SYNTHESIS AND ANTICANCER ACTIVITY EVALUATION OF THIOPYRANO[2,3-d]THIAZOLE DERIVATIVES WITH THE INDOLE FRAGMENT IN THE MOLECULE
DOI:
https://doi.org/10.11603/2312-0967.2024.3.14866Keywords:
thiopyrano[2,3-d]thiazoles, antitumor activity, SwissADMEAbstract
The aim of the work. To carry out the synthesis of thiopyrano[2,3-d]thiazoles with an indole fragment and evaluate their antiсancer activity within the framework of the DTP NCI program of the US National Cancer Institute.
Materials and Methods. During the research, organic synthesis methods were used, and physicochemical analysis of the synthesized compounds was performed. Anticancer activity determination was performed according to the methodology of the DTP NCI program of the US National Cancer Institute. For the hit compound 3.7, an in silico drug similarity screening was performed using the SwissADME online service.
Results and Discussion. As a result of antitumor activity screening, hit compound 3.7 was identified, which showed the highest level of activity at the micromolar level against leukemia lines K-562, SR, epithelial cancer line HCT-116, CNS cancer U251, ovary OVCAR-8 and breast cancer line HS 578T.
Conclusions. The results indicate the presence of pronounced anticancer activity of thiopyrano[2,3-d]thiazoles with an indole fragment, which actualizes the in-depth study of this class of heterocyclic compounds.
References
Chhabria MT, Patel S, Modi P, Brahmkshatriya PS. Thiazole: A review on chemistry, synthesis and therapeutic importance of its derivatives. Current topics in medicinal chemistry. 2016;16(26):2841-62.
Kryshchyshyn A, Roman O, Lozynskyi A, Lesyk R. Thiopyrano[2,3-d]thiazoles as new efficient scaffolds in medicinal chemistry. Scientia Pharmaceutica. 2018;86(2):26.
Metwally NH, Badawy MA, Okpy DS. Synthesis and anticancer activity of some new thiopyrano[2,3-d]thiazoles incorporating pyrazole moiety. Chemical and Pharmaceutical Bulletin. 2015;63(7):495-503.
Ivasechko I, Lozynskyi A, Senkiv J, Roszczenko P, Kozak Y, Finiuk N, Klyuchivska O, Kashchak N, Manko N, Maslyak Z, Lesyk D, Karkhut A, Polovkovych S, Czarnomysy R, Szewczyk O, Kozytskiy A, Karpenko O, Khyluk D, Gzella A, Bielawski K, Bielawska A, Dzubak P, Gurska S, Hajduch M, Stoika R, Lesyk R. Molecular design, synthesis and anticancer activity of new thiopyrano[2,3-d]thiazoles based on 5-hydroxy-1,4-naphthoquinone (juglone). European journal of medicinal chemistry. 2023;252: 115304.
Metwally NH, Badawy MA, Okpy DS. Synthesis, biological evaluation of novel thiopyrano[2,3-d]thiazoles incorporating arylsulfonate moiety as potential inhibitors of tubulin polymerization, and molecular modeling studies. Journal of Molecular Structure. 2022;1258:132648.
Metwally NH, El-Desoky EA. Novel thiopyrano[2,3-d]thiazole-pyrazole hybrids as potential nonsulfonamide human carbonic anhydrase IX and XII inhibitors: design, synthesis, and biochemical studies. ACS omega. 2023;8(6):5571-92.
Szychowski KA, Skóra B, Kryshchyshyn-Dylevych A, Kaminskyy D, Tobiasz J, Lesyk RB, Gmiński J. 4-Thiazolidinone-based derivatives do not affect differentiation of mouse embryo fibroblasts (3T3-L1 cell line) into adipocytes. Chemico-Biological Interactions. 2021;345:109538.
Kumari A, Singh RK. Medicinal chemistry of indole derivatives: Current to future therapeutic prospectives. Bioorganic chemistry. 2019;89:103021.
Monks A, Scudiero D, Skehan P, Shoemaker R, Paull K, Vistica D. hose C, langley J, Cronise P, Vaigro-Wolff A, Gray-Goodrich M, Campbell H, Mayo J, Boyd M. Feasibility of a high-flux anticance r drug screen using a diverse panel of cultured human tumor cel l lines. J. Natl. Cancer Inst. 1991;83:757-66.
Boyd MR, Paull KD. Some practical considerations and applications of the National Cancer Institute in vitro anticancer drug discovery screen. Drug development research. 1995;34(2):91-109.
Lozynskyi A, Zimenkovsky B, Nektegayev I, Lesyk R. Arylidene pyruvic acids motif in the synthesis of new thiopyrano[2,3-d]thiazoles as potential biologically active compounds. Heterocyclic communications. 2015;21(1):55-9.
Lesyk RB, Zimenkovsky BS. 4-Thiazolidones: centenarian history, current status and perspectives for modern organic and medicinal chemistry. Current Organic Chemistry. 2004;8(16):1547-77.
SwissADME. Available from: http://www.swissadme.ch
Daina A, Michielin O, Zoete V. SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Scientific reports. 2017;7(1):42717.
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2024 Pharmaceutical Review / Farmacevtičnij časopis
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
The authors who publish their materials in this journal agree with the following terms:
- Authors reserve the right to authorship of their work and assign to the journal the right to first publish this work under the terms of the Creative Commons Attribution License, which allows other persons to freely distribute the published work with a mandatory reference to the authors of original work and the first publication of work in this journal
. - Authors have the right to make independent extra-exclusive work agreements in the form they are published by this journal (for example, posting work in an electronic repository of an institution or publishing as part of a monograph), provided that the link to the first publication of the work in this journal is maintained.
Journal policy allows and encourages publication of manuscripts on the Internet (for example, in institutions repositories or on personal websites), both before the publication of this manuscript and during its editorial review, as it contributes to productive scientific discussion and positively affects the efficiency and dynamics of the citation of the published work (see The Effect of Open Access).
