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Original Articles

Synthesis and evaluation of biological activities of 4-cyclopropyl-5-(2-fluorophenyl) arylhydrazono-2,3-dihydrothiazoles as potent antioxidant agents

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Pages 196-210 | Received 21 Aug 2015, Accepted 13 Nov 2015, Published online: 16 Feb 2016

References

  • Atmaca G. Antioxidant effects of sulfur-containing amino acids. Yonsei Med J. 2004;45:776–788. doi: 10.3349/ymj.2004.45.5.776
  • Zelisko N, Atamanyuk D, Vasylenko O, Grellier P, Lesyk R. Synthesis and antitrypanosomal activity of new 6,6,7-trisubstituted thiopyrano[2,3-d][1,3]thiazoles. Bioorg Med Chem Lett. 2012;22:7071–7074. doi: 10.1016/j.bmcl.2012.09.091
  • Aggarwal R, Kumar S, Kaushik P, Kaushik D, Gupta GK. Synthesis and pharmacological evaluation of some novel 2-(5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(coumarin-3-yl)thiazoles. Eur J Med Chem. 2013;62:508–514. doi: 10.1016/j.ejmech.2012.11.046
  • Sharma RN, Xavier FP, Vasu KK, Chaturvedi SC, Pancholi SS. Synthesis of 4-benzyl-1,3-thiazole derivatives as potential anti-inflammatory agents: an analogous-based drug design approach. J Enzyme Inhib Med Chem. 2009;24:890–897. doi: 10.1080/14756360802519558
  • Patt WC, Hamilton HW, Taylor MD, et al. Structure–activity relationship of a series of 2-amino-4-thiazole containing rennin inhibitors. J Med Chem. 1992;35:2562–2572. doi: 10.1021/jm00092a006
  • Hargrave KD, Hess FK, Oliver JT. N-(4-Substituted-thiazolyl)oxamic acid derivatives, new series of potent, orally active antiallergy agents. J Med Chem. 1983;26:1158–1163. doi: 10.1021/jm00362a014
  • Lobo PL, Poojary B, Manjunatha K, et al. Synthesis and antimicrobial evaluation of some new 2-(6-oxo-5,6-dihydro[1,3]thiazolo[3,2-b]-2-aryloxymethyl-1,2,4-triazol-5-yl)-N-arylacetamides. Z Natureforsch. 2010;65:617–624.
  • Jean JC, Wise LD, Caprathe BW, et al. 4-(1,2,5,6-Tetrahydro-1-alkyl-3-pyridinyl)-2-thiazolamines: a novel class of compounds with central dopamine agonist properties. J Med Chem. 1990;33:311–317. doi: 10.1021/jm00163a051
  • Bell FW, Cantrell AS, Hogberg M, et al. Phenethythiazolethiourea (PETT) compounds; a new class of HIV-1 reverse transcriptase inhibitors. Synthesis and basic structure activity relationship studies of PETT analogous. J Med Chem. 1995;38:4929–4936. doi: 10.1021/jm00025a010
  • Carter JS, Kramer S, Talley JJ, et al. Synthesis and activity of sulfonamide-substituted 4,5-diaryl thiazoles as selective cyclooxygenase-2 inhibitors. Bioorg Med Chem Lett. 1999;9:1171–1174. doi: 10.1016/S0960-894X(99)00157-2
  • Vicini P, Geronikakib A, Incertia M, et al. Synthesis and biological evaluation of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases. Bioorg Med Chem. 2003;11:4785–4789. doi: 10.1016/S0968-0896(03)00493-0
  • Osman H, Arshad A, Lam CK, Lam C, Bagley, MC. Microwave-assisted synthesis and antioxidant properties of hydrazinyl thiazolyl coumarin derivatives. Chem Cent J. 2012;6:32–41. doi: 10.1186/1752-153X-6-32
  • An TNM, Kumar MA, Chang SH, Kim MY, Kim J-A, Lee KD. Synthesis, anticancer and antioxidant activity of novel 2,4-disubstituted thiazoles. Bull Korean Chem Soc. 2014;35:1619–1624. doi: 10.5012/bkcs.2014.35.6.1619
  • Alam MS, Liu L, Lee YE, Lee D-U. Synthesis, antibacterial activity and quantum-chemical studies of novel 2-arylidenehydrazinyl-4-arylthiazole analogous. Chem Pharm Bull. 2011;59:568–573. doi: 10.1248/cpb.59.568
  • Makam P, Kumar Thakur P, Kannan T. In vitro and in silico antimalarial activity of 2-(2-hydrazinyl)thiazole derivatives. Eur J Pharm Sci. 2014;52:138–145. doi: 10.1016/j.ejps.2013.11.001
  • Ignat A, Lovasz T, Vasilescu M, et al. Heterocycles 27. Microwave assisted synthesis and antitumour activity of novel phenothiazinyl-thiazolyl-hydrazine derivatives. Arch Pharm Chem Life Sci. 2012;345:574–83. doi: 10.1002/ardp.201100355
  • Karegoudar P, Karthikeyan MS, Prasad DJ, Mahalinga M, Holla BS, Kumari NS. Eur J Med Chem. 2008;44:261–267. doi: 10.1016/j.ejmech.2007.03.014
