Benzoik Asit Temelli Yeni 1,3,4-Tiyadiazollerin Sentezi, Karakterizasyonu, ve Antioksidan Aktiviteleri

Year 2021, , 155 - 163, 31.01.2021

Hasan Yakan

https://doi.org/10.31202/ecjse.794370

Cited By: 2

Abstract

N-aril-1,3,4-tiyadazol türevleri benzoik asit ile N-ariltiyosemikarbazitlerin fosforoksiklorür varlığında halkalaşma tepkimesi sonucu elde edildi. Sentezlenen bileşiklerin yapısı FT–IR, 1H NMR, and 13C NMR, spektroskopik yöntemler ve elementel analiz ile aydınlatılmıştır. Sentezlenen bileşiklerin antioksidan özellikleri DPPH yöntemi ile analiz edildi. IC50 değerleri 25.17-43.55 𝜇M arasında değişmektedir. Bileşik II, sentezlenen bileşikler arasında en iyi antioksidan aktivite göstermiştir. Ayrıca bu çalışmada, farklı fonksiyonel gruplara sahip bileşiklerin radikal yakalama tepkimelerinde yapı-aktivite ilişkisi açıklandı.

Keywords

1,3,4-Tiyadiazoller, DPPH, yapı-aktivite ilişkisi, spektroskopik yöntemler

Project Number

-

Synthesis, Characterization, and Antioxidant Activities of New 1,3,4-Thiadiazoles Based on Benzoic Acid

Abstract

N-aryl-1,3,4-thiadiazole derivatives were obtained by cyclization reaction of benzoic acid and N-arylthiosemicarbazides in the presence of phosphorous oxychloride (POCl3). FT-IR, 1H-NMR, and 13C-NMR, spectroscopic methods, and elemental analysis were used to elucidate the identification of the synthesized molecules. The in vitro antioxidant activity of the synthesized molecules was analysed with the 1,1-diphenyl-2-picryl hydrazyl (DPPH) free-radical–trapping process. IC50 values of these molecules were measured from 25.17 to 43.55 𝜇M. Among the synthesized compounds, compound II had the best antioxidant activity. Moreover, this work explained the structure-activity relationship of the obtained molecules with different substituents in radical trapping reactions.

