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Your search keyword '"3-thiazolidin-4-one"' showing total 3 results
Start Over Descriptor "3-thiazolidin-4-one" Topic 0104 chemical sciences
3 results on '"3-thiazolidin-4-one"'

1. Design and Microwave Synthesis of New (5Z) 5-Arylidene-2-thioxo-1,3-thiazolinidin-4-one and (5Z) 2-Amino-5-arylidene-1,3-thiazol-4(5H)-one as New Inhibitors of Protein Kinase DYRK1A

Author

Rémy Le Guével, Solène Guihéneuf, François Carreaux, Olivier Lozach, Emilie Durieu, Khadidja Bourahla, Mustapha Rahmouni, Thierry Charlier, Ludovic Paquin, Laurent Meijer, Emmanuelle Limanton, Jean Pierre Bazureau, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Synthèse Caractérisation Analyse de la Matière (ScanMAT), Université de Rennes (UR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Plate-forme ImPACcell (ImPACcell), Structure Fédérative de Recherche en Biologie et Santé de Rennes ( Biosit : Biologie - Santé - Innovation Technologique ), Institut de recherche en santé, environnement et travail (Irset), Université d'Angers (UA)-Université de Rennes (UR)-École des Hautes Études en Santé Publique [EHESP] (EHESP)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Structure Fédérative de Recherche en Biologie et Santé de Rennes ( Biosit : Biologie - Santé - Innovation Technologique ), Université Ibn Khaldoun de Tiaret = University of Tiaret, Station biologique de Roscoff (SBR), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), ManRos Therapeutics, This research work was funded by the 'Ministère de l’Enseignement Supérieur et de la Recherche de la République Algérienne Démocratique et Populaire' (PhD fellowship for K.B.) and by the 'Ministère de l’Enseignement Supérieur et de la Recherche de la République Française' (PhD fellowship for S.G.). This research was supported by the 'Cancéropôle Grand Ouest' of French National Cancer Institute (contracts PRIR 04-8390 and ACI 04-2254). This research was supported by grants from the 'Fondation Jérôme Lejeune' (L.M.), the 'Agence Nationale pour la Recherche (ANR)' (DYRK-DOWN) (L.M.), the 'Fonds Unique Interministériel' (FUI) PHARMASEA and TRIAD (L.M., J.-P.B., F.C.) projects, an FP7-KBBE-2012 grant (BlueGenics) (L.M.). This project has received funding from the European Union’s Horizon 2020 research and innovation program under grant agreement No 848077. This reflects only the authors’ view and the European Commission is not responsible for any use that may be made of the information it contains., ANR-18-CE16-0020,DYRK-DOWN,DYRK-DOWN: DYRK1A, un gene sensible aux effets de dose à la croisée du développement et du fonctionnement du cerveau pour traiter la Trisomie 21(2018), European Project: 311848,EC:FP7:KBBE,FP7-KBBE-2012-6-singlestage,BLUEGENICS(2012), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Centre National de la Recherche Scientifique (CNRS)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut de Chimie du CNRS (INC), Université d'Angers (UA)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-École des Hautes Études en Santé Publique [EHESP] (EHESP)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Structure Fédérative de Recherche en Biologie et Santé de Rennes ( Biosit : Biologie - Santé - Innovation Technologique ), Jonchère, Laurent, APPEL À PROJETS GÉNÉRIQUE 2018 - DYRK-DOWN: DYRK1A, un gene sensible aux effets de dose à la croisée du développement et du fonctionnement du cerveau pour traiter la Trisomie 21 - - DYRK-DOWN2018 - ANR-18-CE16-0020 - AAPG2018 - VALID, BlueGenics – From gene to bioactive product: Exploiting marine genomics for an innovative and sustainable European blue biotechnology industry - BLUEGENICS - - EC:FP7:KBBE2012-08-01 - 2016-07-31 - 311848 - VALID, Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Structure Fédérative de Recherche en Biologie et Santé de Rennes ( Biosit : Biologie - Santé - Innovation Technologique )-Institut National de la Santé et de la Recherche Médicale (INSERM)-École des Hautes Études en Santé Publique [EHESP] (EHESP)-Université de Rennes 1 (UR1), and Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Université d'Angers (UA)

Subjects
microwave, Stereochemistry, 3-thiazolidin-4-one, Pharmaceutical Science, cell lines, 01 natural sciences, 03 medical and health sciences, Pharmacy and materia medica, [CHIM] Chemical Sciences, Drug Discovery, [CHIM]Chemical Sciences, Protein kinase A, IC50, sulphur/nitrogen displacement, 030304 developmental biology, Knoevenagel condensation, 0303 health sciences, 010405 organic chemistry, Cell growth, Kinase, Chemistry, 1,3-thiazolidin-4-one, protein kinase, DYRK1A, In vitro, inhibition, 0104 chemical sciences, 3. Good health, RS1-441, Medicine, Molecular Medicine, Casein kinase 1, Pharmacophore
Abstract

