Abstract
Here we synthesized novel 1, 2-diazet and pyrrole derivatives and screened for their anti-inflammatory activity. In vivo anti-inflammatory evaluation results revealed that compounds (XVI), (XIV) and (XI) exhibited the highest anti-inflammatory potencies all over the 4 hours, while compounds (VII), (V) and (XV) exhibited the lowest potencies when compared to indomethacin group. Molecular docking study was used to predict the binding mode towards c-Jun N-Terminal Kinase. In addition, ADME (absorption, distribution, metabolism, and excretion) prediction and QSAR (quantitative structure–activity relationship) study of compounds was carried out respectively.
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REFERENCES
Muszynska, B., Grzywacz-Kisielewskaa, A., and Kała, K., J. Food Chem., 2018, vol. 243, pp. 373–381. https://doi.org/10.1016/j.foodchem.2017.09.149
Waetzig, V. and Herdegen, T., Br. J. Pharmacol., 2005, vol. 26, pp. 455–461. https://doi.org/10.1016/j.tips.2005.07.006
Dhillon, A.S., Hagan, S., Rath, O., and Kolch, W., Oncogene, 2007, vol. 26, pp. 3279–3290. https://doi.org/10.1038/sj.onc.1210421
Kim, E.K. and Choi, E., Biochim. Biophys. Acta, 2010, vol. 1802, pp. 396–405. https://doi.org/10.1016/j.bbadis.2009.12.009
Lee, Y.H., Giraud, J., Davis, R.J., and White, M.F., J. Biol. Chem., 2003, vol. 278, pp. 2896–2902. doi https://doi.org/10.1074/jbc.m208359200
Hirosumi, J., Tuncman, G., Chang, L., Görgün, C.Z., Uysal, K.T., Maeda, K., Karin, M., and Hotamisligil, G.S., Nature, 2002, vol. 420, pp. 333–336. https://doi.org/10.1038/nature01137
Han, Z., Boyle, D.L., Aupperle, K.R., Bennett, B., Manning, A.M., and Firestein, G.S., J. Pharmacol. Exp. Ther., 1999, vol. 291, pp. 124–130.
Bogoyevitch, M.A., BioEssays, 2006, vol. 28, pp. 923–934. https://doi.org/10.1002/bies.20458
Khramtsov, V.V., Utepbergenov, D.I., Woldman, Ya.Yu., Vlassenko, L.P., Markel, A.L., Kiriljuk, I.A., Grigor’ev, I.A., Mazhukin, D.G., Tikhonov, A.Ya., and Volodarsky, L.B., Biochemistry (Moscow), 1996, vol. 61, pp. 1731–1742.
Severina, I.S., Ryaposova, I.K., Volodarsky, L.B., Mozhuchin D.C., Tichonov A.Ya., Schwartz G.Ya., Granik V.G., Grigoryev D.A., and Grigoryev N.B., Biochem. Mol. Biol. Int., 1993, vol. 30, pp. 357–366.
Severina, I.S., Belushkina, N.N., and Grigoryev, N.B., Biochem. Mol. Biol. Int., 1990, vol. 55, pp. 1717–1724.
Kirilyuk, I.A., Utepbergenov, D.I., Mazhukin, D.G., Fechner, K., Mertsch, K., Khramtsov, V.V., Blasig, I.E., and Haseloff, R., J. Med Chem., 1998, vol. 41, pp. 1027–1033.
Wang, G.P., Xian, M., Tang, X., Wu, X., Wen, Z., Cai, T., Janczuk, A., J. Chem. Rev., 2002, vol. 102, pp. 1091–1134.
Yelinova, V.I., Bobko, A.A., Mazhukin, D.G., Markel, A.L., and Khramtsov, V.V., Russ. J. Bioorg. Chem., 2003, vol. 29, pp. 74–81. https://doi.org/10.3109/10715762.2012.746460
Utepbergenov, D.I., Khramtsov, V.V., Vlassenko, L.P., Markel, A.L., Mazhukin, D.G., Tikhonov, A.Ya., and Voldarsky, L.B., Biochem. Biophys. Res. Commun., 1995, vol. 214, pp 1023–1032.
Severina, I.S., Ryaposova, I.K., Volodarsky, L.B., Mozhuchin, D.C., Tichonov, A.Ya., Schwartz, G.Ya., Granik, V.G., Grigoryev, D.A., and Grigoryev, N.B., Biochem. Mol. Biol. Int., 1993, vol. 30, pp. 357–366.
