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Bazı Yeni 3-Alkil-4-[3-metoksi-4-(p-nitrobenzoksi)-benzilidenamino]-4,5-dihidro-1H-1,2,4-triazol-5-on Bileşiklerinin in vitro Antioksidan ve Antimikrobiyal Özellikleri

Yıl 2022, Cilt: 22 Sayı: 2, 275 - 281, 30.04.2022

Sevda Manap Haydar Yüksek Zeynep Ekinci Elif Sel

https://doi.org/10.35414/akufemubid.1008079

Öz

Bu çalışmada, dokuz yeni 3-alkil-4-[3-metoksi-4-(p-nitrobenzoksi)-benzilidenamino]-4,5-dihidro-1H-1,2,4-triazol-5-on (3) bileşiği 3-alkil-4-amino-4,5-dihidro-1H-1,2,4-triazol-5-on (1) bileşiklerinin 3-metoksi-4-hidroksibenzaldehidin trietilaminli ortamda p-nitrobenzoil klorür ile reaksiyonundan elde edilen 3-metoksi-4-(p-nitrobenzoksi)-benzaldehid (2) ile reaksiyonundan sentezlenmiştir. Sentezlenen yeni bileşikler IR, 1H NMR ve 13C NMR spektrum verileri kullanılarak karakterize edilmiştir. Çalışmada, ayrıca, yeni bileşiklerin in vitro antibakteriyal etkinlikleri altı bakteriye karşı agar kuyucuk yöntemi ile belirlenmiştir. İn vitro ortamda sentezlenen yeni bileşiklerin antioksidan aktiviteleri üç farklı yöntemle tayin edilmiştir.

Anahtar Kelimeler

Schiff bazı 1,2,4-Triazol-5-on Sentez Antioksidan aktivite Antimikrobiyal aktivite

Teşekkür

Antimikrobiyal ve antioksidan aktivite incelemelerindeki katkılarından dolayı Dr. Muzaffer ALKAN ve Dr. Özlem GÜRSOY KOL’a teşekkür ederiz.

