j. fac. pharm. ankara

Journal of Faculty of Pharmacy of Ankara University

1015-3918 2564-6524

Ankara University

10.33483/jfpau.580011

Pharmacology and Pharmaceutical Sciences

Eczacılık ve İlaç Bilimleri

YENİ N'-SÜBSTİTÜE-2-((5-(TİYOFEN-2-İLMETİL)-4H-1,2,4-TRİAZOL-3-İL)TİYO) ASETOHİDRAZİTLERİN SENTEZ YÖNTEMİ

METHOD OF SYNTHESIS NOVEL N'-SUBSTITUTED2-((5-(THIOPHEN-2-YLMETHYL)-4H-1,2,4-TRIAZOL-3-YL)THIO) ACETOHYDRAZIDES

https://orcid.org/0000-0003-2861-1826

Safonov

Andrey

05 31 2020

44 2 242 252 06 19 2019 04 18 2020

1971

Journal of Faculty of Pharmacy of Ankara University

Amaç: Bu çalışmanın amacı, bir seri yeni N'-sübstitüe-2-((5-(tiyofen-2-ilmetil)-4H-1,2,4-triazol-3-il)tiyo)asetohidrazit sentezlemektir.Gereç ve Yöntem: Bileşik (3) (2-((3-(tiyofen-2-ilmetil)-1H-1,2,4-triazol-5-il)tiyo)asetohidrazit), izopropil 2-((3-(tiyofen-2-ilmetil)-1H-1,2,4-triazol-5-il)tiyo)asetat (1)'e hidrazin hidrat ilave edilerek sentezlenmiş ve propan-2-ol içerisinde 3-4 saat geri çeviren soğutucuda bekletilmiştir. Bileşikler (5a-s) (N'-sübstitüe-2-(((3-(tiyofen-2-ilmetil)-1H-1,2,4-triazol-5-il)tiyo)asetohidrazit), 3-(tiyofen-2-ilmetil)-1H-1,2,4-triazol-5-il)tiyo)asetohidrazit (3) aromatik veya heterosiklik aldehit ilave edilerek sentezlenmiştir. Çözücü olarak asetik asit kullanılmıştır. Sentezlenen bileşiklerin yapısı, Elementel analiz (CHNS), 1H-NMR ve Kromatografik kütle spektral analizi kullanılarak doğrulanmıştır.Sonuç ve Tartışma: Bileşik (3), Bileşik (1)'e hidrazin hidrat ilave edilerek sentezlenmiş ve NH = 2,01 ppm’de (NH2) nedeniyle bir singlet formunda 1H-NMR pik ile karakterize edilmiştir. Bileşikler (5a-s), Bileşik (3)’e aromatik veya heterosiklik aldehit ilave edilerek asetik asit ortamda sentezlenmiştir. Bileşikler (5a-s) için önerilen yapı, 1H-NMR sinyalleri ile doğrulanmıştır. Temel kimyasal yapılarını doğrulamak için sentezlenen bileşikler üzerinde elementel analiz (CHNS) yapılmış ve hesaplanan yüzdelerle kabul edilebilir bir uyum sağladığı gösterilmiştir.

Objective: The purpose of this work is to synthesize new series of N'-substituted-2-((5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-3-yl)thio)acetohydrazides.Material and Method: The compound (3) (2-((3-(thiophen-2-ylmethyl)-1H-1,2,4-triazol-5-yl)thio)acetohydrazide) was synthesized by adding hydrazine hydrate to isopropyl 2-((3-(thiophen-2-ylmethyl)-1H-1,2,4-triazol-5-yl)thio)acetate (1) and refluxed for 3-4 h in propan-2-ol. Synthesis of (5a-s) (N'-substituted-2-((3-(thiophen-2-ylmethyl)-1H-1,2,4-triazol-5-yl)thio)acetohydrazide) was carried out by adding aromatic or heterocyclic aldehyde to 2-((3-(thiophen-2-ylmethyl)-1H-1,2,4-triazol-5-yl)thio)acetohydrazide (3) in acetic acid. The structure of synthesized compounds is confirmed using Elemental analysis (CHNS), 1H-NMR and Chromatographic mass spectral analysis.Result and Discussion: The compound (3) was synthesized by adding hydrazine hydrate to compound (1) and compound (3) characterized by 1H-NMR peak, as a singlet due to (NH2) at δ=2.01ppm. Synthesis of (5a-s) was carried out by adding aromatic or heterocyclic aldehyde to compound (3) in acetic acid. The signals of 1H NMR for (5a-s) are consented with the proposed structure. The elemental analysis (CHNS) was accomplished for synthesized compounds to confirm their basic chemical structures and revealed acceptable agreement with the calculated percentages.

