle Scholar
• Koçak R, Turan Akin E, et al. Synthesis of some novel norbornene-fused pyridazines as potent inhibitors of carbonic anhydrase and acetylcholinesterase. J Heterocyclic Chem 2015. [Epub ahead of print]. http://dx.doi.org/10.1002/jhet.2558
   PubMed Web of Science ®Google Scholar
• Mueller SG, Weiner MW, Thal LJ, et al. Ways toward an early diagnosis in Alzheimer's disease: the Alzheimer's disease neuroimaging initiative (ADNI) Alzheimers Dement 2005;1:55–66
   PubMedGoogle Scholar
• Gülçin İ, Scozzafava A, Supuran CT, et al. Rosmarinic acid inhibits some metabolic enzymes including glutathione S-transferase, lactoperoxidase, acetylcholinesterase, butyrylcholinesterase, and carbonic anhydrase isoenzymes. J Enzyme Inhib Med Chem 2016. [Epub ahead of print]. http://dx.doi.org/10.3109/14756366.2015.1135914
   Web of Science ®Google Scholar
• Maryamabadi A, Hasaninejad A, Nowrouzi N, et al. Application of PEG-400 as a green biodegradable polymeric medium for the catalyst-free synthesis of spirodihydropyridines and their use as acetyl and butyrylcholinesterase inhibitors. Bioorg Med Chem 2016;24:1408–17
   PubMed Web of Science ®Google Scholar
• Ozmen Ozgun D, Yamali C, Gül Hİ, et al. Inhibitory effects of isatin mannich bases on carbonic anhydrases, acetylcholinesterase and butyrylcholinesterase. J Enzyme Inhib Med Chem 2016. [Epub ahead of print]. http://dx.doi.org/10.3109/14756366.2016.1149479
   Web of Science ®Google Scholar
• Makhaeva GF, Boltneva NP, Lushchekina SV, et al. Synthesis, molecular docking and biological evaluation of N, N-disubstituted 2-aminothiazolines as a new class of butyrylcholinesterase and carboxylesterase inhibitors. Bioorg Med Chem 2016;24:1050–62
   PubMed Web of Science ®Google Scholar
• Khunnawutmanotham N, Chimnoi N, Saparpakorn P, Techasakul S. Synthesis and anti-acetylcholinesterase activity of scopoletin derivatives. Bioorg Chem 2016;65:137–45
   PubMed Web of Science ®Google Scholar
• Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nat Rev Drug Discov 2011;10:767–77
   PubMed Web of Science ®Google Scholar
• Göksu H, Topal M, Keskin A, et al. 9,10-Dibromo-N-aryl-9,10-dihydro-9,10-[3,4]epipyrroloanthracene-12,14-diones; synthesis and investigation of their effects on carbonic anhydrase isozymes I, II, IX, and XII. Arch Pharm 2016. [Epub ahead of print]. http://dx.doi.org/10.1002/ardp.201300143
   Web of Science ®Google Scholar
• Şentürk M, Gülçin İ, Beydemir Ş, et al. In vitro inhibition of human carbonic anhydrase I and II isozymes with natural phenolic compounds. Chem Biol Drug Des 2011;77:494–9
   PubMed Web of Science ®Google Scholar
• Öztürk Sarıkaya SB, Topal F, Şentürk M, et al. In vitro inhibition of α-carbonic anhydrase isozymes by some phenolic compounds. Bioorg Med Chem Lett 2011;21:4259–62
   PubMed Web of Science ®Google Scholar
• Nar M, Çetinkaya Y, Gülçin İ, Menzek A. (3,4-Dihydroxyphenyl) (2,3,4-trihydroxyphenyl)methanone and its derivatives as carbonic anhydrase isoenzymes inhibitors. J Enzyme Inhib Med Chem 2013;28:402–6
   PubMed Web of Science ®Google Scholar
• Özgeriş B, Göksu S, Köse Polat L, et al. Acetylcholinesterase and carbonic anhydrase inhibitory properties of novel urea and sulfamide derivatives incorporating dopaminergic 2-aminotetralin scaffolds. Bioorg Med Chem 2016;24:2318–29
   PubMed Web of Science ®Google Scholar
• Öztürk Sarıkaya SB, Gülçin İ, Supuran CT. Carbonic anhydrase inhibitors: inhibition of human erythrocyte isozymes I and II with a series of phenolic acids. Chem Biol Drug Des 2010;75:515–20
   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
• Şentürk M, Gülçin İ, Daştan 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
