Özlem GÜRSOY KOL, Murat BEYTUR, Önder ALBAYRAK, Faruk KARDAŞ, Haydar YÜKSEK, Muzaffer ALKAN, Sevda MANAP

Yeni 2-Etoksi-6-[(4,5-dihidro-1H-1,2,4-triazol-5-on-4-il) iminometil]fenil 4-nitrobenzoat Türevlerinin Sentezi ve Biyolojik Değerlendirmesi

Bu çalışmada, 3-alkil(aril)-4-amino-4,5-dihidro-1H-1,2,4-triazol-5-on (1) bileşikleri 3-etoksi-2- (4-nitrobenzoksi)-benzaldehid (2) ile reaksiyona sokularak 2-etoksi-6-[(3-alkil/aril-4,5-dihidro- 1H-1,2,4- triazol-5-on-4-il)iminometil]fenil 4-nitrobenzoat (3) bileşikleri elde edildi. Yeni dokuz adet bileşiğin yapısı elementel analiz ve IR, 1 H NMR ve 13C NMR spektrum verileri ile aydınlatıldı. Sentezlenen bileşiklerin in vitro potansiyel antioksidan aktiviteleri üç farklı yöntemle analiz edildi. Ayrıca, yeni bileşiklerin antimikrobiyal aktiviteleri incelendi.

Synthesis and Biological Evaluation of New 2-Ethoxy-6-[(4,5- dihydro-1H-1,2,4-triazol-5-one-4-yl)iminomethyl]phenyl 4-nitro-benzoate Derivatives

In the present study, 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (1) reacted with 3-ethoxy-2-(4- nitrobenzoxy)-benzaldehyde (2) to afford 2-ethoxy-6-[(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl) iminomethyl]phenyl 4-nitrobenzoates (3). The structures of new nine compounds were established from the elemental analyses, IR, 1 H NMR and 13C NMR spectral data. The synthesized compounds were analyzed for their in vitro potential antioxidant activities in three different methods. In addition, these new compounds were screened for their antimicrobial activities.

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Y.V. Yuan, D.E. Bone, M.F. Carrington, Antioxidant activity of dulse (Palmaria palmata) extract evaluated in vitro, Food Chemistry, 91 (2005) 484.
I. Gulcin, Antioxidant and antiradical activities of l-carnitine, Life Sciences, 78 (2006) 803.
R.C. Lindsay, Food additives, in O.R. Fennema (Ed.) Food Chemistry, Marcel Dekker Inc., New York (1996).
M.H. Gordon, Food Antioxidants, Elsevier, London (1990).
I. Calis, M. Hosny, T. Khalifa, S. Nishibe, Secoiridoids from Fraxinus angustifolia, Phytochemistry, 33 (1993) 1453.
A.E. Finefrock, A.I. Bush, P.M. Doraiswamy, Current status of metals as therapeutic targets in Alzheimer’s disease, J. Am. Geriatr. Soc., 51 (2003) 1143.
M. Strlic, T. Radovic, J. Kolar, B. Pihlar, Anti- and prooxidative properties of gallic acid in fenton-type systems, J. Agr. Food Chem., 50 (2002) 6313.
F. Yamaguchi, T. Ariga, Y. Yoshimura, H. Nakazawa, Antioxidative and anti-glycation activity of garcinol from Garcinia indica fruit rind, J. Agric. Food Chem., 48 (2000) 180.
P.D. Duh, Y.Y. Tu, G.C. Yen, Antioxidant activity of water extract of Harng Jyur (Chrysanthemum morifolium Ramat), Food Sci. Technol.-Leb., 32 (1999) 269.
J.R. Soares, T.C.P. Dinis, A.P. Cunha, L.M. Almeida, Antioxidant activities of some extracts of Thymus zygis., Free Radical Res., 26 (1997) 469.
J. Baumann, G.,Wurn, V. Bruchlausen,. Prostaglandin synthetase inhibiting O2 - radical scavenging properties of some flavonoids and related phenolic compounds, Naunyn- Schmiedebergs Arch. Pharmacol., 308 (1979) R27.
A. Yildirim, A. Mavi, A.A. Kara, Determination of antioxidant and antimicrobial activities of Rumex crispus L. extracts, J. Agr. Food Chem., 49 (2001) 4083.
S. Meir, J. Kanner, B. Akiri, S. Philosophhadas, Determination and involvement of aqueous reducing compounds in oxidative defense systems of various senescing leaves, J. Agr. Food Chem., 43 (1995) 1813.
I. Ahmad, Z. Mehmood, F. Mohammad, Screening of some Indian medicinal plants for their antimicrobial properties, J. Ethnopharmacol., 62 (1998) 183.
C. Perez, M. Pauli, P. Bazerque, An antibiotic assay by the agar-well diffusion method, Acta. Biol. Med. Exp., 15 (1990) 113.
T.C.P. Dinis, V.M.C. Madeira, L.M. Almeida, Action of phenolic derivatives (acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipidperoxidation and as peroxyl radical scavengers, Arch. Biochem. Biophys., 315 (1994) 161.
M. Oyaizu, Studies on products of browning reaction prepared from glucosamine, Japan. Nutri., 44 (1986) 307. 15. M.S. Blois, Antioxidant determinations by the use of a stable free radical, Nature, 181 (1958) 1199.
D.J. McClements, E.A. Decker, Lipid oxidation in oilin-water emulsions: Impact of molecular environment on chemical reactions in heterogeneous food systems, J. Food Sci., 65 (2000) 1270.
H.H. Hussain, G. Babic, T. Durst, J.S. Wright, M. Flueraru, A. Chichirau, L.L. Chepelev, Development of novel antioxidants: Design, synthesis, and reactivity, J. Org. Chem., 68 (2003) 7023.
Ö. Aktaş-Yokuş, H. Yüksek, Ö. Gürsoy-Kol, Ş. AlpayKaraoğlu, Synthesis and biological evaluation of new 1,2,4-triazole derivatives with their potentiometric titrations, Med. Chem. Res., 24 (2015) 2813.
H. Yüksek, O. Akyıldırım, M.L. Yola, Ö. Gürsoy-Kol, M. Çelebier, D. Kart, Synthesis, in vitro antimicrobial and antioxidant activities of some new 4,5-dihydro-1H1,2,4-triazol-5-one derivatives, Arch. Pharm. Chem. Life Sci., 346 (2013) 470.
H. Yuksek, A. Demirbas, A. Ikizler, C.B. Johansson, C. Celik, A.A. Ikizler, Synthesis and antibacterial activities of some 4,5-dihydro-1H-1,2,4-triazol-5-ones, Arzneim.-Forsch., 47 (1997) 405.
A.A. İkizler, A. İkizler, H. Yüksek, M. Serdar, Antitumor activities of some 4,5-dihydro-1H-1,2,4-triazol-5-ones, Modell. Meas. & Control C, AMSE press, 57 (1998) 25.
E.S. Al-Abdullah, H.M. Al-Tuwaijri, H.M. Hassan, M.E. Haiba, E.E. Habib, A.A. El-Emam, Antimicrobial and hypoglycemic activities of novel N-Mannich bases derived from 5-(1-adamantyl)-4-substituted-1,2,4- triazoline-3-thiones, Int. J. Mol. Sci., 15 (2014) 22995.
C.B. Zhang, C.W. Yang, X.Q. Deng, Z.S. Quan, Design and synthesis of 6-alkyoxyl[1,2,4]triazolo[1,5-a] quinazoline derivatives with anticonvulsant activity, Med. Chem. Res., 21 (2012) 3294.
K.A. Ali, E.A. Ragab, T.A. Farghaly, M.M. Abdalla, Synthesis of new functionalized 3-subsitituted [1,2,4] triazolo [4,3-a]pyrimidine derivatives: Potential antihypertensive agents, Acta Pol. Pharm., 68 (2011) 237.
A. Uzgoren-Baran, B.C. Tel, D. Sarigol, E.I. Ozturk, I. Kazkayasi, G. Okay, M. Ertan, B. Tozkoporan, Thiazolo[3,2-b]-1,2,4-triazole-5(6H)-one substituted with ibuprofen: Novel non-steroidal anti-inflammatory agents with favorable gastrointestinal tolerance, Eur. J. Med. Chem., 57 (2012) 398-406.
N. Chidananda, B. Poojary, V. Sumangala, N.S. Kumari, P. Shetty, T. Arulmoli, Facile synthesis, characterization and pharmacological activities of 3,6-disubstituted 1,2,4-triazolo[3,4-b][1,3,4] thiadiazoles and 5,6-dihydro-3,6-disubstituted-1,2,4- triazolo[3,4-b][1,3,4]thiadiazoles, Eur. J. Med. Chem., 51 (2012) 124.
B. Kahveci, M. Ozil, E. Mentese, O. Bekircan, K. Buruk, Microwave-assisted synthesis and antifungal activity of some new 1H-1,2,4-triazole derivatives, Russ. J. Org. Chem., 44 (2008) 1816.
M.A. Henen, S.A.A. El Bialy, F.E. Goda, M.N.A. Nasr, H.M. Eisa, [1,2,4]Triazolo[4,3-a]quinoxaline: Synthesis, antiviral, and antimicrobial activities. Med. Chem. Res., 21 (2012) 2368.