Kaynakça

  • Ahmad, A., Varshney, H., Rauf, A., Sherwani, A. and Owais, M., 2017. Synthesis and anticancer activity of long chain substituted 1,3,4-oxadiazol-2-thione,1,2,4-triazol-3-thione and 1,2,4-triazolo [3,4-b]-1,3,4-thiadiazine derivatives. Arabian Journal of Chemistry, 10, S3347-S3357.
  • Amir, M., Kumar, H. and Javed, S.A., 2008. Condensed bridgehead nitrogen heterocyclic system: Synthesis and pharmacological activities of 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole derivatives of ibuprofen and biphenyl-4-yloxy acetic acid. European Journal of Medicinal Chemistry, 43(10), 2056-2066.
  • Aktaş-Yokuş, Ö., Yüksek, H., Gürsoy-Kol, Ö. and Alpay-Karaoğlu, S., 2015. Synthesis and biological evaluation of new 1,2,4-triazol derivatives with their potentiometric titrations. Medicinal Chemistry Research, 24, 2813–2824.
  • Blois, M., 1958. Antioxidant determinations by the use of a stable free radical. Nature, 181, 1199-1200.
  • Çiftçi, E., Beytur, M., Calapoğlu, M., Gürsoy Kol, Ö., Alkan, M., Toğay, V.A., Manap, S. and Yüksek, H., 2018. Synthesis, characterization, antioxidant and antimicrobial activities and DNA damage of some novel 2-[3-alkyl (aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-phenoxyacetic acids in Human Lymphocytes. Research Journal of Pharmaceutical, Biological and Chemical Sciences, 9(5), 1760-1771.
  • Demirbas, N., Ugurluoglu, R. and Demirbas, A., 2002. Synthesis of 3-alkyl(Aryl)-4-alkylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-ones and 3-alkyl-4-alkylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones as antitumor agents. Bioorganic and Medicinal Chemistry, 10(12), 3717-3723.
  • Dinis, T.C.P., Madeira, V.M.C. and Almeida, L.M., 1994. Action of phenolic derivatives (Acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers. Archives of Biochemistry and Biophysics, 315(1), 161-169.
  • Eswaran, S., Adhikari, A.V. and Shetty, N.S., 2009. Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety. European Journal of Medicinal Chemistry, 44(11), 4637-4647.
  • Gürsoy-Kol, O., Yuksek, H. and Islamoglu, F., 2013. Synthesis and in vitro antioxidant activities of novel 4-(3-methyl-2-thienylmethyleneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives with their acidic properties. Journal of the Chemical Society of Pakistan, 35(4), 1179–1190.
  • Gürsoy-Kol, Ö.,Yüksek, H., Manap, S. and Tokalı, F. S., 2016. Synthesis, characterization, and antioxidant activities of novel 1-(morpholine-4-yl-methyl)-3-alkyl(aryl)-4-[4-(dimethylamino)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones. JOTCSA, Journal of the Turkish Chemical Society, Section A: Chemistry, 3 (3), 105-120.
  • İkizler, A.A. and Ün, R., 1979. Reactions of ester ethoxycarbonylhydrazones with some amine type compounds. Chimica Acta Turcica, 7, 269-290.
  • İkizler, A. and Yüksek, H., 1993. Acetylation of 4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones. Organic Preparations and Procedures International, 25(1), 99-105.
  • Lu, L., Li, Z., Shan, C., Ma, S., Nie, W., Wang, H., Chen, G., Li, S. and Shu, C., 2021. Whole transcriptome analysis of schinifoline treatment in Caenorhabditis elegans infected with Candida albicans. Molecular Immunology, 135, 312-319.
  • Malbec, F., Milcent, R., Vicart, P. and Bure, A.M., 1984. Synthesis of new derivatives of 4‐amino‐2,4‐dihydro‐1,2,4‐triazol‐3‐one as potential antibacterial agents. Journal of Heterocyclic Chemistry, 21(6), 1769-1774.
  • Manap, S., Gürsoy-Kol, Ö., Alkan, M. and Yüksek, H., 2020. Synthesis, in vitro antioxidant and antimicrobial activities of some novel 3-substitued-4-(3-methoxy-4-isobutyryloxy-benzylideneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives. Indian Journal of Chemistry -Section B, 59B (02), 271-282.
  • Mercan, U., 2004.Toksikolojide Serbest Radikallerin Önemi. Yüzüncü Yıl Üniversitesi Veteriner Fakültesi Dergisi, 15, 91-96.
  • Oyaizu, M., (1986). Studies on products of browning reaction. Antioxidative activities of products of browning reaction prepared from glucosamine. The Japanese Journal of Nutrition and Dietetics, 44(17), 307-315.
  • Perez, C., Pauli, M. and Bazerque, P., 1990. An antibiotic assay by the well agar method. Acta Biologia et Medicine Experimentals, 15, 113-115.
  • Salgin-Goksen, U., Gokhan-Kelekci, N., Goktas, O., Köysal, Y., Kılıç, A., Işık, Ş., Aktay, G. and Özalp, M., 2007. 1-Acylthiosemicarbazides, 1,2,4-triazole-5(4H)-thiones, 1,3,4-thiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: synthesis, analgesic-anti-inflammatory and antimicrobial activities. Bioorganic & Medicinal Chemistry, 15(17), 5738-5751.
  • Shaker, R.M., Mahmoud, A.F. and Abdel-Latif, F.F., 2005. Synthesis and biological activities of novel 1,4-bridged bis-1,2,4-triazoles, bis-1,3,4-thiadiazoles and bis-1,3,4-oxadiazoles. Phosphorus, Sulfur, and Silicon and the Related Elements, 180(2), 397-406.
  • Sztanke, K., Tuzimski, T., Rzymowska. J., Pasternak, K. and Kandefer-Szerszen, M., 2008. Synthesis, determination of the lipophilicity, anticancer and antimicrobial properties of some fused 1,2,4-triazole derivatives. European Journal of Medicinal Chemistry, 43(2), 404-419.
  • Yüksek, H., Demirbaş, A., İkizler, A., Johansson, C.B., Çelik, C. and İkizler, A.A., 1997. Synthesis and antibacterial activities of some 4,5-dihydro-1H-1,2,4-triazol-5-ones. Arzneimittel Forschung-Drug Research, 47, 405-409.
  • Yüksek, H., Akyıldırım, O., Yola, M.L., Gürsoy-Kol, Ö., Çelebier, M., Kart, D. (2013). Synthesis, in vitro antimicrobial and antioxidant activities of some new 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives. Archiv Der Pharmazie, 346(6), 470–480.
  • Yüksek, H., Koca, E., Gürsoy-Kol, Ö., Akyıldırım, O. and Çelebier, M., 2015. Synthesis, in vitro antioxidant activity, and physicochemical properties of novel 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives. Journal of Molecular Liquids, 206, 359–366.
  • Zhao, W., Wang, X., Zhao, C. and Yan, Z., 2021. Immunomodulatory mechanism of Bacillus subtilis R0179 in RAW 264.7 cells against Candida albicans challenge. Microbial Pathogenesis, 157, 104988.