1H-NMR heterocyclic compounds synthesis 1.2.4-triazole

1H-NMR heterosiklik bileşikler sentez 1.2.4-triazol

Pattan, S., Gadhave, P., Tambe, V., Dengale, S., Thakur, D., Hiremath, S. V., & Deotarse, P. (2012). Synthesis and evaluation of some novel 1, 2, 4-triazole derivatives for antmicrobial, antitubercular and anti-inflammatory activities. Indian Journal of Chemistry Section B 51(1):297-301.

Chen, W., Su, H., Xu, Y., Jin, C. Scientific Reports. 2017.; 7:405–414.

Rodionova N., Manukovskaya M., Kolomnikova Ya. et. al. Vestnik Voronezhskogo gosudarstvennogo universiteta inzhenernyih tehnologiy. 2015.; Vol. 66, Iss. 4: 98–103.

Shcherbyna R.O. Farmatsevtychnyi chasopys. 2014.; 4: 145–150.

Aksonova I. I., Shcherbyna R. O., Panasenko O. I. et. al. Ukrainskyi biofarmatsevtychnyi zhurnal. 2014.; 6: 78–82.

Cervantes-Elizarrarás, A., Piloni-Martini, J., Ramírez-Moreno, E., Alanís-García, E., Güemes-Vera, N., Gómez-Aldapa, C. A., del Socorro Cruz-Cansino, N. Ultrasonics Sonochemistry. 2017; Vol. 34: 371–379.

Thakkar, S. S., Thakor, P., Doshi, H., & Ray, A. (2017). 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. Bioorganic & Medicinal Chemistry. 25(15):4064-4075. doi: 10.1016/j.bmc.

Kumar, G. S., Prasad, Y. R., & Chandrashekar, S. M. (2013). Synthesis and pharmacological evaluation of novel 4-isopropylthiazole-4-phenyl-1, 2, 4-triazole derivatives as potential antimicrobial and antitubercular agents. Medicinal Chemistry Research, 22(2), 938-948.

Patel, N. B., Khan, I. H., Pannecouque, C., & De Clercq, E. (2013). Anti-HIV, antimycobacterial and antimicrobial studies of newly synthesized 1, 2, 4-triazole clubbed benzothiazoles. Medicinal Chemistry Research, 22(3), 1320-1329.

Rud, A. M., Kaplaushenko, A. G., Pruglo, Y. S., & Frolova, Y. S. (2018). Establishment Of Diuretic Activity Indicators For (3-Thio-4-R-4-H-1,2,4-triazole-5-yl)(phenyl)methanols And Their Derivatives. Aktualʹnì Pitannâ Farmacevtičnoï ì Medičnoï Nauki ta Praktiki, 2018(2), 215-219.

Saidov, G., Sverdlova, O. and Bakhshiev, N. (1995). Prakticheskoe rukovodstvo po molekuli︠a︡rnoĭ spektroskopii. 1st ed. Sankt-Peterburg: Izd-vo Sankt-Peterburgskogo universiteta.

Kazitsena, L. and Kupletskaya, N. (1979). Primenenie UF-, IK-, YaMR - i MАSS - spectrometrii v orhanicheskoy khimii. 2nd ed. Moskow: University of Moscow, p.240.

Varynskyi, B., Knysh, Y., Parchenko, V., Panasenko, O., & Kaplaushenko, A. (2015). The study of retention regularities for the potential drug substances of 1,2,4-triazol-3-ylthioacetic acids and their salts series by the method of HPLC/DAD-MS. Journal Of Organic And Pharmaceutical Chemistry, 13(4), 68-75.

Tkachenko, A., Zazharsky, V., Bilan, M., & Kovaleva, L. (2010). Some peculiarities of bovis tuberculosis display in long not favourably farm. News of Dniproptrovsk State Agrarian and Economic University, (1), 100-103