Generic placeholder image

Current Microwave Chemistry

Editor-in-Chief

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

Research Article

Microwave Assisted Synthesis, Characterization and Antimicrobial Screening of Thiazolidin-4-one Substituted Pyrazole Derivatives

Author(s): Meenu Beniwal* and Neelam Jain

Volume 6, Issue 1, 2019

Page: [44 - 53] Pages: 10

DOI: 10.2174/2213335606666190722144956

Abstract

Background: This paper describes the synthesis of novel thiazolidin-4-one substituted pyrazole derivatives from the condensation reaction of hydrazide with acetophenone derivatives. Herein we describe the synthesis of fourteen compounds by microwave irradiation method. The synthesized compounds are in excellent yield by utilizing microwave irradiation heating.

Objective: Compounds using different aromatic or heteroaromatic compounds should be synthesized and screened for their antibacterial activity to explore the possibility of pyrazole substituted thiazolidin- 4-ones as a novel series of antimicrobials.

Methods: Synthesis of thiazolidin-4-one substituted pyrazole derivatives was carried out under microwave radiation.

Results: These compounds were identified on the basis of melting point range, Rf values, IR, 1HNMR and mass spectral analysis. These compounds were evaluated for their in vitro antimicrobial activity and their Minimum Inhibitory Concentration (MIC) was determined. Among them Comp. 4b and Comp. 4k possess appreciable antimicrobial and antifungal activities.

Conclusion: A novel series of Thiazolidin-4-one substituted pyrazole were synthesized under microwave irradiation method and identified on the basis of melting point range, Rf values, IR, 1HNMR, mass spectral data and elemental analysis. The compounds were subjected to in vitro antimicrobial screening and their Minimum Inhibitory Concentrations (MIC) were determined. Among all the tested compounds, two compounds 4b and 4k exhibited moderate to significant activity against all the tested strains of bacteria and fungus were found to have appreciable antimicrobial activities. The results of antibacterial activity showed that compounds containing electron withdrawing groups were found to be more active than the compounds containing electron releasing groups.

Keywords: Thiazolidin-4-one, 1-H Pyrazole, vilsmeier haack reagent (DMF/POCl 3), microwave irradiation method, antimicrobial activity, Minimum Inhibitory Concentration (MIC).

