New Heterocyclic Scaffolds with Thiophene and 1,2,4-triazole Rings

Mykola Tupychak1 tupychakmykola [at] gmail.com
Olga Shyyka1
Nazariy Pokhodylo1
Mykola Obushak1
  1. Department of Organic Chemistry, Ivan Franko National University of Lviv, Kyryla i Mefodiya St. 6, Lviv 79005, Ukraine
Abstract 

Some chemical modifications of the Gewald 2-amino-thiophenes and 3-aminothiophenes were established. A number of new substituted thienotriazolopyrimidines, thienotriazoles and thiophenyl-triazolothiadiazine were obtained. This study provides new approaches to the construction of substituted 1H-1,2,4-triazoles bearing thiophene core and allows to use data in medical chemistry for further drug discovery.

References 

[1]. R.M. Mohareb, A.E.M. Abdallah, M.H.E. Helal, S.M.H. Shaloof, “Synthesis and structure elucidation of some novel thiophene and benzothiophene derivatives as cytotoxic agents”, Acta Pharm., vol. 66, pp. 53–68, 2016.

[2]. N.B. Saidov, V.A Georgiyants, E.Yu. Lipakova, “Synthesis and pharmacological potential of new 3-mercapto-4-amino(pyrrolyl-1)-5-(thienyl-2)-1,2,4- triazole(4H) derivatives”, Pharm. Chem. J., vol. 51, no. 1, pp. 26−29, 2017.

[3]. S. Botros, O.M. Khalil, M.M Kamel, Ya.S. El-Dash, “Synthesis, Characterization and Cytotoxicity of Substituted [1]Benzothieno[3,2-e][1,2,4]triazolo[4,3-a]pyrimidines”, Acta Chim. Slov., vol. 64, pp. 102– 116, 2017.

[4]. H.N. Hafez, S.A. Alsalaman, A-R.B.A. El-Gazzar, «Synthesis of thiophene and N-substituted thieno[3,2-d] pyrimidine derivatives as potent antitumor and antibacterial agents” Acta Pharm., vol. 67, pp. 275 292, 2017.

[5]. B. Zhang,, Y.-H. Li, Y. Liu, Y.-R. Chen, E.-S. Pan, W.-W. You, P.-L. Zhao, “Design, synthesis and biological evaluation of novel 1,2,4-triazolo[3,4-b] [1,3,4]thiadiazines bearing furan and thiophene nucleus” Eur. J. Med. Chem., vol. 103, pp. 335−350, 2015.

[6]. N.D. Obushak, N.T. Pokhodylo, I.I. Krupa, V.S. Matiichuk, “Synthesis of Substituted 4-([1,2,4] Triazolo[3,4-b]-[1,3,4]thiadiazol-6-yl)-quinolines”, Russ. Journ. of Org. Chem., vol. 43, no. 8, pp. 1223−1227, 2007.

[7]. N.T. Pokhodylo, V. S. Matiychuk., M.D. Obushak, “New convenient synthesis of 2,3-diaminothieno[2,3-d]pyrimidin-4(3H)-one derivates from substituted alkyl 2-(1H-tetrazol-1-yl)thiophene- 3-carboxylates”, Tetrahedron, vol. 64, no. 7, pp. 1430−1434, 2008.