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Synthesis, Characterization and Anticancer Activity of (5,1-Substituted)-3-(indoline-4-(thiophene-2-yl-methylene)-2-(p-tolyl)-2-methylene)-4,3-dihydro-1H-imidazole-5-one Derivatives
Corresponding Author(s) : Chandraprakash Bayya
Asian Journal of Chemistry,
Vol. 33 No. 9 (2021): Vol 33 Issue 9, 2021
Abstract
The synthesis of novel imidazole-5-one derivatives (5a-j) was allowed in a conventional method by way of Erlenmeyer and Schiff base mechanism. Compound 2a was synthesized by Erlenmeyer reaction of N-(4-methoxy benzoyl)glycine with 2-thiophene-carboxaldehyde in the presence of acetic anhydride and anhydrous sodium acetate. Finally, it undergoes dehydration reaction with Schiff bases of isatin derivatives (4a-j) to yield final compounds 5a-j. The organic potentials of the newly synthesized imidazole-5-one derivatives have been evaluated for their in vitro anticancer activity by MTT assay method. It against MCF-7 cells as comparison with doxorubicin popular drug. The synthesized compounds 5e, 5f and 5j exhibited excellent anticancer activity against MCF-7 cell lines.
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D.A. Shabalin and J.E. Camp, Org. Biomol. Chem., 18, 3950 (2020); https://doi.org/10.1039/D0OB00350F
H.C. Steel, G.R. Tintinger and R. Anderson, Chem. Biol. Drug Des., 72, 225 (2008); https://doi.org/10.1111/j.1747-0285.2008.00694.x
A. Gursoy and N. Karal, Eur. J. Med. Chem., 38, 633 (2003); https://doi.org/10.1016/S0223-5234(03)00085-0
S.K. Sridhar and A. Ramesh, Biol. Pharm. Bull., 24, 1149 (2001); https://doi.org/10.1248/bpb.24.1149
M. Verma, S.N. Pandeya, K.N. Singh and J.P. Stables, Acta Pharm., 54, 49 (2004).
Y.-L. Fan, X.-H. Jin, Z.-P. Huang, H.-F. Yu, Z.-G. Zeng, T. Gao, L.-S. Feng, Eur. J. Med. Chem., 150, 347 (2018); https://doi.org/10.1016/j.ejmech.2018.03.016
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M. Vineet, S. Arun, K. Pallavi and M. Udayabanu, Asian J. Pharm. Clin. Res., 9, 144 (2016).
V. Glover, J.M. Halket, P.J. Watkins, A. Clow, B.L. Goodwin and M. Sandier, J. Neurochem., 51, 656 (1988); https://doi.org/10.1111/j.1471-4159.1988.tb01089.x
H. Kumar, S.A. Javed, S.A. Khan and M. Amir, Eur. J. Med. Chem., 43, 2688 (2008); https://doi.org/10.1016/j.ejmech.2008.01.039
M. Akhter, A. Husain, B. Azad and M. Ajmal, Eur. J. Med. Chem., 44, 2372 (2009); https://doi.org/10.1016/j.ejmech.2008.09.005
G.A. Idrees, O.M. Aly, G.E.A.A. Abuo-Rahma and M.F. Radwan, Eur. J. Med. Chem., 44, 3973 (2009); https://doi.org/10.1016/j.ejmech.2009.04.026
S. Muthusamy, S.A. Babu and M. Nethaji, Tetrahedron, 59, 8117 (2003); https://doi.org/10.1016/j.tet.2003.08.041
M.M. Blanco, M.D. Maso, M.S. Shmidt and I.A. Perillo, Synthesis, 43, 829 (2007).
R. Shakir, A. Ariffin and M. Abdulla, Molecules, 19, 3436 (2014); https://doi.org/10.3390/molecules19033436
R.J. Ruch, S. Cheng and J.E. Klaunig, Carcinogenesis, 10, 1003 (1989); https://doi.org/10.1093/carcin/10.6.1003
A. Solankee, K. Kapadia, K. Upadhyay and J. Patel, Orient. J. Chem., 17, 315 (2001).
A. Venkanna, B. Siva, B. Poornima, P.R. Rao Vadaparthi, K.R. Prasad, K.A. Reddy, G.B.P. Reddy and K.S. Babu, Fitoterapia, 95, 102 (2014); https://doi.org/10.1016/j.fitote.2014.03.003
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