The Experts below are selected from a list of 4920 Experts worldwide ranked by ideXlab platform
Jean Pierre Bazureau - One of the best experts on this subject based on the ideXlab platform.
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efficient combination of task specific ionic liquid and microwave dielectric heating applied to one pot three component synthesis of a small library of 4 Thiazolidinones
Tetrahedron, 2003Co-Authors: Joan Fragadubreuil, Jean Pierre BazureauAbstract:Abstract The first report of the use of task-specific ionic liquid as synthetic equivalent of ionic liquid-phase matrice for the preparation of a small library of 4-Thiazolidinones is reported in this paper. The starting (ethyleneglycol)ionic liquid-phase is functionalized in good yields with 4-(formylphenoxy)butyric acid by using usual esterification reaction conditions (DCC/DMAP as catalyst). The synthesis of the ionic liquid-phase bound 4-Thiazolidinones was performed by a one-pot three-component condensation under microwave dielectric heating. The final cleavage under microwave/catalysis strategy provides the expected 4-Thiazolidinones in high purity after flash-chromatography purification. According to the ionic liquid-phase organic synthesis (IoLiPOS) methodology, it was found that optimized reaction conditions were performed by standard analytical methods (NMR, TLC). The 1H, 13C NMR spectrum of some representative 4-Thiazolidinones and ionic liquid-phase bound benzaldehyde are also reported.
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Efficient combination of task-specific ionic liquid and microwave dielectric heating applied to one-pot three component synthesis of a small library of 4-Thiazolidinones
Tetrahedron, 2003Co-Authors: Joan Fraga-dubreuil, Jean Pierre BazureauAbstract:The first report of the use of task-specific ionic liquid as synthetic equivalent of ionic liquid-phase matrice for the preparation of a small library of 4-Thiazolidinones is reported in this paper. The starting (ethyleneglycol)ionic liquid-phase is functionalized in good yields with 4-(formylphenoxy)butyric acid by using usual esterification reaction conditions (DCC/DMAP as catalyst). The synthesis of the ionic liquid-phase bound 4-Thiazolidinones was performed by a one-pot three-component condensation under microwave dielectric heating. The final cleavage under microwave/catalysis strategy provides the expected 4-Thiazolidinones in high purity after flash-chromatography purification. According to the ionic liquid-phase organic synthesis (IoLiPOS) methodology, it was found that optimized reaction conditions were performed by standard analytical methods (NMR, TLC). The1H,13C NMR spectrum of some representative 4-Thiazolidinones and ionic liquid-phase bound benzaldehyde are also reported. © 2003 Elsevier Ltd. All rights reserved.
Boris S. Zimenkovsky - One of the best experts on this subject based on the ideXlab platform.
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Development of rational strategy for selective COX-2 inhibitors searching as potential anticancer drugs
Fabad Journal of Pharmaceutical Sciences, 2009Co-Authors: M. Senthilraja, Vasyl V. Atamanyuk, Roman B. Lesyk, Danylo V. Atamanyuk, O. Roman Pinyazhko, I. O. Nektegayev, Boris S. ZimenkovskyAbstract:Mol. docking for 145 compds. (4-Thiazolidinone derivs. and related heterocyclic systems) has shown in vitro anticancer activity into the active site of enzyme COX-2 using crystallog. models 1CX2 and 6COX (www.rcsb.org). In silico investigations were performed stage-by-stage with OpenEye Scientific Software program package. As a result selected 20 compds., that are thiopyrano [2,3-d] thiazole-2-ones, 5-arylidene-4-thioxo-2-Thiazolidinone and 2-thioxo-(heteryl, imino or oxo)-4-Thiazolidinone derivs. selective COX-2 inhibition with blockage of COX-2 pathway in cancerogenesis, which dets. a role of selective COX-2 inhibitors in prevention and treatment of cancer. [on SciFinder(R)]
Roman Lesyk - One of the best experts on this subject based on the ideXlab platform.
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Drug design: 4-Thiazolidinones applications. Part 1. Synthetic routes to the drug-like molecules
Journal of the Medical Sciences, 2020Co-Authors: Roman LesykAbstract:4-Thiazolidinones, as examples of privileged scaffolds, have been the focus of medicinal chemistry since 60th. Among them, 5-substituted Thiazolidinones with a C5 exocyclic bond (5-ene derivatives) are of special interest due to chemical characteristics and pharmacological profiles, possessing anticancer, antimicrobial, and antiviral properties, as well as being high-affinity ligands to a number of biological targets. A new medicinal chemistry trend claims that the aforementioned compounds are frequent hitters or pan assay interference compounds, which are useless because of the possible low selectivity. This is argued by the Michael acceptor property of 5-ene-4-Thiazolidinones, which is actively discussed in the literature and requires further investigation. Based on SAR analysis, the main vectors for the design of 5-ene-4-Thiazolidinone-based molecules were proposed: complication of C5 fragment; introduction of the substituents in the N3 position; synthesis of isosteric heterocycles; combination with other pharmacologically attractive fragments; annealing of Thiazolidinone core; utilisation of 5-ene-Thiazolidinones in synthesis of other compounds. The affinity of 5-ene-4-Thiazolidinones toward various targets can be regarded as an advantage in polypharmacological approaches. Michael acceptors are considered as the “new old tool” for new drug creation, especially anticancer agents. One of the possible solutions within privileged substructure-based diversity-oriented synthesis is the fixation of 5-ene-4-Thiazolidinone fragment in the fused heterocycles, for example, thiopyrano[2,3-d]thiazoles obtained from 5-ene-Thiazolidinones.
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Thiazole-Bearing 4-Thiazolidinones as New Anticonvulsant Agents
Scientia Pharmaceutica, 2020Co-Authors: Mariia Mishchenko, Danylo Kaminskyy, Sergiy Shtrygol, Roman LesykAbstract:Here, we describe the synthesis and anticonvulsant activity of thiazole-bearing hybrids based on 2-imino-4-Thiazolidinone and 2,4-dioxothiazolidine-5-carboxylic acid cores. The structure of target compounds was based on the following: (i) A combination of two thiazole cores; (ii) similarity to ralitolin’s structure; (iii) the compliance with structural requirements for the new anticonvulsants. Target compounds were synthesized via known approaches based on Knoenavegel reaction, alkylation reaction, and one-pot three-component reaction. Anticonvulsant properties of compounds were evaluated in two different models—pentylenetetrazole-induced seizures and maximal electroshock seizure tests. Among the tested compounds 5Z-(3-nitrobenzylidene)-2-(thiazol-2-ylimino)-thiazolidin-4-one Ib, 2-[2,4-dioxo-5-(thiazol-2- ylcarbamoylmethyl)-thiazolidin-3-yl]-N-(2-trifluoromethylphenyl)acetamide IId and (2,4-dioxo-5- (thiazol-2-ylcarbamoylmethylene)-thiazolidin-3-yl)acetic acid ethyl ester IIj showed excellent anticonvulsant activity in both models. The directions of compounds modification based on SAR aspects were discussed. The results of the study provide a basis for further study of the anticonvulsant properties of selected thiazole-Thiazolidinones.
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Isothiochromenothiazoles-A Class of Fused Thiazolidinone Derivatives with Established Anticancer Activity That Inhibits Growth of Trypanosoma brucei brucei.
Scientia Pharmaceutica, 2018Co-Authors: Anna Kryshchyshyn, Danylo Kaminskyy, I. O. Nektegayev, Philippe Grellier, Roman LesykAbstract:Recently, Thiazolidinone derivatives have been widely studied as antiparasitic agents. Previous investigations showed that fused 4-Thiazolidinone derivatives (especially thiopyranothiazoles) retain pharmacological activity of their synthetic precursors—simple 5-ene-4-Thiazolidinones. A series of isothiochromeno[4a,4-d][1,3] thiazoles was investigated in an in vitro assay towards bloodstream forms of Trypanosoma brucei brucei. All compounds inhibited parasite growth at concentrations in the micromolar range. The established low acute toxicity of this class of compounds along with a good trypanocidal profile indicates that isothiochromenothiazole derivatives may be promising for designing new antitrypanosomal drugs.
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5-Ene-4-Thiazolidinones - An efficient tool in medicinal chemistry.
European Journal of Medicinal Chemistry, 2017Co-Authors: Danylo Kaminskyy, Anna Kryshchyshyn, Roman LesykAbstract:Abstract The presented review is an attempt to summarize a huge volume of data on 5-ene-4-Thiazolidinones being a widely studied class of small molecules used in modern organic and medicinal chemistry. The manuscript covers approaches to the synthesis of 5-ene-4-Thiazolidinone derivatives: modification of the C5 position of the basic core; synthesis of the target compounds in the one-pot or multistage reactions or transformation of other related heterocycles. The most prominent pharmacological profiles of 5-ene derivatives of different 4-Thiazolidinone subtypes belonging to hit-, lead-compounds, drug-candidates and drugs as well as the most studied targets have been discussed. Currently target compounds (especially 5-en-rhodanines) are assigned as frequent hitters or pan-assay interference compounds (PAINS) within high-throughput screening campaigns. Nevertheless, the crucial impact of the presence/nature of C5 substituent (namely 5-ene) on the pharmacological effects of 5-ene-4-Thiazolidinones was confirmed by the numerous listed findings from the original articles. The main directions for active 5-ene-4-Thiazolidinones optimization have been shown: i) complication of the fragment in the C5 position; ii) introduction of the substituents in the N3 position (especially fragments with carboxylic group or its derivatives); iii) annealing in complex heterocyclic systems; iv) combination with other pharmacologically attractive fragments within hybrid pharmacophore approach. Moreover, the utilization of 5-ene-4-Thiazolidinones in the synthesis of complex compounds with potent pharmacological application is described. The chemical transformations cover mainly the reactions which involve the exocyclic double bond in C5 position of the main core and correspond to the abovementioned direction of the 5-ene-4-Thiazolidinone modification.
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Study of novel anticancer 4-Thiazolidinone derivatives.
Chemico-Biological Interactions, 2016Co-Authors: Konrad A. Szychowski, Danylo Kaminskyy, Roman Lesyk, Marcin L. Leja, Urszula E. Binduga, Oleh R. Pinyazhko, Jan GmińskiAbstract:Abstract 4-Thiazolidinones are a known class of prospective drug-like molecules, especially in the design of new anticancer agents. Two of the most prominent subtypes of these compounds are 5-ene-2-amino(amino)-4-Thiazolidinones and thiopyrano[2,3-d]thiazoles. The latter are considered to be cyclic mimetics of biologically active 5-ene-4-Thiazolidinones with similar pharmacological profiles. Therefore, the aim of this study was to evaluate the impact of 4-Thiazolidinone-based compounds on cytotoxicity, the apoptotic process, and metabolism in the human squamous carcinoma (SCC-15) cell line. The SCC-15 cells were cultured in phenol red-free DMEM/F12 medium supplemented with 10% FBS, hydrocortisone, and exposed to rising concentrations (1 nM–100 μM) of the studied compounds for 6, 24 and 48 h. Afterwards, reactive oxygen species (ROS) formation, cell viability, caspase-3 activity, and cell metabolism were measured. The obtained results showed that all of the studied compounds in a wide range of concentrations (1 nM–100 μM) increased DCF fluorescence which suggests a stimulation of ROS production. Nevertheless, these new compounds showed cytotoxic and proapoptotic properties only at high (10–100 μM) concentrations. Our studies are the first to be carried out on these compounds and require further investigation to clarify the mechanism of action of their anticancer potential.
Alexandre J S Goes - One of the best experts on this subject based on the ideXlab platform.
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synthesis of thiosemicarbazone and 4 Thiazolidinone derivatives and their in vitro anti toxoplasma gondii activity
Bioorganic & Medicinal Chemistry Letters, 2005Co-Authors: Romulo P Tenorio, Cristiane S Carvalho, Carla S Pessanha, Jose G De Lima, Antonio Rodolfo De Faria, Antonio J Alves, Edesio J T De Melo, Alexandre J S GoesAbstract:Thiosemicarbazone and 4-Thiazolidinone derivatives were synthesized in one and two step, respectively, from thiosemicarbazide, in satisfactory yields. Then, the synthesized compounds were submitted to evaluation against host cells infected with Toxoplasma gondii. The present studies showed that thiosemicarbazones 2 and 4-Thiazolidinone derivatives 3 were effective against intracellular T. gondii.
Kishor H Chikhalia - One of the best experts on this subject based on the ideXlab platform.
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an efficient alkynylation of 4 Thiazolidinone with terminal alkyne under c h functionalisation
RSC Advances, 2016Co-Authors: Mohammedumar M Shaikh, Sulochana S Mudaliar, Kishor H ChikhaliaAbstract:A method of palladium catalysed efficient alkynylation through the cross coupling reaction of terminal alkynes with the slightly more acidic C–H bonds of 4-Thiazolidinone has been developed. This method allows the direct introduction of an ethynyl group into the 4-Thiazolidinone moiety. Mild reaction conditions involving aerial oxidation and one pot synthesis make this reaction more efficient for the formation of sp3(C)–sp(C) bond.
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An efficient alkynylation of 4-Thiazolidinone with terminal alkyne under C–H functionalisation
RSC Advances, 2016Co-Authors: Mohammedumar M Shaikh, Sulochana S Mudaliar, Kishor H ChikhaliaAbstract:A method of palladium catalysed efficient alkynylation through the cross coupling reaction of terminal alkynes with the slightly more acidic C–H bonds of 4-Thiazolidinone has been developed. This method allows the direct introduction of an ethynyl group into the 4-Thiazolidinone moiety. Mild reaction conditions involving aerial oxidation and one pot synthesis make this reaction more efficient for the formation of sp3(C)–sp(C) bond.
