Copyright (c) 2025 laxmi madhuri rupakula, prof
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Moleculoar Docking and Antidiabetic Studies of Some 3,5-Disubstituted Thiazolidinediones
Corresponding Author(s) : G. Rajitha
Asian Journal of Chemistry,
Vol. 37 No. 3 (2025): Vol 37 Issue 3, 2025
Abstract
Novel thiazolidinedione derivatives incorporating a naphthylidene moiety were synthesized through Knoevenagel condensation reaction. The structural confirmation of the synthesized compounds was achieved through IR, mass and NMR spectral analyses. These compounds were assessed for their antidiabetic effects in alloxan-induced diabetic rats and in vivo antidiabetic analysis indicated that the compounds IIg and IIh exhibited significant antidiabetic activity. Molecular docking studies on the PPARγ receptor were performed to gain insights into the binding interactions of these designed compounds. The molecular docking studies identified compounds IIg and IIh as particularly effective against the PPARγ receptor. ADME properties were predicted using the QikProp module from the Schrödinger suite and all compounds complied with Lipinski’s rule of five, suggesting good oral absorption. Thus, compounds IIg and IIh may further be considered as potential antidiabetic agents.
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- M.A.B. Khan, M.J. Hashim, J.K. King, R.D. Govender, H. Mustafa and J. Al Kaabi, J. Epidemiol. Glob. Health, 10, 107 (2019); https://doi.org/10.2991/jegh.k.191028.001
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- Sucheta, S. Tahlan and P.K. Verma, Chem. Cent. J., 12, 129 (2018); https://doi.org/10.1186/s13065-018-0496-0
References
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R. Pradeepa and V. Mohan, Indian J. Ophthalmol., 69, 2932 (2021); https://doi.org/10.4103/ijo.IJO_1627_21
A.T. Kharroubi and H.M. Darwish, World J. Diabetes, 6, 850 (2015); https://doi.org/10.4239/wjd.v6.i6.850
P.K. Prabhakar, Asian J. Pharm. Clin. Res., 9, 32 (2016).
H.E. Lebovitz, Curr. Diab. Rep., 19, 151 (2019); https://doi.org/10.1007/s11892-019-1270-y
D. Swapna, B. Sivagami, K. Manasa, G. Rajitha and V. Alagarsamy, Int. Res. J. Pharm., 7, 5 (2016).
P.L. Madhuri and G. Rajitha, Int. J. Life Sci. Pharm. Res., 13, 25 (2023).
S. Tyagi, P. Gupta, A.S. Saini, C. Kaushal and S. Sharma, J. Adv. Pharm. Technol. Res., 2, 236 (2011); https://doi.org/10.4103/2231-4040.90879
J.R. Greenfield and D.J. Chisholm, Exp. Clin. Pharmacol., 27, 67 (2004).
S. Makar, T. Saha and S.K. Singh, Eur. J. Med. Chem., 161, 252 (2019); https://doi.org/10.1016/j.ejmech.2018.10.018
M.-H. Huang, S.-N. Wu, J.-P. Wang, C.-H. Lin, S.-I. Lu, L.-F. Liao and A.-Y. Shen, Drug Dev. Res., 60, 261 (2003); https://doi.org/10.1002/ddr.10327
M. Badawneh, P.L. Ferrarini, V. Calderone, C. Manera, E. Martinotti, C. Mori, G. Saccomanni and L. Testai, Eur. J. Med. Chem., 36, 925 (2001); https://doi.org/10.1016/S0223-5234(01)01277-6
G.A. Idrees, O.M. Aly, G.E.-D.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
G.P. Rajani and P. Ashok, Indian J. Pharmacol., 41, 227 (2009); https://doi.org/10.4103/0253-7613.58513
R. Kalariya, V. Pandya, N. Gohil, G. Bhattacharjee, V. Singh, P.D. Rajani, R. Bhosale and J.S. Yadav, Eur. J. Med. Chem. Rep., 6, 100078 (2022).
P. Mahesha and N.S. Shetty, ChemistrySelect, 9, e202400522 (2024); https://doi.org/10.1002/slct.202400522
G. Bruno, L. Costantino, C. Curinga, R. Maccari, F. Monforte, F. Nicolo, R. Ottana and M.G. Vigorita, Bioorg. Med. Chem., 10, 1077 (2002); https://doi.org/10.1016/S0968-0896(01)00366-2
Y. Momose, T. Maekawa, T. Yamano, M. Kawada, H. Odaka, H. Ikeda and T. Sohda, J. Med. Chem., 45, 1518 (2002); https://doi.org/10.1021/jm010490l
T. Sohda, Y. Momose, K. Meguro, Y. Kawamatsu, Y. Sugiyama and H. Ikeda, Arzneimittelforschung, 40, 37 (1990).
S. Shukla, P. Kumar, N. Das, N.S.H.N. Moorthy, S.K. Shrivastava, P. Trivedi and R.S. Srivastava, Med. Chem., 8, 834 (2012); https://doi.org/10.2174/157340612802084388
P.G. Anna and Nikalje, Eur. J. Exp. Biol., 2, 343 (2012).
A. Najmi, M.S. Alam, N. Thangavel, M.M.E. Taha, A.M. Meraya, M. Albratty, H.A. Alhazmi, W. Ahsan, A. Haque and F. Azam, Sci. Rep., 13, 19869 (2023); https://doi.org/10.1038/s41598-023-47157-x
L.F.C. da Costa Leite, R.H. Veras Mourão, M.C.A. de Lima, S.L. Galdino, M.Z. Hernandes, F. de Assis Rocha Neves, S. Vidal, J. Barbe and I. da Rocha Pitta, Eur. J. Med. Chem., 42, 1263 (2007); https://doi.org/10.1016/j.ejmech.2007.02.015
G. Rajitha, K.V.S.R.G. Prasad, A. Umamaheswari, D. Pradhan and K. Bharathi, Med. Chem. Res., 23, 5204 (2014); https://doi.org/10.1007/s00044-014-1091-0
P. Varakumar, K. Rajagopal, F. Islam, K. Raman, G. Byran, S. Prema, M. Gurunathan, T. Murugesan, P. Chitrapu, R. Barua, S.F. Ahmad, S.M. Attia and T.B. Emran, J. Biol. Regul. Homeost. Agents, 37, 6511 (2023); https://doi.org/10.23812/j.biol.regul.homeost.agents.20233712.616
K.B. Juybari, A. Hosseinzadeh and A.M. Sharifi, J. Recept. Signal Transduc., 39, 1 (2019); https://doi.org/10.1080/10799893.2018.1557206
F. Ntie-Kang, J.A. Mbah, L.L. Lifongo, L.C. Owono-Owono, E. Megnassan, L. Meva’a Mbaze, P.N. Judson, W. Sippl and S.M.N. Efange, Org. Med. Chem. Lett., 3, 10 (2013); https://doi.org/10.1186/2191-2858-3-10
M.J. Naim, M.J. Alam, F. Nawaz, V.G.M. Naidu, S. Aaghaz, M. Sahu, N. Siddiqui and O. Alam, Bioorg. Chem., 73, 24 (2017); https://doi.org/10.1016/j.bioorg.2017.05.007
S. Hosen, R. Dash, M. Khatun, R. Akter, M. Bhuiyan, M. Karim, N. Mouri, F. Ahamed, K. Islam and S. Afrin, J. Appl. Pharm. Sci., 7, 120 (2017); https://doi.org/10.7324/JAPS.2017.70116
Sucheta, S. Tahlan and P.K. Verma, Chem. Cent. J., 12, 129 (2018); https://doi.org/10.1186/s13065-018-0496-0
