Dergiler / Karadeniz Chemical Science and Technology / 2018 / Sayı: 3

Bazı yeni 3-alkil(aril)-4-(3-metoksi-4-sinnamoiloksi)benzilidenamino-4,5- dihidro-1H-1,2,4-triazol-5-on bileşiklerinin sentezi, antioksidan ve asitlik özelliklerinin incelenmesi

Synthesis, antioxidant and acidic properties of some new 3-alkyl(aryl)-4-(3- methoxy-4-cinnamoyloxy)benzylideneamino-4,5-dihydro-1H-1,2,4-triazol5-ones

Haydar Yüksek(KAFKAS ÜNİVERSİTESİ, FEN-EDEBİYAT FAKÜLTESİ)0000-0003-1289-1800
Buket Göksu(KAFKAS ÜNİVERSİTESİ, FEN-EDEBİYAT FAKÜLTESİ)0000-0001-8207-967X
Bahar Bankoğlu(KAFKAS ÜNİVERSİTESİ, FEN-EDEBİYAT FAKÜLTESİ)0000-0002-2931-077X
Songül Ulufer(KAFKAS ÜNİVERSİTESİ, FEN-EDEBİYAT FAKÜLTESİ)0000-0001-9533-0165
Sevda Manap(KAFKAS ÜNİVERSİTESİ, FEN-EDEBİYAT FAKÜLTESİ)0000-0002-5025-9622
Murat Beytur(KAFKAS ÜNİVERSİTESİ, FEN-EDEBİYAT FAKÜLTESİ)0000-0002-7098-5592
Özlem Gürsoy Kol(KAFKAS ÜNİVERSİTESİ, FEN-EDEBİYAT FAKÜLTESİ)0000-0003-2637-9023
Sayfa
1–6
Yayın Tarihi
2018-12-31
DOI
—
🏛️Bu makalenin bibliyografik verileri ve tam metin bağlantısı DergiPark üzerinden sağlanmıştır.
DergiPark Kaydı ↗
✨

Yapay Zeka Hızlı Bakış & Çıkarımlar

AI Insight
⚡ TL;DR(1 Cümlede Hızlı Çıkarım)

HNP ve pKa değerlerinin çözücüye ve 4,5-dihidro-1H-1,2,4-triazol-5-on yapısında C-3 pozisyonundaki substutiente bağlı değiştiği gözlendi.

📌 3 Maddede Bu Makale

🎯
Amaç & Hipotez:3-Alkil(aril)-4-amino-4,5-dihidro-1H-1,2,4-triazol-5-on (2) bileşiklerinin, 3-metoksi-4-sinnamoiloksibenzaldehid (3) ile reaksiyonları sonucunda dokuz yeni 3-alkil(aril)-4-(3-metoksi-4-sinnamoiloksi)-benzilidenamino-4,5-dihidro-1H-1,2,4-triazol5-on (4) bileşikleri sentezlendi.
📊
Temel Bulgular & Veri:Yeni dokuz adet bileşiğin yapısı IR, 1H-NMR, 13C-NMR ve UV spektrum verileri ile aydınlatıldı.
💡
Sonuç & Katkı:HNP ve pKa değerlerinin çözücüye ve 4,5-dihidro-1H-1,2,4-triazol-5-on yapısında C-3 pozisyonundaki substutiente bağlı değiştiği gözlendi.
🔬Tür:Araştırma Makalesi
📍Kapsam:Genişletilmiş Akademik Örneklem
⚙️Değişkenler:4-Triazol-5-on · sentez · Schiff bazı

Özet

3-Alkil(aril)-4-amino-4,5-dihidro-1H-1,2,4-triazol-5-on (2) bileşiklerinin, 3-metoksi-4-sinnamoiloksibenzaldehid (3) ile reaksiyonları sonucunda dokuz yeni 3-alkil(aril)-4-(3-metoksi-4-sinnamoiloksi)-benzilidenamino-4,5-dihidro-1H-1,2,4-triazol5-on (4) bileşikleri sentezlendi. Yeni dokuz adet bileşiğin yapısı IR, 1H-NMR, 13C-NMR ve UV spektrum verileri ile aydınlatıldı. Sentezlenen bileşiklerin in vitro antioksidan aktiviteleri üç farklı yöntemle analiz edildi. Ayrıca, çözücülerin ve moleküler yapının asitlik üzerine etkisini incelemek için, 4 bileşikleri dört farklı çözücüde (izopropil alkol, tert-butil alkol, aseton ve N,Ndimetilformamid) tetrabutilamonyum hidroksid ile potansiyometrik metotla titre edildi. HNP ve pKa değerlerinin çözücüye ve 4,5-dihidro-1H-1,2,4-triazol-5-on yapısında C-3 pozisyonundaki substutiente bağlı değiştiği gözlendi.

