SYNTHESIS AND BIOLOGICAL EVALUATION OF NOVEL THIAZOLE-PYRAZOLE INTEGRATED CHALCONES AS ANTIOXIDANT AND ANTI-INFLAMMATORY AGENTS
Keywords:Thiazole,, Pyrazole,, Chalcone,, Antioxidant activity,, Anti-inflammatory activity
Objective: The objective of the present study was to synthesize the thiazole-pyrazole integrated chalcones and their in vitro antioxidant and anti- inflammatory evaluation.
Methods: The designed hybrid thiazole-pyrazole integrated chalcones (3a-j) were synthesized by Claisen–Schmidt reaction of substituted 1-(4-methyl-2-phenylthiazol-5-yl) ethanone and substituted pyrazole aldehyde in the presence of 10% NaOH in ethanol solvent under reflux condition. The chemical structures of synthesized compounds were confirmed by IR, 1H nuclear magnetic resonance (NMR), 13C NMR, and high- resolution mass spectra.
Results: All the title compounds were screened for their in vitro antioxidant and anti-inflammatory activity. The screening data indicated that tested compounds showed potent antioxidant activity with moderate anti-inflammatory potential.
Conclusion: Antioxidant screening data reveal that most of the synthesized compounds possess excellent 1,1-diphenyl-2-picrylhydrazyl and NO radical scavenging activity. Most of the compounds found to possess marked anti-inflammatory potential by effectively inhibiting the heat-induced albumin denaturation.
Khatib S, Nerya O, Musa R, Shmuel A, Tamir S, Vaya J. Chalcones as potent tyrosinase inhibitors: The importance of a 2,4-substituted resorcinol moiety. Bioorg Med Chem 2005;13:433-41.
Chavan HV, Bandgar BP, Adsul LK, Dhakane VD, Bhale PS, Thakare VN, et al. Design, synthesis, characterization and anti- inflammatory evaluationof novel pyrazole amalgamated flavones. Bioorg Med Chem Lett 2013;23:1315-21.
Climent MJ, Corma A, Iborra S, Velty A. Activated hydrotalcites as catalysts for the synthesis of chalcones of pharmaceutical interest. J Catal 2004;221:474-82.
Fukui K, Matsumoto T, Nakamura S, Nakayama M. Synthetic studies of the flavone derivatives. VII. The synthesis of jaceidin. Bull Chem Soc Jpn 1968;41:1413-7.
Eddarir S, Cotelle N, Bakkour Y, Rolando C. An efficient synthesis of chalcones based on the Suzuki reaction. Tetrahedron Lett 2003;44:5359 63.
Ganguly AK, Kaur S, Mahata PK, Biswas D, Pramanik BN, Chan TM. Synthesis and properties of 3-acyl-_-pyrones, a novel class of flavones and chromones. Tetrahedron Lett 2005;46:4119- 21.
Bhale PS, Chavan HV, Dongare SB, Shringare SN, Mule YB, Nagane SS, et al. Synthesis of extended conjugated indolyl chalcones as potent anti-breast cancer, anti-inflammatory and antioxidant agents. Bioorg Med Chem Lett 2017;27:1502-7.
Honda T, Yoshizawa H, Sundararajan C, David E, Lajoie MJ, Favaloro FG Jr., et al. Tricyclic compounds containing nonenolizable cyano enones. A novel class of highly potent anti-inflammatory and cytoprotective agents. J Med Chem 2011;54:1762-78.
Al-Masum M, Ng E, Wai MC. Palladium-catalyzed direct cross-coupling of potassium styryltrifluoroborates and benzoyl chlorides-a one-step method for chalcone synthesis. Tetrahedron Lett 2011;52:1008-10.
Narender T, Papi Reddy K. A simple and highly efficient method for the synthesis of chalcones by using borontrifluoride-etherate. Tetrahedron Lett 2007;48:3177-80.
Srivastava YK. Ecofriendly microwave assisted synthesis of some chalcones. Rasa J Chem 2008;1:884-6.
Zangade S, Mokle S, Vibhute A, Vibhute Y. An efficient and operationally simple synthesis of some new chalcones by using grinding. Tech Chem Sci J 2011;2:1-6.
Ayati A, Esmaeili R, Moghimi S, Oghabi Bakhshaiesh T, Eslami-S Z, Majidzadeh-A K, et al. Synthesis and biological evaluation of 4-amino-5-cinnamoylthiazoles as chalcone-like anticancer agents. Eur J Med Chem 2018;145:404-12.
(a) Rai US, Isloor AM, Shetty P, Pai HK, Fun HK. Synthesis and in vitro biological evaluation of new pyrazole chalcones and heterocyclic diamides as potential anticancer agents. Arab J Chem 2015;8:317-21. (b) Bekhit AA, Haimanot T, Hymete A. Evaluation of some 1H-pyrazole derivatives as a dual acting antimalarial and anti-leishmanial agents. Pak J Pharm Sci 2014;27:1767-73.
Alsarahni A, Muhi-Eldeen Z, Al-Kaissi E, Al-Adham I, Al-Muhtase N. Synthesis and structural elucidation of amino acetylenic and thiocarbamates derivatives for 2-mercaptobenzothiazole as antimicrobial agents. Int J Pharm Pharm Sci 2017;9:192-7.
Pisal P, Deodhar M, Kale A, Nigade G, Pawar S. Design, synthesis, docking studies and biological evaluation of 2-phenyl-3-(substituted benzo[d] thiazol-2-ylamino)-quinazoline-4(3h)-one derivatives as antimicrobial agents. Int J Pharm Pharm Sci 2018;10:57-61.
Sashidhara KV, Rao KB, Kushwaha P, Modukuri RK, Singh P, Soni I, et al. Novel chalcone-thiazole hybrids as potent inhibitors of drug resistant Staphylococcus aureus. ACS Med Chem Lett 2015;6:809 13.
Jadhav SY, Bhosale RB, Shirame SP, Hublikar MG, Sonawane KD, Shaikh RV. Synthesis and biological evaluation of fluoro-hydroxy submitted pyrazolechalcones as anti-inflammatory antioxidant and antibacterial agents. Int J Pharm Biosci 2013;4:390-7.
Sunil K, Rathore DS, Garg G, Khatri K, Saxena R, Sanjeev KS. Synthesis and evaluation of some benzothiazole derivatives as antidiabetic agents. Int J Pharm Pharm Sci 2017;9:60-8.
Sivakumar D, Geetha G, Molecular docking studies on thiadiazole derivatives as protein kinase inhibitors. Int J Pharm Pharm Sci 2018;10:70-4.
Bhale PS, Bandgar BP, Dongare SB, Shringare SN, Sirsat DM, Chavan HV. Ketene dithioacetal mediated synthesis of 1,3,4,5-tetrasubstituted pyrazolederivativesand their biological evaluation. Phosphorus Sulfur Silicon Relat Elem 2019:1-7. [doi: 10.1080/10426507.2019.1565760].
Liaras K, Geronikaki A, Glamočlija J, Cirić A, Soković M. Thiazole-based chalcones as potent antimicrobial agents. Synthesis and biological evaluation. Bioorg Med Chem 2011;19:3135-40.
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