The preparation and assessment of carbonic anhydrase and paraoxonase enzyme inhibition properties of 3-(2-(5-amino-4-(4-bromophenyl)-3-methyl-1H-pyrazol-1-yl)ethoxy)phthalonitrile (2) and its nitrogen-containing non-peripheral phthalocyanine derivatives (3 and 4) are reported for the first time. The new phthalonitrile and its phthalocyanine derivatives have been elucidated by FT-IR spectroscopy, ¹H-NMR, $^{13}$ $^{13}$ C-NMR, mass and UV-vis spectroscopy. The results demonstrated that all synthesized compounds moderately inhibited carbonic anhydrase and paraoxonase enzymes. Among the compounds, the most active ones were found to be compound 4 for PON (Ki : 0.14 $μ$ $μ$ M), compound 3 for hCA I (Ki : 22.52 $μ$ $μ$ M) and compound 1 for hCA II (Ki : 13.62 $μ$ $μ$ M).

Keywords:

Most comprehensive & up-to-date research on PORPHYRINS
Handbook of Porphyrin Science now available in 46 volumes

References

1. Watson AD, Berliner JA, Hama SY, La Du BN, Faull KF, Fogelman AM and Navab M . J. Clin. Invest. 1995; 96: 2882–2891. Crossref, Web of Science, Google Scholar
2. Mackness MI, Arrol S and Durrington PN . FEBS Lett. 1991; 286: 152–154. Crossref, Web of Science, Google Scholar
3. Gao BB, Clermont A, Rook S, Fonda SJ, Srinivasan VJ, Wojtkowski M, Fujimoto JG, Avery RL, Arrigg PG, Bursell SE, Aiello LP and Feener EP . Nat. Med. 2007; 13: 181–188. Crossref, Web of Science, Google Scholar
4. Alterio V, Di Fiore A, D’Ambrosio K, Supuran CT and De Simone G . Chem. Rev. 2012; 112: 4421–4468. Crossref, Web of Science, Google Scholar
5. İşci Ü, Caner C, Zorlu Y, Gürek AG, Dumoulin F and Ahsen V . Dalt. Trans. 2014; 43: 17916–17919. Crossref, Web of Science, Google Scholar
6. Jiang Y, Lu Y, Lv X, Han D, Zhang Q, Niu L and Chen W . ACS Catal. 2013; 3: 1263–1271. Crossref, Web of Science, Google Scholar
7. Çimen Y, Ermiş E, Dumludağ F, Özkaya AR, Salih B and Bekaroğlu Ö . Sensors Actuators, B Chem. 2014; 202: 1137–1147. Crossref, Web of Science, Google Scholar
8. Arıcan D, Erdoğmuş A and Koca A . Thin Solid Films 2014; 550: 669–676. Crossref, Web of Science, Google Scholar
9. Ince M, Yum JH, Kim Y, Mathew S, Gratzel M, Torres T. and Nazeeruddin MK . J. Phys. Chem. C 2014; 118: 17166–17170. Crossref, Web of Science, Google Scholar
10. Güzel E, Şişman İ, Gül A and Koçak MB . J. Porphyr. Phthalocyanines 2019; 23: 279–286. Link, Web of Science, Google Scholar
11. Urbani M, de la Torre G, Nazeeruddin MK and Torres T . Chem. Soc. Rev. 2019; 48: 2738–2766. Crossref, Web of Science, Google Scholar
12. Harish TS and Viswanath P . Thin Solid Films 2016; 598: 170–176. Crossref, Web of Science, Google Scholar
13. Duro JA, Torre G, Barberá J, Serrano JL and Torres T . Chem. Mater. 1996; 8: 1061–1066. Crossref, Web of Science, Google Scholar
14. Güzel E, Arslan BS, Atmaca GY, Nebioğlu M and Erdoğmuş A . ChemistrySelect 2019; 4: 515–520. Crossref, Web of Science, Google Scholar
15. Sen P, Managa M and Nyokong T . Inorganica Chim. Acta 2019; 491: 1–8. Crossref, Web of Science, Google Scholar
16. Ferreira JT, Pina J, Ribeiro CAF, Fernandes R, Tomé JPC, Morgade MSR and Torres T . J. Mater. Chem. B 2017; 5: 5862–5869. Crossref, Web of Science, Google Scholar
17. Güzel E, Atsay A, Nalbantoglu S, S̈aki N, Dogan AL, Gül A and Koçak MB . Dyes Pigments 2013; 97: 238–243. Crossref, Web of Science, Google Scholar
18. Lo PC, Rodriguez-Morgade MS, Pandey RK, Ng DKP, Torres T, Dumoulin F . Chem. Soc. Rev. 2020; 49: 1041–1056. Crossref, Web of Science, Google Scholar
19. Güzel E, Koçyiğit ÜM, Arslan BS, Ataş M, Taslimi P, Gökalp F, Nebioğlu M, Şişman İ and Gulçin İ . Arch. Pharm. (Weinheim) 2019; 352: e1800292. Crossref, Web of Science, Google Scholar
