Synthesis and Antioxidant Activity Studies of Some 5-Chloro-3-substituted 2(3H)-Benzoxazolone Derivatives

Z. Soyer; S. Uysal; F.A. Kose; A. Pabuccuoglu

doi:10.14233/ajchem.2014.17086

Issue

Vol. 26 No. 19 (2014): Vol 26 Issue 19

Issue Published : September 16, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Antioxidant Activity Studies of Some 5-Chloro-3-substituted 2(3H)-Benzoxazolone Derivatives

https://doi.org/10.14233/ajchem.2014.17086

Z. Soyer

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ege University, 35100 Bornova, Izmir, Turkey

S. Uysal

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ege University, 35100 Bornova, Izmir, Turkey

F.A. Kose

Department of Biochemistry, Faculty of Pharmacy, Ege University, 35100 Bornova, Izmir, Turkey

A. Pabuccuoglu

Department of Biochemistry, Faculty of Pharmacy, Ege University, 35100 Bornova, Izmir, Turkey

Corresponding Author(s) : Z. Soyer

zeynep.soyer@ege.edu.tr

Asian Journal of Chemistry, Vol. 26 No. 19 (2014): Vol 26 Issue 19
Article Published : September 19, 2014

Abstract

2(3H)-Benzoxazolone derivatives are versatile heterocyclic compounds since they display a wide range of pharmacological properties. On the other hand, anilide pharmacophore has been known in medicinal chemistry as an useful template in various pharmacological states. In this study, we synthesized eleven 5-chloro-2(3H)-benzoxazolone-3-alkananilide derivatives and evaluated their antioxidant activities. The structural confirmation of the title compounds was achieved by spectral and analytical data. The antioxidant capacity of the synthesized compounds was determined by the 2,2-diphenyl-2-picrylhydrazyl hydrate (DPPH) and 2,2-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radicals scavenging assays. The results indicated that the majority of the compounds were effective in both tests. The most active compound in the series was compound 6, bearing 4-methoxy substituent on the N-phenyl ring of the propionanilide skeleton.

Keywords

2(3H)-Benzoxazolone Anilide Antioxidant activity DPPH 2,2-Azinobis(3-ethylbenzothiazoline-6-sulfonic acid)

Soyer, Z., Uysal, S., Kose, F., & Pabuccuoglu, A. (2014). Synthesis and Antioxidant Activity Studies of Some 5-Chloro-3-substituted 2(3H)-Benzoxazolone Derivatives. Asian Journal of Chemistry, 26(19), 6642–6646. https://doi.org/10.14233/ajchem.2014.17086

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References

M. Valko, C.J. Rhodes, J. Moncol, M. Izakovic and M. Mazur, Chem. Biol. Interact., 160, 1 (2006); doi:10.1016/j.cbi.2005.12.009.
W. Droge, Physiol. Rev., 82, 47 (2002).
D.V. Ratnam, D.D. Ankola, V. Bhardwaj, D.K. Sahana and M.N.V.R. Kumar, J. Control. Release, 113, 189 (2006); doi:10.1016/j.jconrel.2006.04.015.
R. Hardeland, Endocrine, 27(2), 119, (2005).
E.R.V. Rios, E.T. Venancio, N.F.M. Rocha, D.J. Woods, S. Vasconcelos, D. Macedo, F.C.F. Sousa and M.M.F. Fonteles, Int. J. Neurosci., 120, 583 (2010); doi:10.3109/00207454.2010.492921.
R. Hardeland, S.R. Pandi-Perumal and D.P. Cardinali, Int. J. Biochem. Cell Biol., 38, 313 (2006); doi:10.1016/j.biocel.2005.08.020.
L.A. Thompson and A.J. Ellman, Chem. Rev., 96, 555 (1996); doi:10.1021/cr9402081.
I. Chiarotto, M. Feroci, M. Orsini, G. Sotgiu and A. Inesi, Tetrahedron, 65, 3704 (2009); doi:10.1016/j.tet.2009.02.057.
B.-L. Deng, M.D. Cullen, Z. Zhou, T.L. Hartman, R.W. Buckheit Jr., C. Pannecouque, E.D. Clercq, P.E. Fanwick and M. Cushman, Bioorg. Med. Chem., 14, 2366 (2006); doi:10.1016/j.bmc.2005.11.014.
Y.Ivanova, G.Momekov, O.Petrov, M.Karaivanova and V.Kalcheva, Eur. J. Med. Chem., 42, 1382 (2007); doi:10.1016/j.ejmech.2007.02.019.
S. Unlu, T. Onkol, Y. Dundar, B. Okcelik, E. Kupeli, E. Yesilada, N. Noyanalpan and M.F. Sahin, Arch. Pharm., 336, 353 (2003); doi:10.1002/ardp.200300746.
M. Koksal, N. Gokhan, E. Kupeli, E. Yesilada and H. Erdogan, Arch. Pharm., 338, 117 (2005); doi:10.1002/ardp.200400937.
T. Onkol, S. Ito, E. Yildirim, K. Erol and M.F. Sahin, Arch. Pharm., 334, 17 (2001); doi:10.1002/1521-4184(200101)334:1<17::AID-ARDP17>3.0.CO;2-Z.
M. Koksal, N. Gokhan, H. Erdogan, M. Ozalp and M. Ekizoglu, Il Farmaco, 57, 535 (2002); doi:10.1016/S0014-827X(02)01244-2.
H. Ucar, K. Van derpoorten, S. Cacciaguerra, S. Spampinato, J.P. Stables, P. Depovere, M. Isa, B. Masereel, J. Delarge and J.H. Poupaert, J. Med. Chem., 41, 1138 (1998); doi:10.1021/jm970682+.
M. Courtois, Z. Mincheva, F. Andreu, M. Rideau and M.C. Viaud-Massuard, J. Enzyme Inhib. Med. Chem., 19, 559 (2004); doi:10.1080/14756360400004615.
Z. Soyer, M. Bas, A. Pabuçcuoglu and V. Pabuçcuoglu, Arch. Pharm., 338, 405 (2005); doi:10.1002/ardp.200500106.
T.B. Ng, F. Liu and L. Zhao, J. Neural Transm., 107, 1243 (2000); doi:10.1007/s007020070014.
H. Orhan, D.S. Dogruer, B. Çakir, G. Sahin and M.F. Sahin, Exp. Toxicol. Pathol.,51, 397 (1999); doi:10.1016/S0940-2993(99)80028-1.
R.J. Nachman, J. Heterocycl. Chem., 19, 1545 (1982); doi:10.1002/jhet.5570190660.
D.E.F. Gangi, J. Am. Pharm. Assoc., XLIV, 135 (1955).
K.J. Wang, Y.J. Zhang and C.R. Yang, Chem. Biodivers., 3, 1317 (2006); doi:10.1002/cbdv.200690135.
R. Re, N. Pellegrini, A. Proteggente, A. Pannala, M. Yang and C. Rice-Evans, Free Radic. Biol. Med., 26, 1231 (1999); doi:10.1016/S0891-5849(98)00315-3.
U. Calis, H.G. Pilli and F. Ozkanli, Hacettepe Univ. J. Fac. Pharmacy, 12, 71 (1992).
M. Hesse, H. Meier and B. Zeeh, Spectroscopic Methods in Organic Chemistry, Georg Thieme Verlag: Stutgart, New York (1997).
K. Nakanishi and P.H. Solomon, Infrared Absorption Spectroscopy, Holden-Day Inc. San Francisco, edn 2 (1977).

References

M. Valko, C.J. Rhodes, J. Moncol, M. Izakovic and M. Mazur, Chem. Biol. Interact., 160, 1 (2006); doi:10.1016/j.cbi.2005.12.009.

W. Droge, Physiol. Rev., 82, 47 (2002).

D.V. Ratnam, D.D. Ankola, V. Bhardwaj, D.K. Sahana and M.N.V.R. Kumar, J. Control. Release, 113, 189 (2006); doi:10.1016/j.jconrel.2006.04.015.

R. Hardeland, Endocrine, 27(2), 119, (2005).

E.R.V. Rios, E.T. Venancio, N.F.M. Rocha, D.J. Woods, S. Vasconcelos, D. Macedo, F.C.F. Sousa and M.M.F. Fonteles, Int. J. Neurosci., 120, 583 (2010); doi:10.3109/00207454.2010.492921.

R. Hardeland, S.R. Pandi-Perumal and D.P. Cardinali, Int. J. Biochem. Cell Biol., 38, 313 (2006); doi:10.1016/j.biocel.2005.08.020.

