An Efficient and Convenient Approach for the Synthesis of Novel Pyrazolo[1,2-a]triazole-triones and Evaluation of their Antimicrobial Activities
Pooja Saluja A , Jitender M. Khurana A C , Chetan Sharma B and Kamal R. Aneja B
+ Author Affiliations
- Author Affiliations
A Department of Chemistry, University of Delhi, Delhi 110007, India.
B Department of Microbiology, Kurukshetra University, Kurukshetra 136119, Haryana, India.
C Corresponding author. Email: jmkhurana1@yahoo.co.in
Australian Journal of Chemistry 67(6) 867-874 https://doi.org/10.1071/CH13586
Submitted: 30 October 2013 Accepted: 24 January 2014 Published: 19 February 2014
Abstract
A new protocol for the efficient synthesis of novel pyrazolo[1,2-a]triazole-1,3,5-triones has been developed. The synthesis was achieved by reaction of aromatic aldehydes, Meldrum’s acid, and 4-phenylurazole in the presence of a catalytic amount of glacial AcOH at 80°C. The structural assignment has been unambiguously confirmed by X-ray analysis. The present finding provides an environmentally benign, efficient, and promising synthetic strategy for the synthesis of libraries with diversity. These compounds were tested in vitro for their antibacterial activity against four strains, namely Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa and antifungal activity against two fungal strains, namely Aspergillus niger and Aspergillus flavus.
References
[1] (a) A. Kumar, G. Gupta, S. Srivastava, Green Chem. 2011, 13, 2459.| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtV2hsr3M&md5=2db18659fc1c03a446d15f50b9cf572eCAS |
(b) A. Kumar, M. K. Gupta, M. Kumar, Green Chem. 2012, 14, 290.
| Crossref | GoogleScholarGoogle Scholar |
(c) K. Tanaka, T. Sugino, F. Toda, Green Chem. 2000, 2, 303.
| Crossref | GoogleScholarGoogle Scholar |
(d) C. L. Raston, J. L. Scott, Green Chem. 2000, 2, 49.
| Crossref | GoogleScholarGoogle Scholar |
(e) P. T. Anastas, J. C. Warner, Green Chemistry: Theory and Practice 1998 (Oxford University Press: Oxford)
(f) J. McNulty, P. Das, Eur. J. Org. Chem. 2009, 2009, 4031.
| Crossref | GoogleScholarGoogle Scholar |
(g) J. McNulty, P. Das, Tetrahedron Lett. 2009, 50, 5737.
| Crossref | GoogleScholarGoogle Scholar |
(h) J. McNulty, P. Das, D. McLeod, Chem. – Eur. J. 2010, 16, 6756.
| Crossref | GoogleScholarGoogle Scholar |
(i) P. Das, D. McLeod, J. McNulty, Tetrahedron Lett. 2011, 52, 199.
| Crossref | GoogleScholarGoogle Scholar |
[2] (a) A. Domling, Chem. Rev. 2006, 106, 17.
| Crossref | GoogleScholarGoogle Scholar | 16402771PubMed |
(b) J. Zhu, H. Bienayme, Multicomponent Reactions 2005 (Wiley-VCH: Weinheim)
(c) D. J. Ramon, M. Yus, Angew. Chem. Int. Ed. 2005, 44, 1602.
| Crossref | GoogleScholarGoogle Scholar |
[3] (a) A. Dömling, W. Wang, K. Wang, Chem. Rev. 2012, 112, 3083.
| Crossref | GoogleScholarGoogle Scholar | 22435608PubMed |
(b) C. de Graaff, E. Ruijter, R. V. A. Orru, Chem. Soc. Rev. 2012, 41, 3969.
| Crossref | GoogleScholarGoogle Scholar |
(c) M. M. Sánchez Duque, C. Allais, N. Isambert, T. Constantieux, J. Rodriguez, Top. Heterocycl. Chem. 2010, 23, 227.
(d) B. B. Touré, D. G. Hall, Chem. Rev. 2009, 109, 4439.
| Crossref | GoogleScholarGoogle Scholar |
[4] P. A. Clarke, S. Santos, W. H. C. Martin, Green Chem. 2007, 9, 438.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXmslyqtro%3D&md5=05eccefb72826dcb76156826a3ad8c36CAS |
[5] C. R. Jacobson, A. D’Adamo, C. E. Cosgrove, U.S. Patent 3663564A 1972.
