Antimicrobial Activity of Some Novel 1-(3-(4-Chlorophenylimino)-3,4- dihydroquinoxalin-2-yl)-3-substituted phenyl-1H-pyrazole-4-carbaldehyde

Author(s): Dhanapal Visagaperumal*, Vineeth Chandy

Journal Name: Anti-Infective Agents
Formerly Anti-Infective Agents in Medicinal Chemistry

Volume 18 , Issue 2 , 2020


DOI : 10.2174/2211352517666190117143604

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Graphical Abstract:


Abstract:

Background: In this study, synthesis of some novel 1-(3-(4-chlorophenylimino)-3,4- dihydroquinoxalin-2-yl)-3-substituted phenyl-1H-pyrazole-4-carbaldehyde were done by cyclization of dehydrated hemiketal using VilsmeierHaack reaction. The structures of synthesized compounds were in accordance of the basis of IR, 1HNMR, Mass spectral data and elemental analyses. The synthesized compounds had given good yields and high purity.

Methods: The antimicrobial activity of the synthesized compounds was preliminarily screened by paper disc diffusion technique. The determination of minimum inhibitory concentrations (MIC) of the synthesized compounds were done by using tube dilution method.

Results and Conclusion: All the screened compounds showed antibacterial and antifungal activity against selected strains of Gram positive and Gram negative bacteria and two strains of fungus, respectively but exhibited considerably less activity when compared to the reference drug ciprofloxacin and Fluconazole for antibacterial and antifungal activity, respectively. Among the synthesized compounds VV5 exhibited significant activity.

Keywords: Quinoxaline, pyrazole-4-carbaldehyde, vilsmeier haack reaction, antimicrobial activity, 1HNMR, gram negative bacteria.

