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Multi-Step Synthesis, Characterization and Bioevaluation of Novel 2-(3-Methoxy-9H-carbazol-9-yl)-N-phenyl Acetamide Analogues
Corresponding Author(s) : Lakshman Shaik
Asian Journal of Chemistry,
Vol. 36 No. 5 (2024): Vol 36 Issue 5, 2024
Abstract
In this work, the multi-step synthesis and characterization of novel 2-(3-methoxy-9H-carbazol-9-yl)-N-phenyl acetamide analogues is presented. These analogues were synthesized from 2-(3-methoxy-9H-carbzol-9-yl)acetyl chloride with substituted aromatic primary amines in the presence of organic base such as triethylamine and methylene dichloride under reflux conditions. The elemental analysis and structures of these novel compounds were elucidated by analyzing spectral data obtained through 1H NMR, 13C NMR and LCMS techniques. The bioevaluation of these newly synthesized compounds has been studied by evaluating their antibacterial and antifungal activities against various kinds of bacterial and fungal strains, respectively.
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- S.A. Patil, S.A. Patil, E.A. Ble-González, S.R. Isbel, S.M. Hampton, and A. Bugarin, Molecules, 27, 6575 (2022); https://doi.org/10.3390/molecules27196575
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- A. van Dijken, J.J.A.M. Bastiaansen, N.M.M. Kiggen, B.M.W. Langeveld, C. Rothe, A. Monkman, I. Bach, P. Stössel and K. Brunner, J. Am. Chem. Soc., 126, 7718 (2004); https://doi.org/10.1021/ja049771j
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- K.R. Justin Thomas, J.T. Lin, Y.-T. Tao and C.-W. Ko, J. Am. Chem. Soc., 123, 9404 (2001); https://doi.org/10.1021/ja010819s
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- P. Rajakumar, K. Sekar, V. Shanmugaiah and N. Mathivanan, Eur. J. Med. Chem., 44, 3040 (2009); https://doi.org/10.1016/j.ejmech.2008.07.031
- A.E. Martin and K.J.R. Prasad, Acta Pharm., 56, 79 (2006).
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- T.K. Chaitanya and R. Nagarajan, Tetrahedron Lett., 48, 2489 (2007); https://doi.org/10.1016/j.tetlet.2007.02.031
- T. Mandala and J. Dash, Org. Biomol. Chem., 19, 9797 (2021); https://doi.org/10.1039/D1OB01471D
- A.H. Banskota, Y. Tezuka, K. Midorikawa, K. Matsushige and S. Kadota, J. Nat. Prod., 63, 1277 (2000); https://doi.org/10.1021/np000143z
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References
S.A. Patil, S.A. Patil, E.A. Ble-González, S.R. Isbel, S.M. Hampton, and A. Bugarin, Molecules, 27, 6575 (2022); https://doi.org/10.3390/molecules27196575
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Y. Tachibana, H. Kikuzaki, N.H. Lajis and N. Nakatani, J. Agric. Food Chem., 51, 6461 (2003); https://doi.org/10.1021/jf034700+
A. van Dijken, J.J.A.M. Bastiaansen, N.M.M. Kiggen, B.M.W. Langeveld, C. Rothe, A. Monkman, I. Bach, P. Stössel and K. Brunner, J. Am. Chem. Soc., 126, 7718 (2004); https://doi.org/10.1021/ja049771j
