Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Substituted Imidazole-Pyrazole Clubbed Scaffolds: Microwave Assisted Synthesis and Examined Their In-vitro Antimicrobial and Antituberculosis Effects

Author(s): Keyur M. Pandya*, Janki J. Patel, Arpan H. Patel, Navin B. Patel and Piyush. S. Desai

Volume 18, Issue 7, 2021

Published on: 19 August, 2020

Page: [574 - 582] Pages: 9

DOI: 10.2174/1570178617999200819164729

Price: $65

Abstract

A series of substituted imidazole-pyrazole fused compounds were designed & fused synthesized by employing Debus-Radziszewski one-pot synthesis reaction. Azoles are an extensive and comparatively new class of synthetic compounds including imidazoles and pyrazoles. The current clinical treatment uses compounds of azole framework. Azoles act by inhibiting ergosterol synthesis pathway (a principal component of the fungal cell wall). In addition, a literature review shows that the compounds that include imidazoles and pyrazoles have significant anti-bacterial and anti-mycobacterial effects. In light of the above findings, a series of compounds with imidazole and pyrazole scaffolds were sketched and developed to examine anti-bacterial, antifungal and antimycobacterial activities. The structures of the synthesized compounds were characterized using 1HNMR, 13CNMR, elemental analysis, and MS spectral data. The target compounds were screened for their in-vitro antimicrobial activity against gram-positive and gram-negative bacterial species by disc diffusion method according to the NCCLS (National Committee for Clinical Laboratory Standards) and anti-mycobacterial activity against the Mycobacterium tuberculosis H37Rv strain. The results revealed that imidazole-pyrazole fused scaffold compounds have potential antibacterial, antifungal and anti-mycobacterial activities which can be further optimized to get a lead compound.

Keywords: Debus-Radziszewski, imidazole, pyrazole, antimicrobial activity, antituberculosis activity.

