New thiosemicarbazides and 1,2,4-triazolethiones derived from 2-(Ethylsulfanyl) benzohydrazide as potent antioxidants

Molecules

Volumn 19, Issue 8, 2014, Pages 11520-11537

  Nazarbahjat, Nafal ^a,b   Nordin, Nurdiana ^a   Abdullah, Zanariah ^a   Abdulla, Mahmood Ameen ^a   Yehye, Wageeh A ^a   Halim, Siti Nadiah Abdul ^a   Kee, Chin Hui ^a   Ariffin, Azhar ^a  

^a UNIVERSITY OF MALAYA   (Malaysia)

^b MIDDLE TECHNICAL UNIVERSITY   (Iraq)

Author keywords

1,2,4 triazoles; Antioxidant activity; Thioethers; Thiosemicarbazide derivatives; X ray structure determination

Indexed keywords

ANTIOXIDANT; AZIDE; FERRIC ION; MERCAPTOTRIAZOLE; SCAVENGER; SEMICARBAZIDE DERIVATIVE; THIOSEMICARBAZIDE; TRIAZOLE DERIVATIVE;

CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; SYNTHESIS;

ANTIOXIDANTS; AZIDES; FERRIC COMPOUNDS; FREE RADICAL SCAVENGERS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; SEMICARBAZIDES; TRIAZOLES;

EID: 84906713398     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules190811520     Document Type: Article

References (30)

1. Lee, W.-L.; Huang, J.-Y.; Shyur, L.-F. Phytoagents for cancer management: Regulation of nucleic acid oxidation, ros, and related mechanisms. Oxid. Med. Cell. Longev. 2013, 2013, doi:10.1155/2013/925804.
2. Grimm, S.; Höhn, A.; Grune, T. Oxidative protein damage and the proteasome. Amino Acids 2012, 42, 23-38.
3. Yin, H.; Xu, L.; Porter, N.A. Free radical lipid peroxidation: Mechanisms and analysis. Chem. Rev. 2011, 111, 5944-5972.
4. Kadenbach, B.; Ramzan, R.; Vogt, S. Degenerative diseases, oxidative stress and cytochrome c oxidase function. Trends Mol. Med. 2009, 15, 139-147.
5. Diplock, A.T.; Charleux, J.-L.; Crozier-Willi, G.; Kok, F.J.; Rice-Evance, C.; Roberfroid, M.; Stahl, W.; Viña-Ribes, J. Functional food science and defence against reactive oxidative species. Br. J. Nutr. 1998, 80, S77-S112.
6. Singh, N.; Rajini, P.S. Free radical scavenging activity of an aqueous extract of potato peel. Food Chem. 2004, 85, 611-616.
7. Jaishree, V.; Ramdas, N.; Sachin, J.; Ramesh, B. In vitro antioxidant properties of new thiazole derivatives. J. Saudi Chem. Soc. 2012, 16, 371-376.
8. Ani, V.; Naidu, K. Antioxidant potential of bitter cumin (centratherum anthelminticum (l.) kuntze) seeds in in vitro models. BMC Complem. Altern. M. 2011, 11, 40.
9. He, J.; Wang, X.; Zhao, X.; Liang, Y.; He, H.; Fu, L. Synthesis and antitumor activity of novel quinazoline derivatives containing thiosemicarbazide moiety. Eur. J. Med. Chem. 2012, 54, 925-930.
10. Ezabadi, I.R.; Camoutsis, C.; Zoumpoulakis, P.; Geronikaki, A.; Soković, M.; Glamočilija, J.; Ćirić, A. Sulfonamide-1,2,4-triazole derivatives as antifungal and antibacterial agents: Synthesis, biological evaluation, lipophilicity, and conformational studies. Bioorg. Med. Chem. 2008, 16, 1150-1161.
11. Revelant, G.; Gadais, C.; Mathieu, V.; Kirsch, G.; Hesse, S. Synthesis and antiproliferative studies of 5-aryl-2-(3-thienylamino)-1,3,4-thiadiazoles. Bioorg. Med. Chem. Lett. 2014, 24, 2724-2727.
12. 2-d-galactopyranosyl)thiosemicarbazide. Eur. J. Med. Chem. 2013, 60, 199-207.
13. Amorati, R.; Fumo, M.G.; Menichetti, S.; Mugnaini, V.; Pedulli, G.F. Electronic and hydrogen bonding effects on the chain-breaking activity of sulfur-containing phenolic antioxidants. J. Org. Chem. 2006, 71, 6325-6332.
14. Tozkoparan, B.; Gökhan, N.; Aktay, G.; Yeşilada, E.; Ertan, M. 6-benzylidenethiazolo[3,2-b]-1,2,4-triazole-5(6h)-onessubstituted with ibuprofen: Synthesis, characterizationand evaluation of anti-inflammatory activity. Eur. J. Med. Chem. 2000, 35, 743-750.
15. Varvaresou, A.; Siatra-Papastaikoudi, T.; Tsotinis, A.; Tsantili-Kakoulidou, A.; Vamvakides, A. Synthesis, lipophilicity and biological evaluation of indole-containing derivatives of 1,3,4-thiadiazole and 1,2,4-triazole. Il Farmaco 1998, 53, 320-326.
16. Küçükgüzel, S.G.; Rollas, S.; Erdeniz, H.; Kiraz, M. Synthesis, characterization and antimicrobial evaluation of ethyl 2-arylhydrazono-3-oxobutyrates. Eur. J. Med. Chem. 1999, 34, 153-160.
17. Benzie, I.F.F.; Strain, J.J. The ferric reducing ability of plasma (frap) as a measure of "Antioxidant power": The frap assay. Anal. Biochem. 1996, 239, 70-76.
18. Prior, R.L.; Wu, X.; Schaich, K. Standardized methods for the determination of antioxidant capacity and phenolics in foods and dietary supplements. J. Agric. Food Chem. 2005, 53, 4290-4302.
19. Karadag, A.; Ozcelik, B.; Saner, S. Review of methods to determine antioxidant capacities. Food Anal. Method. 2009, 2, 41-60.
20. Delley, B. An all-electron numerical method for solving the local density functional for polyatomic molecules. J. Chem. Phys. 1990, 92, 508-517.
21. Delley, B. From molecules to solids with the dmol3 approach. J. Chem. Phys. 2000, 113, 7756-7764.
22. Liu, Z.-Q.; Wu, D. How many peroxyl radicals can be scavenged by hydroxyl-substituted schiff bases in the oxidation of linoleic acid? J. Phys. Org. Chem. 2009, 22, 308-312.
23. Laarhoven, L.J.J.; Mulder, P.; Wayner, D.D.M. Determination of bond dissociation enthalpies in solution by photoacoustic calorimetry. Accunts Chem. Res. 1999, 32, 342-349.
24. pro; Agilent Technologies Inc. SantaClara, CA, USA, 2013.
25. Sheldrick, G.M. A short history of shelx. Acta Crystallogr. A 2007, 64, 112-122.
26. Barbour, L.J. X-seed - A software tool for supramolecular crystallography. J. Supramol. Chem. 2001, 1, 189-191.
27. Gerhäuser, C.; Klimo, K.; Heiss, E.; Neumann, I.; Gamal-Eldeen, A.; Knauft, J.; Liu, G.-Y.; Sitthimonchai, S.; Frank, N. Mechanism-based in vitro screening of potential cancer chemopreventive agents. Mutat. Res. 2003, 523, 163-172.
28. Frisch, M.; Trucks, G.; Schlegel, H.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G.A.; et al. Gaussian 03; Gaussian Inc.: Wallington, CT, USA, 2003.
29. Becke, A.D. Density-functional thermochemistry - The role of exact exchange. J. Chem. Phys. 1993, 98, 5648-5652.
30. Perdew, J.P.; Burke, K.; Ernzerhof, M. Generalized gradient approximation made simple. Phys. Rev. Lett. 1996, 77, 3865-3868.