  • Sarıgüney AB, Saf AÖ, Coskun A. A newly synthesized thiazole derivative as a fluoride ion chemosensor: Naked-eye, spectroscopic, electrochemical and NMR studies. Spectro Chim Acta A. 2014;128:575–582. doi: 10.1016/j.saa.2014.02.032
  • Nagesh GY, Mruthyunjayaswamy BHM. Synthesis, characterization and biological relevance of some metal (II) complexes with oxygen, nitrogen and oxygen (ONO) donor Schiff base ligand derived from thiazole and 2-hydroxy-1-naphthaldehyde. J Mol Struct. 2015;1085:198–206. doi: 10.1016/j.molstruc.2014.12.058
  • Nagesh GY, Mahendra Raj K, Mruthyunjayaswamy BHM. Synthesis, characterization, thermal study and biological evaluation of Cu(II), Co(II), Ni(II) and Zn(II) complexes of Schiff base ligand containing thiazole moiety. J Mol Struct. 2015;1079:423–432. doi: 10.1016/j.molstruc.2014.09.013
  • Ismail FMD. Important fluorinated drugs in experimental and clinical use. J Fluorine Chem. 2002;118:27–33. doi: 10.1016/S0022-1139(02)00201-4
  • Kirk KL. The use of selective fluorination in drug design and development. Curr Top Med. Chem. 2006;6:1445–1445. doi: 10.2174/156802606777951118
  • Kumar BNP, Mohana KN, Mallesha L. Synthesis and antiproliferative activity of some new fluorinated Schiff bases derived from 1,2,4-triazoles. J Fluorine Chem. 2013;156:15–20. doi: 10.1016/j.jfluchem.2013.08.008
  • Guan A, Qin Y, Wang J, Li B. Synthesis and insecticidal activity of novel dihalopropene derivatives containing benzoxazole moiety: a structure–activity relationship study. J Fluorine Chem. 2103;156:120–123. doi: 10.1016/j.jfluchem.2013.09.003
  • Jaitak V, Sharma K, Kalia K, et al. Antioxidant activity of Potentilla fulgens: an alpine plant of western Himalaya. J Food Compost Anal. 2010;23:142–147. doi: 10.1016/j.jfca.2009.02.013
  • Sharifzadeh B, Mahmoodi NO, Mamaghani M, Tabatabaeian K, Chirani AS, Nikokar I. Facile regioselective synthesis of novel bioactive thiazolyl-pyrazoline derivatives via a three-component reaction and their antimicrobial activity. Bioorg Med Chem Lett. 2013;23:548–551. doi: 10.1016/j.bmcl.2012.11.024
  • Mahmoodi NO, Parvizi J, Sharifzadeh B, et al. Facile regioselective synthesis of novel bis-thiazole derivatives and their antimicrobial activity. Arch Pharm Chem Life Sci. 2013;346:860–864. doi: 10.1002/ardp.201300187
  • Mahmoodi NO, Safari N, Sharifzadeh B. One-pot synthesis of novel 2-(thiazol-2-yl)-4,5-dihydropyridazin-3(2H)-one derivatives catalyzed by activated KSF. Synth Commun. 2014;44:245–250. doi: 10.1080/00397911.2013.801077
  • Mahmoodi NO, Ramzanpour S, Ghanbari Pirbasti F. One-pot multi-component synthesis of 1,4-dihydropyridines using Zn2+@KSF and evaluation their antibacterial and antioxidant activities. Arch Pharm. 2015;348:275–282. doi: 10.1002/ardp.201400414
  • Metzger JV. Thiazole and its derivatives, part 1. New York: John Wiley & Sons; 1979. p. 166–310.
  • Pan X, Huang R, Zhang J, et al. Efficient synthesis of prasugrel, a novel P2Y12 receptor inhibitor. Tetrahedron Lett. 2012;53:5364–5366. doi: 10.1016/j.tetlet.2012.07.071
  • Abbasi Shiran J, Yahyazadeh A, Yamin BM, et al. Basic ionic liquid as catalyst and reaction media for the one-pot three-component regioselective synthesis of various thiazol-2-imine derivatives. J Heterocyclic Chem. Article in press. 10.1002/jhet.2406
  • Hassan AA, Ibrahim YR, El-Sheref EM, Abdel-Aziz M, Bräse S, Nieger M. Synthesis and antibacterial activity of 4-aryl-2-(1-substituted ethylidene)thiazoles. Arch. Pharm. Chem. Life Sci. 2013;346:562–570. 10.1002/ardp.201300099 doi: 10.1002/ardp.201300099
  • Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biol Med. 1999;9–10:1231–1237. doi: 10.1016/S0891-5849(98)00315-3
  • Bondet V, Brand-Williams W, Berset C. Kinetics and mechanisms of antioxidant using the DPPH• free radical method. Food Sci Technol. 1997;30:609–615.
  • Jaishree V, Ramdas N, Sachin J, Ramesh B. In vitro antioxidant properties of new thiazole derivatives. J Saudi Chem Soc. 2012;16:371–376. doi: 10.1016/j.jscs.2011.02.007
  • Jin L, Zhang Y, Yan L, Guo Y, Niu L. Phenolic compounds and antioxidant activity of bulb extracts of six Lilium species native to China. Molecules. 2012;17:9361–9378. doi: 10.3390/molecules17089361

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