Structural characterization, photoluminescence, computational studies and bioassay of newly synthesized N-(3-oxo-3-morpholino-1-phenyl-propyl) benzo sulfonamide with multifunctional application
- 133 Downloads
N-(3-oxo-3-morpholino-1-phenyl-propyl) benzo sulfonamide (BMS) (C19H22N2O4S) has been synthesized and characterized by FT-IR, 1H and 13C NMR, and ESI-mass spectrometric methods. The 2-D NMR (COSY, HSQC, DEPT and TOCSY spectra) of BMS is recorded to study the correlation between protons and carbons. The optimized geometry, harmonic vibrational frequencies and infrared intensities are calculated using B3LYP/6-311++(2d,p) basis set on the Gaussian. 13C and 1H NMR chemical shifts are calculated using the gauge independent atomic orbital method with B3LYP/6-311++(2d,p) basis set. The detailed analysis of experimental NMR chemical shifts as well as IR vibrations is supported by quantum chemical calculations using the Gaussian approach. The HOMO and LUMO energy calculation and Mulliken charges were calculated by the DFT approach. The UV–Vis and photoluminescence study confirms the light emitting nature of the molecule. BMS showed better antimicrobial activities against resistant and non-resistant strains. Further, the anticancer activity of the compound is studied against the PC-3 cancer cell line in comparison to mitoxantrone. Comparative docking study of BMS with mitoxantrone and doxorubicin has been carried out on the p53 tumor suppressor-DNA complex. Effective binding is observed at ARG-248, which is an experimentally proved mutated site of the p53 protein.
KeywordsSulfonamide BMS PL p53 Antimicrobial activity Anticancer activity
The authors thank University Grants Commission-Rajiv Gandhi National Fellowship for ST students, New Delhi, India (F1-17.1/2014-15/RGNF-2014-15-ST-HIM-84222/(SAIII/Website)) for giving the financial assistance. We would like to thank Director, NIT Hamirpur for providing infrastructure facilities. The facilities provided by the NMR Centre and computational lab, IIT Roorkee, Uttarakhand are highly acknowledged. Authors are thankful to Prof. Ritu Barthwal Department of Biotechnology IIT Roorkee for her NMR and computational discussion. The paper is the original research of the authors, and the work is also being filed as a patent with Indian Patent Application No. 201711026145.
Compliance with ethical standards
Conflict of interests
There is no conflict to declare.
- 5.Y. Ozawa, N.H. Sugi, T. Watanabe, T. Nagasu, N. Koyanagi, K. Kitoh, Proc. 9th NCI-EORTC Ann. Oncol. Suppl. 7, 140 (1996)Google Scholar
- 8.R. Mohammadpur, S. Safarian, S. Farahnak, S. Hasheminasl, N. Sheibani, J. Cell. Mol. Biol. 10, 41 (2012)Google Scholar
- 10.M. Mirian, A. Zarghi, S. Sadeghi, P. Tabaraki, M. Tavallaee, O. Dadrass, A.H. Sadeghi, Iran. J. Pharm. Res. 10, 741 (2011)Google Scholar
- 11.A.M. Badawi, S.H.E. Ali, D.A. Ismail, Aust. J. Basic Appl. Sci. 2, 301 (2008)Google Scholar
- 12.K. Tsukahara, T. Watanabe, N.H. Sugi, K. Yoshimatsu, H. Okayama, T. Nagasu, Am. Soc. Pharma. Exp. Ther. Mol. Pharmacol. 60, 1254 (2001)Google Scholar
- 13.U. Kalidhar, R. Kumar, A. Kaur, Res. J. Pharma. Bio. Chem. Sci. 3, 1072 (2012)Google Scholar
- 15.A. Yokoi, J. Kuromitsu, T. Kawai, Mol. Cancer Ther. 1, 275 (2002)Google Scholar
- 16.D. Rai, R.K. Singh, Indian J. Chem. 50, 931 (2011)Google Scholar
- 17.F.A. Davis, Am. Chem. Soc. 71(24), 8993 (2006)Google Scholar
- 19.T. Eichhorn, C. Hiller, K. Hirschfelder, M. Frank, T. Efferth, Cancer Genom. Proteom. 10, 35 (2013)Google Scholar
- 20.R.K. Mahajan, V.P. Patial, P. Sharma, Indian J. Chem. 41B, 2635 (2002)Google Scholar
- 24.A.L. Barry, M.B. Coyle, C. Thornberry, E.H. Gerlach, R.W. Hawkinson, J. Clin. Microbiol. 10, 885 (1979)Google Scholar
- 25.V.K. Rastogi, M.A. Palafox, V. Kumar, H.P. Mital, R. Sharma, Sci. Access 2, 150 (2004)Google Scholar
- 26.M. Silverstein, G. C. Basseler, C. Morill (Wiley, New York, 1981)Google Scholar