Yates, F.S., Comprehensive Heterocyclic Chemistry, Boulton, A.J., McKillop, A., Eds., Oxford: Pergamon, 1984, vol. 2, pp. 511–524.
Jones, R.A., Pyrroles, New York: Wiley, 1992.
Corvo, M.C. and Pereira, M.A., Tetrahedron Lett., 2002, vol. 43, pp. 455–458.
Daidone, G., Maggio, B., and Schillari, D., Pharmazie, 1990, vol. 45, p. 441.
Almerico, A.M., Diana, P., Barraja, P., Dattolo, G., Mingoia, F., Loi, A.G., Scintu, F., Milia, C., Puddu, I., and La Colla, P., Farmaco, 1998, vol. 53, pp. 33–40. https://doi.org/10.1016/s0014-827x(97)00002-5
Almerico, A.M., Diana, P., Barraja, P., Dattalo, G., Mingoia, F., Putzolu, M., Perra, G., Milia, C., Musiu, C., and Marongiu, M.E., Farmaco, 1997, vol. 52, pp. 667–672.
Kimura, T., Kawara, A., Nakao, A., Ushiyama, S., Shimozato, T., and Suzuki, K., PCt Int. Appl. WO, no. 0001688 A1 20000113, 2002.
Kaiser, D.G. and Glenn, E.M., J. Pharm Sci., 1972, vol. 61, pp. 1908–1911.
Lehuede, J., Fauconneau, B., Barrier, L., Ourakow, M., Piriou, A., and Vierfond, J.M., Eur. J. Med. Chem., 1999, vol. 34, pp. 991–996.
Synthèse de dérivés de la 4-(méthylnitroasamino)-1-(3-pyridyl)-1-butanone (NNK), Org. Synth., 1941, coll. vol. 1, p. 94; 1921, vol. 1, p. 33.
Winter, C.A., Risley, E.A., and Nuss, G.W., Proc. Soc. Exp. Biol. Med.,1962, vol. 111, pp. 544–547. https://doi.org/10.3181/00379727-111-27849
El Kadya, W.M., Salama, A.A.A., Desoukey, S.Y., Hagag, E.G., El-Shenawy, S.M., and El-Shanawany, M.A., Bull. Fac. Pharm. Cairo Univ., 2015, vol. 53, pp. 129–145, https://doi.org/10.1016/j.bfopcu.2015.07.001
Guma, M. and Firestein, G.S., Open Rheumatol. J., 2012, vol. 6, pp. 220–231.
Guma, M., Ronacher, L.M., Firestein, G.S., and Karin, M., Arthritis Rheum., 2011, vol. 63, pp. 1603–1612. https://doi.org/10.1002/art.30271
Guma, M., Kashiwakura, J., Crain, B., Kawakami, Y., Beutler, B., Firestein, G.S., Kawakami, T., Karin, M., Proc. Natl. Acad. Sci. U. S. A., 2010, vol. 107, pp. 22 122–22 127.
Hazem, A.M., Mohammed, K.I., Ahmed, M.M., Amany, B., Ahmed, B.M.M., Kamal, M.A. El-G., Abdou, El-Sh., Mostafa, A.E.l., Mohamed, M.R., Mahmoud, A.E.l., and Ibrahim, H.E., Bioorg. Chem., 2020, vol. 94, pp. 103 422–103 446. https://doi.org/10.1016/j.bioorg.2019.103422
El-Helby, A.A., Sakr, H., Eissa, I.H., Al-Karmalawy, A.A., and El-Adl, K., Arch. Pharm., 2019, vol. 352, pp. 1–19. https://doi.org/10.1002/ardp.201900113
Swiss ADME predictor. http://www.swissadme.ch/index.php.
Daina, A., Michielin, O., and Zoete, V., Sci Rep., 2017, vol. 7, pp. 1–13. https://doi.org/10.1038/srep42717
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El-Serwy, W.S., El-Serwy, W.S., Mohamed, N.A. et al. Synthesis, Biological Evaluation, Molecular Docking, ADME Predictions and QSAR Studies of Novel 1,2-Diazet and Pyrrole Derivatives as Anti-Inflammatory Agents. Russ J Bioorg Chem 47, 183–198 (2021). https://doi.org/10.1134/S1068162021010040
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DOI: https://doi.org/10.1134/S1068162021010040