Generic placeholder image

Current Microwave Chemistry

Editor-in-Chief

ISSN (Print): 2213-3356
ISSN (Online): 2213-3364

General Research Article

Conventional Versus Microwave Induced Synthesis and Biological Evolution of Coumarin Substituted Thioaryl Pyrazolyl Pyrazoline

Author(s): Parin V. Shaikh* and Dinkar I. Brahmbhatt

Volume 10, Issue 2, 2023

Published on: 27 November, 2023

Page: [223 - 229] Pages: 7

DOI: 10.2174/0122133356267953231101093319

Price: $65

Abstract

Aim: This is a comparative study of some new coumarin substituted thioaryl pyrazolyl pyrazoline.

Methods: The target compounds were synthesized using both conventional as well as microwave irradiation by reaction of coumarin chalcones with different substituted hydrazine hydrates and aryl hydrazines to give the resultant pyrazoline derivatives. Microwave reaction, enhanced organic reactions, and reduced reaction time led to better yields and selectivity than conventional methods.

Results: The obtained compounds were characterized by different spectroscopic analysis including IR, 1H-NMR, 13C-NMR, mass spectroscopy and elemental-analysis and evaluated for their antimicrobial screening against a representative panel of bacteria (Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Salmonella typhi) and fungi (Aspergillus niger, Candida albicans).

Conclusion: In the present study, we have synthesized coumarin pyrazoline derivatives clubbed with benzofuran pyrazole via both conventional and microwave irradiation and also subjected to antibacterial and antifungal studies. Synthesis of target compounds by the microwave irradiation enhanced reaction rate and reduced reaction time led to better yields and selectivity than conventional methods. The study of antibacterial and antifungal activities revealed that all the compounds exhibited reasonable to excellent activities against the pathogenic strains.

Keywords: Coumarin, pyrazoline derivatives, microwave irradiation, conventional synthesis, antimicrobial activity.

