Analysis of the relationship between the predicted biological activity and the chemical structure of S-derivatives of 5-(5-bromofuran-2-yl)-4R-1,2,4-triazole-3-thiols




bromfuran 1,2,4-triazoles, prediction of biological activity, dependence “structure – action”


1,2,4-Triazole derivatives are actively used as components in the development of new drugs, plant protection products, polymeric materials, anti-corrosion agents and etc. Chemical modeling of substituted 1,2,4-triazoles due to the introduction of different pharmacophores into the structure is very popular among scientists in various fields. Today it is known that some S-derivatives of 5-(5-bromofuran-2-yl)-4R-1,2,4-triazole-3-thiols have antimicrobial activity.

The aim of the work is to analyze the relationships between the predicted biological activity and the chemical structure of S-derivatives of 5-(5-bromofuran-2-yl) -4R-1,2,4-triazole-3-thiols.

Materials and methods. Virtual screening of compounds was performed using the computer program PASS (Prediction of activity spectra for substances). The results of the forecast were issued in the form of a list of names of probable types of activity with estimates of the probabilities of presence (Pa) and absence of each activity (Pi), which had values from 0 to 1.

Results. Analyzing the prediction of biological activity on protein targets from the group of enzymes, we can said that derivatives of 5-(5-bromofuran-2-yl)-4R-1,2,4-triazole-3-thiols were active in the group of oxyreductases (Glutathione reductase, mitochondrial; Cyclooxygenase-2; Hypoxia-inducible factor prolyl hydroxylase 2), which catalyzed oxidation reactions, the transfer of electrons from one molecule (reducer, electron donor) to another (oxidant, electron acceptor). These compounds can demonstrate antioxidant, antihypoxic activity.

Conclusions. The conducted forecast of biological activity revealed that derivatives of 5-(5-bromofuran-2-yl)-4R-1,2,4-triazole-3-thiols are the most active and there is a probability to show antitumor, antiviral, antibacterial, diuretic, actoprotective, and antioxidant activity.

Author Biography

O. A. Bigdan, Zaporizhzhia State Medical University, Ukraine

PhD, Associate Professor of the Department of Clinical Pharmacy, Pharmacotherapy, Pharmacognosy and Pharmaceutical Chemistry


Parchenko, V. V. (2012). Novi S-pokhidni 1,2,4-tryazolu, yak potentsiini oryhinalni vitchyzniani veterynarni likarski zasoby [New S-derivatives of 1,2,4-triazoles as potential original home of veterinary pharmaceuticals]. Farmatsevtychnyi zhurnal, (3), 42-48. [in Ukrainian].

Parchenko, V. V. (2014). Syntez, peretvorennia, fizyko-khimichni ta biolohichni vlastyvosti v riadi 5-furylzamishchenykh 1,2,4-triazol3-tioniv (Dis. dokt. farm. nauk). [Synthesis, transformation, physico-chemical and biological properties in the number of 5-furylsubstituted 1,2,4-triazole-3-thiones (Doctoral dissertation)]. Zaporizhzhia State Medical University, Zaporizhzhia. [in Ukrainian].

Zazharskyi, V., Parchenko, M., Parchenko, V., Davydenko, P., Kulishenko, O., & Zazharska, N. (2020). Physicochemical properties of new S-derivatives of 5-(5-bromofuran-2-yl)-4-methyl-1,2,4-triazol-3-thiols. Voprosy khimii i khimicheskoi tekhnologii, (6), 50-58.

Zazharskyi, V., Parchenko, M., Fotina, T., Davydenko, P., Kulishenko, O., Zazharskaya, N., & Borovik, I. (2019). Synthesis, structure, physicochemical properties and antibacterial activity of 1,2,4-triazoles-3-thiols and furan derivatives. Voprosy khimii i khimicheskoi tekhnologii, (6), 74-82.

Lipinski, C. A., Lombardo, F., Dominy, B. W., & Feeney, P. J. (2001). Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Advanced drug delivery reviews, 46(1-3), 3-26.

Gao, F., Wang, T., Xiao, J., & Huang, G. (2019). Antibacterial activity study of 1,2,4-triazole derivatives. European journal of medicinal chemistry, 173, 274-281.