20. Arslan T, Biyiklioglu Z and Şentürk M . RSC Adv. 2018; 8: 10172–10178. Crossref, Web of Science, Google Scholar
21. Almeida-Marrero V, van de Winckel E, Anaya-Plaza E, Torres T, de la Escosura A . Chem. Soc. Rev. 2018; 47: 7369–7400. Crossref, Web of Science, Google Scholar
22. Demirbaş Ü, Barut B, Özel A and Kantekin H . J. Mol. Struct. 2019; 1187: 8–13. Crossref, Web of Science, Google Scholar
23. Kasımoğulları R, Bülbül M, Arslan BS and Gökçe B . Eur. J. Med. Chem. 2010; 45: 4769–4773. Crossref, Web of Science, Google Scholar
24. Yu M, Lizarzaburu M, Motani A, Fu Z, Du X, Liu JJ, Jiao X, Lai S, Fan P, Fu A, Liu Q, Murakoshi M, Nara F, Oda K, Okuyama R, Reagan JD, Watanabe N, Yamazaki M, Xiong Y, Zhang Y, Zhuang R, Lin DCH, Houze JB, Medina JC and Li L . ACS Med. Chem. Lett. 2013; 4: 829–834. Crossref, Web of Science, Google Scholar
25. Samanta S, Debnath B, Basu A, Gayen S, Srikanth K and Jha T . Eur. J. Med. Chem. 2006; 41: 1190–1195. Crossref, Web of Science, Google Scholar
26. Kane JL, Hirth BH, Liang B, Gourlie BB, Nahill S and Barsomian G . Bioorg. Med. Chem. Lett. 2003; 13: 4463 Sen P, Managa M and Nyokong T. 4466. Crossref, Web of Science, Google Scholar
27. Kordik CP, Luo C, Zanoni BC, Dax SL, McNally JJ, Lovenberg TW, Wilson SJ and Reitz AB . Bioorg. Med. Chem. Lett. 2001; 11: 2283–2286. Crossref, Web of Science, Google Scholar
28. Gudmundsson KS, Johns BA and Allen SH . Bioorg. Med. Chem. Lett. 2008; 18: 1157–1161. Crossref, Web of Science, Google Scholar
29. Abu-Melha S . Arch. Pharm. (Weinheim). 2013; 346: 912–921. Crossref, Web of Science, Google Scholar
30. Worachartcheewan A, Nantasenamat C, Prachayasittikul S, Aiemsaard A and Prachayasittikul V . Med. Chem. Res. 2017; 26: 2699–2706. Crossref, Web of Science, Google Scholar
31. Kamenecka T, Habel J, Duckett D, Chen W, Ling YY, Frackowiak B, Jiang R, Shin Y, Song X and LoGrasso P . J. Biol. Chem. 2009; 284: 12853–61. Crossref, Web of Science, Google Scholar
32. Alterio V, Di Fiore A, D’Ambrosio K, Supuran CT and De Simone G . Chem. Rev. 2012; 112: 4421–4468. Crossref, Web of Science, Google Scholar
33. Nas A, Biyiklioglu Z, Fandaklı S, Sarkı G, Yalazan H and Kantekin H . Inorganica Chim. Acta 2017; 466: 86–92. Crossref, Web of Science, Google Scholar
34. Atmaca GY, Yakan H, Kutuk H, Nebioğlu M, Guzel E and Erdogmuş A . J. Porphyr. Phthalocyanines 2019; 23: 821–827. Link, Web of Science, Google Scholar
35. Günsel A, Bilgiçli AT, Güzel E, Yarasir MN and Gündüz B . Res. Chem. Intermed. 2018; 44: 6197–6217. Crossref, Web of Science, Google Scholar
36. Nair SK, Ludwig PA and Christianson DW . Am. Chem. Soc. 1994; 116: 3659–3660. Crossref, Web of Science, Google Scholar
37. Boztaş M, Çetinkaya Y, Topal M, Gülçin I, Menzek A, Şahin E, Tanc M and Supuran CT . J. Med. Chem. 2015; 58: 640–650. Crossref, Web of Science, Google Scholar
38. Karataş MO, Çalgın G, Alıcı B, Gökçe B, Gençer N, Tok TT, Arslan O, Kılıç-Cıkla I and Özdemir N . Appl. Organomet. Chem. 2019; 33: e5130. Crossref, Web of Science, Google Scholar
39. Erzengin M, Basaran I, Cakir U, Aybey A and Sinan S . Appl. Biochem. Biotechnol. 2012; 168: 1540–1548. Crossref, Web of Science, Google Scholar
40. Işgör MM and Beydemir Ş . Eur. J. Pharmacol. 2010; 645: 135–142. Crossref, Web of Science, Google Scholar
41. Caglar S, Dilek E, Alisir SH and Caglar B . J. Coord. Chem. 2016; 69: 2482–2492. Crossref, Web of Science, Google Scholar
42. Alim Z, Kilic D, Koksal Z, Beydemir S and Ozdemir H . J. Biochem. Mol. Toxicol. 2017; 31: e21950. Crossref, Web of Science, Google Scholar
43. Beydemir Ş and Demir Y . J. Biochem. Mol. Toxicol. 2017; 31: e21889. Crossref, Web of Science, Google Scholar