Graphical Abstract
[1]
Loupy, A. Microwaves in organic synthesis. Tetrahedron, 2001, 57, 9199.
[2]
Kappe, C.O. Controlled microwave heating in modern organic synthesis. Angew. Chem. Int. Ed. Engl., 2004, 43(46), 6250-6284.
[3]
Zhang, S.; Arvidsson, P. Facile synthesis of N-protected amino acid esters assisted by microwave irradiation. Int. J. Pept. Res. Ther., 2008, 14, 219-222.
[4]
Zhou, Y.L.; Zeng, M.H.; Wei, L.Q.; Li, B.W.; Kurmoo, M. Traditional and microwave-assisted solvo thermal synthesis and surface modification of Co7 brucite disk clusters and their magnetic properties. Chem. Mater., 2010, 22, 4295-4303.
[5]
Mogilaiah, K.; Reddy, N.V.; Reddy, P.R. Microwave assisted synthesis of pyrazolyl-1, 8-naphthyridines. Ind. J. Heterocycl. Chem., 2001, (10), 267.
[6]
Verma, R.S. Advances in Green Chemistry: Chemical Synthesis using Microwave Irradiation. In: Astra Zeneca Research Foundation; ; , 2002.
[7]
Mahendrasinh, M.R.; Hemtul, V.P.; Lata, R.; Naynika, K.P. Synthesis, characterization and in vitro antimicrobial evaluation of some novel heterocyclic compounds. Int. J. Res. Pharm. Chem., 2013, 3, 2231-2781.
[8]
Verma, A.K.; Martin, A.; Singh, A.K. Evaluation of Anti- Inflammatory and Analgesic Activity of Novel Pyrazole Derivatives. Asian J. Biomed. Pharm. Sci, 2014, 4, 21-25.
[9]
Bondock, S.; Fadaly, W.; Metwally, M.A. Synthesis and antimicrobial activity of some new thiazole, thiophene and pyrazole derivatives containing benzothiazole moiety. Eur. J. Med. Chem., 2010, 45(9), 3692-3701.
[10]
Jain, S.; Goyal, A. Synthesis and antibacterial screening of some 1-phenyl-3-(4-(3-propanoloxy) phenyl)-5-aryl-1-H- pyrazoles. Der. Chem. Sin., 2012, 3, 249-254.
[11]
Mistry, B.D. Conventional and microwaveassisted synthesis of pyrazole derivatives and screening of their antibacterial and antifungal activities. Indian J. Chem., 2012, 51(2), 246-751.
[12]
Priyadarshini, P.; Ujwala, B.; Venkata, R.C.; Madhava, R.V. Synthesis and antimicrobial activity of some novel pyrazoles. Der. Pharm. Lett, 2012, 4(2), 1123-1128.
[13]
Gokhan-Kelekc, N.; Yabanog˘lu, S.; Ku¨peli, E.; Salgın, U.; Ozgen, O.; Ucar, G.; Yesilada, E.; Kendi, E.; Yesiladaf, Y.; Altan Bilgin, A. ‘Synthesis and biological evaluation of some thiazole and thiadiazolyl derivatives of 1H-pyrazole as anti-inflammatory antimicrobial’. Bioorg. Med. Chem., 2007, 15, 5775-5786.
[14]
Bekhit, A.A.; Hymete, A.; Asfaw, H. Bekhit, Ael-D. Synthesis and biological evaluation of some pyrazole derivatives as anti-malarial agents. Arch. Pharm. (Weinheim), 2012, 345(2), 147-154.
[15]
Nitulescu, G.M.; Draghici, C.; Olaru, O.T.; Matei, L.; Ioana, A.; Dragu, L.D.; Bleotu, C. Synthesis and apoptotic activity of new pyrazole derivatives in cancer cell lines. Bioorg. Med. Chem., 2015, 23(17), 5799-5808.
[16]
Nitulescu, G.M.; Matei, L.; Aldea, I.M.; Draghici, C.; Olaru, O.T.; Bleotu, C. Ultrasound-assisted synthesis and anticancer evaluation of new pyrazole derivatives as cell cycle inhibitors. Arab. J. Chem., 2015, 12, 816-824.
[17]
Sharath, V.; Kumar, H.V.; Naik, N. Synthesis of novel indole based scaffolds holding pyrazole ring as anti-inflammatory and antioxidant agents. J. Pharm. Res., 2013, 6, 785-790.
[18]
Bandgar, B.P.; Gawande, S.S.; Bodade, R.G.; Gawande, N.M.; Khobragade, C.N. Synthesis and biological evaluation of a novel series of pyrazole chalcones as anti-inflammatory, antioxidant and antimicrobial agents. Bioorg. Med. Chem., 2009, 17(24), 8168-8173.
[19]
Arunakumar, D.B.; Prakash, G.K.; Kumaranswamy, M.N.; Nandeshwarappa, B.P.; Sherigara, B.S.; Mahadevan, K.M. A novel method for the synthesis of formyl pyrazoles using vilsmeier-haack reaction. Ind. J. Chem., 46B 2007,
[20]
Attaryana, O.S.; Antanosyana, S.K.; Panosyanb, G.A.; Asratyana, G.V.; Matsoyana, S.G. Vilsmeier haak formylation of 3, 5-dimethylpyrazoles. Russ. J. Gen. Chem., 2006, 76(11), 1817-1819.
[21]
Vilsmeier, A.; Haack, A. The classical vilsmeier haack reactions. Chem. Ber., 1927, 60, 199.
[22]
Marson, C.M.; Giles, P.R. Synthesis Using Vilsmeier Reagents. In:CRC Press; Boca Raton, FL, 1994.
[23]
Rajput, A.P.; Rajput, S.S. A novel method for the synthesis of formyl pyrazoles using vilsmeier-haack reaction. Int. J. Pharm. Pharm. Sci., 2011, 3(4), 346-351.
[24]
Beniwal, M.; Jain, N. Review article on Vilsmeier Haack reaction and its application. Eur. J Biomed. Pharm. Sci., 2015, (2), 1340-1374.
[25]
Judge, V.; Narasimhan, B.; Ahuja, B.; Dharmajan, S.; Yogeeswari, P. Balzarini. J. Med. Chem., 2013, 9(1), 53-76.
[26]
Ahsan, M.J.; Saini, V. Design and synthesis of 3-(4-aminophenyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1 carboxamide/ carbothioamide analogues as antitubercular agents. Beni. Suef. Univ. J. Basic Appl. Sci., 2015, 4, 41-46.
[27]
Cappucino, J.G.; Sherman, N. Microbiology-A laboratory manual, 4th ed. ; Addison wesley longman inc: Harlow, England; . , 1999.
[28]
Gaud, R.S.; Gupta, G.D. Practical microbiology. In: Nirali Prakashan, , 5th ed;; , 2006.
[29]
Ericsson, H.M.; Sherris, J.C. Antibiotic sensitivity testing. Report of an international collaborative study. Acta Pathol. Microbiol. Scand. B. Microbiol. Immunol., 1971, 217(Suppl. 217), 1-90.

© 2024 Bentham Science Publishers | Privacy Policy