Microwave and ultrasound promoted greener synthesis of thiazolyl-pyrazoline derivatives and investigation of their biological activities

Abstract

Six thiazolyl-pyrazoline derivatives were synthesized starting from corresponding chalcone compounds for their antioxidant capacity and antiurease inhibitory activities. In addition to the conventional method, ultrasonic sonication and microwave irradiation methods which are environmental methods were used in the synthesis stage. Compound 2-(5-(3-bromophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)-4-phenyl thiazole (5a) exhibited the most potent antiurease activity with IC₅₀ of 2,28±0,02, which was comparable to the positive control.

Keywords

• Thiazole,microwave irradiation,Ultrasound sonication,Biological activity

References

1. 1. Rostom SAF, El-Ashmawy IM, El Razik H.A.A, Badr MH, Ashour HMA. Design and synthesis of some thiazolyl and thiadiazolyl derivatives of antipyrine as potential non-acidic anti-inflammatory, analgesic and antimicrobial agents. Bioorg Med Chem. 2009; 17: 882-895. 2. Al-Saadi MS, Faidallah HM, Rostom SAF. Synthesis and biological evaluation of some 2,4,5‐trisubstituted thiazole derivatives as potential antimicrobial and anticancer agents. Arch Pharm Chem Life Sci. 2008; 341: 424-434.
2. 3. Li Z, Yang Q, Qian X. Novel thiazonaphthalimides as efficient antitumor and DNA photocleaving agents: Effects of intercalation, side chains, and substituent groups. Bioorg Med Chem. 2005; 13: 4864-4870.
3. 4. Li FY, Guo XF, Fan ZJ, Zhang YQ, Zong GN, Qian XL, Ma LY, Chen L, Zhu YJ, Tatiana K, Morzherin YY, Belskaya NP. Synthesis and biological activities of novel 2-amino-1,3-thiazole-4-carboxylic acid derivatives. Chinese Chem Lett. 2015; 26: 1315-1318.
4. 5. Tenórioa RP, Carvalho CS, Pessanha CS, de Lima JG, de Faria AR, Alves AJ, de Melo EJT, Góes AJS. Synthesis of thiosemicarbazone and 4-thiazolidinone derivatives and their in vitro anti-Toxoplasma gondii activity. Bioorg Med Chem. Lett. 2005; 15: 2575-2578.
5. 6. Milne GWA. Ashgate Handbook of Antineoplastic Agents, Gower, London, UK, 2000. 7. Karthikeyan, MS. Synthesis, analgesic, anti-inflammatory and antimicrobial studies of 2,4- 8. Scherman WR, Dickson DE. 4-(5-Nitro-2-furyl)thiazoles1a. J Org Chem. 1952; 27: 1351-1355.
6. 9. de Aquino TM, Liesen AP, da Silva REA, Lima VT, Carvalho CS, de Faria AR, de Araújo JM, de Lima JG, Alves AJ, de Melo EJT, Góes AJS. Synthesis, anti-Toxoplasma gondii and antimicrobial activities of benzaldehyde 4-phenyl-3-thiosemicarbazones and 2-[(phenylmethylene)hydrazono]-4-oxo-3-phenyl-5-thiazolidineacetic acids. Bioorg Med Chem. 2008; 16: 446-456. 10. Taha M, Ismail NH, Imran S, Wadood A, Rahim F, Khan KM, Riaz M. Hybrid benzothiazole analogs as antiurease agent: Synthesis and molecular docking studies. Bioorg Chem. 2016; 66: 80-87.
7. 11. Tuncbilek M, Altanlar N. Synthesis of New 3‐(substituted phenacyl)‐5‐[3′‐(4h‐4‐oxo‐1‐benzopyran ‐2‐yl)‐benzylidene]‐2,4‐thiazolidinediones and their antimicrobial activity. Arch Pharm Chem Life Sci. 2006; 339: 213-216.
8. 12. Parmar SS, Pandey BR, Dwivedi C, Harbison RD. Anticonvulsant activity and monoamine oxidase inhibitory properties of 1, 3, 5‐trisubstituted pyrazolines. J Pharm Sci. 1974; 63: 1152-1155.

9. 13. Can OD, Ozkay UD, Kaplancıklı ZA, Ozturk Y. Effects of some 1,3,5-trisubstitued-2-pyrazoline derivatives on depression and anxiety parameters of mice. Arch Pharm Research. 2009; 32:1293-1299.
10. 14. Palaska E, Erol D, Demirdamar R. Synthesis and antidepressant activities of some 1,3,5-triphenyl-2-pyrazolines. Eur J Med Chem. 1996; 31: 43-47. 15. Zitouni GT, Chevallet P, Kilic FS, Erol K. Synthesis of some thiazolyl-pyrazoline derivatives and preliminary investigation of their hypotensive activity. Eur J Med Chem. 2000; 35: 635-641.
11. 16. Bondavalli F, Bruno O, Ranise A, Schenone F, Addonizio P, De Novellis V, Loffreda A, Marmo E. 3,5-Diphenyl-1H-pyrazole derivatives. I--Esters and N-substituted carbamates of 1-(2-hydroxyethyl)-3,5-diphenyl-1H-pyrazole and its 4-bromo derivative with depressant, antiarrhythmic, analgesic and other activities. Farmaco. 1988; 43: 725-743.
12. 17. Martins MAP, Pereira CMP, Moura S, Frizzo CP, Beck P, Bonacorso HG, Zanatta N, Flores AFC. Microwave assisted regiospecific synthesis of 5‐trifluoro methyl‐4,5‐dihydropyrazoles and pyrazoles. J Heterocycl Chem. 2007; 44: 1195-1199.
13. 18. Martins MAP, Pereira CMP, Beck P, Machado P, Moura S, Teixeira MV, Bonacorso HG, Zanatta N. Microwave-assisted synthesis of 5-trichloromethyl substituted 1-phenyl-1H-pyrazoles and 1, 2-dimethylpyrazolium chlorides. Tetrahedron Lett. 2003; 44: 6669-6672.
14. 19. Stefani HA, Pereira CMP, Almeida RB, Braga RC, Guzen KP, Cella R. A mild and efficient method for halogenation of 3, 5-dimethyl pyrazoles by ultrasound irradiation using N-halosuccinimides. Tetrahedron Lett. 2005; 46: 6833-6837.
15. 20. Stefani HA, Cella R, Dörr FA, Pereira CMP, Gomes FP, Zeni G. Ultrasound-assisted synthesis of functionalized arylacetylenes. Tetrahedron Lett. 2005; 46: 2001-2003.
16. 21. Stefani HA, Oliveira CB, Almeida RB, Pereira CMP, Braga RC, Cella R, Borges VC, Savegnago L, Nogueira CW. Dihydropyrimidin-(2H)-ones obtained by ultrasound irradiation: a new class of potential antioxidant agents. Eur J Med Chem. 2006; 41: 513-518.
17. 22. Pereira CMP, Stefani HA, Guzen KP, Órfão ATG. Improved synthesis of benzotriazoles and 1-acylbenzotriazoles by ultrasound irradiation. Lett Org Chem. 2007; 4: 43-46.
18. 23. Guzen KP, Guarezemini AS, Órfão ATG, Cella R, Pereira CMP, Stefani HA. Eco-friendly synthesis of imines by ultrasound irradiation. Tetrahedron Lett. 2007; 48: 1845-1848.
19. 24. Pizzuti L, Piovesan LA, Flores AFC, Quina FH, Pereira CMP. Environmentally friendly sonocatalysis promoted preparation of 1-thiocarbamoyl-3, 5-diaryl-4, 5-dihydro-1H-pyrazoles. Ultrason Sonochem. 2009; 16: 728-731. 25. Silva FAN, Galluzzi MP, Pizzuti L, Gressler V, Rivelli DP, Barros SBM, Pereira CMP. Ultrasound irradiation promoted large-scale preparation in aqueous media and antioxidant activity of azoles. Lett Drug Des Discov. 2009; 6: 323-326.
20. 26. Pizzuti L, Martins PLG, Ribeiro BA, Quina FH, Pinto E, Flores AFC, Venzke D, Pereira CMP. Efficient sonochemical synthesis of novel 3, 5-diaryl-4, 5-dihydro-1H-pyrazole-1-carboximidamides. Ultrason Sonochem. 2010; 17: 34-37.
21. 27. Duarte A, Cunico W, Pereira CMP, Flores AFC, Freitag RA, Siqueira GM. Ultrasound promoted synthesis of thioesters from 2-mercaptobenzoxa (thia) zoles. Ultrason Sonochem. 2010; 17: 281-283.
22. 28. Holm L, Sander C. An evolutionary treasure: unification of a broad set of amidohydrolases related to urease. Proteins. 1997; 28: 72-82.
23. 29. Mobley HL, Island MD, Hausinger RP. Molecular biology of microbial ureases. Microbiol. Rev. 1995; 59: 451-480.
24. 30. Venzke D, Flores AFC, Quina F.H, Pizzuti L, Pereira CMP. Ultrasound promoted greener synthesis of 2-(3, 5-diaryl-4, 5-dihydro-1H-pyrazol-1-yl)-4-phenylthiazoles. Ultrason Sonochem. 2011; 18: 370-374.
25. 31. Lipinski CA, Lombardo L, Dominy BW, Feeney P. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev. 1997; 23: 3-25.
26. 32. Zhao Y, Abraham MH, Lee J, Hersey A, Luscombe NC, Beck G, Sherborne B, Cooper I. Rate-limited steps of human oral absorption and QSAR studies. Pharm Res. 2002; 19: 1446-1457.
27. 33. Blois MS. Antioxidant determinations by the use of a stable free radical. Nature. 1958; 181: 1199-1200.
28. 34. Benzie IFF, Strain JJ. [2] Ferric reducing/antioxidant power assay: Direct measure of total antioxidant activity of biological fluids and modified version for simultaneous measurement of total antioxidant power and ascorbic acid concentration. Methods Enzymol. 1999; 299: 15-27.
29. 35. Apak R, Guclu K, Ozyurek M, Karademir SE. Novel total antioxidant capacity index for dietary polyphenols and vitamins C and E, using their cupric ion reducing capability in the presence of neocuproine: CUPRAC method. J Agric Food Chem. 2004; 52: 7970-7981.
30. 36. Weatherburn MW. Estimation of ammonia nitrogen by colorimetric method. Anal Chem. 1967; 39: 971-974.