Synthesis, characterization, and investigation of the antioxidant activity of some 1,2,4-benzothiadiazine-1,1-dioxides bearing sulfonylthioureas moieties
[en] A series of 1,2,4-benzothiadiazine-1,1-dioxides bearing a sulfonylthiourea moiety were synthesized, characterized, and screened for their antioxidant activity, using six antioxidant analytical assays comparatively to reference compounds, ascorbic acid and quercetin. The results indicated that several compounds demonstrated strong antioxidant activity in DPPH, ABTS, H2O2, and lipid peroxidation assays where some of them were either as active as or more active than reference compounds. However, all compounds were largely less active than references compounds in the reducing power assay. The results indicated that the thiourea moiety probably played a crucial role in the antioxidant activity of the target compounds, as a thiolate ion. The most favorable R1 groups were the hydrogen atom and methyl group, followed by phenyl and benzyl groups, whereas the most favorable R2 group was iPr, followed by the phenyl and methyl groups. The combination of benzothiadiazine ring with sulfonylthiourea moieties led to valuable new antioxidants, which could be used in the treatment or the prevention of certain diseases or in the field of cosmetics, which needs further investigations in the future.
Disciplines :
Pharmacy, pharmacology & toxicology
Author, co-author :
Harrouche, Kamel; Laboratoire de Phytochimie et de Pharmacologie, Département de Chimie, Faculté des Sciences Exactes et Informatique, Université Mohamed Seddik Ben Yahia Jijel, Jijel, Algeria
Lahouel, Asma; Laboratoire de Phytochimie et de Pharmacologie, Département de Chimie, Faculté des Sciences Exactes et Informatique, Université Mohamed Seddik Ben Yahia Jijel, Jijel, Algeria
Belghobsi, Mebrouk; Laboratoire de Phytochimie et de Pharmacologie, Département de Chimie, Faculté des Sciences Exactes et Informatique, Université Mohamed Seddik Ben Yahia Jijel, Jijel, Algeria
Pirotte, Bernard ; Université de Liège - ULiège > Unités de recherche interfacultaires > Centre Interdisciplinaire de Recherche sur le Médicament (CIRM)
Khelili, Smail; Laboratoire de Phytochimie et de Pharmacologie, Département de Chimie, Faculté des Sciences Exactes et Informatique, Université Mohamed Seddik Ben Yahia Jijel, Jijel, Algeria
Language :
English
Title :
Synthesis, characterization, and investigation of the antioxidant activity of some 1,2,4-benzothiadiazine-1,1-dioxides bearing sulfonylthioureas moieties
This work was supported by the Algerian Ministry of Higher Education and Scientific Research and Laboratory of Phytochemistry and Pharmacology (University of Mohamed Seddik Ben Yahia, Jijel). The authors gratefully acknowledge the technical assistance of M. Aibech Riad.This work was supported by the Algerian Ministry of Higher Education and Scientific Research and Laboratory of Phytochem-istry and Pharmacology (University of Mohamed Seddik Ben Yahia, Jijel). The authors gratefully acknowledge the technical assistance of M. Aibech Riad.
Rubin, A. A.; Roth, F. E.; Taylor, R. M.; Rosenkilde, H. J. Pharmacol. Exp. Ther. 1962, 136 (3), 344.
Rubin, A. A.; Taylor, R. M.; Roth, F. E. Ann. N.Y. Acad. Sci. 1968, 150 (2), 457. doi:10.1111/j.1749-6632.1968.tb19070.x.
De Tullio, P.; Dupont, L.; Francotte, P.; Counerotte, S.; Lebrun, P.; Pirotte, B. J. Med. Chem. 2006, 49 (23), 6779. doi:10.1021/jm060534w.
Dabrowski, M.; Ashcroft, F. M.; Ashfield, R.; Lebrun, P.; Pirotte, B.; Egebjerg, J.; Hansen, J. P.; Wahl, P. Diabetes 2002, 51 (6), 1896. doi:10.2337/diabetes.51.6.1896.
Pirotte, B.; Ouedraogo, R.; De Tullio, P.; Khelili, S.; Somers, F.; Boverie, S.; Dupont, L.; Fontaine, J.; Damas, J.; Lebrun, P. J. Med. Chem. 2000, 43 (8), 1456. doi:10.1021/jm991069o.
Lebrun, P.; Arkhammar, P.; Antoine, M. H.; Nguyen, Q. A.; Hansen, J. B.; Pirotte, B. Diabetologia 2000, 43 (6), 723. doi:10.1007/s001250051370.
Novello, F. C.; Bell, S. C.; Abrams, E. L.; Ziegler, C.; Sprague, J. M. J. Org. Chem. 1960, 25 (6), 970. doi:10.1021/jo01076a028.
Ford, R. Curr. Ther. Res. 1961, 3, 320.
Di Bella, M.; Monzani, A.; Andrisano, M. G.; Fabio, U.; Quaglio, G. P. Farmaco. Sci. 1983, 38 (7), 466.
Di Bella, M.; Rinaldi, M.; Coppi, G.; Fabio, U.; Manicardi, G. Farmaco 1974, 29, 915.
Dröge, W. Physiol. Rev. 2002, 82, 47. doi:10.1152/physrev.00018.2001.
Maiese, K.; Morhan, S. D.; Chong, Z. Z. Curr. Neurovasc. Res. 2007, 4, 63. doi:10.2174/156720207779940653.