L.A. Thompson and A.J. Ellman, Chem. Rev., 96, 555 (1996); doi:10.1021/cr9402081.

I. Chiarotto, M. Feroci, M. Orsini, G. Sotgiu and A. Inesi, Tetrahedron, 65, 3704 (2009); doi:10.1016/j.tet.2009.02.057.

B.-L. Deng, M.D. Cullen, Z. Zhou, T.L. Hartman, R.W. Buckheit Jr., C. Pannecouque, E.D. Clercq, P.E. Fanwick and M. Cushman, Bioorg. Med. Chem., 14, 2366 (2006); doi:10.1016/j.bmc.2005.11.014.

Y.Ivanova, G.Momekov, O.Petrov, M.Karaivanova and V.Kalcheva, Eur. J. Med. Chem., 42, 1382 (2007); doi:10.1016/j.ejmech.2007.02.019.

S. Unlu, T. Onkol, Y. Dundar, B. Okcelik, E. Kupeli, E. Yesilada, N. Noyanalpan and M.F. Sahin, Arch. Pharm., 336, 353 (2003); doi:10.1002/ardp.200300746.

M. Koksal, N. Gokhan, E. Kupeli, E. Yesilada and H. Erdogan, Arch. Pharm., 338, 117 (2005); doi:10.1002/ardp.200400937.

T. Onkol, S. Ito, E. Yildirim, K. Erol and M.F. Sahin, Arch. Pharm., 334, 17 (2001); doi:10.1002/1521-4184(200101)334:1<17::AID-ARDP17>3.0.CO;2-Z.

M. Koksal, N. Gokhan, H. Erdogan, M. Ozalp and M. Ekizoglu, Il Farmaco, 57, 535 (2002); doi:10.1016/S0014-827X(02)01244-2.

H. Ucar, K. Van derpoorten, S. Cacciaguerra, S. Spampinato, J.P. Stables, P. Depovere, M. Isa, B. Masereel, J. Delarge and J.H. Poupaert, J. Med. Chem., 41, 1138 (1998); doi:10.1021/jm970682+.

M. Courtois, Z. Mincheva, F. Andreu, M. Rideau and M.C. Viaud-Massuard, J. Enzyme Inhib. Med. Chem., 19, 559 (2004); doi:10.1080/14756360400004615.

Z. Soyer, M. Bas, A. Pabuçcuoglu and V. Pabuçcuoglu, Arch. Pharm., 338, 405 (2005); doi:10.1002/ardp.200500106.

T.B. Ng, F. Liu and L. Zhao, J. Neural Transm., 107, 1243 (2000); doi:10.1007/s007020070014.

H. Orhan, D.S. Dogruer, B. Çakir, G. Sahin and M.F. Sahin, Exp. Toxicol. Pathol.,51, 397 (1999); doi:10.1016/S0940-2993(99)80028-1.

R.J. Nachman, J. Heterocycl. Chem., 19, 1545 (1982); doi:10.1002/jhet.5570190660.

D.E.F. Gangi, J. Am. Pharm. Assoc., XLIV, 135 (1955).

K.J. Wang, Y.J. Zhang and C.R. Yang, Chem. Biodivers., 3, 1317 (2006); doi:10.1002/cbdv.200690135.

R. Re, N. Pellegrini, A. Proteggente, A. Pannala, M. Yang and C. Rice-Evans, Free Radic. Biol. Med., 26, 1231 (1999); doi:10.1016/S0891-5849(98)00315-3.

U. Calis, H.G. Pilli and F. Ozkanli, Hacettepe Univ. J. Fac. Pharmacy, 12, 71 (1992).

M. Hesse, H. Meier and B. Zeeh, Spectroscopic Methods in Organic Chemistry, Georg Thieme Verlag: Stutgart, New York (1997).

K. Nakanishi and P.H. Solomon, Infrared Absorption Spectroscopy, Holden-Day Inc. San Francisco, edn 2 (1977).

Issue

Vol. 26 No. 19 (2014): Vol 26 Issue 19

Synthesis and Antioxidant Activity Studies of Some 5-Chloro-3-substituted 2(3H)-Benzoxazolone Derivatives

Corresponding Author(s) : Z. Soyer

Abstract

Keywords

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