Some 2,5-Disubstitue-1,3,4-Oxadiazoles as New Antioxidants

Year 2019, , 10 - 15, 30.06.2019

Nurhan Gümrükçüoğlu , Bahar Bilgin Sökmen

https://doi.org/10.31466/kfbd.528553

Abstract

Many heterocyclic compound, a pharmacologically
used as the starting compound for the synthesis of new structures which are
important. Groups of these azole compounds, due to their various biological
activities, in recent years have become common classes of compounds
synthesized. Heterocyclic compounds containing five-membered ring, compounds of
pharmacological class have entered popular in recent years due to properties. In
this study, antioxidant activities of some 2,5-disubstitue-1,3,4-oxadiazoles (1-3) were evaluated for according to ABTS
(2,2’-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) diammonium salt), 2,2-diphenyl-1-picrylhydrazyl
(DPPH) radical scavenging activities and iron reducing
power capacity. The obtained results showed that the synthesized
compounds (1-3) had effective
antioxidant activities.

Keywords

2.5-Disubstitue-1.3.4-oxadiazoles, Antioxidant, ABTS Radical Scavenging Activity

Yeni Antioksidanlar Olarak Bazı 2,5-Disübstitüye-1,3,4-Oksadiazoller

Abstract

Birçok heterosiklik bileşik, farmakolojik açıdan
önemli olan yeni yapıların sentezi için başlangıç bileşiği olarak
kullanılmaktadır. Bunlardan azol gurubu bileşikler, sahip oldukları değişik
biyolojik aktivitelerden dolayı son yıllarda sıklıkla sentezlenen bileşik
sınıfları haline gelmiştir. Beş üyeli halka içeren heterosiklik bileşikler,
farmakolojik özelliklere sahip olmasından dolayı son yıllarda popüler
bileşikler sınıfına girmiştir. Bu çalışmada, bazı 2,5-disübstitüye-1,3,4-oksadiazollerin
(1-3) antioksidan aktiviteleri, ABTS
(2,2’-Azino-bis(3-etilbenzenothiazoline-6-sülfonik asid), DPPH
(1,1-difenil-2-pikrilhidrazil) radikal giderme aktiviteleri ve demir indirgeme
gücü kapasitesine göre incelendi. Elde edilen sonuçlar,
sentezlenen bileşiklerin (1-3)
etkili antioksidan aktiviteye sahip olduğunu gösterdi.

Keywords

2.5-Disübstitüye-1.3.4-oksadiazoller, Antioksidan, ABTS Radikal Giderme Aktivitesi

References

• Akhtar, T., Hameed ,S., Al-Masoudi, N.A., Loddo, R., Colla, P.L. (2010). In Vitro Antitumor and Antiviral Activities of New Benzothiazole and 1,3,4-oxadiazole-2-thione Derivatives. Acta Pharmazie, 58, 135-149.
• Akhter, M., Husain, A., Azad, B., Ajmal, M. (2008). Aroylpropionic Acid Based 2,5- Disubstituted-1,3,4-oxadiazoles: Synthesis and Their Anti-İnflammatory and Analgesic Activities. European Journal of Medicinal Chemistry, 44, 2372-2378.
• Arnao, M.B., Cano, A., Acosta, M. (2001). The hydrophilic,and lipophilic contribution to total antioxidant activity. Food Chemistry, 73, 239-244.
• Bala, S., Kamboj, S., Kumar, A. (2010). Heterocyclic 1, 3, 4-oxadiazole compounds with diverse biological activities, Journal of Pharmacy Research, 3(12), 2993-2997. Bharathi, D., Hemalatha, S., Devadass, G., Kumar, P.R., Shanmugasundaram, P., Aanandhi, M.V. (2010). Synthesis, Characterisation and in-vitro Antiinflammatory and Anthelmintic activities of 1,3,4-Oxadiazole derivatives. International Journal of Chem Tech Research, 2(4), 1867-1870.
• Brand-Williams, W., Cuvelier, M. V. and Berset, C. (1995). Use of a Free Radical Method to Evaluated Antioxidant Activity. LWT-Food Science Technology, 26, 25-30.
• Dasuri, K., Zhang, L., Keller, J.N. (2013). Oxidative stress, neurodegeneration, and the balance of protein degradation and protein synthesis, Free Radical Biology & Medicine, 62, 170-185.
• Grodstein, F., O'Brien, J., Kang, J. H., Dushkes, R., Cook, N. R., Okereke, O., Manson, J.E., Glynn, R.J., Buring, J.E., Gaziano, M., Sesso, H.D. (2013). Long-term multivitamin supplementation and cognitive function in men: A randomized trial. Annals of Internal Medicine, 159, 806-814.
• Gumrukcuoglu, N., Serdar, M., Çelik, E., Sevim, E., Demirbaş N. (2007). Synthesis and Antimicrobial Activities of Some New 3,5-dialkyl-1,2,4-Triazole Derivatives. Turkish Journal of Chemistry, 31, 335-348.
• James, N.D., Growcott, J.W. (2009). Zibotentan. Drugs Future, 34, 624-633.
• Jayashankar, B., Rai, K.M.L., Baskaran, N., Sathish, H.S. (2009). Synthesis and Pharmacological Evaluation of 1,3,4-Oxadiazole Bearing Bis(Heterocycle) Derivatives as Anti-inflammatory and Analgesic Agents. European Journal of Medicinal Chemistry, 44, 3898-902.
• Kade, I.J., Paixão, M.W., Rodrigues, O.E.D., Ibukun, E.O., Braga, A.L., Zeni, G., Nogueira, C.W., Rocha, J.B.T. (2009). Studies on the antioxidant effect and interaction of diphenyl diselenide and dicholesteroyl diselenide with hepatic d-aminolevulinic acid dehydratase and isoforms of lactate dehydrogenase, Toxicology in Vitro, 23:14-20.
• Kanthiah, S., Kalusalingam, A., Velayutham, R., Vimala, A.T., Beyatricks, J. (2011). 5-(2-Aminophenyl)-1,3,4-oxadiazole2(3H)-thione Derivatives Synthesis, characterization and antimicrobial evaluation. International Journal of Pharmaceutical Sciences Review and Research, 6(1), 64-67.
• Kotaiah, Y.; Harikrishna, N.; Nagaraju, K.; Rao, C. V. 2012, Synthesis and antioxidant activity of 1,3,4-oxadiazole tagged thieno[2,3-d]pyrimidine derivatives, European Journal of Medicinal Chemistry, 58, 340- 345.
• Liu, S., Lee, I. M., Song, Y., Van Denburgh, M., Cook, N. R., Manson, J. E., Buring, J.E. (2006). Vitamin E and risk of type 2 diabetes in the women's health study randomized controlled trial. Diabetes, 55, 2856-2862.
• Naveena, C.S., Boja, P., Kumari, N.S. (2010). Synthesis, Characterization and Antimicrobial Activity of Some Disubstituted 1,3,4-Oxadiazoles Carrying 2-(Aryloxymethyl)phenyl Moiety. European Journal of Medicinal Chemistry, 45, 4708-4719.
• Nordberg, J.; Arnér, E. S. J. 2001, Reactive oxygen species, antioxidants, and the mammalian thioredoxin system, Free Radical Biology and Medicine, 31(11), 1287-1312
• Oliveira, C., Lira, B., Barbosa-Filho, J., Lorenzo, J.G.F., AthaydeFilho, P. (2012). Synthetic Approaches and Pharmacological Activity of 1,3,4-Oxadiazoles: A Review of the Literature from 2000-2012. Molecules, 17, 10192-10291.
• Oyaizu, M.( 1986). Studies on products of browning reactions: Antioxidative activities of products of browning reaction prepared from glucosamine. The Japanese Journal of Nutrition and Dietetics, 44, 307-315.
• Rostom, S.A.F., Shalaby, M.A., ElDemellawy, M.A. (2003). Synthesis of New 1-(4- Chlorophenyl)-4-hydroxy-1H-pyrazole- 3-carboxylic Acid Hydrazide Analogs and Some Derived Ring Systems. A Novel Class of Potential Antitumor and Anti-HCV Agents. European Journal of Medicinal Chemistry, 38, 959-74.
• Savarino, A. (2006). A Historical Sketch of the Discovery and Development of HIV-1 Integrase Inhibitors. Expert Opinion on Investigational Drugs, 15, 1507-1522.
• Serdar, M., Gumrukcuoglu, N., Karaoğlu, Ş. A., Demirbaş, N. (2007). Synthesis of Some Novel 3,5-Diaryl-1,2,4-Triazole Derivatives and Investigation of Their Antimicrobial Activities, Turkish Journal of Chemistry, 31, 315-326.
• Shyma, P.C., Balakrishna, K., Peethambar, S.K., Vijesh, A.M. (2015). Synthesis, Characterization, Antidiabetic and Antioxidant Activity of 1,3,4-oxadiazole Derivatives Bearing 6-Methyl Pyridine Moiety, Der Pharma Chemica, 7(12), 137-145.
• Sosa, V., Moliné, T., Somoza, R., Paciucci, R., Kondoh, H., LLeonart, M.E. (2013). Oxidative stress and cancer: An overview. Ageing Research Reviews, 12, 376-390.
• Sridhara, A.M., Reddy, K.R.V., Keshavayya, J., Goud, P.S.K., Somashekar, B.C., Bose, P. (2010). Synthesis and Antimicrobial Activity of 2-Substituted[4-(1,3,4-Oxadiazol-2-yl methyl)] phthalazin1(2H)-one derivatives, European Journal of Medicinal Chemistry, 45, 4983-4989.
• Uttara, B., Singh, A.V., Zamboni, P., Mahajan, R.T. (2009).Oxidative Stress and Neurodegenerative Diseases: A Review of Upstream and Downstream Antioxidant Therapeutic Options, Current Neuropharmacology, 7(1), 65-74.