Aruoma, O. I. Mutat. Res. 2003, 523–524, 9. doi:10.1016/S0027-5107(02)00317-2.
Roussel, A. M.; Ferry, M. Nutr. Clin. Métabol. 2002, 16 (4), 285. doi:10.1016/S0985-0562(02)00173-5.
Valko, M.; Rhodes, C. J.; Moncol, J.; Izakovic, M.; Mazur, M. Chem. Biol. Interact. 2006, 160 (1), 1. doi:10.1016/j.cbi.2005.12.009.
Braugghler, J. M.; Duncan, C. A.; Chase, L. R. J. Biol. Chem. 1986, 261 (22), 10282. PMID:3015924.
Mohammad, W.; Barry, H.; Martin, G.; Christoper, P. M.; Duncan, C. S. H.; Harold, B. Biochem. J. 1987, 243, 867. doi:10.1042/bj2430867.
Kelner, M. J.; Bagnell, R.; Welch, K. J. J. Biol. Chem. 1990, 265 (3), 1306.
Kim, S. G.; Kim, H. J.; Yang, C. H. Chem. Biol. Interact. 1999, 117 (2), 117. doi:10.1016/S0009-2797(98)00101-X.
Venkatesh, P.; Pandey, S. N. Int. J. Chemtech. Res. 2009, 1 (3), 733.
Mahdavi, M.; Shirazi, M. S.; Taherkhani, R.; Saeedi, M.; Alipour, E.; Moghadam, F. H.; Moradi, A.; Nadri, H.; Emami, S.; Firoozpour, L.; Shafiee, A.; Foroumadi, A. Eur. J. Med. Chem. 2014, 82, 308. doi:10.1016/j. ejmech.2014.05.054.
Curtis, W. E.; Muldrow, M. E.; Parker, N. B.; Barkleyt, R.; Linas, S. L.; Repine, J. E. Proc. Natl. Acad. Sci. U.S.A. 1988, 85 (10), 3422. doi:10.1073/pnas. 85.10.3422.
Nathalie, B.; Parker, P.H.D.; Elaine, M.; Berger, B. S.; William, E.; Curtis, B. S.; Maegaret, E.; Muldrow, B. S.; Stuart, L.; Linas, M. D.; John, E.; Repine, M. D. J. Free Radic. Biol. Med. 1985, 1 (5–6), 415. doi:10.1016/0748-5514(85)90155-2.
Dong, Y.; Venkatachalam, T. K.; Narla, R. K.; Trieu, V. N.; Sudbeck, E. A.; Uckun, F. M. Bioorg. Med. Chem. Lett. 2000, 10 (1), 87. doi:10.1016/S0960-894X(99)00581-8.
Fox, R. B. J. Clin. Invest. 1984, 74 (4), 1456. doi:10.1172/JCI111558.
Topliss, J. G.; Konzelman, L. M.; Shapiro, E. P.; Sperber, N.; Roth, F. E. J. Med. Chem. 1964, 7 (3), 269. doi:10.1021/jm00333a005.
Hennig, U. G. G.; Moskalyk, R. E.; Chatten, L. G.; Chan, S. F. J. Pharm. Sci. 1981, 70 (3), 317. doi:10.1002/jps.2600700324.
Hennig, U. G. G.; Chatten, L. G.; Moskalyk, R. E.; Ediss, C. Analyst 1981, 106, 557. doi:10.1039/AN9810600557.
Hennig, U. G. G.; Moskalyk, R. E.; Chatten, L. G.; Rabenstein, D. L. Analyst 1981, 106, 565. doi:10.1039/AN9810600565.
Ross, M. A. J. Chromatogr. B 1994, 657 (1), 197. doi:10.1016/0378-4347(94)80087-1.
Lemanska, K.; Van Der Woude, H.; Szymusiak, H.; Boersma, M. G.; Gliszczynska-Swigło, A.; Rietjens Ivonne, M. C. M.; Tyrakowska, B. Free Radic. Res. 2004, 38 (6), 639. doi:10.1080/10715760410001694062.
Huang, D.; Ou, B.; Prior, R. L. J. Agric. Food Chem. 2005, 53 (6), 1841. doi:10. 1021/jf030723c.
Prior, R. L.; Wu, X.; Schaich, K. J. Agric. Food Chem. 2005, 53 (10), 4290. doi:10.1021/jf0502698.
Jiménez, A.; Selga, A.; Torres, J. L.; Julià, L. Org. Lett. 2004, 6 (24), 4583. doi:10.1021/ol048015f.
Barton, J. P.; Packer, J. E.; Sims, R. J. J. Chem. Soc. Perkin Trans. 2 1973, 1547. doi:10.1039/P29730001547.
Poole, L. B.; Karplus, P. A.; Claiborne, A. Annu. Rev. Pharmacol. Toxicol. 2004, 44, 325. doi:10.1146/annurev.pharmtox.44.101802.121735.
Nagy, P.; Ashby, M. T. J. Am. Chem. Soc. 2007, 129 (45), 14082. doi:10.1021/ja0737218.
Winterbourn, C. C.; Hampton, M. B. Free Radic. Biol. Med. 2008, 45 (5), 549. doi:10.1016/j.freeradbiomed.2008.05.004.
Luo, D.; Smith, S. W.; Anderson, B. D. J. Pharm. Sci. 2005, 94 (2), 304. doi:10. 1002/jps.20253.