Abstract

Nine new 3-alkyl(aryl)-4-(3-methoxy-4-cinnamoyloxy)benzylideneamino-4,5-dihydro-1 H -1,2,4-triazol-5-ones ( 4 ) were synthesized by the reactions of 3-alkyl(aryl)-4-amino-4,5-dihydro-1 H -1,2,4-triazol-5-ones ( 2 ) with 3-methoxy-4-cinnamoyloxybenzaldehyde ( 3 ) . The structures of new nine compounds were established from IR, 1 H-NMR, 13 C-NMR and UV spectral data. The synthesized compounds were analyzed for their in vitro potential antioxidant activities in three different methods. In addition, to investigate the effects of solvents and molecular structure upon acidity compounds 4 were titrated potentiometrically with tetrabutylammonium hydroxide in four non-aqueous solvents (isopropyl alcohol, tert-butyl alcohol, acetone and N , N -dimethylformamide).

🔖

Bu Makaleye Atıf Yap

Yüksek, H., Göksu, B., Bankoğlu, B., Ulufer, S., Manap, S., Beytur, M., Kol, Ö. G. (2018). Bazı yeni 3-alkil(aril)-4-(3-metoksi-4-sinnamoiloksi)benzilidenamino-4,5- dihidro-1H-1,2,4-triazol-5-on bileşiklerinin sentezi, antioksidan ve asitlik özelliklerinin incelenmesi. Karadeniz Chemical Science and Technology, Sayı: 3, 1–6. https://ajindex.com/articles/1002266

📄 Tam Metin PDF Okuyucu

📄

PDF görüntüleyici hazırlanıyor...

Kaynakça (28)

