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Current Drug Discovery Technologies

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ISSN (Print): 1570-1638
ISSN (Online): 1875-6220

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Research Article

Green Chemistry Approach for the Synthesis of Isoxazole Derivatives and Evaluation of their Anti-epileptic Activity

Author(s): Krishna Chandra Panda*, Ravi Kumar Venkata Varaha Bera, Biswa Mohan Sahoo and Parijat Swain

Volume 20, Issue 3, 2023

Published on: 27 March, 2023

Article ID: e150223213697 Pages: 8

DOI: 10.2174/1570163820666230215125043

Price: $65

Abstract

Background: Green strategy involves the design, synthesis, processing, and use of chemical substances by eliminating the generation of chemical hazards. This approach focuses on atom economy, use of safer solvents or chemicals, consumption of energy, and decomposition of the chemical substances to non-toxic materials which are eco-friendly.

Objective: So, the microwave irradiated heating method is considered a green and sustainable technique for the development of novel heterocyclic scaffold-like isoxazole derivatives via chalcones. Isoxazole derivatives play a vital role due to their diverse pharmacological activities such as antibiotic (Sulfamethoxazole, Cloxacillin, Flucloxacillin, Cycloserine), anti-fungal (Drazoxolon), Antirheumatic (Leflunomide), antidepressant (Isocarboxazid), antineoplastic (Acivicin), anticonvulsant (Zonisamide), antipsychotic (Risperidone) and anti-inflammatory drugs (Valdecoxib), etc.

Methods: The isoxazole derivatives were synthesized with the help of microwave irradiation that follows green chemistry protocol.

Results: The titled compounds were subjected to antiepileptic evaluation to determine their therapeutic potential.

Conclusion: The use of microwave radiation enhances the rate of the reaction which leads to high selectivity with improved product yields in comparison with the traditional heating methods. The tested compounds exhibited promising antiepileptic activity as compared to the standard drug (Phenytoin).

Keywords: Epilepsy, isoxazole, chalcone, pharmacological activities, cloxacillin, heterocyclic compounds.

Graphical Abstract

[1]
Gupta P, Mahajan A. Green chemistry approaches as sustainable alternatives to conventional strategies in the pharmaceutical industry. RSC Adv 2015; 5(34): 26686-705.
[http://dx.doi.org/10.1039/C5RA00358J]
[2]
Clarke CJ, Tu WC, Levers O, Bröhl A, Hallett JP. Green and sustainable solvents in chemical processes. Chem Rev 2018; 118(2): 747-800.
[http://dx.doi.org/10.1021/acs.chemrev.7b00571] [PMID: 29300087]
[3]
Sahoo BM. Microwave Assisted Drug Synthesis (MADS): A green technology in medicinal chemistry. J App Pharm 2016; 8(1): 1-2.
[4]
Mavandadi F, Lidström P. Microwave - assisted chemistry in drug discovery. Curr Top Med Chem 2004; 4(7): 773-92.
[http://dx.doi.org/10.2174/1568026043451078] [PMID: 15032686]
[5]
Sahoo BM, Panda J, Banik BK. Thermal and non-thermal effects of microwaves in synthesis. J Indian Chem Soc 2018; 95: 1311-9.
[6]
Polshettiwar V, Nadagouda MN, Varma RS. Microwave-assisted chemistry: A rapid and sustainable route to the synthesis of organics and nanomaterials. Aust J Chem 2009; 62(1): 16-26.
[http://dx.doi.org/10.1071/CH08404]
[7]
Kapubalu SK, Reddya KT, Vamsikantha A. Synthesis and characterization of some novel isoxazoles via chalcone intermediates. Pharma Chem 2011; 3(5): 113-22.
[8]
Ajay Kumar K, Jayaroopa P. Isoxazoles: Molecules with potential medicinal properties. Int J Pharm Chem Biol Sci 2013; 3(2): 294-304.
[9]
Chikkula KV. , S R. Isoxazole-A potent pharmacophore. Int J Pharm Pharm Sci 2017; 9(7): 13-24.
[http://dx.doi.org/10.22159/ijpps.2017.v9i7.19097]
[10]
Sahoo BM, Sahoo B, Panda J, Kumar A. Microwave-induced synthesis of substituted isoxazoles as potential antimicrobial agents. Curr Microw Chem 2017; 4(2): 146-51.
[http://dx.doi.org/10.2174/2213335603666160926101734]
[11]
Parikh AR, Merja BC, Joshi AM, Parikh KA. Synthesis and biological evaluation of isoxazoline derivatives. Indian J Chem 2004; 43B: 955-9.
[12]
Lincy J, Mathew G. Evaluation of in vivo and in-vitro anti-inflammatory activity of novel isoxazole series. Eur Int J Sc Tech 2016; 5: 35-42.
[13]
Sevim R, Sila K, Bedia KK, Suna OT, Julide A. Synthesis and evaluation of cytotoxic activities of some substitutedisoxazolone derivatives. Marmara Pharm J 2011; 15: 94-9.
[14]
Renuka S, Kota RK. Medicinal and biological significance of isoxazole a highly important scaffold for drug discovery. Asian J Res Chem 2011; 4(7): 1038-42.
[15]
Balaji NV. HariBabu B, Rao UV, Subbaraju GV, Nagasree KP, Kumar MMK. Synthesis, screening, and docking analysis of hispolonpyrazoles and isoxazoles as potential antitubercular agents. Curr Top Med Chem 2019; 19: 662-82.
[http://dx.doi.org/10.2174/1568026619666190305124954] [PMID: 30834836]
[16]
Pradeep KY, Ruthu M, Chetty CM, Prasanthi G, Reddy VJ. Pharmacological activities of isoxazole derivatives. J Glob Trends Pharm Sci 2011; 2(1): 55-62.
[17]
Shaik A, Kishor P, Kancharlapalli V. Synthesis of novel and potential antimicrobial, antioxidant and anticancer chalcones and dihydropyrazoles bearing isoxazole scaffold. Proceedings 2020; 41(1): 1-12.
[18]
Hamama WS, Ibrahim ME, Zoorob HH. Synthesis and biological evaluation of some novel isoxazole derivatives. J Heterocycl Chem 2017; 54(1): 341-6.
[http://dx.doi.org/10.1002/jhet.2589]
[19]
Mahapatra DK, Bharti SK, Asati V. Chalcone derivatives: Anti-inflammatory potential and molecular targets perspectives. Curr Top Med Chem 2017; 17(28): 3146-69.
[http://dx.doi.org/10.2174/1568026617666170914160446] [PMID: 28914193]
[20]
Singh S, Sharma PK, Verma NK, Dudhe R. A Review on a versatile molecule: Chalcone. Asian J Pharm Biol Res 2011; 1(3): 412-8.
[21]
Sahu NK, Balbhadra SS, Choudhary J, Kohli DV. Exploring pharmacological significance of chalcone scaffold: A review. Curr Med Chem 2012; 19(2): 209-25.
[http://dx.doi.org/10.2174/092986712803414132] [PMID: 22320299]
[22]
Lidström P, Tierney J, Wathey B, Westman J. Microwave assisted organic synthesis - A review. Tetrahedron 2001; 57(45): 9225-83.
[http://dx.doi.org/10.1016/S0040-4020(01)00906-1]
[23]
Santagada V, Frecentese F, Perissutti E, Fiorino F, Severino B, Caliendo G. Microwave assisted synthesis: A new technology in drug discovery. Mini Rev Med Chem 2009; 9(3): 340-58.
[http://dx.doi.org/10.2174/1389557510909030340] [PMID: 19275727]
[24]
Panda KC, Kumar BVVR, Sahoo BM. Microwave assisted facile synthesis and in vitro anti-microbial activities of some novel isoxazole derivatives via chalcones. Nat Volat Essent Oils J 2021; 11: 503-10.
[25]
Vogel HG. Drug Discovery and Evaluation: Pharmacological Assays 2nd. Springer 2006; pp. 25-8.
[http://dx.doi.org/10.1007/3-540-29804-5]
[26]
Rubio C, Rubio-Osornio M, Retana-Márquez S, Lopez M, Custodio V, Paz C. In vivo experimental models of epilepsy. Cent Nerv Syst Agents Med Chem 2010; 10(4): 298-309.
[http://dx.doi.org/10.2174/187152410793429746] [PMID: 20868357]
[27]
Porter RJ. Antiepileptic drug development program. Prog Clin Biol Res 1983; 127: 53-66.
[PMID: 6351101]
[28]
Dunham NW, Miya TS. A note on a simple apparatus for detecting neurological deficit in rats and mice. J Am Pharm Assoc 1957; 46(3): 208-9.
[http://dx.doi.org/10.1002/jps.3030460322] [PMID: 13502156]
[29]
Khobare R, Pawar RP, Warad KD, Tayade A, Mane CB. An efficient synthesis of substituted isoxazole derivatives using ultra sound sonication method. Eur J Mol Clin Med 2020; 7(7): 319-25.
[30]
Hushare VJ, Rajput PR. Synthesis, characterization and antimicrobial activity of some novel isoxazoles. Rasayan J Chem 2012; 5(1): 121-6.
[31]
Goel A, Madan AK. Structure-activity study of antiepilepticN-aryl-isoxazolecarboxamides/N-isoxazolylbenzamide analogs using Wiener’s topological index. Struct Chem 1997; 8(2): 155-9.
[http://dx.doi.org/10.1007/BF02262851]
[32]
Barmade MA, Murumkar PR, Sharma MK, Yadav MR. Medicinal chemistry perspective of fused isoxazole derivatives. Curr Top Med Chem 2016; 16(26): 2863-83.
[http://dx.doi.org/10.2174/1568026616666160506145700] [PMID: 27150366]
[33]
Zimmermann LA, de Moraes MH, da Rosa R, et al. Synthesis and SAR of new isoxazole-triazole bis-heterocyclic compounds as analogues of natural lignans with antiparasitic activity. Bioorg Med Chem 2018; 26(17): 4850-62.
[http://dx.doi.org/10.1016/j.bmc.2018.08.025] [PMID: 30173929]
[34]
Banik BK, Sahoo BM, Ravi Kumar BVV, Panda KC. Microwave induced green chemistry approach towards the synthesis of heterocyclic compounds via C-N bond forming reactions. Curr Microw Chem 2021; 8(3): 204-14.
[http://dx.doi.org/10.2174/2213335608666210923144201]
[35]
Sahoo BM, Banik BK, Panda JR. Microwave-assisted green chemistry approach: A potential tool for drug synthesis in medicinal chemistry. CRC Press: Boca Raton 2018; pp. 475-508.
[http://dx.doi.org/10.1201/9781351240499-12]

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