Copyright (c) 2024 GURVINDER PAL SINGH GURVINDER, K. Sarvanan, Gyanendra Kumar Sharma
This work is licensed under a Creative Commons Attribution 4.0 International License.
Microwave Assisted Synthesis of Some New 2-(4-Substituted phenyl)-3-(1H-indol-4-yl)imidazo[4,5-b]indoles of Biological Interest
Corresponding Author(s) : Gurvinder Pal Singh
Asian Journal of Chemistry,
Vol. 36 No. 12 (2024): Vol 36 Issue 12, 2024
Abstract
A novel series of imidazo-indole hybrid compounds, focusing on their antibacterial, anticancer and anthelmintic efficacy was designed and synthesized. All the compounds, 2-(4-substituted phenyl)-3-(1H-indol-4-yl)imidazo[4,5-b]indoles (1b-10b) were characterized by FT-IR, 1H NMR, 13C NMR, mass spectrometry and elemental analysis. Conventional heating and microwave irradiation were both used in the synthesis process, although the microwave irradiation provided better efficiency, faster response times and safer environmental conditions. The synthesized compounds were screened for their antibacterial activity against Gram-positive and Gram-negative pathogens, revealing promising efficacy in several compounds, particularly 2b, 5b and 6b. Furthermore, their anticancer potential was evaluated using the EAC cell line approach, with compounds 1b, 2b, 4b and 5b exhibiting excellent activity, with CTC50 values of 31.25 µg/mL, 51.61 µg/mL, 44.21 µg/mL and 31.25 µg/mL, respectively. Additionally, most compounds also displayed moderate to good anthelmintic activity, highlighting their potential as therapeutic agents.
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F. Bellina, S. Cauteruccio and R. Rossi, Tetrahedron, 63, 4571 (2007); https://doi.org/10.1016/j.tet.2007.02.075
D.G. Daraji, N.P. Prajapati and H.D. Patel, J. Heterocycl. Chem., 56, 2299 (2019); https://doi.org/10.1002/jhet.3641
S.M. Umer, M. Solangi, K.M. Khan and R.S.Z. Saleem, Molecules, 27, 7586 (2022); https://doi.org/10.3390/molecules27217586
N.K. Kaushik, N. Kaushik, P. Attri, N. Kumar, C.H. Kim, A.K. Verma and E.H. Choi, Molecules, 18, 6620 (2013); https://doi.org/10.3390/molecules18066620
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M. Chauhan, A. Saxena and B. Saha, Eur. J. Med. Chem., 218, 113400 (2021); https://doi.org/10.1016/j.ejmech.2021.113400
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T. Sumiya, M. Ishigaki and K. Oh, Int. J. Chem. Eng. Appl., 8, 233 (2017); https://doi.org/10.18178/ijcea.2017.8.3.662
B. Jasiewicz, K. Babijczuk, B. Warzajtis, U. Rychlewska, J. Starzyk, G. Cofta and L. Mrówczynska, Molecules, 28, 708 (2023); https://doi.org/10.3390/molecules28020708
K. Benkli, S. Demirayak, N. Gundogdu-Karaburun, N. Kiraz, G. Iscan and U. Ucucu, Indian J. Chem., 43B, 174 (2004).
N.J.P. Subhashini, E. Praveen Kumar, N. Gurrapu and V. Yerragunta, J. Mol. Struct., 1180, 618 (2019); https://doi.org/10.1016/j.molstruc.2018.11.029
S. Choudhary, P.K. Singh, H. Verma, H. Singh and O. Silakari, Eur. J. Med. Chem., 151, 62 (2018); https://doi.org/10.1016/j.ejmech.2018.03.057
H.M.S. Kumar, L. Herrmann and S.B. Tsogoeva, Bioorg. Med. Chem. Lett., 30, 127514 (2020); https://doi.org/10.1016/j.bmcl.2020.127514
B. Meunier, Acc. Chem. Res., 41, 69 (2008); https://doi.org/10.1021/ar7000843
A.M. Altaher, M.A. Adris, S.H. Aliwaini, A.M. Awadallah and R. Morjan, Asian Pac. J. Cancer Prev., 23, 2943 (2022); https://doi.org/10.31557/APJCP.2022.23.9.2943
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K.N. Venugopala, M. Habeebuddin, B.E. Aldhubiab and A.H. Asif, Molecules, 26, 5235 (2021); https://doi.org/10.3390/molecules26175235
M.S. Akhtar, Z. Iqbal, M.N. Khan and M. Lateef, Small Rumin. Res., 38, 99 (2000); https://doi.org/10.1016/S0921-4488(00)00163-2
S. Chaudhary, H.C. Verma, M.K. Gupta, R.K. Gupta, A. Kumar and A.N. El-Shorbagi, Asian J. Pharm. Clin. Res., 12, 310 (2019); https://doi.org/10.22159/ajpcr.2019.v12i1.30094