[6] T. Shgematsu, M. Tomita, T. Shibahara, M. Nakazawa, S. Munakata, Chem. Abstr. 1977, 87, 168017f.[Jpn. Patent, 52083562A, 1977].
[7] T. Jikihara, K. Matsuya, H. Ohta, S. Suzuki, O. Wakabayashi, Chem. Abstr. 1981, 95, 62219y.[U.S. Patent 4249934A, 1981].
[8] R. A. Izydore, I. H. Hall, Chem. Abstr. 1990, 112, 151876x.[U.S. Patent 4866058, 1990].
[9] B. V. Bredow, H. Brechbuehler, Chem. Abstr. 1974, 80, 140210s.[Ger. Offen. 2343347A1, 1974].
[10] I. H. Hall, O. T. Wong, R. Simlot, M. C. Miller, R. Izydore, Anticancer Res. 1992, 12, 1355.
| 1:CAS:528:DyaK3sXptl2jtw%3D%3D&md5=57f8cbb7084aca4d22fe46300e6cb768CAS | 1444191PubMed |
[11] (a) S. Mallakpour, Z. Rafiee, Polym. Bull. 2006, 56, 293.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xhs1SjtLo%3D&md5=ab860f2cb339cd4aa8b7a2430cd3ba45CAS |
(b) S. Mallakpour, Z. Rafiee, J. Appl. Polym. Sci. 2007, 103, 947.
| Crossref | GoogleScholarGoogle Scholar |
[12] A. M. Boldi, C. E. Johnson, H. O. Eissa, Tetrahedron Lett. 1999, 40, 619.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXntFGiuw%3D%3D&md5=ae7f139d43e63df8cafc94648bc177bcCAS |
[13] M. Cecere, F. Gozzo, S. Lorusso, C. Garavaglia, Chem. Abstr. 1981, 94, 121551.[Ger. Offen. 13 1980].
[14] W. E. Bottomley, G. V. Boyd, R. L. Monteil, J. Chem. Soc., Perkin Trans. 1 1980, 1, 843.
| Crossref | GoogleScholarGoogle Scholar |
[15] (a) A. M. Celli, D. Donati, M. Scotton, Tetrahedron 1989, 45, 7929.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXktVGnsLc%3D&md5=9f2571a148de5292881f71b8e003bec9CAS |
(b) J. P. Ryall, T. J. Dines, B. Z. Chowdhry, S. A. Leharne, R. Withnall, J. Chem. Phys. 2010, 373, 219.
| Crossref | GoogleScholarGoogle Scholar |
[16] G. M. Sheldrick, Acta Crystallogr. 2008, 64, 112.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhsVGhurzO&md5=e60798290754f1a9dfe9beb4e8e0b93dCAS |
[17] L. J. Farrugia, WinGX Version 1.80.05: An Integrated System of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-Ray Diffraction Data 1997–2009 (Department of Chemistry, University of Glasgow: Glasgow).
[18] K. R. Aneja, C. Sharma, R. Joshi, Int. J. Pediatr. Otorhinolaryngol. 2010, 74, 604.
| Crossref | GoogleScholarGoogle Scholar | 1:STN:280:DC%2BC3czjt1Gnug%3D%3D&md5=a49d6e25a8dba6148dccb2eabf4ddd0aCAS | 20347163PubMed |
[19] K. R. Aneja, C. Sharma, R. Joshi, Jundishapur J. Microbiol. 2011, 4, 175.
[20] J. M. Andrews, J. Antimicrob. Chemother. 2001, 48, 5.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXlsVegtr8%3D&md5=d2b3a6818ac95f43e56c977a3f91c04dCAS | 11420333PubMed |
[21] S. K. S. Al-Burtamani, M. O. Fatope, R. G. Marwah, A. K. Onifade, S. H. Al-Saidi, J. Ethnopharmocol. 2005, 96, 107.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhtVaqsLfO&md5=c5aa79b33d4eec14b679ebe81ef876faCAS |