L. Hu, Z. Li, Y. Li, J. Qu, Y.-H. Ling, J. Jiang and D.W. Boykin, J. Med. Chem., 49, 6273 (2006); https://doi.org/10.1021/jm060546h
V. Dhayalan, J.A. Clement, R. Jagan and A.K. Mohanakrishnan, J. Org. Chem., 2009, 531 (2009); https://doi.org/10.1002/ejoc.200801018
H. Knolker and K.R. Reddy, Chem. Rev., 102, 4303 (2002); https://doi.org/10.1021/cr020059j
R.H. Friend, R.W. Gymer, A.B. Holmes, J.H. Burroughes, R.N. Marks, C. Taliani, D.D.C. Bradley, D.A.D. Santos, J.L. Brédas, M. Lögdlund and W.R. Salaneck, Nature, 397, 121 (1999); https://doi.org/10.1038/16393
K.R. Justin Thomas, J.T. Lin, Y.-T. Tao and C.-W. Ko, J. Am. Chem. Soc., 123, 9404 (2001); https://doi.org/10.1021/ja010819s
P.-L.T. Boudreault, S. Wakim, N. Blouin, M. Simard, C. Tessier, Y. Tao and M. Leclerc, J. Am. Chem. Soc., 129, 9125 (2007); https://doi.org/10.1021/ja071923y
X. Gong, M.R. Robinson, J.C. Ostrowski, D. Moses, G.C. Bazan and A.J. Heeger, Adv. Mater., 14, 581 (2002); https://doi.org/10.1002/1521-4095(20020418)14:8<581::AIDADMA581>3.0.CO;2-B
V.K. Ol’khovik and A.G. Baran, Russ. J. Org. Chem., 46, 1185 (2010); https://doi.org/10.1134/S1070428010080130
S. Wakim, J. Bouchard, M. Simard, N. Drolet, Y. Tao and M. Leclerc, Chem. Mater., 16, 4386 (2004); https://doi.org/10.1021/cm049786g
P. Rajakumar, K. Sekar, V. Shanmugaiah and N. Mathivanan, Eur. J. Med. Chem., 44, 3040 (2009); https://doi.org/10.1016/j.ejmech.2008.07.031
A.E. Martin and K.J.R. Prasad, Acta Pharm., 56, 79 (2006).
M. Bennasar, T. Roca and F. Ferrando, J. Org. Chem., 71, 1746 (2006); https://doi.org/10.1021/jo052428s
M.P. Kumar, G. Mahantesh, P. Amaladass, C. Manikandan and V. Dhayalan, RSC Adv., 13, 32596 (2023); https://doi.org/10.1039/D3RA06396H
I.C.F.R. Ferreira, M.-J.R.P. Queiroz and G. Kirsch, Tetrahedron Lett., 44, 4327 (2003); https://doi.org/10.1016/S0040-4039(03)00952-3
M. Mudadu, A. Singh and R.P. Thummel, J. Org. Chem., 73, 6513 (2008); https://doi.org/10.1021/jo801132w
T.K. Chaitanya and R. Nagarajan, Tetrahedron Lett., 48, 2489 (2007); https://doi.org/10.1016/j.tetlet.2007.02.031
T. Mandala and J. Dash, Org. Biomol. Chem., 19, 9797 (2021); https://doi.org/10.1039/D1OB01471D
A.H. Banskota, Y. Tezuka, K. Midorikawa, K. Matsushige and S. Kadota, J. Nat. Prod., 63, 1277 (2000); https://doi.org/10.1021/np000143z
R. Benassi, in eds.: A.R. Katritzky, C.W. Rees and E.F.V. Scriven, Comprehensive Heterocyclic Chemistry II, Oxford: Pergamon, vol. 2, p.. 259 (1996).
K. Kawasaki, M. Masubuchi, K. Morikami, S. Sogabe, T. Aoyama, H. Ebiike, S. Niizuma, M. Hayase, T. Fujii, K. Sakata, H. Shindoh, Y. Shiratori, Y. Aoki, T. Ohtsuka and N. Shimma, Bioorg. Med. Chem. Lett., 13, 87 (2003); https://doi.org/10.1016/S0960-894X(02)00844-2
S. Alper-Hayta, M. Arisoy, Ö. Temiz-Arpaci, I. Yildiz, E. Aki, S. Özkan and F. Kaynak, Eur. J. Med. Chem., 43, 2568 (2008); https://doi.org/10.1016/j.ejmech.2007.12.019
K.M. Dawood, H. Abdel-Gawad, E.A. Rageb, M. Ellithey and H.A. Mohamed, Bioorg. Med. Chem., 14, 3672 (2006); https://doi.org/10.1016/j.bmc.2006.01.033