In vitro Antioxidant and Antimicrobial Activities of Some Novel 3-Alkyl-4-[3-methoxy-4-(p-nitrobenzoxy)-benzylideneamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones

Yıl 2022, Cilt: 22 Sayı: 2, 275 - 281, 30.04.2022

Sevda Manap Haydar Yüksek Zeynep Ekinci Elif Sel

https://doi.org/10.35414/akufemubid.1008079

Öz

In this study, nine novel 3-alkyl-4-[3-methoxy-4-(p-nitrobenzoxy)-benzylideneamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones (3) were synthesized from the reactions of 3-alkyl-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (1) with 3-methoxy-4-(p-nitrobenzoxy)-benzaldehyde (2), which was synthesized by the reaction of 3-methoxy-4-hydroxybenzaldehyde with p-nitrobenzoyl chloride by using triethylamine. The structures of novel compounds were established from IR, 1H NMR and 13C NMR spectral data. In addition, in vitro antibacterial capacities of the new compounds were determined against six bacteria by mains of agar well diffusion method. Furthermore, newly synthesized compounds antioxidant capacities were performed by three different methods.

Anahtar Kelimeler

Schiff base 1,2,4-Triazol-5-one Syntheses Antioxidant activity Antimicrobial activity

Kaynakça

  • Ahmad, A., Varshney, H., Rauf, A., Sherwani, A. and Owais, M., 2017. Synthesis and anticancer activity of long chain substituted 1,3,4-oxadiazol-2-thione,1,2,4-triazol-3-thione and 1,2,4-triazolo [3,4-b]-1,3,4-thiadiazine derivatives. Arabian Journal of Chemistry, 10, S3347-S3357.
  • Amir, M., Kumar, H. and Javed, S.A., 2008. Condensed bridgehead nitrogen heterocyclic system: Synthesis and pharmacological activities of 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole derivatives of ibuprofen and biphenyl-4-yloxy acetic acid. European Journal of Medicinal Chemistry, 43(10), 2056-2066.
  • Aktaş-Yokuş, Ö., Yüksek, H., Gürsoy-Kol, Ö. and Alpay-Karaoğlu, S., 2015. Synthesis and biological evaluation of new 1,2,4-triazol derivatives with their potentiometric titrations. Medicinal Chemistry Research, 24, 2813–2824.
  • Blois, M., 1958. Antioxidant determinations by the use of a stable free radical. Nature, 181, 1199-1200.
  • Çiftçi, E., Beytur, M., Calapoğlu, M., Gürsoy Kol, Ö., Alkan, M., Toğay, V.A., Manap, S. and Yüksek, H., 2018. Synthesis, characterization, antioxidant and antimicrobial activities and DNA damage of some novel 2-[3-alkyl (aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-phenoxyacetic acids in Human Lymphocytes. Research Journal of Pharmaceutical, Biological and Chemical Sciences, 9(5), 1760-1771.
  • Demirbas, N., Ugurluoglu, R. and Demirbas, A., 2002. Synthesis of 3-alkyl(Aryl)-4-alkylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-ones and 3-alkyl-4-alkylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones as antitumor agents. Bioorganic and Medicinal Chemistry, 10(12), 3717-3723.
  • Dinis, T.C.P., Madeira, V.M.C. and Almeida, L.M., 1994. Action of phenolic derivatives (Acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers. Archives of Biochemistry and Biophysics, 315(1), 161-169.
  • Eswaran, S., Adhikari, A.V. and Shetty, N.S., 2009. Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety. European Journal of Medicinal Chemistry, 44(11), 4637-4647.
  • Gürsoy-Kol, O., Yuksek, H. and Islamoglu, F., 2013. Synthesis and in vitro antioxidant activities of novel 4-(3-methyl-2-thienylmethyleneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives with their acidic properties. Journal of the Chemical Society of Pakistan, 35(4), 1179–1190.
  • Gürsoy-Kol, Ö.,Yüksek, H., Manap, S. and Tokalı, F. S., 2016. Synthesis, characterization, and antioxidant activities of novel 1-(morpholine-4-yl-methyl)-3-alkyl(aryl)-4-[4-(dimethylamino)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones. JOTCSA, Journal of the Turkish Chemical Society, Section A: Chemistry, 3 (3), 105-120.
