Abstract
In this study sulfonamide ligand, 3-methyl-2-(phenylsulfonamido)butanoic acid, has been synthesized and introduced in complexation with metals Cu, Zn, Fe, Ni, and Cd. Diorganotin and triorganotin complexes have been also prepared. The synthesized ligand and its metal complexes have been characterized by FTIR and mass spectrometry, and single crystal X-ray diffraction. The molecules are connected with each other via N–H···O–Hbond forming 2D polymeric network in the crystallographic plane (001) with base vectors [100] and [010]. Intermolecular interactions have been also studied by Hirshfeld surface analysis. Biological activities of the compounds including radical scavenging, total antioxidant potential, enzyme inhibition, antifungal, and antibacterial have been tested. Triorganotin carboxylates demonstrate high activity against four bacterial strains and one fungi (Aspergillus niger). Transition metal carboxylates (Ni and Fe) have demonstrated moderate antioxidant activity. Among Sn carboxylates dialkylstannyl complex has exhibited some response. In case of enzymes inhibition, Ni carboxylates have demonstrated the highest activity against butyrylcholine esterase but moderate activity against acetylcholine esterase.
Similar content being viewed by others
REFERENCES
Mincione, F., Benedini, F., Biondi, S., Cecchi, A., Temperini, C., Formicola, G., Pacileo, I., Scozzafava, A., Masini, E., and Supuran, C.T., Bioorg. Med. Chem. Lett., 2011, vol. 21, no. 11, p. 3216. https://doi.org/10.1016/j.bmcl.2011.04.046
Innocenti, A., Vullo, D., Scozzafava, A., and Supuran, C.T., Bioorg. Med. Chem. Lett., 2008, vol. 18, no. 5, p. 1583. https://doi.org/10.1016/j.bmcl.2008.01.077
Supuran, C.T., Expert Opin. Investig. Drugs, 2003, vol. 12, no. 2, p. 283. https://doi.org/10.1517/13543784.12.2.283
Rathish, I., Javed, K., Ahmad, S., Bano, S., Alam, M., Pillai, K., Singh, S., and Bagchi, V., Bioorg. Med. Chem. Lett., 2009, vol. 19, no. 1, p. 255. https://doi.org/10.1016/j.bmcl.2008.10.105
Bouasla, R., Berredjem, M., Hessainia, S., Chereait, Z., Berredjem, H., and Aouf, N.E., J. Chem. Chem. Eng., 2011, vol. 5, no. 12, p. S1095.
Tfelt-Hansen, P., De, Vries, P., and Saxena, P.R., Drugs, 2000, vol. 60, no. 6, p. 1259. https://doi.org/10.2165/00003495-200060060-00003
Sakurai, H., Kojima, Y., Yoshikawa, Y., Kawabe, K., and Yasui, H., Coord. Chem. Rev., 2002, vol. 226, no. 2, p. 187. https://doi.org/10.1016/S0010-8545(01)00447-7
Budiasih, K.S., Anwar, C., Santosa, S.J., Ismail, H., and Sari, I.P., J. Chem. Pharm. Res., 2013, vol. 5, no. 9, p. 34.
Danish, M., Butt, R.A., Akbar, S., Ashfaq, M., and Smith, G., J. Chem. Crystallogr., 2016, vol. 46, no. 10, p. 421. https://doi.org/10.1007/s10870-016-0671-x
Danish, M., Ghafoor, S., Tahir, M.N., Ahmad, N., and Hamid, M., Acta Cryst. E, 2010, vol. 66, no. 10, p. m1268. https://doi.org/10.1107/S1600536810036512
Danish, M., Tahir, M.N., Ahmad, N., Raza, A.R., and Ibrahim, M., Acta Cryst. E, 2009, vol. 65, no. 5, p. m609. https://doi.org/10.1107/S1600536809015475
Danish, M., Tahir, M.N., Ahmad, N., Ali, S., and Badshah, A., Acta Cryst. E, 2009, vol. 65, no. 12, p. m1614. https://doi.org/10.1107/S1600536809048314
Jabeen, N., Mushtaq, M., Danish, M., Tahir, M.N., and Raza, M.A., Acta Cryst. E, 2015, vol. 71, no. 11, p. o902. https://doi.org/10.1107/S205698901502014918
Geoghegan, K., Kelleher, S., and Evans, P., J. Org. Chem., 2011, vol. 76, no. 7, p. 2187. https://doi.org/10.1021/jo200023r
Mahmood, S., Ali, S., Bhatti, M.H., Mazhar, M., Iqbal, R., Khan, K.M., and Maharvi, G.M., Turk. J. Chem., 2003, vol. 27, no. 5, p. 657.
Danish, M., Ali, S., Badshah, A., Mazhar, M., Masood, H., Malik, A., and Kehr, G., Synth. React. Inorg. M., 1997, vol. 27, no. 6, p. 863. https://doi.org/10.1080/00945719708000234
Badshah, A., Danish, M., Ali, S., Mazhar, M., Mahmood, S., and Chaudhry, M.I., Synth. React. Inorg. M., 1994, vol. 24, no. 7, p. 1155. https://doi.org/10.1080/00945719408001391
Bhatti, M.H., Ali, S., Mazhar, M., Danish, M., and Chaudhary, M.A., Turk. J. Chem., 1999, vol. 23, no. 3, p. 329.
Wolff, S., Grimwood, D., McKinnon, J., Turner, M., Jayatilaka, D., and Spackman, M., Crystal Explorer, University of Western Australia Crawley, Australia, 2012.
Spackman, M.A. and Jayatilaka, D., CrystEngComm., 2009, vol. 11. no. 1, p. 19. https://doi.org/10.1039/B818330A
Ashfaq, M., Tahir, M.N., Kuznetsov, A., Mirza, S.H., Khalid, M., and Ali, A., J. Mol. Struct., 2019, vol. 1180, p. 199. https://doi.org/10.1016/j.molstruc.2019.127041
Tahir, M.N., Ashfaq, M., Alexander, F., Caballero, J., Hernández-Rodríguez, E.W., and Ali, A., J. Mol. Struct., 2019, vol. 1193, p. 185. https://doi.org/10.1016/j.molstruc.2019.05.003
Turner, M.J., McKinnon, J. J., Jayatilaka, D., and Spackman, M.A., CrystEngComm., 2011, vol. 13, no. 6, p. 1804. https://doi.org/10.1039/C0CE00683A
Sheldrick, G.M., Acta Cryst. A, 2008, vol. 64, no. 1, p. 112. https://doi.org/10.1107/S0108767307043930
Sheldrick, G.M., Acta Cryst. A, 2015, vol. 71, vol. 1, p. 3. https://doi.org/10.1107/S2053229614024218
Bruker, S., Bruker AXS. Inc, Madison, Wisconsin, USA, 2013.
Farrugia, L.J., J. Appl. Cryst., 2012, vol. 45, no. 4, p. 849. https://doi.org/10.1107/S0021889812029111
Shahid, S., Raza, M.A., and Ur-Rehman, S., Afr. J. Biotechnol., 2009, vol. 8, no. 19, p. 5116.
Shahwar, D., Raza, M.A., Mughal, M.A.S., Abbasi, M.A., and Ahmad, V.U., J J. Chem. Soc. Pak., 2010, vol. 32, no. 3, p. 357.
Ellman, G.L., Courtney, K.D., Andres, Jr.V., Featherstone, R.M., Biochem. Pharmacol., 1961, vol. 7, no. 2, p. 88. https://doi.org/10.1016/0006-2952(61)90145-9
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
No conflict of interest was declared by the authors.
Rights and permissions
About this article
Cite this article
Danish, M., Jabeen, N., Raza, M.A. et al. 3-Methyl-2-(phenylsulfonamido)butanoic Acid and Its Metal Complexes: Synthesis, Crystal Structure, Antimicrobial, and Enzyme Inhibition Activity. Russ J Gen Chem 91, 294–301 (2021). https://doi.org/10.1134/S1070363221020183
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363221020183