Synthesis and Antimicrobial Evaluation of Chiral 3, 5-Diaryl-5, 6-dihydrothiazolo[ 2, 3-c][1, 2, 4]triazoles

Author(s): Pawankumar R. Tiwari, Marina E. John, Anil V. Karnik*

Journal Name: Letters in Organic Chemistry

Volume 16 , Issue 12 , 2019

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Graphical Abstract:


Disclosed herein is a general approach for the synthesis of chiral thiazolo triazoles 5a-e. An efficient 3-step synthetic strategy has been developed to obtain the fused heterocycles in good yields. The key step involves formation of a secondary carbocation under acidic condition and intramolecular attack of the nitrogen of the 1,2,4-triazolo part leads to the formation of fused bicyclic compound in a regioselective manner. A new chiral center was created during the reaction and Chiral HPLC analyses confirmed the presence of the same and the racemic nature of the synthesized compounds. Their antimicrobial activities were evaluated by broth micro-dilution method and expressed as the minimum inhibitory concentration. The preliminary bioassay results demonstrate that most of the target compounds exhibit a significantly wide spectrum activity against S. aureus and E. coli comparable to ampicillin. The efficacies of compounds against C. albicans are either more or similar compared to Griseofulvin.

Keywords: Thaizolo[2, 3-c][1, 2, 4]triazoles, chiral HPLC, antimicrobial activity, intramolecular cyclization, chirality, fused heterocycles.

Khose, V.N.; John, M.E.; Pandey, A.D.; Karnik, A.V. Tetrahedron Asymmetry, 2017, 28, 1233-1289.
Gilchrist, T. Heterocyclic Chemistry 3rd 1984, edition; pp. 1, Pearson Education, India
Khose, V.N.; John, M.E.; Pandey, A.D.; Borokov, V.; Karnik, A.V. Symmetry , 2018, 10, 34.
Tawde, T.S.; Wagh, S.J.; Sapre, J.V.; Khose, V.N.; Badani, P.M.; Karnik, A.V. Tetrahedron Asymmetry, 2016, 27, 130-135.
Gawin, R.; Pieczycolan, M.; Malinska, M.; Wozniak, K.; Grela, K. Synlett, 2013, 24, 1250-1254.
Reiderer, S.K.U.; Bechlars, B.; Herrmann, W.A.; Kuhn, F.E. Dalton Trans., 2011, 40, 41.
Banerjee, S.; Ganguly, S.; Sen, K. J. Adv. Pharm. Educ. Res., 2013, 3(3), 102-115.
Burch, H.A.; Smith, W.O. J. Med. Chem., 1966, 9, 405.
Rollas, S.; Kalyoncuoglu, N.; Stur-Altiner, D. Yegenoglu.; Y. Pharmazie, 1993, 48, 308.
Foroumadi, A.; Mansouri, S.; Kiani, Z.; Rahmani, A. Eur. J. Med. Chem., 2003, 38, 851.
Ram, V.J.; Mishra, L.; Pandey, N.H.; Kushwaha, D.S.; Pieters, L.A.C.; Vlietinck, A.J. J. Heterocycl. Chem., 1990, 27, 351.
Kalyoncuoglu, N.; Rollas, S. Sur- Altiner, D.; Yegenoglu, Y.; Ang, O. Pharmazie, 1992, 47, 796.
Ergenc, N.; Ilhan, E.; Otuk, G. Pharmazie, 1992, 47, 59.
Karnik, A.V.; Kulkarni, A.M.; Malviya, N.J.; Mourya, B.R.; Jadhav, B.L. Eur. J. Med. Chem., 2008, 43(11), 2615-2617.
Karnik, A.V.; Malviya, N.J.; Kulkarni, A.M.; Jadhav, B.L. Eur. J. Med. Chem., 2006, 41(7), 891-895.
Karnik, A.V.; Malviya, N.J.; Kulkarni, A.M.; Jaimini, D.; Jadhav, B.L. J. Heterocycl. Chem., 2006, 43(2), 489-493.
Tiwari, P.R.; John, M.E.; Karnik, A.V. Synth. Commun., 10.1080/00397911.2018.1514052
Dayama, D.S.; Khatale, P.N.; Khedekar, S.A.; Nazarkar, S.R.; Vedpathak, P.A. Pharma Chem., 2014, 6(5), 123-127.
Ledeti, I.V.; Bercean, V.N.; Badea, V.; Balan, M. Rev. Chim. (Bucharest), 2010, 61(9), 833-837.
Karnik, A.; Patil, S.; Patnekar, S.; Semwal, A. New J. Chem., 2004, 28, 1420.
Wagh, S.J.; Tawde, T.S.; Sapre, J.V.; Khose, V.N.; Karnik, A.V. Indian J. Chem., 2016, 55B, 707-712.
Henry, D. Clinical microbiology handbook, Isenberg, 2 nd Edition, vol.II, Chapter 5, pp. 5.0.1.
Desai, N.C.; Shihora, P.N.; Moradia, D.L. Indian J. Chem., 2007, 46B, 550.
Wayne, P.A. National Committee for Clinical Laboratory Standards. Methods for Dilution, Antimicrobial Susceptibility Tests for Bacteria that grow Aerobically Approved Standard, (M 7A5), 5th ed , 2000.
Shadomy, S. Manual of Clinical Microbiology; Albert, B., Ed.; ASM Press: Washington, DC, 1991, p. 1173.
Rattan, A. Antimicrobials in Laboratory Medicine; BI Churchill Livingstone: India, 2000, p. 85.

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Article Details

Year: 2019
Published on: 08 October, 2019
Page: [978 - 982]
Pages: 5
DOI: 10.2174/1570178616666190411102818
Price: $65

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