  • İkizler, A.A. and Ün, R., 1979. Reactions of ester ethoxycarbonylhydrazones with some amine type compounds. Chimica Acta Turcica, 7, 269-290.
  • İkizler, A. and Yüksek, H., 1993. Acetylation of 4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones. Organic Preparations and Procedures International, 25(1), 99-105.
  • Lu, L., Li, Z., Shan, C., Ma, S., Nie, W., Wang, H., Chen, G., Li, S. and Shu, C., 2021. Whole transcriptome analysis of schinifoline treatment in Caenorhabditis elegans infected with Candida albicans. Molecular Immunology, 135, 312-319.
  • Malbec, F., Milcent, R., Vicart, P. and Bure, A.M., 1984. Synthesis of new derivatives of 4‐amino‐2,4‐dihydro‐1,2,4‐triazol‐3‐one as potential antibacterial agents. Journal of Heterocyclic Chemistry, 21(6), 1769-1774.
  • Manap, S., Gürsoy-Kol, Ö., Alkan, M. and Yüksek, H., 2020. Synthesis, in vitro antioxidant and antimicrobial activities of some novel 3-substitued-4-(3-methoxy-4-isobutyryloxy-benzylideneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives. Indian Journal of Chemistry -Section B, 59B (02), 271-282.
  • Mercan, U., 2004.Toksikolojide Serbest Radikallerin Önemi. Yüzüncü Yıl Üniversitesi Veteriner Fakültesi Dergisi, 15, 91-96.
  • Oyaizu, M., (1986). Studies on products of browning reaction. Antioxidative activities of products of browning reaction prepared from glucosamine. The Japanese Journal of Nutrition and Dietetics, 44(17), 307-315.
  • Perez, C., Pauli, M. and Bazerque, P., 1990. An antibiotic assay by the well agar method. Acta Biologia et Medicine Experimentals, 15, 113-115.
  • Salgin-Goksen, U., Gokhan-Kelekci, N., Goktas, O., Köysal, Y., Kılıç, A., Işık, Ş., Aktay, G. and Özalp, M., 2007. 1-Acylthiosemicarbazides, 1,2,4-triazole-5(4H)-thiones, 1,3,4-thiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: synthesis, analgesic-anti-inflammatory and antimicrobial activities. Bioorganic & Medicinal Chemistry, 15(17), 5738-5751.
  • Shaker, R.M., Mahmoud, A.F. and Abdel-Latif, F.F., 2005. Synthesis and biological activities of novel 1,4-bridged bis-1,2,4-triazoles, bis-1,3,4-thiadiazoles and bis-1,3,4-oxadiazoles. Phosphorus, Sulfur, and Silicon and the Related Elements, 180(2), 397-406.
  • Sztanke, K., Tuzimski, T., Rzymowska. J., Pasternak, K. and Kandefer-Szerszen, M., 2008. Synthesis, determination of the lipophilicity, anticancer and antimicrobial properties of some fused 1,2,4-triazole derivatives. European Journal of Medicinal Chemistry, 43(2), 404-419.
  • Yüksek, H., Demirbaş, A., İkizler, A., Johansson, C.B., Çelik, C. and İkizler, A.A., 1997. Synthesis and antibacterial activities of some 4,5-dihydro-1H-1,2,4-triazol-5-ones. Arzneimittel Forschung-Drug Research, 47, 405-409.
  • Yüksek, H., Akyıldırım, O., Yola, M.L., Gürsoy-Kol, Ö., Çelebier, M., Kart, D. (2013). Synthesis, in vitro antimicrobial and antioxidant activities of some new 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives. Archiv Der Pharmazie, 346(6), 470–480.
  • Yüksek, H., Koca, E., Gürsoy-Kol, Ö., Akyıldırım, O. and Çelebier, M., 2015. Synthesis, in vitro antioxidant activity, and physicochemical properties of novel 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives. Journal of Molecular Liquids, 206, 359–366.
  • Zhao, W., Wang, X., Zhao, C. and Yan, Z., 2021. Immunomodulatory mechanism of Bacillus subtilis R0179 in RAW 264.7 cells against Candida albicans challenge. Microbial Pathogenesis, 157, 104988.
Toplam 25 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Organik Kimya
Bölüm Makaleler
Yazarlar

