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Figure 4. Scavenging effect of compound 3b on DPPH radicals.
Data are reported as mean ± S.D. of 3 independent experiments. The
values are expressed in percentage of control (C) (100 %) (one-way
ANOVA followed by the Newman– Keuls' test).
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In the DPPH assay, antioxidants could reduce the stable
radical DPPH by donating hydrogen to a free radical to remove
the extra electron (which is responsible for the activity of free
radicals). Moreover, protonated radical ABTS is used for
evaluating the scavenger activity of proton radicals.23 Our results
revealed that the compound 3b was an effective scavenger
against the ABTS radical species, but there was no scavenging
activity for DPPH radical. In this regard, we believed that the
antioxidant effect of compound 3b is related to protonated
radical-scavenger activity. The different effect of compound 3b
in DPPH and ABTS assays can be due to the different chemical
structure of these two radicals. Moreover, it could be rationalized
that nitrogen atom into pyridine ring is important to scavenger
activity of proton radicals. As evidenced by Luchese and
collaborators (2012),24 bis(2-pyridyl) diselenide has excellent
antioxidant potential and it is a better antioxidant that other
disubstituted diaryl diselenides due the presence of pyridine ring.
However, in line with our results, it is important to highlight that
ABTS radicals scavenging activity of compound 3b is better than
bis(2-pyridyl) diselenide.
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K. I.; Jain, V. K. J. Organomet. Chem. 2012, 713, 42. (b) Bhasin,
K. K.; Jain, V. K.; Kumar, H.; Sharma, S.; Mehta, S. K.; Singh, J.
Synth. Comm. 2003, 33, 977. (c) Kienitz, C. O.; Thöne, C.; Jones,
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Chem. Rev. 2013, 257, 1409.
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V.; Panov, V. A.; Khabibulina, A. G.; Amosova, S. V.; Bhasin, K.
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Iwaokac, M.; Priyadarsini, K. I. Org. Biomol. Chem. 2014, 12,
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M. K.; Engman, L. J. Org. Chem. 2015, 80, 7385.
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Iraci, N.; Santi, C.; Pannecouque, C.; Tabarrini, O. J. Med. Chem.
2015, 58, 9601.
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Chem. 2015, 39, 7948. (b) Cargnelutti, R.; Lang, E. S.; Piquini, P.;
Abram, U. Inorg. Chem. Comm. 2014, 45, 48. (c) Cargnelutti, R.;
Hagenbach, A.; Abram, U.; Burrow, R. A.; Lang, E. S.
Polyhedron 2015, 96, 33. (d) Cargnelutti, R.; Land, E. S.;
Schumacher, R. F. Tetrahedron Lett. 2015, 56, 5218.
11. Crystal data for 3b: Orthorhombic, space group Fdd2, T = 100(2)
K, a = 12.5638(4) Å, b = 23.6753(9) Å, c = 7.6802(4) Å, α = 90°,
β = 90°, γ = 90°, V = 2284.49(16) Å3, Z = 8, Bruker APEX-II
CCD, Mo Kα radiation (λ = 0.71073 Å), μ = 6.450 mm−1,
absorption correction: multi-scan, Tmin = 0.5002, Tmax = 0.7461.
Structure solution and refinement: SHELXL-2014, [G. M.
Sheldrick, SHELXS-2014, Program for Crystal Structure Solution,
University of Göttingen, 2014]. R1 = 0.0159, wR2 = 0.0335, GooF
= 1.053, CCDC deposit number: 1555010.
12. Brandenburg, K. DIAMOND 3.2i, Crystal Impact GbR, Bonn,
Germany, 1997–2012.
13. Radatz, C. S.; Alves, D.; Schneider, P. H. Tetrahedron 2013, 69,
1316.
14. Ma, X.; Liu, Q.; Jia, X.; Su, C.; Xu, Q. RSC Adv. 2016, 6, 56930.
15. Perin, G.; Silveira, M. B.; Barcellos, A. M.; Araujo, D. R.; Jacob,
R. G.; Barcellos, T.; Lenardão, E. J. Arkivoc 2017, 138.
16. Grutzendler, J.; Morris, J. C. Drugs 2001, 61, 41.
17. Porcel, J.; Montalban, X. J. Neurol. 2006, 245, 177.
18. (a) Birks, J., Cochrane Database Syst. Rev. 2006, 25, CD005593.
(b) Yang, Y. D.; Cheng, X. M.; Liu, W.; Chou, G. X.; Wang, Z.
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3. Conclusion
In summary, we have developed a simple and efficient method
for the synthesis of bis(2-pyridyl) diselenides using 2-
chloropyridynes in acid medium. This method allowed to prepare
the bis(3-amino-2-pyridyl) diselenide, which reactivity was
tested to synthesize a new class of 2-aryl[1,3]selenazolo[5,4-
b]pyridines, 2-(alkylselanyl)pyridin-3-amino and 2-phenyl-3H-
pirido[2,3-b][1,4]selenazine. These compounds were obtained by
simple and environmentally benign protocols in good to excellent
yields. On the other hand, results obtained after preliminary
biological assays shown that the compound 3b has an important
potential to act against the oxidative stress and as inhibitor of
AChE activity. In addition, other compounds of this class are
being studied and additional pharmacological aspects are being
elucidated.
Acknowledgments
The authors thank CNPq, CAPES, FAPERGS (ARD 16/2551-
0000358-0, PRONEM 16/2551-0000240-1) and FINEP for the
financial support. CNPq is also acknowledged for the fellowship
for G.P. and C.L. We also thank the CIA-FURG for the NMR
analyzes performed.
19. Halliwell, B. Biochem Soc Trans. 2007, 35, 1147.
20. (a) Méndez-Armenta, M.; Nava-Ruíz, C.; Juárez-Rebollar, D.;
Rodríguez-Martínez, E.; Yescas Gómez, P. Oxid Med Cell
Longev. 2014, 293689. (b) Thanan, R.; Oikawa, S.; Hiraku, Y.;
Ohnishi, S.; Ma, N.; Pinlaor, S.; Yongvanit, P.; Kawanishi, S.;
Murata, M. Int. J. Mol. Sci. 2014, 16, 193. (c) Marseglia, L.;
Manti, S.; D'Angelo, G.; Nicotera, A.; Parisi, E.; Di Rosa, G.;
Gitto, E.; Arrigo, T. Int. J. Mol. Sci. 2014, 16, 378.
References and notes
1. (a) Santi, C. Organoselenium Chemistry: Between Synthesis and
Biochemistry, Bentham Science: Sharjah, e-book, DOI: