Bazı Sübstitüe Fenil/Piridin-4-il Halkası İçeren 1,2,4-triazolo[3,4-b][1,3,4]tiyadiazol Bileşiklerinin Sentezi ve Karakterizasyonu
DOI:
https://doi.org/10.5281/zenodo.18209758Anahtar Kelimeler:
Sübstitüe aromatik karboksilik asitler, Fosfor oksiklorür, Halkalanma reaksiyonları, 1 2 4-triazolÖzet
Bu çalışmada, 4-amino-3-fenil/(piridin-4-il)-5-merkapto-4H-1,2,4-triazol bileşiği ile farklı halojen ve metil sübstitüentleri içeren karboksilli asitler fosfor oksiklorür ortamında reaksiyona sokularak altı adet yeni 1,2,4-triazolo-tiyadiazol yapısını içeren bileşik sentezlenmiştir. Fosfor oksiklorür yapılan halka kapanması reaksiyonunda etken reaktiftir. Sentezlenen bileşiklerin yapısal özelliklerinin belirlenmesi amacıyla Fourier dönüşümlü kızılötesi spektroskopisi, proton nükleer manyetik rezonans spektroskopisi ve elektrosprey iyonizasyon kütle spektrometrisi analiz yöntemleri kullanılarak karakterize edilmiştir. FTIR spektrumları, bileşiklerde bulunan temel fonksiyonel gruplar hakkında bilgi vermiş, 1H-NMR spektrumları proton ortamlarına ilişkin genel yapısal değerlendirmeye ve ESI-MS analizlerinde gözlenen [M+H]+ moleküler iyonları ise, moleküler kütlelerin belirlenmesine olanak sağlamıştır. Uygulanan analizlerden elde edilen bulgular, sentezlenen 1,2,4-triazolo-tiyadiazol türevlerinin uygun şekilde oluştuğunu göstermiştir.
Referanslar
Abdelli, A., Azzouni, S., Plais, R., Gaucher, A., Efrit, M.L., Prim, D., 2021. Recent advances in the chemistry of 1,2,4-triazoles: synthesis, reactivity and biological activities. Tetrahedron Letters, 86: 153518.
Ali, A.A., 2020. 1,2,3-triazoles: synthesis and biological application. In: Azoles: synthesis, properties, applications and perspectives. IntechOpen.
Alsehli, M., Aljuhani, A., Ihmaid, S.K., El-Messery, S.M., Othman, D.I.A., El-Sayed, A.A.A., Ahmed, H.E.A., Rezki, N., Aouad, M.R., 2022. Design and synthesis of benzene homologues tethered with 1,2,4-triazole and 1,3,4-thiadiazole motifs revealing dual MCF-7/HepG2 cytotoxic activity with prominent selectivity via histone demethylase LSD1 inhibitory effect. International Journal of Molecular Sciences, 23: 8796.
Beytur, M., Avinca, İ., 2021. Molecular, electronic, nonlinear optical and spectroscopic analysis of heterocyclic 3-substituted-4-(3-methyl-2-thienylmethyleneamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones: experiment and DFT calculations. Heterocyclic Communications, 27: 1–16.
Bodzioch, A., Pomikło, D., Celeda, M., Pietrzak, A., Kaszyński, P., 2019. 3-substituted benzo[e][1,2,4]triazines: synthesis and electronic effects of the C(3) substituent. The Journal of Organic Chemistry, 84(10): 6377–6394.
Caceres, M., Kesternich, V., Pérez-Fehrmann, M., Castroagudín, M., Nelson, R., Quezada, V., Christen, P., Castro-Álvarez, A., Cárcamo, J.G., 2025. Ultrasound-assisted synthesis of substituted chalcone-linked 1,2,3-triazole derivatives as antiproliferative agents: in vitro antitumor activity and molecular docking studies. International Journal of Molecular Sciences, 26: 3389.
Dai, J., Tian, S., Yang, X., Liu, Z., 2022. Synthesis methods of 1,2,3-/1,2,4-triazoles: a review. Frontiers in Chemistry, 10: 891484.
Depa, N., Erothu, H., 2022. Synthesis and biological active compounds of nitrogen-containing heterocyclic compounds: a review. Rasayan Journal of Chemistry.
Ebenezer, O., Amra-Jordaan, M., Carena, G., Bono, T., Shapi, M., Tuszynski, J.A., 2022. An overview of the biological evaluation of selected nitrogen-containing heterocycle medicinal chemistry compounds. International Journal of Molecular Sciences, 23: 8117.
El-Reedy, A.A.M., Soliman, N.K., 2020. Synthesis, biological activity and molecular modeling study of novel 1,2,4-triazolo[4,3-b][1,2,4,5]tetrazines and 1,2,4-triazolo[4,3-b][1,2,4]triazines. Scientific Reports, 10: 62977.
Gençer, K., Çevik, A., Levent, S., Sağlık, B., Korkut, B., Özkay, Y., Ilgın, S., Öztürk, Y., 2017. New benzimidazole-1,2,4-triazole hybrid compounds: synthesis, anticandidal activity and cytotoxicity evaluation. Molecules, 22: 507.
Guan, Q., Xing, S., Wang, L., Zhu, J., Guo, C., Xu, C., Zhao, Q., Wu, Y., Chen, Y., Sun, H., 2024. Triazoles in medicinal chemistry: physicochemical properties, bioisosterism, and application. Journal of Medicinal Chemistry, 67: 7788–7824.
Guo, H.-Y., Chen, Z.-A., Shen, Q.-K., Quan, Z.-S., 2021. Application of triazoles in the structural modification of natural products. Journal of Enzyme Inhibition and Medicinal Chemistry, 36(1): 1115–1144.
Irfan, M., Khan, H.A., Bibi, S., Wu, G., Ali, A., Khan, S.G., Alhokbany, N., Rasool, F., Chen, K., 2024. Exploration of nonlinear optical properties of 4-methyl-4H-1,2,4-triazol-3-yl)thio)-N-phenylpropanamide based derivatives: experimental and DFT approach. Scientific Reports, 14: 51788.
Karpun, Y., Polishchuk, N., 2021. Synthesis and antimicrobial activity of S-substituted derivatives of 1,2,4-triazole-3-thiol. ScienceRise: Pharmaceutical Science, 3(31).
Khilkovets, A., Karpenko, Y., Bigdan, O., Parchenko, M., Parchenko, V., 2022. Synthetic and biological aspects of studying the properties of 1,2,4-triazole derivatives. Scientific Journal of Polonia University, 51(2).
Martins, P., Jesus, J., Santos, S., Raposo, L.R., Roma-Rodrigues, C., Baptista, P.V., Fernandes, A.R., 2015. Heterocyclic anticancer compounds: recent advances and the paradigm shift towards the use of nanomedicine’s tool box. Molecules, 20: 16852–16891.
Matin, M.M., Matin, P., Rahman, M.R., Ben Hadda, T., Almalik, F.A., Mahmud, S., Ghoneim, M.M., Alruwaily, M., Alshehri, S., 2022. Triazoles and their derivatives: chemistry, synthesis, and therapeutic applications. Frontiers in Molecular Biosciences, 9: 864286.
Salma, U., Ahmad, S., Alam, M.Z., Khan, S.A., 2023. A review: synthetic approaches and biological applications of triazole derivatives. Journal of Molecular Structure, 1301: 137240.
Thakur, D., Kumar, V., Tyagi, S.K., Parmar, R.S., 2023. A review on the medicinal significance of heterocyclic compounds. International Journal for Research in Applied Science & Engineering Technology, 11(7).
Xiao, P., Song, X., Xiong, X., Peng, D., Nie, X., 2023. Synthesis, crystal structure, spectral characterization and antifungal activity of novel phenolic acid triazole derivatives. Molecules, 28: 6970.
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Telif Hakkı (c) 2026 EJONS Uluslararası Matematik, Mühendislik ve Doğa Bilimleri Dergisi
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