Sevda Manap 0000-0002-5025-9622

Haydar Yüksek 0000-0003-1289-1800

Zeynep Ekinci Bu kişi benim 0000-0002-1527-5416

Elif Sel Bu kişi benim 0000-0002-5887-8516

Yayımlanma Tarihi 30 Nisan 2022
Gönderilme Tarihi 11 Ekim 2021
Yayımlandığı Sayı Yıl 2022 Cilt: 22 Sayı: 2

Kaynak Göster

APA Manap, S., Yüksek, H., Ekinci, Z., Sel, E. (2022). Bazı Yeni 3-Alkil-4-[3-metoksi-4-(p-nitrobenzoksi)-benzilidenamino]-4,5-dihidro-1H-1,2,4-triazol-5-on Bileşiklerinin in vitro Antioksidan ve Antimikrobiyal Özellikleri. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, 22(2), 275-281. https://doi.org/10.35414/akufemubid.1008079
AMA Manap S, Yüksek H, Ekinci Z, Sel E. Bazı Yeni 3-Alkil-4-[3-metoksi-4-(p-nitrobenzoksi)-benzilidenamino]-4,5-dihidro-1H-1,2,4-triazol-5-on Bileşiklerinin in vitro Antioksidan ve Antimikrobiyal Özellikleri. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. Nisan 2022;22(2):275-281. doi:10.35414/akufemubid.1008079
Chicago Manap, Sevda, Haydar Yüksek, Zeynep Ekinci, ve Elif Sel. “Bazı Yeni 3-Alkil-4-[3-Metoksi-4-(p-Nitrobenzoksi)-Benzilidenamino]-4,5-Dihidro-1H-1,2,4-Triazol-5-on Bileşiklerinin in Vitro Antioksidan Ve Antimikrobiyal Özellikleri”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 22, sy. 2 (Nisan 2022): 275-81. https://doi.org/10.35414/akufemubid.1008079.
EndNote Manap S, Yüksek H, Ekinci Z, Sel E (01 Nisan 2022) Bazı Yeni 3-Alkil-4-[3-metoksi-4-(p-nitrobenzoksi)-benzilidenamino]-4,5-dihidro-1H-1,2,4-triazol-5-on Bileşiklerinin in vitro Antioksidan ve Antimikrobiyal Özellikleri. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 22 2 275–281.
IEEE S. Manap, H. Yüksek, Z. Ekinci, ve E. Sel, “Bazı Yeni 3-Alkil-4-[3-metoksi-4-(p-nitrobenzoksi)-benzilidenamino]-4,5-dihidro-1H-1,2,4-triazol-5-on Bileşiklerinin in vitro Antioksidan ve Antimikrobiyal Özellikleri”, Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, c. 22, sy. 2, ss. 275–281, 2022, doi: 10.35414/akufemubid.1008079.
ISNAD Manap, Sevda vd. “Bazı Yeni 3-Alkil-4-[3-Metoksi-4-(p-Nitrobenzoksi)-Benzilidenamino]-4,5-Dihidro-1H-1,2,4-Triazol-5-on Bileşiklerinin in Vitro Antioksidan Ve Antimikrobiyal Özellikleri”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 22/2 (Nisan 2022), 275-281. https://doi.org/10.35414/akufemubid.1008079.
JAMA Manap S, Yüksek H, Ekinci Z, Sel E. Bazı Yeni 3-Alkil-4-[3-metoksi-4-(p-nitrobenzoksi)-benzilidenamino]-4,5-dihidro-1H-1,2,4-triazol-5-on Bileşiklerinin in vitro Antioksidan ve Antimikrobiyal Özellikleri. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. 2022;22:275–281.
MLA Manap, Sevda vd. “Bazı Yeni 3-Alkil-4-[3-Metoksi-4-(p-Nitrobenzoksi)-Benzilidenamino]-4,5-Dihidro-1H-1,2,4-Triazol-5-on Bileşiklerinin in Vitro Antioksidan Ve Antimikrobiyal Özellikleri”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, c. 22, sy. 2, 2022, ss. 275-81, doi:10.35414/akufemubid.1008079.
Vancouver Manap S, Yüksek H, Ekinci Z, Sel E. Bazı Yeni 3-Alkil-4-[3-metoksi-4-(p-nitrobenzoksi)-benzilidenamino]-4,5-dihidro-1H-1,2,4-triazol-5-on Bileşiklerinin in vitro Antioksidan ve Antimikrobiyal Özellikleri. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. 2022;22(2):275-81.
 Kapak Resmi İndir