Copyright (c) 2024 Gyanendra Kumar Sharma Gyanendra Kumar Sharma, Gurvinder Pal Singh Gurvinder, Harsh Bhardwaj, Manish Pal Singh, Himanshu Bhardwaj, Akhileshar Prasad Mishra
This work is licensed under a Creative Commons Attribution 4.0 International License.
Conventional and Microwave Assisted Synthesis of Some Novel 2-(Substituted phenyl)-4,5-diphenyl-1-(thiazol-2-yl)-1H-imidazoles of Biological Interest
Corresponding Author(s) : Gyanendra Kumar Sharma
Asian Journal of Chemistry,
Vol. 36 No. 9 (2024): Vol 36 Issue 9, 2024
Abstract
In present investigation, a straightforward approach to design and synthesize 2-(substituted phenyl)-4,5-diphenyl-1-(thiazol-2-yl)-1H-imidazoles (5a-j) using two methods viz. traditional heating and microwave irradiation and characterized with elemental, FT-IR, 1H NMR, 13C NMR, mass spectrophotometric techniques. The microwave irradiation method offers excellent yields, lesser reaction time and eco-environmental friendly reactions as compared to conventional method. The synthesized compounds were evaluated for their antimicrobial, anticancer and free radical scavenging activity. The findings on the compounds’ in vitro antibacterial activity against Gram-positive and Gram-negative pathogens showed that compounds 5b, 5c and 5g showed potential antibacterial and fungicide efficacy. Using Dalton’s Lymphoma Ascites (DLA) cell lines, the synthesized compounds were further examined for its in vitro anticancer efficacy. Among the synthesized compounds, 5b, 5f, 5g and 5j exhibited excellent anticancer activity with CTC50 value of 31.25 µg/mL, 51.61 µg/mL, 44.21 µg/mL and 31.25 µg/mL, respectively. The synthesized compounds have also shown a marked free radical scavenging capacity in all the concentrations but specifically compounds 5a, 5d, 5e, 5f, 5i and 5j have shown good antioxidant potential with an IC50 value of 25.18 µmol/L, 44.22 µmol/L 35.61 µmol/L, 28.09 µmol/L, 44.47 µmol/L and 39.46 µmol/L, respectively.
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- M.M. Heravi and V. Zadsirjan, RSC Adv., 10, 44247 (2020); https://doi.org/10.1039/D0RA09198G
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References
M.M. Heravi and V. Zadsirjan, RSC Adv., 10, 44247 (2020); https://doi.org/10.1039/D0RA09198G
J. Jampilek, Molecules, 24, 3839 (2019); https://doi.org/10.3390/molecules24213839
A.P. Taylor, R.P. Robinson, Y.M. Fobian, D.C. Blakemore, L.H. Jones and O. Fadey, Org. Biomol. Chem., 14, 6611 (2016); https://doi.org/10.1039/c6ob00936k
A. De, S. Sarkar and A. Majee, Chem. Heterocycl. Comp., 57, 410 (2021); https://doi.org/10.1007/s10593-021-02917-3
B.A. Bhongade, S. Talath, R.A. Gadad and A.K. Gadad, J. Saudi Chem. Soc., 20, 463 (2016); https://doi.org/10.1016/j.jscs.2013.01.010
I. Althagafi, N. El-Metwaly and T.A. Farghaly, Molecules, 24, 1741 (2019); https://doi.org/10.3390/molecules24091741
V. Gupta and V. Kant, Sci. Int. (Lahore), 1, 253 (2013); https://doi.org/10.17311/sciintl.2013.253.260
P. Mohanty, S. Behera, R. Behura, L. Shubhadarshinee, P. Mohapatra, A.K. Barick and B.R. Jali, Biointerface Res. Appl. Chem., 12, 2171 (2022); https://doi.org/10.33263/BRIAC125.60786092
