BibTex RIS Kaynak Göster

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

Yıl 2017, Cilt: 45 Sayı: 2, 153 - 161, 01.06.2017

Öz

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.

Kaynakça

  • 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.

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

Yıl 2017, Cilt: 45 Sayı: 2, 153 - 161, 01.06.2017

Öz

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

Kaynakça

  • 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.
Toplam 31 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Research Article
Yazarlar

Haydar Yüksek Bu kişi benim

Faruk Kardaş Bu kişi benim

Sevda Manap Bu kişi benim

Muzaffer Alkan Bu kişi benim

Önder Albayrak Bu kişi benim

Murat Beytur Bu kişi benim

Özlem Gürsoy-kol Bu kişi benim

Yayımlanma Tarihi 1 Haziran 2017
Yayımlandığı Sayı Yıl 2017 Cilt: 45 Sayı: 2

Kaynak Göster

APA Yüksek, H., Kardaş, F., Manap, S., Alkan, M., vd. (2017). 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. Hacettepe Journal of Biology and Chemistry, 45(2), 153-161.
AMA Yüksek H, Kardaş F, Manap S, Alkan M, Albayrak Ö, Beytur M, Gürsoy-kol Ö. 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. HJBC. Haziran 2017;45(2):153-161.
Chicago Yüksek, Haydar, Faruk Kardaş, Sevda Manap, Muzaffer Alkan, Önder Albayrak, Murat Beytur, ve Özlem Gürsoy-kol. “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”. Hacettepe Journal of Biology and Chemistry 45, sy. 2 (Haziran 2017): 153-61.
EndNote Yüksek H, Kardaş F, Manap S, Alkan M, Albayrak Ö, Beytur M, Gürsoy-kol Ö (01 Haziran 2017) 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. Hacettepe Journal of Biology and Chemistry 45 2 153–161.
IEEE H. Yüksek, “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”, HJBC, c. 45, sy. 2, ss. 153–161, 2017.
ISNAD Yüksek, Haydar vd. “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”. Hacettepe Journal of Biology and Chemistry 45/2 (Haziran 2017), 153-161.
JAMA Yüksek H, Kardaş F, Manap S, Alkan M, Albayrak Ö, Beytur M, Gürsoy-kol Ö. 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. HJBC. 2017;45:153–161.
MLA Yüksek, Haydar vd. “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”. Hacettepe Journal of Biology and Chemistry, c. 45, sy. 2, 2017, ss. 153-61.
Vancouver Yüksek H, Kardaş F, Manap S, Alkan M, Albayrak Ö, Beytur M, Gürsoy-kol Ö. 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. HJBC. 2017;45(2):153-61.

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