Keywords

1,3,4-thiadiazoles, DPPH, structure–activity relationship, spectroscopic methods

Supporting Institution

-

Project Number

-

References

• [1] Jain, A.K.; Sharma, S.; Vaidya, A.; Ravichandran, V.; Agrawal, R.K. 1,3,4‐Thiadiazole and its derivatives: A review on recent progress in biological activities. Chemical Biology & Drug Design. 2013; 81(5): 557-576.
• [2] Çevik, U. A.; O. Derya; Levent, S.; Sağlik, B. N.; Çavuşoğlu, B.K; Karaduman, A.B.; Özkay, Y.; Kaplancikli, Z.A.; "Synthesis and biological evaluation of novel 1, 3, 4-thiadiazole derivatives as possible anticancer agents." Acta Pharmaceutica 2020; 70(4): 499-513.
• [3] Khan, I.; Ali, S.; Hameed, S.; Rama, N.H.; Hussain, M.T.; Wadood, A.; Uddin, R.; Ul-Haq, Z.; Khan, A.; Ali, S. Synthesis, antioxidant activities and urease inhibition of some new 1,2,4-triazole and 1,3,4-thiadiazole derivatives. European Journal of Medicinal Chemistry. 2010; 45(11): 5200-5207.
• [4] Kumar, H.; Javed, S.A.; Khan, S.A.; Amir, M. 1,3,4-Oxadiazole/thiadiazole and 1,2, 4-triazole derivatives of biphenyl-4-yloxy acetic acid: synthesis and preliminary evaluation of biological properties. European Journal of Medicinal Chemistry. 2008; 43(12): 2688-2698.
• [5] Muğlu, H.; Şener, N.; Emsaed, H.A.M.; Özkınalı, S.; Özkan, O.E.; Gür, M. Synthesis and characterization of 1,3,4-thiadiazole compounds derived from 4-phenoxybutyric acid for antimicrobial activities. Journal of Molecular Structure. 2018; 1174: 151-159.
• [6] Muğlu, H.; Yakan, H.; Shouaib, H.A. New 1,3,4-thiadiazoles based on thiophene-2-carboxylic acid: Synthesis, characterization, and antimicrobial activities. Journal of Molecular Structure. 2020; 1203: 127470.
• [7] Behrouzi-Fardmoghadam, M.; Poorrajab, F.; Ardestani, S.K.; Emami, S.; Shafiee, A.; Foroumadi, A. Synthesis and in vitro anti-leishmanial activity of 1-[5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl] and 1-[5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-yl]-4-aroylpiperazines. Bioorganic & medicinal chemistry. 2008; 16(8): 4509-4515.
• [8] Kamboj, V.K.; Kapoor, A.; Jain, S. Synthesis, antimicrobial, and antioxidant screening of aryl acetic acid incorporated 1, 2, 4‐triazolo‐1, 3, 4‐thiadiazole derivatives. Journal of Heterocyclic Chemistry. 2019; 56(4): 1376-1382.
• [9] Jakovljević, K.; Matić, I.Z.; Stanojković, T.; Krivokuća, A.; Marković, V.; Joksović, M.D.; Mihailović, N.; Nićiforović, M.; Joksović, L. Synthesis, antioxidant and antiproliferative activities of 1, 3, 4-thiadiazoles derived from phenolic acids. Bioorganic & Medicinal Chemistry Letters. 2017; 27(16): 3709-3715.
• [10] Gowda, K.; Swarup, H.A.; Nagarakere, S.C.; Rangappa, S.; Kanchugarkoppal, R.S.; Kempegowda, M. Structural studies of 2, 5-disubstituted 1, 3, 4-thiadiazole derivatives from dithioesters under the mild condition: Studies on antioxidant, antimicrobial activities, and molecular docking. Synthetic Communications. 2020; 50(10): 1528-1544.
• [11] Hu, Y.; Li, C.-Y.; Wang, X.-M.; Yang, Y.-H.; Zhu, H.-L. 1,3,4-Thiadiazole: synthesis, reactions, and applications in medicinal, agricultural, and materials chemistry. Chemical reviews. 2014; 114(10): 5572-5610.
• [12] Halliwell, B.; Gutteridge, J.M. Free radicals in biology and medicine: Oxford University Press, USA; 2015.
• [13] Tyagi, Y.K.; Kumar, A.; Raj, H.G.; Vohra, P.; Gupta, G.; Kumari, R.; Kumar, P.; Gupta, R.K. Synthesis of novel amino and acetyl amino-4-methylcoumarins and evaluation of their antioxidant activity. European journal of medicinal chemistry. 2005; 40(4): 413-420.
• [14] Brand-Williams, W.; Cuvelier, M.-E.; Berset, C. Use of a free radical method to evaluate antioxidant activity. LWT-Food science and Technology. 1995; 28(1): 25-30.
• [15] Demir, F., Aliyazıcıoğlu, Y., Demir, S., Investigation of the Effect of Acidification Process on Antioxidant Properties of Laurocerasus officinalis Extracts. El-Cezerî Journal of Science and Engineering, 2017, 4(3); 365-373.
• [16] Naik, N.; Vijay Kumar, H.; Vidyashree, P.B. Synthesis and evaluation of antioxidant potential of novel isatin analogues. J Pharm Res. 2011; 4(8): 2686-2689.
• [17] Frankel, E.N.; Meyer, A.S. The problems of using one‐dimensional methods to evaluate multifunctional food and biological antioxidants. Journal of the Science of Food and Agriculture. 2000; 80(13): 1925-1941.
• [18] Luszczki, J.J.; Karpińska, M.; Matysiak, J.; Niewiadomy, A. Characterization and preliminary anticonvulsant assessment of some 1, 3, 4-thiadiazole derivatives. Pharmacological Reports. 2015; 67(3): 588-592.
• [19] Tahtaci, H.; Er, M.; Karakurt, T.; Sancak, K. Synthesis of 1, 3, 4-thiadiazol-2 (3H)-one derivatives via an unexpected intramolecular addition-elimination reaction of 1, 3, 4-thiadiazoles. Tetrahedron. 2017; 73(30): 4418-4425.
• [20] Williams, D.; Fleming, I. RNA structure and NMR spectroscopy. Spectroscopic Methods in Organic Chemistry. McGraw-Hill, New York; 1996.
• [21] Shahidi, F. Antioxidants: Principles and applications. Handbook of antioxidants for food preservation: Elsevier; 2015, 1-14.
• [22] Wanasundara, P.; Shahidi, F. Antioxidants: Science, technology, and applications. 6th ed. Vol. 1. Hoboken, NJ, USA: Wiley Interscience; 2005.
• [23] Mohammadpour, M.; Sadeghi, A.; Fassihi, A.; Saghaei, L.; Movahedian, A.; Rostami, M. Synthesis and antioxidant evaluation of some novel ortho-hydroxypyridine-4-one iron chelators. Research in pharmaceutical sciences. 2012; 7(3): 171-179.
• [24] Santos-Sánchez, N.F.; Salas-Coronado, R.; Villanueva-Cañongo, C.; Hernández-Carlos, B. Antioxidant compounds and their antioxidant mechanism. Antioxidants: IntechOpen; 2019.
• [25] Bendary, E.; Francis, R.; Ali, H.; Sarwat, M.; El Hady, S. Antioxidant and structure–activity relationships (SARs) of some phenolic and anilines compounds. Annals of Agricultural Sciences. 2013; 58(2): 173-181.
• [26] Božić, A.; Filipović, N.; Novakovic, I.; Bjelogrlić, S.; Nikolić, J.; Drmanić, S.; Marinković, A. Synthesis, antioxidant and antimicrobial activity of carbohydrazones. Journal of the Serbian Chemical Society. 2017; 82(5): 495-508.
• [27] Queiroz, M.-J.R.; Ferreira, I.C.; Calhelha, R.C.; Estevinho, L.M. Synthesis and antioxidant activity evaluation of new 7-aryl or 7-heteroarylamino-2, 3-dimethylbenzo [b] thiophenes obtained by Buchwald–Hartwig C–N cross-coupling. Bioorganic & medicinal chemistry. 2007; 15(4): 1788-1794.