E. Gougoula, D.J. Cole and N.R. Walker, J. Phys. Chem. A, 124, 2649 (2020); https://doi.org/10.1021/acs.jpca.0c00544
G.M. Rosair, A. Kraft and A. Tominey, Acta Cryst., A61, C354 (2005); https://doi.org/10.1107/S0108767305084928
E. Gougoula , C.N. Cummings, Y. Xu, T. Lu, G. Feng and N.R. Walker, J. Chem. Phys., 158, 114307 (2023); https://doi.org/10.1063/5.0143024
A.J.K. Atia, Molecules, 14, 2431 (2009); https://doi.org/10.3390/molecules14072431
A. Siwach and P.K. Verma, BMC Chem., 15, 12 (2021); https://doi.org/10.1186/s13065-020-00730-1
S.S. Alghamdi, R.S. Suliman, K. Almutairi, K. Kahtani and D. Aljatli, Drug Des. Devel. Ther., 15, 3289 (2021); https://doi.org/10.2147/DDDT.S307113
A.-M. Borcea, I. Ionut, O. Crisan and O. Oniga, Molecules, 26, 624 (2021); https://doi.org/10.3390/molecules26030624
K. K. Rajagopal, S. Dhandayutham, M. Nandhagopal, M. Narayanasamy, M.I. Elzagheid, L. Rhyman and P. Ramasami, J. Mol. Struct., 1255, 132374 (2022); https://doi.org/10.1016/j.molstruc.2022.132374
M.F. Arshad, A. Alam, A.A. Alshammari, M.B. Alhazza, I.M. Alzimam, M.A. Alam, G. Mustafa, M.S. Ansari, A.M. Alotaibi, A.A. Alotaibi, S. Kumar, S.M.B. Asdaq, M. Imran, P.K. Deb, K.N. Venugopala and S. Jomah, Molecules, 27, 3994 (2022); https://doi.org/10.3390/molecules27133994
A. Rouf and C. Tanyeli, Eur. J. Med. Chem., 97, 911 (2015); https://doi.org/10.1016/j.ejmech.2014.10.058
J. Guo, Z. Xie, W. Ruan, Q. Tang, D. Qiao and W. Zhu, Eur. J. Med. Chem., 259, 115689 (2023); https://doi.org/10.1016/j.ejmech.2023.115689
K.U. Sadek, R.A. Mekheimer, M. Abd-Elmonem, F.A. Abo-Elsoud, A.M. Hayallah, S.M. Mostafa, M.H. Abdellattif, M.A.S. Abourehab, T.A. Farghaly and A. Elkamhawy, J. Mol. Struct., 1286, 135616 (2023); https://doi.org/10.1016/j.molstruc.2023.135616
N.G. Heatley, Biochem. J., 38, 61 (1944); https://doi.org/10.1042/bj0380061
J.B. Patel, F.R. Cockerill, P.A. Bradford, G.M. Eliopoulos, J.A. Hindler, S.G. Jenkins, J.S. Lewis, B. Limbago, L.A. Miller, D.P. Nicolau, M. Powell, J.M. Swenson, M.M. Traczewski, J.D. Turnidge, M.P. Weinstein and B.L. Zimmer, Performance Standards for Antimicrobial Susceptibility Testing; Twenty-Fifth Informational Supplement (M100-S25), Clinical and Laboratory Standard Institute, Wayne, Pennsylvania, pp. 132-135 (2015).
S. Arikan and J.H. Rex, in eds.: L. Collier, A. Balows, M. Sussman, L. Ajello and R.J. Hay, Resistance to Antifungal Agents, Topley & Wilson’s Microbiology and Microbial Infections, London: Arnold Publishing, edn., 10, pp. 168-181 (2005).
F. Abbate, A. Casini, T. Owa, A. Scozzafava and C.T. Supuran, Bioorg. Med. Chem. Lett., 14, 217 (2004); https://doi.org/10.1016/j.bmcl.2003.09.062
R. Kuttan, P. Bhanumathy, K. Nirmala and M.C. George, Cancer Lett., 29, 197 (1985); https://doi.org/10.1016/0304-3835(85)90159-4
A. Foroumadi, A. Asadipour, M. Mirzaei, J. Karimi and S. Emami, Farmaco, 57, 765 (2002); https://doi.org/10.1016/S0014-827X(02)01277-6
N. Kaushik, N. Kumar and A. Kumar, Indian J. Pharm. Sci., 78, 352 (2016); https://doi.org/10.4172/pharmaceutical-sciences.1000125
R. Malviya, P.K. Sharma and S.K. Dubey, Marmara Pharm. J., 21, 701 (2017); https://doi.org/10.12991/marupj.323594