• Çoban TA, Beydemir Ş, Gülçin İ, Ekinci D. The effect of ethanol on erythrocyte carbonic anhydrase isoenzymes activity: an in vitro and in vivo study. J Enzyme Inhib Med Chem 2008;23:266–70
   PubMed Web of Science ®Google Scholar
• Çoban TA, Beydemir Ş, Gülçin İ, Ekinci D. Morphine inhibits erythrocyte carbonic anhydrase in vitro and in vivo. Biol Pharm Bull 2007;30:2257–61
   PubMed Web of Science ®Google Scholar
• Hisar O, Beydemir Ş, Gülçin İ, et al. The effect of melatonin hormone on carbonic anhydrase enzyme activity in rainbow trout (Oncorhynchus mykiss) erythrocytes in vitro and in vivo. Turk J Vet Anim Sci 2005;29:841–5
   Web of Science ®Google Scholar
• Hisar O, Beydemir Ş. Gülçin, et al. Effect of low molecular weight plasma inhibitors of rainbow trout (Oncorhyncytes mykiss) on human erythrocytes carbonic anhydrase-II isozyme activity in vitro and rat erythrocytes in vivo. J Enzyme Inhib Med Chem 2005;20:35–9
   PubMed Web of Science ®Google Scholar
• ArasHisar Ş, Hisar O, Beydemir Ş, et al. Effect of vitamin E on carbonic anhydrase enzyme activity in rainbow trout (Oncorhynchus mykiss) erythrocytes in vitro and in vivo. Acta Vet Hung 2004;52:413–22
   PubMed Web of Science ®Google Scholar
• Beydemir Ş, Gülçin İ. Effects of melatonin on carbonic anhydrase from human erythrocytes in vitro and from rat erythrocytes in vivo. J Enzyme Inhib Med Chem 2004;19:193–7
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Beydemir Ş, Büyükokuroğlu ME. In vitro and in vivo effects of dantrolene on carbonic anhydrase enzyme activities. Biol Pharm Bull 2004;27:613–16
   PubMed Web of Science ®Google Scholar
• Polat Kose L, Gülçin İ, Özdemir H, et al. The effects of some avermectins on bovine carbonic anhydrase enzyme. J Enzyme Inhib Med Chem 2015. [Epub ahead of print]. http://dx.doi.org/10.3109/14756366.2015.1064406
   PubMed Web of Science ®Google Scholar
• Oktay K, Polat Köse L, Şendil K, et al. The synthesis of (Z)-4-Oxo-4-(arylamino)but-2-enoic acids derivatives and determination of theirs inhibition properties against human carbonic anhydrase I, and II isoenzymes. J Enzyme Inhib Med Chem 2015. [Epub ahead of print]. http://dx.doi.org/10.3109/14756366.2015.1071808
   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
• Gülçin İ, Scozzafava A, Supuran CT, et al. The effect of caffeic acid phenethyl ester (CAPE) metabolic enzymes including acetylcholinesterase, butyrylcholinesterase, glutathione s-transferase, lactoperoxidase and carbonic anhydrase ısoenzymes I, II, IX and XII. J Enzyme Inhib Med Chem 2015. [Epub ahead of print]. http://dx.doi.org/10.3109/14756366.2015.1094470
   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
• Ellman GL, Courtney KD, Andres V, Featherston RM. A new and rapid colorimetric deermination of acetylcholinesterase activity. Biochem Pharmacol 1961;7:88–95
   PubMed Web of Science ®Google Scholar
• Thomas AW, Ley SV. Modern synthetic methods for copper-mediated C(aryl)[bond]O, C(aryl)[bond]N, and C(aryl)[bond]S bond formation. Angew Chem Int Ed Engl 2003;42:5400–49
   PubMed Web of Science ®Google Scholar
• Beletskaya IP, Cheprakov AV. Copper in cross-coupling reactions the post-Ullmann. Chem Coord Chem Rev 2004;248:2337–64
   Web of Science ®Google Scholar
• Taslimi P, Gülçin İ, Öztaşkın N, et al. The effects of some bromophenols on human carbonic anhydrase isoenzymes. J Enzyme Inhib Med Chem 2016;31:603–7
   PubMed Web of Science ®Google Scholar
• Gül Hİ, 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
   PubMed Web of Science ®Google Scholar
• Yılmaz S, Akbaba Y, Özgeriş B, et al. Synthesis and inhibitory properties of some carbamates on carbonic anhydrase and acetylcholine esterase. J Enzyme Inhib Med Chem 2016. [Epub ahead of print]. http://dx.doi.org/10.3109/14756366.2016.1149477
   Web of Science ®Google Scholar