Kummari, L. K., Butler, M. S., Furlong, E., Blundell, R., Nouwens, A., Silva, A. B., Kappler, U., Fraser, J. A., Kobe, B., Cooper, M. A., & Robertson, A. (2018). Antifungal benzo[b]thiophene 1,1-dioxide IMPDH inhibitors exhibit pan-assay interference (PAINS) profiles. Bioorganic & medicinal chemistry, 26(20), 5408-5419.

Küçükgüzel, Ş. G., & Çıkla-Süzgün, P. (2015). Recent advances bioactive 1,2,4-triazole-3-thiones. European journal of medicinal chemistry, 97, 830-870.

Sharba, A. H., Al-Bayati, R. H., Aouad, M., & Rezki, N. (2005). Synthesis of oxadiazoles, thiadiazoles and triazoles derived from benzo[b]thiophene. Molecules, 10(9), 1161-1168.

Marques, A. F., Esser, D., Rosenthal, P. J., Kassack, M. U., & Lima, L. M. (2013). Falcipain-2 inhibition by suramin and suramin analogues. Bioorganic & medicinal chemistry, 21(13), 3667-3673.

Hessle, L., Johnson, K. A., Anderson, H. C., Narisawa, S., Sali, A., Goding, J. W., Terkeltaub, R., & Millan, J. L. (2002). Tissue-nonspecific alkaline phosphatase and plasma cell membrane glycoprotein-1 are central antagonistic regulators of bone mineralization. Proceedings of the National Academy of Sciences of the United States of America, 99(14), 9445-9449.

Ali, K. A., Ragab, E. A., Farghaly, T. A., & Abdalla, M. M. (2011). Synthesis of new functionalized 3-substituted [1,2,4]triazolo [4,3-a]pyrimidine derivatives: potential antihypertensive agents. Acta poloniae pharmaceutica, 68(2), 237-247.

Di Virgilio F. (2012). Purines, purinergic receptors, and cancer. Cancer research, 72(21), 5441-5447.

Raper, E. S. (1996). Complexes of heterocyclic thionates. Part 1. Complexes of monodentate and chelating ligands. Coordination Chemistry Reviews. Elsevier.

Amir, M., & Shikha, K. (2004). Synthesis and anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation activities of some new 2-[(2,6-dichloroanilino) phenyl]acetic acid derivatives. European journal of medicinal chemistry, 39(6), 535-545.

Goel, R. K., Singh, D., Lagunin, A., & Poroikov, V. (2011). PASS-assisted exploration of new therapeutic potential of natural products. Medicinal Chemistry Research, 20, 1509-1514.

Lagunin, A., Zakharov, A., Filimonov, D., & Poroikov, V. (2011). QSAR Modelling of Rat Acute Toxicity on the Basis of PASS Prediction. Molecular informatics, 30(2-3), 241-250.

Lagunin, A., Stepanchikova, A., Filimonov, D., & Poroikov, V. (2000). PASS: prediction of activity spectra for biologically active substances. Bioinformatics, 16(8), 747-748.

Daina, A., Michielin, O., & Zoete, V. (2017). SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Scientific reports, 7, 42717.

Sushko, I., Novotarskyi, S., Körner, R., Pandey, A. K., Rupp, M., Teetz, W., Brandmaier, S., Abdelaziz, A., Prokopenko, V. V., Tanchuk, V. Y., Todeschini, R., Varnek, A., Marcou, G., Ertl, P., Potemkin, V., Grishina, M., Gasteiger, J., Schwab, C., Baskin, I. I., Palyulin, V. A., … Tetko, I. V. (2011). Online chemical modeling environment (OCHEM): web platform for data storage, model development and publishing of chemical information. Journal of computer-aided molecular design, 25(6), 533-554.



How to Cite

Bigdan OA. Analysis of the relationship between the predicted biological activity and the chemical structure of S-derivatives of 5-(5-bromofuran-2-yl)-4R-1,2,4-triazole-3-thiols. CIPM [Internet]. 2021Jun.1 [cited 2023Dec.8];14(2):167-72. Available from:



Original research