Abstract
A series of N-substituted-6-methyl-4-{4-[5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl]methoxyphenyl}-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides have been synthesized by the condensation of newly synthesized {4-[5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl]methoxy}benzaldehyde with variously substituted acetoacetanilides and urea in the presence of ethanol. The synthesized compounds have been characterized by 1H, 13C NMR, IR spectroscopy, and mass spectrometry. All synthesized compounds were evaluated for in vitro antidiabetic activity using the α-amylase inhibition assay with the 3,5-dinitrosalicylic acid (DNSA) reagent.
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REFERENCES
Kappe, O.C. and Stadler, A., Org. React., 2004, vol. 63, p. 1. https://doi.org/10.1002/0471264180.or063.01
Lalpara, J.N., Hadiyal, S.D., Radia, A.J., Dhalani, J.M., and Dubal, G.G., Polycyclic Aromat. Compd., 2020. https://doi.org/10.1080/10406638.2020.1852586
Mallikarjunaswamy, C., Mallesha, L., Bhadregowda, D.G., and Pinto, O., Arabian J. Chem., 2017, vol. 10, p. S484. https://doi.org/10.1016/j.arabjc.2012.10.008
Wang, S.-B., Deng, X.-Q., Zheng, Y., Yuan, Y.-P., Quan, Z.-S., and Guan, L.-P., Eur. J. Med. Chem., 2012, vol. 56, p. 139. https://doi.org/10.1016/j.ejmech.2012.08.027
Mohamed, M.S., Kamel, R., and Fatahala, S.S., Eur. J. Med. Chem., 2010, vol. 45, p. 2994. https://doi.org/10.1016/j.ejmech.2010.03.028
Abu-Hashem, A.A., Youssef, M.M., and Hussein, H.A.R., J. Chin. Chem. Soc., 2011, vol. 58, p. 41. https://doi.org/10.1002/jccs.201190056
Gaber, A.A., Bayoumi, A.H., El-morsy, A.M., Sherbiny, F.F., Mehany, A.B.M., and Eissa, I.H., Bioorg. Chem., 2018, vol. 80, p. 375. https://doi.org/10.1016/j.bioorg.2018.06.017
Vaidya, A., Jain, S., Jain, P., Jain, P., Tiwari, N., Jain, R., Jain, R., Jain, A.K., and Agrawal, R.K., Mini-Rev. Med. Chem., 2016, vol. 16, p. 825. https://doi.org/10.2174/1389557516666160211120835
Azzam, R.A. and Mohareb, R.M., Chem. Pharm. Bull. (Tokyo), 2015, vol. 63, p. 1055. https://doi.org/10.1248/cpb.c15-00685
El-Abadelah, M.M., Nazer, M.Z., Hussein, A.Q., Awadallah, A.M., Rademacher, P., and Woydt, M., J. Heterocycl. Chem., 1991, vol. 28, p. 1229. https://doi.org/10.1002/jhet.5570280513
Nirmali Wickramaratne, M., Punchihewa, J.C., and Wickramaratne, D.B.M., BMC Complementary Altern. Med., 2016, vol. 16, p. 466. https://doi.org/10.1186/s12906-016-1452-y
Radia, A.J., Lalpara, J.N., Modasiya, I.J., and Dubal, G.G., J. Heterocycl. Chem., 2020. https://doi.org/10.1002/jhet.4200
ACKNOWLEDGMENTS
The authors are grateful to the Department of Chemistry, School of Science, RK University (Rajkot) for providing laboratory facilities and National Facility for Drug Discovery (NFDD) for providing spectral data. The authors express their gratitude to the Department of Microbiology, School of Science, RK University, Rajkot for antidiabetic screening.
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Lalpara, J.N., Vachhani, M.D., Hadiyal, S.D. et al. Synthesis and in vitro Antidiabetic Screening of Novel Dihydropyrimidine Derivatives. Russ J Org Chem 57, 241–246 (2021). https://doi.org/10.1134/S1070428021020159
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DOI: https://doi.org/10.1134/S1070428021020159