Copyright (c) 2023 B. DURGA VARAPRASADU, K. SHIVA KUMAR, B. PULLA RAO
This work is licensed under a Creative Commons Attribution 4.0 International License.
Design, Synthesis, Characterization and Antibacterial Activity of Some Novel Furan Supported 1,2,4-Triazoles
Corresponding Author(s) : B. DURGA VARAPRASADU
Asian Journal of Chemistry,
Vol. 35 No. 10 (2023): Vol 35 Issue 10, 2023
Abstract
A methodical approach to synthesize several novel 2-phenyl-4-methylfuran [2,3-e][1,2,4]triazolo [1,5-c]pyrimidine derivatives (5a-c) as final compounds, N-(4-imino-4-methylfuro [2,3-d]pyrimidin-3(4H)-ylbenzamides (4a-c) by involving 2-amino-3-cyano-4-methyl furan (1) and N-(3-cyano-4-methylfuran)formimidic ethyl ether (2) and N’-((Z-(3-cyano-4-methylfuran-2-ylimino)methyl)benzohydrazides (3a-c) as intermediates and their antibacterial activity was tested. The chemical structures of all the newly synthesized intermediates and title compounds have been characterized by 1H NMR, IR, HRMS and elemental analysis. Compounds 4a-c and 5a-c showed antibacterial activity against different bacterial strains.
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- R. Paprocka, M. Wiese, A. Eljaszewicz, A. Helmin-Basa, A. Gzella, B. Modzelewska-Banachiewicz and J. Michalkiewicz, Bioorg. Med. Chem. Lett., 25, 2664 (2015);https://doi.org/10.1016/j.bmcl.2015.04.079
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- S. Pathania, R.K. Narang and R.K. Rawal, Eur. J. Med. Chem., 180, 486 (2019);https://doi.org/10.1016/j.ejmech.2019.07.043
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References
R. Paprocka, M. Wiese, A. Eljaszewicz, A. Helmin-Basa, A. Gzella, B. Modzelewska-Banachiewicz and J. Michalkiewicz, Bioorg. Med. Chem. Lett., 25, 2664 (2015);https://doi.org/10.1016/j.bmcl.2015.04.079
D. Kumudha, T. Kalavathi and B.A. Viswanath, World J. Pharm. Res., 7, 1614 (2018).
E. Stingaci, M. Zveaghinteva, S. Pogrebnoi, L. Lupascu, V. Valica, L. Uncu, A. Smetanscaia, M. Drumea, A. Petrou, A. Ciric, J. Glamoclija, M. Sokovic, V. Kravtsov, A. Geronikaki and F. Macaev, Bioorg. Med. Chem. Lett., 30, 127368 (2020);https://doi.org/10.1016/j.bmcl.2020.127368
N.K. Maddali, V.K.V. Ivaturi, L.N. Murthy Yellajyosula, V. Malkhed, P.K. Brahman, S.K.S.S. Pindiprolu, V. Kondaparthi and S.R. Nethinti, ChemistrySelect, 6, 6788 (2021);https://doi.org/10.1002/slct.202101387
J. Haber, Cas. Lek. Cesk., 140, 596 (2001).
S. Pathania, R.K. Narang and R.K. Rawal, Eur. J. Med. Chem., 180, 486 (2019);https://doi.org/10.1016/j.ejmech.2019.07.043
F. Foroumadi, S. Mansouri, Z. Kiani and A. Rahmani, Eur. J. Med. Chem., 38, 851 (2003);https://doi.org/10.1016/S0223-5234(03)00148-X
Z. Karczmarzyk, M. Swatko-Ossor, W. Wysocki, M. Drozd, G. Ginalska, A. Pachuta-Stec and M. Pitucha, Molecules, 25, 6033 (2020);https://doi.org/10.3390/molecules25246033
V. Klimešová, L. Zahajská, K. Waisser, J. Kaustová and U. Möllmann, Il Farmaco, 59, 279 (2004);https://doi.org/10.1016/j.farmac.2004.01.006
R. Romeo, D. Iannazzo, L. Veltri, B. Gabriele, B. Macchi, C. Frezza, F. Marino-Merlo and S.V. Giofrè, Molecules, 24, 1718 (2020);https://doi.org/10.3390/molecules24091718
A.R. Trivedi, B.H. Dholariya, C.P. Vakhariya, D.K. Dodiya, H.K. Ram, V.B. Kataria, A.B. Siddiqui and V.H. Shah, Med. Chem. Res., 21, 1887 (2012);https://doi.org/10.1007/s00044-011-9712-3
B. Tylinska, B. Wiatrak, Z. Czyznikowska, A. Ciesla-Niechwiadowicz, E. Gebarowska and A. Janicka-Klos, Int. J. Mol. Sci., 22, 3825 (2021);https://doi.org/10.3390/ijms22083825
N. Atatreh, A.M. Youssef, M.A. Ghattas, M. Al-Sorkhy, S. Alrawashdeh, K.B. Al-Harbi, I.M. El-Ashmawy, T.I. Almundarij, A.A. Abdelghani and A.S. Abd-El-Aziz, Bioorg. Chem., 86, 393 (2019);https://doi.org/10.1016/j.bioorg.2019.02.014
J. Majeed and M. Shaharyar, J. Enzyme Inhib. Med. Chem., 26, 819 (2011);https://doi.org/10.3109/14756366.2011.557022
S. Manohar, U.C. Rajesh, S.I. Khan, B.L. Tekwani and D.S. Rawat, ACS Med. Chem. Lett., 3, 555 (2012);https://doi.org/10.1021/ml3000808
N. Irshad, A.-U. Khan, Alamgeer, S. Khan and M.S. Iqbal, Biomed. Pharma., 139, 111567 (2021);https://doi.org/10.1016/j.biopha.2021.111567
Indian Pharmacopoeia, Microbiological Assay and Test, vol. II, A-100 (1996).