« Previous
Graphical Abstract
[1]
Yoneyama, H.; Katsumata, R. Biosci. Biotechnol. Biochem., 2006, 70(5), 1060-1075.
[http://dx.doi.org/10.1271/bbb.70.1060] [PMID: 16717405]
[2]
Molton, J.S.; Tambyah, P.A.; Ang, B.S.; Ling, M.L.; Fisher, D.A. Clin. Infect. Dis., 2013, 56(9), 1310-1318.
[http://dx.doi.org/10.1093/cid/cit020] [PMID: 23334810]
[3]
Ichiyama, S. Clin. J. Med., 1992, 50, 992-997.
[4]
Yasunaka, K.; Kono, K. Microb. Drug Resist., 1999, 5(3), 207-213.
[http://dx.doi.org/10.1089/mdr.1999.5.207] [PMID: 10566871]
[5]
Takeda, S.; Yasunaka, K.; Kono, K.; Arakawa, K. Int. J. Antimicrob. Agents, 2000, 14(1), 39-43.
[http://dx.doi.org/10.1016/S0924-8579(99)00148-X] [PMID: 10717499]
[6]
(a)Viegas-Junior, C.; Danuello, A.; da Silva Bolzani, V.; Barreiro, E.J.; Fraga, C.A.M. Curr. Med. Chem., 2007, 14(17), 1829-1852.
[http://dx.doi.org/10.2174/092986707781058805] [PMID: 17627520]
(b)Gong, H.H.; Addla, D.; Lv, J.S.; Zhou, C.H. Curr. Top. Med. Chem., 2016, 16(28), 3303-3364.
[http://dx.doi.org/10.2174/1568026616666160506145943] [PMID: 27150364]
(c)Peng, X.M.; Peng, L.P.; Li, S.; Avula, S.R.; Kannekanti, V.K.; Zhang, S.L.; Tam, K.Y.; Zhou, C.H. Future Med. Chem., 2016, 8(16), 1927-1940.
[http://dx.doi.org/10.4155/fmc-2016-0002] [PMID: 27668522]
[7]
Zhang, H.Z.; Jeyakkumar, P.; Kumar, K.V. Zhou. C.H. New. J. Chem., 2015, 39, 5776-5796.
[http://dx.doi.org/10.1039/C4NJ01932F]
[8]
(a)Pavlovic´, D. ACS Med. Chem. Lett., 2011, 2, 331-336.
[PMID: 24900314]
(b)Siddiqui, N. Med. Chem. Res., 2016, 25, 1390-1402.
[http://dx.doi.org/10.1007/s00044-016-1570-6]
(c)Walsh, J.J.; Bell, A. Curr. Pharm. Des., 2009, 15(25), 2970-2985.
[http://dx.doi.org/10.2174/138161209789058183] [PMID: 19754373]
[9]
Plech, T.; Wujec, M.; Kosikowska, U.; Malm, A. M. Eur. J. Med. Chem., 2013, 60, 128-134.
[http://dx.doi.org/10.1016/j.ejmech.2012.11.040]
[10]
Pandya, K.M. Some Aspects on Novel Heterocyclic Compounds and Their Microbicidal Activity; ProQuest Dissertations Publishing: USA, 2019, p. 27750600.
(b)Pandya, K.M. P.S. Adv. J Chem. A., 2020, 3(4), 378-390.
[http://dx.doi.org/10.33945/SAMI/AJCA.2020.4.1]
(c)Pandya, K.M.; Patel, A.H.; Desai, P.S. Chem Afr., 2019, 3, 89-98.
[http://dx.doi.org/10.1007/s42250-019-00096-5]
[11]
Sharma, D.; Narasimhan, B.; Kumar, P.; Judge, V.; Narang, R.; De Clercq, E.; Balzarini, J. Eur. J. Med. Chem., 2009, 44(6), 2347-2353.
[http://dx.doi.org/10.1016/j.ejmech.2008.08.010] [PMID: 18851889]
[12]
Zampieri, D.; Mamolo, M.G.; Vio, L.; Banfi, E.; Scialino, G.; Fermeglia, M.; Ferrone, M.; Pricl, S. Bioorg. Med. Chem., 2007, 15(23), 7444-7458.
[http://dx.doi.org/10.1016/j.bmc.2007.07.023] [PMID: 17888669]
[13]
Olender, D.; Zwawiak, J.; Lukianchuk, V.; Lesyk, R.; Kropacz, A.; Fojutowski, A.; Zaprutko, L. Eur. J. Med. Chem., 2009, 44(2), 645-652.
[http://dx.doi.org/10.1016/j.ejmech.2008.05.016] [PMID: 18590938]
[14]
Pandya, K.M. Synthesis and cytotoxicity of azaheterocyclic compounds Rowan University: New Jersey, 2018. https://rdw.rowan.edu/etd/2549 dissertation
[15]
Suzuki, F.; Kuroda, T.; Tamura, T.; Sato, S.; Ohmori, K.; Ichikawa, S. J. Med. Chem., 1992, 35(15), 2863-2870.
[http://dx.doi.org/10.1021/jm00093a020] [PMID: 1495017]
[16]
Puratchikodya, A.; Doble, M. Bioorg. Med. Chem., 2007, 15, 1083.
[http://dx.doi.org/10.1016/j.bmc.2006.10.025] [PMID: 17079151]
[17]
Pinza, M.; Farina, C.; Cerri, A.; Pfeiffer, U.; Riccaboni, M.T.; Banfi, S.; Biagetti, R.; Pozzi, O.; Magnani, M.; Dorigotti, L. J. Med. Chem., 1993, 36(26), 4214-4220.
[http://dx.doi.org/10.1021/jm00078a011] [PMID: 8277504]
[18]
(a)Ansari, A.; Ali, A.; Asif, M. New J. Chem., 2017, 41, 16-41.
[http://dx.doi.org/10.1039/C6NJ03181A]
(b)Pandya, K.M.; Desai, P.S. Rasayan J. Chem., 2020, 13(2), 1054-1062.
[http://dx.doi.org/10.31788/RJC.2020.1325628]
(c)Karrouchi, K.; Radi, S.; Ramli, Y.; Taoufik, J.; Mabkhot, Y.N.; Al-aizari, F.A.; Ansar, M. Molecules, 2018, 23, 134.
[http://dx.doi.org/10.3390/molecules23010134]
[19]
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. N. Engl. J. Med., 2000, 342(26), 1946-1952.
[http://dx.doi.org/10.1056/NEJM200006293422603] [PMID: 10874062]
[20]
Friedrich, G.; Rose, T.; Rissler, K. Chromatogr, J. B766, , 295-305.2002
[21]
Hampp, C.; Hartzema, A.G.; Kauf, T.L. Value Health, 2008, 11(3), 389-399.
[http://dx.doi.org/10.1111/j.1524-4733.2007.00281.x] [PMID: 18179661]
[22]
Luttinger, D.; Hlasta, D.L. Annu. Rep. Med. Chem., 1987, 22, 21-30.
[http://dx.doi.org/10.1016/S0065-7743(08)61151-3]
[23]
Eseola, A.O.; Adepitan, O.; Govls, H.; Plass, W. New J. Chem., 2012, 36, 891-902.
[http://dx.doi.org/10.1039/c2nj20880f]
[24]
Gomleksiz, M.; Alkan, C.; Erdem, B. S. Afr. J. Chem., 2013, 66, 107-112.
[25]
Patel, A.; Sharo, S.Y.; Hall, K.; Lewis, W. Org. Biomol. Chem., 2016, 14(16), 3889-3905.
[http://dx.doi.org/10.1039/C6OB00471G] [PMID: 27035072]
[26]
N.C.C.L.S. Twelfth Informational Supplement 2002.
[27]
Rattan, A.; Churchill, B.I. Antimicrobials in Laboratory Medicine; Livingstone New Delhi, 2000, p. 85.
[28]
Jeyakkumar, P.; Zhang, L.; Avula, S.R.; Zhou, C.H. Eur. J. Med. Chem., 2016, 122, 205-215.
[http://dx.doi.org/10.1016/j.ejmech.2016.06.031] [PMID: 27371924]
[29]
Pascal, R.; Nadine, A. Eur. J. Med. Chem., 2002, 37, 671.
[30]
Cao, R.; Müller, P.; Lippard, S.J. J. Am. Chem. Soc., 2010, 132(49), 17366-17369.
[http://dx.doi.org/10.1021/ja108212v] [PMID: 21090678]
[31]
Fernandez-Ferri, P.; Ubeda, A.; Guillen, I.; Lasri, J. J. Eur. J. Med. Chem., 2003, 38, 289-296.
[http://dx.doi.org/10.1016/S0223-5234(03)00013-8]

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