Synthesis of novel 5-substituted 2-pyrazolylthiazol-4-ones as potential bioligically active compounds


  • I. M. Yushyn Danylo Halytsky Lviv National Medical University, Ukraine,
  • A. V. Lozynskyi Danylo Halytsky Lviv National Medical University, Ukraine,
  • O.-M. V. Fedusevych Danylo Halytsky Lviv National Medical University, Ukraine,
  • O. Yа. Vovchuk Danylo Halytsky Lviv National Medical University, Ukraine,
  • R. B. Lesyk Danylo Halytsky Lviv National Medical University, Ukraine,



hybrid-pharmacophore approach, thiazolo-pyrazoline conjugates, [2 3]-cyclocondensation reaction, NMR spectroscopy


One of the effective strategies in potential “drug-like” molecules design is using a molecular hybridization approach based on the combination of several pharmacological scaffolds in one molecule. The main argument for using this approach is a polypharmacological theory based on the interaction of mentioned hybrid molecules with multiple bio-targets based on selectivity and the resulting reduction of toxicity.

The aim of the work is to synthesize a number of new 5-substituted 2-pyrazolylthiazol-4-ones as potentional biologically active compounds.

Materials and methods. Organic synthesis, 1H NMR spectroscopy.

Results. The synthesis of new 5-ene-2-pyrazolylthiazol-4-ones was carried out via a three-component [2+3]-cyclocondensation reaction of 3-methyl-5-aryl-4,5-dihydropyrazole-1-carbothiamides with chloroacetic acid and the corresponding carbonyl compounds in acetic acid medium. The structure of the synthesized compounds was confirmed by elemental analysis and 1H NMR spectroscopy.

Conclusions. As a result of chemical transformations, a library of new thiazole-pyrazoline conjugates was synthesized based on a hybrid-pharmacophore approach to further anticancer activity evaluation within the DTP NCI protocol.



Lesyk, R. B., & Zimenkovsky, B. S. (2004). 4-thiazolidones: Centena­rian history, current status and perspectives for modern organic and medicinal chemistry. Current Organic Chemistry, 8(16), 1547-1577.

Havrylyuk, D., Zimenkovsky, B., Vasylenko, O., Gzella, A., & Lesyk, R. (2012). Synthesis of New 4-Thiazolidinone-, Pyrazoline-, and Isatin-Based Conjugates with Promising Antitumor Activity. Journal of Medicinal Chemistry, 55(20), 8630-8641.

Saeed, A., Mahesar, P. A., Channar, P. A., Larik, F. A., Abbas, Q., Hassan, M., Raza, H., & Seo, S. Y. (2017). Hybrid Pharmacophoric Approach in the Design and Synthesis of Coumarin Linked Pyra­zolinyl as Urease Inhibitors, Kinetic Mechanism and Molecular Docking. Chemistry & Biodiversity, 14(8), Article e1700035.

Kumar, P., Duhan, M., Kadyan, K., Sindhu, J., Kumar, S., & Sharma, H. (2017). Synthesis of novel inhibitors of α-amylase based on the thiazolidine-4-one skeleton containing a pyrazole moiety and their configurational studies. MedChemComm, 8(7), 1468-1476.

Saczewski, J., Paluchowska, A., Klenc, J., Raux, E., Barnes, S., Sullivan, S., … Strekowskia, L. (2009). Synthesis of 4-substituted 2-(4-methylpiperazino)pyrimidines and quinazoline analogs as serotonin 5-HT2A receptor ligands. Journal of Heterocyclic Chemistry, 46(6), 1259-1265.

Abu-Hashem, A. A., & Aly, A. S. (2012). Synthesis of new pyrazole, triazole, and thiazolidine-pyrimido [4, 5-b] quinoline derivatives with potential antitumor activity. Archives of pharmacal research, 35(3), 437-445.

Abeed, A., El-Emary, T. I., & Youssef, M. (2019). A Facile Synthesis and Reactions of Some Novel Pyrazole-based Heterocycles. Current organic synthesis, 16(3), 405-412.

Gondru, R., Sirisha, K., Raj, S., Gunda, S. K., Kumar, C. G., Pasupuleti, M., & Bavantula, R. (2018). Design, Synthesis, In Vitro Evaluation and Docking Studies of Pyrazole-Thiazole Hybrids as Antimicrobial and Antibiofilm Agents. Chemistryselect, 3(28), 8270-8276.

Abdellatif, K. R. A., Abdelgawad, M. A., Elshemy, H. A. H., Kahk, N. M., & El Amir, D. M. (2017). Design, Synthesis, Antioxidant and Anticancer Activity of New Coumarin Derivatives Linked with Thiazole, Isoxa­zole or Pyrazole Moiety. Letters in Drug Design & Discovery, 14(7), 773-781.

Kryshchyshyn, A., Kaminskyy, D., Karpenko, O., Gzella, A., Grellier, P., & Lesyk, R. (2019). Thiazolidinone/thiazole based hybrids – New class of antitrypanosomal agents. European Journal of Medicinal Chemistry, 174, 292-308.

Alvarez, G., Martinez, J., Varela, J., Birriel, E., Cruces, E., … Cerecetto, H. (2015). Development of bis-thiazoles as inhibitors of triosephosphate isomerase from Trypanosoma cruzi. Identification of new non-mutagenic agents that are active in vivo. European Journal of Medicinal Chemistry, 100, 246-256.

Holota, S., Derkach, H., Demchuk, I. L., Vynnytska, R. B., Antoniv, O. I., Furdychko, L. O., Slyvka, N., Nektegayev, I., Lesyk, R. B. (2019). Synthesis and In vivo evaluation of pyrazoline-thiazolidin-4-one hybrid Les-5581 as a potential non-steroidal anti-inflammatory agent. Biopolymers and Cell, 35(6), 437-447.

Kamble, R. D., Meshram, R. J., Hese, S. V., More, R. A., Kamble, S. S., Gacche, R. N., & Dawane, B. S. (2016). Synthesis and in silico investigation of thiazoles bearing pyrazoles derivatives as anti-inflammatory agents. Computational Biology and Chemistry, 61, 86-96.

Abdellatif, K., Fadaly, W., Kamel, G., Elshaier, Y., & El-Magd, M. (2019). Design, synthesis, modeling studies and biological evaluation of thiazolidine derivatives containing pyrazole core as potential anti-diabetic PPAR-γ agonists and anti-inflammatory COX-2 selective inhibitors. Bioorganic Chemistry, 82, 86-99.

Havrylyuk, D., Zimenkovsky, B., Vasylenko, O., Zaprutko, L., Gzella, A., & Lesyk, R. (2009). ChemInform Abstract: Synthesis of Novel Thiazolone-Based Compounds Containing Pyrazoline Moiety and Evaluation of Their Anticancer Activity. European Journal of Medicinal Chemistry, 44(4), 1396-1404.

How to Cite

Yushyn IM, Lozynskyi AV, Fedusevych O-MV, Vovchuk OY, Lesyk RB. Synthesis of novel 5-substituted 2-pyrazolylthiazol-4-ones as potential bioligically active compounds. CIPM [Internet]. 2020Jul.3 [cited 2023Dec.8];13(2). Available from:



Original research