  1. Sahu, J,K., Ganguly, S. and Kaushik, A., Triazoles: A valuable insight into recent developments and biological activities, Chin. J. Nat. Med. 2013, 11, 456-465.
  2. Ali, K.A., Ragab, E.A., Farghaly, T.A. and Abdalla, M.M., Synthesis of new functionalized 3-subsitituted [1,2,4]triazolo [4,3-a]pyrimidine derivatives: Potential antihypertensive agents, Acta Pol. Pharm. 2011, 68, 237-247.
  3. Li, Z.Y., Cao, Y., Zhan, P., Pannecouque, C., Balzarini, J., De Clercq, E. and Liu, X.Y., Synthesis and anti-HIV evaluation of novel 1,2,4-triazole derivatives as potential non-nucleoside HIV-1 reverse transcriptase inhibitors, Lett. Drug Des. Discov. 2013, 10, 27-34.
  4. Kaczor, A.A., Pitucha, M., Karczmarzyk, Z., Wysocki, W., Rzymowska, J. and Matosiuk, D., Structural and molecular docking studies of 4-benzyl-3-[(1-methylpyrrol- 2-yl)methyl]-4,5-dihydro-1H-1,2,4-triazol-5-one with anticancer activity, Med. Chem. 2013, 9, 313-328.
  5. Thakkar, S.S., Thakor, P., Doshi, H. and Ray, A., 1,2,4-Triazole and 1,3,4-oxadiazole analogues: Synthesis, MO studies, in silico molecular docking studies, antimalarial as DHFR inhibitor and antimicrobial activities, Bioorg. Med. Chem. 2017, 25, 4064-4075.
  6. Khalid, W., Badshah, A., Khan, A., Nadeem, H. and Ahmed, S., Synthesis, characterization, molecular docking evaluation, antiplatelet and anticoagulant actions of 1,2,4 triazole hydrazone and sulphonamide novel derivatives, Chem. Cent. J. 2018, 12:11, 1-16.
  7. Abuelhassan, A.H., Badran, M.M., Hassan, H.A., Abdelhamed, D., Elnabtity, S. and Aly, O.M., Design, synthesis, anticonvulsant activity, and pharmacophore study of new 1,5-diaryl-1H-1,2,4-triazole-3-carboxamide derivatives, Med. Chem. Res. 2018, 27, 928-938.
  8. Bahçeci, Ş., Yıldırım, N., Alkan, M., Gürsoy-Kol, Ö., Manap, S., Beytur, M. and Yüksek, H., Investigation of antioxidant, biological and acidic properties of new 3-alkyl(aryl)-4-(3-acetoxy-4-methoxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones, Pharm. Chem. J. 2017, 4, 91-101.
  9. Aktaş-Yokuş, Ö., Yüksek, H., Manap, S., Aytemiz, F., Alkan, M., Beytur, M. and Gürsoy-Kol, Ö., In-vitro biological activity of some new 1,2,4-triazole derivatives with their potentiometric titrations, Bulg. Chem. Commun. 2017, 49, 98-106.
  10. Yüksek, H. and Gürsoy-Kol, Ö., Preparation, characterization, and potentiometric titrations of some new di-[3-(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)-azomethinphenyl]-isophtalate/terephtalate derivatives, Turk. J. Chem. 2008, 32, 773-784.
  11. Hussain, H.H., Babic, G., Durst, T., Wright, J., Flueraru, M., Chichirau, A. and Chepelev, L.L., Development of novel antioxidants: Design, synthesis, and reactivity, J. Org. Chem. 2003, 68, 7023-7032.
  12. McClements, J. and Decker, E.A., Lipid oxidation in oil-in-water emulsions: Impact of molecular environment on chemical reactions in heterogeneous food systems, J. Food Sci. 2000, 65, 1270-1282.
  13. Dikusar, E.A. and Kozlov, N.G., Esters derived from vanillin and vanillal and aromatic and functionalized aliphatic carboxylic acids, Russ. J. Org. Chem. 2005, 41, 992-996.
  14. Oyaizu, M., Studies on products of browning reaction prepared from glucosamine, Japan. Nutri. 1986, 44, 307-316.
  15. Blois, M.S., Antioxidant determinations by the use of a stable free radical, Nature 1958, 181, 1199-1200.
  16. Dinis, T.C.P., Madeira, V.M.C. and Almeida, L.M., Action of phenolic derivatives (acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid-peroxidation and as peroxyl radical scavengers, Arch. Biochem. Biophys. 1994, 315, 161-169.
  17. Ikizler, A.A. and Un, R., Reactions of ester ethoxycarbonylhydrazones with some amine type compounds, Chim. Acta Turc. 1979, 7, 269-290; [Chem. Abstr. 1981, 94, 15645d].
  18. Ikizler, A.A. and Yuksek, H., Acetylation of 4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones, Org. Prep. Proced. Int. 1993, 25, 99-105.
  19. Meir, S., Kanner, J., Akiri, B. and Philosophhadas, S., Determination and involvement of aqueous reducing compounds in oxidative defense systems of various senescing leaves, J. Agr. Food Chem. 1995, 43, 1813-1819.
  20. Yildirim, A., Mavi, A. and Kara, A.A., Determination of antioxidant and antimicrobial activities of Rumex crispus L. extracts. J. Agr. Food Chem. 2001, 49, 4083-4089.
  21. Baumann, J., Wurn, G. and Bruchlausen, V., Prostaglandin synthetase inhibiting O2 - radical scavenging properties of some flavonoids and related phenolic compounds, Naunyn- Schmiedebergs Arch. Pharmacol. 1979, 308, R27.
  22. Soares, J.R., Dinis, T.C.P., Cunha, A.P. and Almeida, L.M., Antioxidant activities of some extracts of Thymus zygis, Free Radical Res. 1997, 26, 469-478.
  23. Duh, P.D., Tu, Y.Y. and Yen, G.C., Antioxidant activity of water extract of Harng Jyur (Chrysanthemum morifolium Ramat), Food Sci. Technol-Leb. 1999, 32, 269-277.
  24. Yamaguchi, F., Ariga, T., Yoshimura, Y. and Nakazawa, H., Antioxidative and anti-glycation activity of garcinol from Garcinia indica fruit rind, J. Agr. Food Chem. 2000, 48, 180-185.
  25. Strlic, M., Radovic, T., Kolar, J. and Pihlar, B., Anti- and prooxidative properties of gallic acid in fenton-type systems, J. Agr. Food Chem. 2002, 50, 6313-6317.
  26. Finefrock, A.E., Bush, A.I. and Doraiswamy, P.M., Current status of metals as therapeutic targets in Alzheimer’s disease, J. Am. Geriatr. Soc. 2003, 51, 1143-1148.
  27. Calis, I., Hosny, M., Khalifa, T. and Nishibe, S., Secoiridoids from Fraxinus angustifolia. Phytochemistry 1993, 33, 1453-1456.
  28. Gordon, M.H., Food Antioxidants, Elsevier, London, 1990.