[1]
Docquier, J.D.; Cusi, M.G. Editorial overview: anti-infectives: towards novel antiviral and antibacterial drugs? Current approaches to address a growing medical need. Curr. Opin. Pharmacol., 2014, 18, 4-6.
[http://dx.doi.org/10.1016/j.coph.2014.10.004] [PMID: 25454403]
[2]
McDermott, P.F.; Walker, R.D.; White, D.G. Antimicrobials: modes of action and mechanisms of resistance. Int. J. Toxicol., 2003, 22(2), 135-143.
[http://dx.doi.org/10.1080/10915810305089] [PMID: 12745995]
[3]
Zampini, I.C.; Cuello, S.; Alberto, M.R.; Ordoñez, R.M.; D’ Almeida, R.; Solorzano, E.; Isla, M.I. Antimicrobial activity of selected plant species from “the Argentine Puna” against sensitive and multi-resistant bacteria. J. Ethnopharmacol., 2009, 124(3), 499-505.
[http://dx.doi.org/10.1016/j.jep.2009.05.011] [PMID: 19467313]
[4]
Tomar, V.; Bhattacharjee, G.; Kamaluddin, ; Kumar, A. Synthesis and antimicrobial evaluation of new chalcones containing piperazine or 2,5-dichlorothiophene moiety. Bioorg. Med. Chem. Lett., 2007, 17(19), 5321-5324.
[http://dx.doi.org/10.1016/j.bmcl.2007.08.021] [PMID: 17719779]
[5]
Sharma, D.; Narasimhan, B.; Kumar, P.; Judge, V.; Narang, R.; De Clercq, E.; Balzarini, J. Synthesis, antimicrobial and antiviral evaluation of substituted imidazole derivatives. Eur. J. Med. Chem., 2009, 44(6), 2347-2353.
[http://dx.doi.org/10.1016/j.ejmech.2008.08.010] [PMID: 18851889]
[6]
Davis, D.C.; Mohammad, H.; Kyei-Baffour, K.; Younis, W.; Creemer, C.N.; Seleem, M.N.; Dai, M. Discovery and characterization of aryl isonitriles as a new class of compounds versus methicillin- and vancomycin-resistant Staphylococcus aureus. Eur. J. Med. Chem., 2015, 101, 384-390.
[http://dx.doi.org/10.1016/j.ejmech.2015.06.031] [PMID: 26164843]
[7]
Qin, W.; Panunzio, M.; Biondi, S. β-Lactam Antibiotics Renaissance. Antibiotics (Basel), 2014, 3(2), 193-215.
[http://dx.doi.org/10.3390/antibiotics3020193] [PMID: 27025744]
[8]
Sharma, D.; Narasimhan, B.; Kumar, P.; Jalbout, A. Synthesis and QSAR Evaluation of (2-(Substituted Phenyl)-1H-Benzimidazol-1-yl)-Pyridin-3-yl-Metahnones. Eur. J. Med. Chem., 2009, 44, 1119-1127.
[http://dx.doi.org/10.1016/j.ejmech.2008.06.009] [PMID: 18657885]
[9]
Tunçbilek, M.; Kiper, T.; Altanlar, N. Synthesis and in vitro antimicrobial activity of some novel substituted benzimidazole derivatives having potent activity against MRSA. Eur. J. Med. Chem., 2009, 44(3), 1024-1033.
[http://dx.doi.org/10.1016/j.ejmech.2008.06.026] [PMID: 18718694]
[10]
Sharma, S.; Gangal, S.; Rauf, A. Convenient one-pot synthesis of novel 2-substituted benzimidazoles, tetrahydrobenzimidazoles and imidazoles and evaluation of their in vitro antibacterial and antifungal activities. Eur. J. Med. Chem., 2009, 44(4), 1751-1757.
[http://dx.doi.org/10.1016/j.ejmech.2008.03.026] [PMID: 18472189]
[11]
Okemo, P.O.; Bais, H.P.; Vivanco, J.M. In vitro activities of Maesa lanceolata extracts against fungal plant pathogens. Fitoterapia, 2003, 74(3), 312-316.
[http://dx.doi.org/10.1016/S0367-326X(03)00039-X] [PMID: 12727503]
[12]
Bouamama, H.; Noël, T.; Villard, J.; Benharref, A.; Jana, M. Antimicrobial activities of the leaf extracts of two Moroccan Cistus L. species. J. Ethnopharmacol., 2006, 104(1-2), 104-107.
[http://dx.doi.org/10.1016/j.jep.2005.08.062] [PMID: 16213684]
[13]
Fustero, S.; Sánchez-Roselló, M.; Barrio, P.; Simón-Fuentes, A. From 2000 to mid-2010: a fruitful decade for the synthesis of pyrazoles. Chem. Rev., 2011, 111(11), 6984-7034.
[http://dx.doi.org/10.1021/cr2000459] [PMID: 21806021]
[14]
Ansari, A.; Ali, A.; Asif, M. Review: biologically active pyrazole derivatives. New J. Chem., 2017, 41, 16-41.
[http://dx.doi.org/10.1039/C6NJ03181A]
[15]
Steinbach, G.; Lynch, P.M.; Phillips, R.K.; Wallace, M.H.; Hawk, E.; Gordon, G.B.; Wakabayashi, N.; Saunders, B.; Shen, Y.; Fujimura, T.; Su, L-K.; Levin, B.; Godio, L.; Patterson, S.; Rodriguez-Bigas, M.A.; Jester, S.L.; King, K.L.; Schumacher, M.; Abbruzzese, J.; DuBois, R.N.; Hittelman, W.N.; Zimmerman, S.; Sherman, J.W.; Kelloff, G. The effect of celecoxib, a cyclooxygenase-2 inhibitor, in familial adenomatous polyposis. N. Engl. J. Med., 2000, 342(26), 1946-1952.
[http://dx.doi.org/10.1056/NEJM200006293422603] [PMID: 10874062]
[16]
Uslaner, J.M.; Parmentier-Batteur, S.; Flick, R.B.; Surles, N.O.; Lam, J.S.; McNaughton, C.H.; Jacobson, M.A.; Hutson, P.H. Dose-dependent effect of CDPPB, the mGluR5 positive allosteric modulator, on recognition memory is associated with GluR1 and CREB phosphorylation in the prefrontal cortex and hippocampus. Neuropharmacology, 2009, 57(5-6), 531-538.
[http://dx.doi.org/10.1016/j.neuropharm.2009.07.022] [PMID: 19627999]
[17]
Friedrich, G.; Rose, T.; Rissler, K. Determination of lonazolac and its hydroxy and O-sulfated metabolites by on-line sample preparation liquid chromatography with fluorescence detection. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 2002, 766(2), 295-305.
[http://dx.doi.org/10.1016/S0378-4347(01)00514-X] [PMID: 11824818]
[18]
Hampp, C.; Hartzema, A.G.; Kauf, T.L. Cost-utility analysis of rimonabant in the treatment of obesity. Value Health, 2008, 11(3), 389-399.
[http://dx.doi.org/10.1111/j.1524-4733.2007.00281.x] [PMID: 18179661]
[19]
Spitz, I.M.; Novis, B.H.; Ebert, R.; Trestian, S.; LeRoith, D.; Creutzfeldt, W. Betazole-induced GIP secretion is not mediated by gastric HCl. Metabolism, 1982, 31(4), 380-382.
[http://dx.doi.org/10.1016/0026-0495(82)90114-7] [PMID: 7078422]
[20]
Luttinger, D.; Hlasta, D.J. Antidepressant Agents. Annu. Rep. Med. Chem., 1987, 22, 21-30.
[http://dx.doi.org/10.1016/S0065-7743(08)61151-3]
[21]
Kameyama, T.; Nabeshima, T. Effects of 1,3-diphenyl-5-(2-dimethylaminopropionamide)-pyrazole[difenamizole] on a conditioned avoidance response. Neuropharmacology, 1978, 17(4-5), 249-256.
[http://dx.doi.org/10.1016/0028-3908(78)90108-9] [PMID: 652137]
[22]
García-Lozano, J.; Server-Carrió, J.; Escrivà, E.; Folgado, J-V.; Molla, C.; Lezama, L. X-ray crystal structure and electronic properties of chlorobis (mepirizole) copper (II) tetrafluoroborate (mepirizole = 4-methoxy-2-(5-methoxy-3-methyl-1H-pyrazol-1-yl)-6-methylpyrimidine). Polyhedron, 1997, 16, 939-944.
[http://dx.doi.org/10.1016/S0277-5387(96)00346-4]
[23]
Bhise, S.B.; Pawar, P.Y. Synthesis and antibacterial activity of some new quinoxalinedione derivatives. Int. J. Chem. Sci., 2007, 5, 700-710.
[24]
Mackie and McCartney: Practical medical microbiology., Eds J.G. Collee, J.P. Duguid, A.G. Fraser & B.P. Marmion, 13th edition;Churchill Livingstone. 1989.
[http://dx.doi.org/10.1016/0195-6701(90)90135-B]
[25]
Silverstein, R.M.; Webster, F.X. Spectrometric Identification of Organic compounds; John Wiley & Sons, Inc.: New York, 1998.


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Article Details

VOLUME: 18
ISSUE: 2
Year: 2020
Published on: 08 June, 2020
Page: [128 - 134]
Pages: 7
DOI: 10.2174/2211352517666190117143604

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