Copyright (c) 2024 B.V. Durgarao, D.V.L. Sirisha, K. Apparao, V. Narasingrao, K. Balageeta, N. Krishna Rao
This work is licensed under a Creative Commons Attribution 4.0 International License.
An Efficient One Pot Synthesis and Biological Activities of 6H-Indolo[2,3-b]quinoxalines Promoted by Palladium Acetate as Catalyst
Corresponding Author(s) : N. Krishna Rao
Asian Journal of Chemistry,
Vol. 36 No. 9 (2024): Vol 36 Issue 9, 2024
Abstract
A multi-component one pot protocol for the synthesis of quinoxalines derivatives by condensation reaction of substituted isatin with substituted o-phenylene diamine in presence palladium acetate as catalyst in strong base such as triphenylphosphine under conventional method has been reported. The molecular structures of the newly synthesized compounds were characterized by elemental analyses, IR, 1H NMR, 13C NMR and LCMS spectral data. The presented method is mild, inexpensive, highly atom economy and easy work up to give the products in good to excellent yields. All the synthesized compounds were also evaluated for in vitro antibacterial assay against Gram-negative (Escherichia coli and Staphylococcus aureus), Gram-positive (Salmonella typhi and Bacillus subtilis) and fungi (Aspergillus niger and Candida albicans) pathogenic bacteria in comparison to the standards streptomycin and fluconazole.
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B. Avula, C.K.R. Reddivari, R.M.R. Muchumarri, S. Eraganaboyina, G.V. Zyryanov and B.R. Nemallapudi, Polycycl. Arom. Comp., 44, 634 (2024); https://doi.org/10.1080/10406638.2023.2167215
L. Biesen and T.J.J. Müller, Adv. Synth. Catal., 363, 980 (2021); https://doi.org/10.1002/adsc.202001219
H. Khatoon and E. Abdulmalek, Molecules, 26, 1055 (2021); https://doi.org/10.3390/molecules26041055
V.E. Melnichenko, T.N. Kudryavtseva, A.Y. Lamanov, T.A. Kudryavcev, L.G. Klimova, Chemical Data Coll., 41, 100929 (2022); https://doi.org/10.1016/j.cdc.2022.100929
M. Srinivas, A. Tejashri, N. Anjaneyulu and K. Satyanarayana, Int. J. Pharm. Sci., 3, 142 (2013).
A. El-Faham, W.N. Hozzein, M.A.M. Wadaan, S.N. Khattab, H.A. Ghabbour, H.-K. Fun and M.R. Siddiqui, J. Chem., 2015, 716987 (2015); https://doi.org/10.1155/2015/716987
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P. Kumar, S. Singh and M.R.F. Pratama, Lett. Appl. NanoBioSci., 9, 961 (2020); https://doi.org/10.33263/LIANBS92.961967
K. Gescher, J. Kühn, W. Hafezi, A. Louis, A. Derksen, E. Lorentzen, A. Deters and A. Hensel, Fitoterapia, 82, 408 (2011); https://doi.org/10.1016/j.fitote.2010.11.022
L.M. Wilhelmsson, N. Kingi and J. Bergman, J. Med. Chem., 51, 7744 (2008); https://doi.org/10.1021/jm800787b
M.O. Shibinskaya, S.A. Lyakhov, A.V. Mazepa, S.A. Andronati, A.V. Turov, N.M. Zholobak and N. Ya. Spivak, Eur. J. Med. Chem., 45, 1237 (2010); https://doi.org/10.1016/j.ejmech.2009.12.014
M.O. Shibinskaya, S.A. Lyakhov, A.V. Mazepa, S.A. Andronati, A.V. Turov, N.M. Zholobak and N.Y. Spivak, Eur. J. Med. Chem., 45, 1237 (2010); https://doi.org/10.1016/j.ejmech.2009.12.014
R.A. Dabhi, M.P. Dhaduk, V.D. Bhatt and B.S. Bhatt, Materials Today: Proc., 65, 367 (2022); https://doi.org/10.1016/j.matpr.2022.06.374
P.B. Arimondo, B. Baldeyrou, W. Laine, C. Bal, F.-A. Alphonse, S. Routier, G. Coudert, J.-Y. Mérour, P. Colson, C. Houssier and C. Bailly, Chimico-Biol. Interactions, 138, 59 (2001); https://doi.org/10.1016/S0009-2797(01)00260-5
M. Santivañez-Veliz, S. Pérez-Silanes, E. Torres and E. Moreno-Viguri, Bioorg. Med. Chem. Lett., 26, 2188 (2016); https://doi.org/10.1016/j.bmcl.2016.03.066
E. Vicente, R. Villar, S. Perez-Silanes, I. Aldana, R.C. Goldman and A. Monge, Infect. Disord. Drug Targets, 11, 196 (2011); https://doi.org/10.2174/187152611795589735
A. Burguete, E. Pontiki, D. Hadjipavlou-Litina, R. Villar, E. Vicente, B. Solano, S. Ancizu, S. Pérez-Silanes, I. Aldana and A. Monge, Bioorg. Med. Chem. Lett., 17, 6439 (2007); https://doi.org/10.1016/j.bmcl.2007.10.002
S. Syed, M.A. Mohammad, M. Naveen, M. Chaithanya, G. Vanaja, M.K. Arunasree, P. Reddanna and M.S. Alam, Eur. J. Med. Chem., 49, 324 (2012); https://doi.org/10.1016/j.ejmech.2012.01.032
S. Sajjadifar, S. Karimian, H. Noorizadeh and H. Veisi, J. Catalysts, 2013, 723903 (2013); https://doi.org/10.1155/2013/723903
M.M. Heravi, K. Bakhtiari, M.H. Tehrani, N.M. Javadi and H.A. Oskooie, ARKIVOC, 16 (2006); https://doi.org/10.3998/ark.5550190.0007.g02
B. Karami and S. Khodabakhshi, J. Serb. Chem. Soc., 76, 1191 (2011); https://doi.org/10.2298/JSC100801104K
E. Kolvari, M.A. Zolfigol and M. Peiravi, Green Chem. Lett. Rev., 5, 155 (2012); https://doi.org/10.1080/17518253.2011.606849
M. Kalhor, M. Shayestefar, M. Khalaj and F. Janghorban, Res. Chem. Intermed., 49, 885 (2023); https://doi.org/10.1007/s11164-022-04914-3
J.-J. Cai, J.-P. Zou, X.-Q. Pan and W. Zhang, Tetrahedron Lett., 49, 7386 (2008); https://doi.org/10.1016/j.tetlet.2008.10.058
A. Trowbridge, S.M. Walton and M.J. Gaunt, Chem. Rev., 120, 2613 (2020); https://doi.org/10.1021/acs.chemrev.9b00462
A.R. Alcántara, Catalysts, 14, 161 (2024); https://doi.org/10.3390/catal14030161
G.S. Reddy, J.S. Kumar, B. Thirupataiah, H. Bhuktar, S. Shukla and M. Pal, Bioorg. Chem., 129, 106195 (2022); https://doi.org/10.1016/j.bioorg.2022.106195