Copyright (c) 2024 Udaya Bhaskar Jekkoju
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization and Antibacterial Activity of Some Novel Pyrido[2,3-b]indole, Morpholine and Chalcone Hybrid Compounds
Corresponding Author(s) : J. Udaya Bhaskar
Asian Journal of Chemistry,
Vol. 36 No. 11 (2024): Vol 36 Issue 11, 2024
Abstract
In present investigation, a novel series of (E)-3-(2-morpholino-9H-pyrido[2,3-b]indol-3-yl)-1-phenylprop-2-en-1-one and its derivatives (5a-f) were synthesized by condensation reaction from the final intermediate, 2-morpholino-9H-pyrido[2,3-b]indol-3-carbaldehyde (4). The synthesis of the title compounds commenced from commercially available 21H-indol-2-amine (1) and by involving N-(1H-indol-2-yl)-acetamide (2) and 2-chloro-9H-pyrido[2,3-b]indole-3-carbaldehyde (3) as reactive intermediates. The chemical structure of synthesized compounds was characterized by IR, 1H NMR, mass spectral data and elemental analysis. The final compounds were used to screen for their antibacterial activity against various strains of bacteria.
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H. Yu and F. Xu, RSC Adv., 13, 8238 (2023); https://doi.org/10.1039/D3RA00400G
B. Zhang and A. Studer, Chem. Soc. Rev., 44, 3505 (2015); https://doi.org/10.1039/C5CS00083A
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A. Ramirez-Villalva, D. Gonzalez-Calderon, C. Gonzalez-Romero, M. Morales-Rodriguez, B. Jauregui Rodriguez, E. Cuevas-Yanez and A. Fuentes-Benites, Eur. J. Med. Chem., 97, 275 (2015); https://doi.org/10.1016/j.ejmech.2015.04.047
P. Zhan, X. Chen, D. Li, Z. Fang, E. de Clercq and X. Liu, Med. Res. Rev., 33(S1), 1 (2013); https://doi.org/10.1002/med.20241
T.L.S. Kishbaugh, Curr. Top. Med. Chem., 16, 3274 (2016); https://doi.org/10.2174/1568026616666160506145141
A.S. Abd El-All, S.A. Osman, H.M.F. Roaiah, M.M. Abdalla, A.A. Abd El Aty and W.H. AbdEl-Hady, Med. Chem. Res., 24, 4093 (2015); https://doi.org/10.1007/s00044-015-1460-3
S.R. Alizadeh and M.A. Ebrahimzadeh, Mini Rev. Med. Chem., 21, 2584 (2021); https://doi.org/10.2174/1389557521666210126143558
F.A. Bassyouni, H.A. Tawfik, A.M. Soliman and M.A. Rehim, Res. Chem. Intermed., 38, 1291 (2012); https://doi.org/10.1007/s11164-011-0413-9
U. Fathy, A. Younis and H. Awad, J. Chem. Pharm. Res., 7, 4 (2015).
V. Antoci, D. Cucu, G. Zbancioc, C. Moldoveanu, V. Mangalagiu, D.A. Mantu, A. Aricu and I.I. Mangalagiu, Future Med. Chem., 12, 207 (2020); https://doi.org/10.4155/fmc-2019-0063
L. El Kaim, L. Grimaud and P. Pravin, Org. Lett., 14, 476 (2012); https://doi.org/10.1021/ol202974w
M.C. Sharma, Interdiscip. Sci. Comput. Life Sci., 6, 197 (2014); https://doi.org/10.1007/s12539-013-0201-x
S.T. Chung, W.H. Huang, C.K. Huang, F.C. Liu, R.-Y. Huang, C.-C. Wu and A.-R. Lee, Res. Chem. Intermed., 42, 1195 (2016); https://doi.org/10.1007/s11164-015-2081-7
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J.A. Bull, J.J. Mousseau, G. Pelletier and A.B. Charette, Chem. Rev., 112, 2642 (2012); https://doi.org/10.1021/cr200251d
G.D. Henry, Tetrahedron, 60, 6043 (2004); https://doi.org/10.1016/j.tet.2004.04.043
V.A.F.F.M. Santos, L.O. Regasini, C.R. Nogueira, G.D. Passerini, I. Martinez, V.S. Bolzani, M.A.S. Graminha, R.M.B. Cicarelli and M.J. Furlan, J. Nat. Prod., 75, 991 (2012); https://doi.org/10.1021/np300077r
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T. Henkel, R.M. Brunne, H. Muller and F. Reichel, Angew. Chem. Int. Ed., 38, 643 (1999); https://doi.org/10.1002/(SICI)1521-3773(19990301)38:5<643::AID-ANIE643>3.0.CO;2-G
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P. Ruiz-Sanchis, S.A. Savina, F. Albericio and M. Álvarez, Chem. Eur. J., 17, 1388 (2011); https://doi.org/10.1002/chem.201001451
A. Boot, A. Brito, T.V. Wezel, H. Morreau, M. Costa and F. Proença, Anticancer Res., 34, 1673 (2014).
S. Kolle, D.S. Barak, A. Ghosh, V. Jaiswal, R. Kant and S. Batra, ACS Omega, 4, 5617 (2019); https://doi.org/10.1021/acsomega.9b00396
K. Ueshima, H. Akihisa-Umeno, A. Nagayoshi, S. Takakura, M. Matsuo and S. Mutoh, Biol. Pharm. Bull., 28, 247 (2005); https://doi.org/10.1248/bpb.28.247
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P.S. Singh, A.J. Shirgaonkar, B.K. Chawathe and R.M. Kamble, J. Chem. Sci., 132, 150 (2020); https://doi.org/10.1007/s12039-020-01851-9
R. Jiang, Y. Wang and Z. Zhou, Tetrahedron, 72, 6444 (2016); https://doi.org/10.1016/j.tet.2016.08.050
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