Abstract
A variety of new derivatives of 9,10-anthracenedione with mono- and bisdithiocarbamate moiety in the non-catalytic conditions have been synthesized. The obtained compounds were screened for their antioxidant capacity using the cupric-reducing antioxidant capacity (CUPRAC) method. Three of the compounds showed CUPRAC-Trolox equivalent antioxidant capacity (TEAC) coefficients higher than trolox. Scavenging effects on reactive oxygen species (ROS), hydroxyl radical scavenging (HRS), hydrogen peroxide scavenging (HPS), and superoxide anion radical scavenging (SARS) of all synthesized compounds were determined. It was established that the results of HRS-, HPS-, and SARS-CUPRAC methods for three compounds are in accordance with TEAC-CUPRAC assay data.
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Spannhoff A, Sippl W, Jung M (2009) Int J Biochem Cell Biol 41:4
Said M, Badshah A, Shah NA, Khan H, Murtaza G, Vabre B, Zargarian D, Khan MR (2013) Molecules 18:10378
Yang Y, Karakhanova S, Werner J, Bazhin AV (2013) Curr Med Chem 20:3677
Hogarth G (2005) Prog Inorg Chem 53:7
Schreck R, Meier B, Mannel DN, Droge W, Baeuerle PA (1992) J Exp Med 175:1181
Meyer M, Schreck R, Baeuerle PA (1993) EMBO J 12:2005
Schenk H, Klein M, Erdbrugger W, Droge W, Schulze-Osthoff K (1994) Proc Natl Acad Sci USA 91:1672
Wolfe JT, Ross D, Cohen GM (1994) FEBS Lett 352:58
Bessho R, Matsubara K, Kubota M, Kuwakado K, Hirota H, Wakazono Y, Lin YW, Okuda A, Kawai M, Nishikomori R, Heike T (1994) Biochem Pharmacol 48:1883
Albrecht H, Tschopp J, Jongeneel CV (1994) FEBS Lett 351:45
Cremlyn RJ (1991) Agrochemicals-Preparation and Mode of Action. John Wiley, Chichester
Nice HR (1962) Org React 12:57
Hidaka S, Funakoshi T, Shimada H, Tsuruoka M, Kojima S (1995) J Appl Toxicol 15:267
Wood MR, Duncalf DJ, Rannard SP, Perrier S (2006) Org Lett 8:553
Ronconi L, Marzano C, Zanello P, Corsini M, Miolo G, Macca C, Trevisan A, Fregona D (2006) J Med Chem 49:1648
Hou XL, Ge ZM, Wang TM, Guo W, Cui JR, Cheng TM, Lai CS, Li RT (2006) Bioorg Med Chem Lett 16:4214
The HIV87 study group1 (1993) AIDS Res Hum Retrov 9:83
Nagano R, Shibata K, Naito T, Fuse A, Asano K, Hashizume T, Nakagawa S (1997) Antimicrob Agents Chemother 41:2278
Safak C, Erdogan H, Yesilada A, Erol K, Cimgi I (1992) Arzneim Forsch 42:123
Arai S, Kato S, Hida MB (1985) Chem Soc Jpn 58:1458
Sattigeri VJ, Soni A, Singhal S, Khan S, Pandya M, Bhateja P, Mathur T, Rattan A, Khanna JM, Mehta A (2005) Arkivoc ii:46
Guérin D, Carlier R, Lorcy D (2000) J Org Chem 65:6069
Azizi N, Aryanasab F, Torkiyan L, Ziyaei A, Saidi MR (2006) J Org Chem 71:3634
Azizi N, Aryanasab F, Saidi MR (2006) Org Lett 8:5275
Bhadra S, Saha A, Ranu BC (2008) Green Chem 10:1224
Clifford M, Lichty JG (1932) J Am Chem Soc 54:1163
Chen Z-C, Jin Y-Y, Stang PJ (1987) J Org Chem 52:4117
Grischuk BD, Gorbova PM, Sviderskaya LP, Dyachuk AA, Tikhonov VP, Ganuschak NI (1990) Russ J Gen Chem 60:432
Klimenko LS, Mainagashev IJ, Fokin EP (1992) Izv Akad Nauk Ser Khim 3:582
Chatterjee T, Bhadra S, Ranu BC (2011) Green Chem 13:1837
Ozyurek M, Bektasoglu B, Guclu K, Apak R (2008) Anal Chim Acta 616:196
Ozyurek M, Bektasoglu B, Guçlu K, Gungor N, Apak R (2010) J Food Compos Anal 23:689
Yu H, Liu X, Xing R, Liu S, Li C, Li P (2005) Bioorg Med Chem Lett 15:2659
Apak R, Guçlu K, Ozyurek M, Karademir SE (2004) J Agric Food Chem 52:7970
Deniz NG, Ozyurek M, Tufan AN, Apak MR (2015) Monatsh Chem 146:2117
Deniz NG, Ibis C, Gokmen Z, Stasevych M, Novikov V, Komarovska-Porokhnyavets O, Ozyurek M, Guclu K, Karakas D, Ulukaya E (2015) Chem Pharm Bull 63:1029
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The authors would like to express their gratitude to the Ministry of Education and Science of Ukraine, Scientific Research Project (Project Number: 0116U004138), and Scientific Research Projects Coordination Unit of Istanbul University (Project Number: NP-45621) for financial support.
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Zvarych, V., Stasevych, M., Lunin, V. et al. Synthesis and investigation of antioxidant activity of the dithiocarbamate derivatives of 9,10-anthracenedione. Monatsh Chem 147, 2093–2101 (2016). https://doi.org/10.1007/s00706-016-1839-y
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DOI: https://doi.org/10.1007/s00706-016-1839-y