Abstract
A combined experimental and theoretical investigation has been reported on N-(alanine)-p-styrene sulfonamide (abbreviated as ASS). The new title compound have been synthesized for the first time from the reaction of p-styrene sulfonyl chloride and (S)-alanine in the mild condition. The ASS was confirmed using FT-IR and 1H-NMR spectra. IR and 1H NMR spectrum, MEP and HOMO–LUMO analysis of the ASS have been investigated using DFT method. 1H-NMR chemical shift values have been compared with experimental data. The potential energy distribution (PED) of the normal modes among the respective internal coordinates have been calculated for ASS using the BALGA program and compared with theoretical and experimental values. The ASS is investigated against Staphylococcus aureus and Escherichia coli. Molecular Docking study has also been reported.
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REFERENCES
N. N. Al-Mohammed et al., Molecules 18, 11978 (2013).
S. S. Stokes et al., Bioorg. Med. Chem. Lett. 22, 7019 (2012).
P. Zoumpoulakis et al., Bioorg. Med. Chem. Lett. 20, 1569 (2012).
S. Br et al., J. Med. Chem. 23, 9855 (2014).
C. T. Supuran et al., Mini. Rev. Med. Chem. 4, 189 (2004).
M. F. Mohamed et al., Appl. Biochem. Biotech. 168, 1153 (2012).
X. Jin et al., Eur. J. Med. Chem. 56, 203 (2012).
F. M. Awadallah et al., Eur. J. Med. Chem. 96, 425 (2015).
M. M. Ghorab, M. Ceruso, M. Alsaid, Y. M. Nissan, R. K. Arafa, and C. T. Supuran, Eur. J. Med. Chem. 87, 186 (2014).
A. Kamal et al., Bioorg. Med. Chem. Lett. 20, 4865 (2010).
K. V. Sashidhara et al., Bioorg. Med. Chem. Lett. 20, 7205 (2010).
M. Mirian et al., Iran. J. Pharm. Res. 10, 741 (2011).
R. Levine et al., Diabetes 6, 263 (1957).
S. Riaz et al., Bioorg. Chem. 63, 64 (2015).
M. Adib et al., Tetrahedron Lett. 51, 5646 (2010).
A. Mascarello et al., Eur. J. Med. Chem. 86, 491 (2014).
A. Alsughayer et al., J. Biomater. Nanobiotechnol. 2, 144 (2011).
N. D. Reddy et al., Chem.-Biol. Interact. 253, 112 (2016).
R. Pingaew et al., Eur. J. Med. Chem. 103, 446 (2015).
A. Yari, E. Mehdipour, and M. Karami, J. Fluoresc. 24, 1415 (2014).
E. Mehdipour et al., J. Phosphorus, Sulfur, Silicon Rel. Elem. 190, 1588 (2015).
N. Yada et al., J. Polym. Sci., Part A 3, 2229 (1968).
M. J. Frisch, H. B. S. G. W. Trucks, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, et al., Gaussian 09, Revision C.01 (Gaussian Inc., Wallingford, CT, 2010).
A. D. Becke, J. Chem. Phys. 98, 5648 (1993).
H. Tavakol and F. Keshavarzipour, Struct. Chem. 26, 1049 (2015).
O. Trott et al., J. Comput. Chem. 31, 455 (2010).
M. J. Nowak and L. Lapinski, Vibrat. Spectrosc. 49, 43 (2009).
A. Lagunin, A. Stepanchikova, D. Filimonov, and V. Poroikov, Bioinformatics 16, 747 (2000).
A. Vina, J. Comput. Chem. 31, 455 (2010).
G. M. Morris, D. S. Goodsell, R. S. Halliday, R. Huey, W. E. Hart, and R. K. Belew, J. Comput. Chem. 19, 1639 (1998).
R. Huey et al., J. Comput. Chem. 28, 1145 (2007).
A. C. Wallace et al., J. Med. Chem., 127 (1996).
NCCLS, Methods for dilution antimicrobial susceptibility test for bacteria that grow aerobically, M7-A4 (1997).
R. G. Parr et al., J. Am. Chem. Soc. 121, 1922 (1999).
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Parvaneh Shafieyoon, Mehdipour, E. & Michalski, J. Synthesis, Characterization, and Biological Investigation of Alanine-Based Sulfonamide Derivative: FT-IR, 1H NMR Spectra: MEP, HOMO–LUMO Analysis, and Molecular Docking. Russ. J. Phys. Chem. 93, 1285–1296 (2019). https://doi.org/10.1134/S0036024419070215
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DOI: https://doi.org/10.1134/S0036024419070215