Graphical Abstract
[1]
Ley, S.V.; Baxendale, I.R. New tools and concepts for modern organic synthesis. Nat. Rev. Drug Discov., 2002, 1(8), 573-586.
[http://dx.doi.org/10.1038/nrd871] [PMID: 12402498]
[2]
Lew, A.; Krutzik, P.O.; Hart, M.E.; Chamberlin, A.R. Increasing rates of reaction: Microwave-assisted organic synthesis for combinatorial chemistry. J. Comb. Chem., 2002, 4(2), 95-105.
[http://dx.doi.org/10.1021/cc010048o] [PMID: 11886281]
[3]
Lidstrom, P.; Tierney, J. Microwave Assisted Organic Synthesis-A Review. Tetrahedron, 2001, 57, 9225-9283.
[http://dx.doi.org/10.1016/S0040-4020(01)00906-1]
[4]
Polshettiwar, V.; Nadagouda, M.N.; Varma, R.S. Microwave-Assisted Chemistry: A rapid and sustainable route to synthesis of organics and nanomaterials. Aust. J. Chem., 2009, 62(1), 16-26.
[http://dx.doi.org/10.1071/CH08404]
[5]
Yadav, J.S.; Reddy, B.V.S.; Basak, A.K.; Narsaiah, A.V. Microwave accelerated SN2' substitution of Baylis–Hillman acetates: A comparative study of conventional heating versus microwave irradiation. J. Mol. Catal. Chem., 2007, 274(1-2), 105-108.
[http://dx.doi.org/10.1016/j.molcata.2007.03.073]
[6]
Katritzky, A.R.; Singh, S.K. Microwave-assisted heterocyclic synthesis. ARKIVOC, 2003, 2003(13), 68-86.
[http://dx.doi.org/10.3998/ark.5550190.0004.d09]
[7]
Abirami, M.; Nadaraj, V. Synthesis of Schiff Base under Solvent-free Condition: As a Green Approach. Int. J. Chemtech Res., 2014, 6, 2534-2538.
[8]
Vekariya, R.; Panchal, S. A One Pot, Solvent Free and Catalyst Free Synthesis of Substituted 2-Amino-5-Aryl-1,3,4-Oxadiazoles under Microwave Irradiation. Curr. Microw. Chem., 2015, 2, 61-68.
[http://dx.doi.org/10.2174/221333560201150212111506]
[9]
Barham, J.P.; Koyama, E.; Norikane, Y.; Ohneda, N.; Yoshimura, T. Microwave Flow: A Perspective on Reactor and Microwave Configurations and the Emergence of Tunable Single-Mode Heating Toward Large-Scale Applications. Chem. Rec., 2019, 19(1), 188-203.
[http://dx.doi.org/10.1002/tcr.201800104] [PMID: 30457695]
[10]
Sharma, A.K.; Bal, A.K. Coumarin in chromosome analysis. Stain Technol., 1953, 28(5), 255-257.
[http://dx.doi.org/10.3109/10520295309105242] [PMID: 13089943]
[11]
Okuyama, N; Takata, T Studies on the anti-tumor-promoting activity of naturally occurring substances. IV. Pd-II [(+)anomalin, (+)praeruptorin B], a seselin-type coumarin, inhibits the promotion of skin tumor formation by 12-O-tetradecanoylphorbol-13-acetate in 7,12-dimethylbenz[a]anthracene-initiated mice. Carcinogenesis., 1990, 11(9), 1557-1561.
[12]
Tsai, I.L.; Wun, M.F.; Teng, C.M.; Ishikawa, T.; Chen, I.S. Anti-platelet aggregation constituents from formosan Toddalia asiatica. Phytochemistry, 1998, 48(8), 1377-1382.
[http://dx.doi.org/10.1016/S0031-9422(97)00678-X] [PMID: 9720317]
[13]
Dawane, B.S.; Konda, S.G.; Mandawad, G.G.; Shaikh, B.M. Poly(ethylene glycol) (PEG-400) as an alternative reaction solvent for the synthesis of some new 1-(4-(4'-chlorophenyl)-2-thiazolyl)-3-aryl-5-(2-butyl-4-chloro-1H-imidazol-5yl)-2-pyrazolines and their in vitro antimicrobial evaluation. Eur. J. Med. Chem., 2010, 45(1), 387-392.
[http://dx.doi.org/10.1016/j.ejmech.2009.10.015] [PMID: 19896247]
[14]
Lombardino, J.G.; Otterness, I.G. Novel immunosuppressive agents. Potent immunological activity of some benzothiopyrano[4,3-c]pyrazol-3-ones. J. Med. Chem., 1981, 24(7), 830-834.
[http://dx.doi.org/10.1021/jm00139a012] [PMID: 7277388]
[15]
Amir, M.; Kumar, H.; Khan, S.A. Synthesis and pharmacological evaluation of pyrazoline derivatives as new anti-inflammatory and analgesic agents. Bioorg. Med. Chem. Lett., 2008, 18(3), 918-922.
[http://dx.doi.org/10.1016/j.bmcl.2007.12.043] [PMID: 18182288]
[16]
Bano, S.; Javed, K.; Ahmad, S.; Rathish, I.G.; Singh, S.; Alam, M.S. Synthesis and biological evaluation of some new 2-pyrazolines bearing benzene sulfonamide moiety as potential anti-inflammatory and anti-cancer agents. Eur. J. Med. Chem., 2011, 46(12), 5763-5768.
[http://dx.doi.org/10.1016/j.ejmech.2011.08.015] [PMID: 22019186]
[17]
Budakoti, A.; Bhat, A.R.; Azam, A. Synthesis of new 2-(5-substituted-3-phenyl-2-pyrazolinyl)-1,3-thiazolino[5,4-b]quinoxaline derivatives and evaluation of their antiamoebic activity. Eur. J. Med. Chem., 2009, 44(3), 1317-1325.
[http://dx.doi.org/10.1016/j.ejmech.2008.02.002] [PMID: 18378360]
[18]
Özdemir, Z.; Kandilci, H.B.; Gümüşel, B.; Çalış, Ü.; Bilgin, A.A. Synthesis and studies on antidepressant and anticonvulsant activities of some 3-(2-furyl)-pyrazoline derivatives. Eur. J. Med. Chem., 2007, 42(3), 373-379.
[http://dx.doi.org/10.1016/j.ejmech.2006.09.006] [PMID: 17069933]
[19]
Tehranchian, S.; Akbarzadeh, T.; Fazeli, M.R.; Jamalifar, H.; Shafiee, A. Synthesis and antibacterial activity of 1-[1,2,4-triazol-3-yl] and 1-[1,3,4-thiadiazol-2-yl]-3-methylthio-6,7-dihydrobenzo[c]thiophen-4(5H)ones. Bioorg. Med. Chem. Lett., 2005, 15(4), 1023-1025.
[http://dx.doi.org/10.1016/j.bmcl.2004.12.039] [PMID: 15686905]
[20]
Pillai, A.D.; Rathod, P.D.; Xavier, F.P.; Padh, H.; Sudarsanam, V.;K.; Vasu, K. Tetra substituted thiophenes as anti-inflammatory agents: Exploitation of analogue-based drug design. Bioorg. Med. Chem., 2005, 13(24), 6685-6692.
[http://dx.doi.org/10.1016/j.bmc.2005.07.044] [PMID: 16125391]
[21]
Russell, R.K. Thiophene systems: Thienopyrimidinedione derivatives as potential antihypertensive agents. J. Med. Chem., 1988, 31, 1786-1793.
[http://dx.doi.org/10.1021/jm00117a019] [PMID: 2842504]
[22]
Chen, Z.; Ku, T.C.; Seley-Radtke, K.L. Thiophene-expanded guanosine analogues of Gemcitabine. Bioorg. Med. Chem. Lett., 2015, 25(19), 4274-4276.
[http://dx.doi.org/10.1016/j.bmcl.2015.07.086] [PMID: 26316465]
[23]
Kundaliya, K.N.; Patel, N.H.; Brahmbhatt, D.I. Microwave-assisted Synthesis of Novel Triazolyl Pyrazolyl Pyrazoline Substituted Coumarins and Their Antimicrobial Activity. >. Bioorg. Med. Chem. Lett., 2002, 9(1), 47-59.
[24]
Bhila, V.G.; Patel, C.V.; Patel, N.H.; Brahmbhatt, D.I. One pot synthesis of some novel coumarins containing 5-(substituted-2-hydroxybenzoyl) pyridine as a new class of antimicrobial and antituberculosis agents. Med. Chem. Res., 2013, 22(9), 4338-4346.
[http://dx.doi.org/10.1007/s00044-012-0437-8]
[25]
Arbačiauskienė, E.; Martynaitis, V.; Krikštolaitytė, S.; Holzer, W.; Šačkus, A. Synthesis of 3-substituted 1-phenyl-1H-pyrazole-4-carbaldehydes and the corresponding ethanones by Pd-catalysed cross-coupling reactions. ARKIVOC, 2011, 2011(11), 1-21.
[http://dx.doi.org/10.3998/ark.5550190.0012.b01]
[26]
National Committee for Clinical Laboratory Standards (NCCLS). Performance Standards for Antimicrobial Susceptibility Testing; Twelfth Informational Supplement., 2002. Available From: https://www.researchgate.net/file.PostFileLoader.html?id=55d77c2f614325f5d38b461b&assetKey=AS:27383670

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy