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

Year 2017, Volume: 45 Issue: 2 , 153 - 161 , 01.06.2017

Haydar Yüksek Faruk Kardaş Sevda Manap Muzaffer Alkan Önder Albayrak Murat Beytur Özlem Gürsoy-kol

https://izlik.org/JA44GE94EC

Abstract

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, 1H 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.

Keywords

Schiff base , Synthesis , Acetylation , antioxidant activity , antimicrobial activity

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

https://izlik.org/JA44GE94EC

Abstract

B u 4-nitrobenzoksi -benzaldehid 2 ile reaksiyona sokularak 2-etoksi-6-[ 3-alkil/aril-4,5-dihidro- 1H-1,2,4triazol-5-on-4-il iminometil]fenil 4-nitrobenzoat 3 bileşikleri elde edildi. Yeni dokuz adet bileşiğin yapısı elementel analiz ve IR, 1H 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

Keywords

Schiff bazı , sentez , asetillendirme , antioksidan aktivite , antimikrobiyal aktivite

References

• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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-1H- 1,2,4-triazol-5-one derivatives, Arch. Pharm. Chem. Life Sci., 346 (2013) 470.
• Ö. Aktaş-Yokuş, H. Yüksek, Ö. Gürsoy-Kol, Ş. Alpay- Karaoğlu, Synthesis and biological evaluation of new 1,2,4-triazole derivatives with their potentiometric titrations, Med. Chem. Res., 24 (2015) 2813.
• 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.
• D.J. McClements, E.A. Decker, Lipid oxidation in oil- in-water emulsions: Impact of molecular environment on chemical reactions in heterogeneous food systems, J. Food Sci., 65 (2000) 1270.
• M. Oyaizu, Studies on products of browning reaction prepared from glucosamine, Japan. Nutri., 44 (1986) 307.
• M.S. Blois, Antioxidant determinations by the use of a stable free radical, Nature, 181 (1958) 1199.
• T.C.P. Dinis, V.M.C. Madeira, L.M. Almeida, Action of phenolic derivatives (acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid- peroxidation and as peroxyl radical scavengers, Arch. Biochem. Biophys., 315 (1994) 161.
• C. Perez, M. Pauli, P. Bazerque, An antibiotic assay by the agar-well diffusion method, Acta. Biol. Med. Exp., 15 (1990) 113.
• I. Ahmad, Z. Mehmood, F. Mohammad, Screening of some Indian medicinal plants for their antimicrobial properties, J. Ethnopharmacol., 62 (1998) 183.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• I. Calis, M. Hosny, T. Khalifa, S. Nishibe, Secoiridoids from Fraxinus angustifolia, Phytochemistry, 33 (1993) 1453.
• M.H. Gordon, Food Antioxidants, Elsevier, London (1990).
• R.C. Lindsay, Food additives, in O.R. Fennema (Ed.) Food Chemistry, Marcel Dekker Inc., New York (1996).
• 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.