Here, we report on the synthesis of libraries of new 5-arylidene-2-thioxo-1,3-thiazolidin-4-ones 3 (twenty-two compounds) and new 2-amino-5-arylidene-1,3-thiazol-4(5H)-ones 5 (twenty-four compounds) with stereo controlled Z-geometry under microwave irradiation. The 46 designed final compounds were tested in order to determine their activity against four representative protein kinases (DYR1A, CK1, CDK5/p25, and GSK3α/β). Among these 1,3-thiazolidin-4-ones, the molecules (5Z) 5-(4-hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one 3e (IC50 0.028 μM) and (5Z)-5-benzo[1,3]dioxol-5-ylmethylene-2-(pyridin-2-yl)amino-1,3-thiazol-4(5H)-one 5s (IC50 0.033 μM) were identified as lead compounds and as new nanomolar DYRK1A inhibitors. Some of these compounds in the two libraries have been also evaluated for their in vitro inhibition of cell proliferation (Huh7 D12, Caco2, MDA-MB 231, HCT 116, PC3, and NCI-H2 tumor cell lines). These results will enable us to use the 1,3-thiazolidin-4-one core as pharmacophores to develop potent treatment for neurological or oncological disorders in which DYRK1A is fully involved.

Published
2021
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2. Synthesis, Characterization, Antibacterial and Antioxidant Potency of NSubstituted- 2-Sulfanylidene-1,3-Thiazolidin-4-one Derivatives and QSAR Study

Author

Harshad Brahmbhatt, Valentina Pavić, Maja Molnar, and Vesna Rastija

Subjects
Quantitative structure–activity relationship, Antioxidant, Antiparasitic, medicine.drug_class, DPPH, Nitrogen, medicine.medical_treatment, Quantitative Structure-Activity Relationship, Chemistry Techniques, Synthetic, Microbial Sensitivity Tests, 010402 general chemistry, 01 natural sciences, Antioxidants, chemistry.chemical_compound, Picrates, Drug Discovery, medicine, N-substituted-2-sulfanylidene-1, 3-thiazolidin-4-one, antibacterial activity, antioxidant activity, QSAR, 010405 organic chemistry, Biphenyl Compounds, Antimicrobial, 3. Good health, 0104 chemical sciences, Anti-Bacterial Agents, Rhodanine, chemistry, Proton NMR, Thiazolidines, Antibacterial activity, Nuclear chemistry
Abstract

Background: Rhodanine is known for its potential and important role in the medicinal chemistry since its derivatives exhibit a wide range of pharmacological activities such as antibacterial, antifungal, antidiabetic, antitubercular, anti-HIV, antiparasitic, antioxidant, anticancer, antiproliferative and anthelmintic agents. Objectives: Since N-substituted rhodanine synthons are rarely commercially available, it is desirable to develop a straightforward synthetic approach for the synthesis of these key building blocks. The objective was to synthesize a series of rhodanine derivatives and to investigate their antimicrobial and antioxidant activity. Also, in order to obtain an insight into their structure-activity relationship, QSAR studies on the antioxidant activity were performed. Methods: 1H and 13C FTNMR spectra were recorded on Bruker Avance 600 MHz NMR Spectrometer, mass analysis was carried out on ESI+ mode by LC-MS/MS API 2000. 2,2-Diphenyl-1- picrylhydrazyl radical scavenging activity (% DPPH) was determined in dimethylsulfoxide (DMSO) as a solvent. The antibacterial activity was assessed against Bacillus subtilis, Staphylococcus aureus (Gram positive) and Escherichia coli, Pseudomonas aeruginosa (Gram negative) bacteria in terms of the minimum inhibitory concentrations (MICs) by a modified broth microdilution method. Results: A series of N-substituted-2-sulfanylidene-1,3-thiazolidin-4-ones were synthesized and characterized by 1H NMR, 13C NMR, FTIR, GC MS, LCMS/MS and C,H,N,S elemental analysis. Most of the synthesized compounds showed moderate to excellent antibacterial activity (MIC values from 125 μg/ml to 15.62 μg/mL) and DPPH scavenging activity (from 3.60% to 94.40%). Compound 2-thioxo-3- (4-(trifluoromethyl)-phenyl)thiazolidin-4-one showed the most potent activity against Escherichia coli (3.125 μg/mL), equivalent to antibiotic Amikacin sulphate and against Staphylococcus aureus (0.097 μg/ml), 100 times superior then antibiotic Amikacin sulphate. It has also shown a potent antioxidant activity (95% DPPH scavenging). Two best QSAR models, obtained by GETAWAY descriptor R7p+, Balabans molecular connectivity topological index and Narumi harmonic topological index (HNar), suggest that the enhanced antioxidant activity is related to the presence of pairs of atoms higher polarizability at the topological distance 7, substituted benzene ring and longer saturated aliphatic chain in N-substituents. Conclusion: A series of novel N-substituted-2-thioxothiazolidin-4-one derivatives were designed, synthesized, characterized and evaluated for their antibacterial and antioxidant activity in vitro. Majority of the compounds showed excellent antibacterial activity compared to ampicillin and few of them have an excellent activity as compared to Chloramphenicol standard antibacterial drug. The QSAR study has clarified the importance of presenting a pairs of atoms higher polarizability, such as Cl and S at the specific distance, as well as the substituted benzene ring and a long saturated aliphatic chain in N-substituents for the enhanced antioxidant activity of 2-sulfanylidene-1,3- thiazolidin-4-one derivatives.

Published
2018

3. Investigation on the synthesis of new 3-[4-(arylalkoxy)phenylethyl]-2-thioxo-1,3-thiazolidin-4-ones and their biological evaluation against cancer cells

Author

Wacothon Karime Coulibaly, Jean Pierre Bazureau, Anne Corlu, Christelle N’ta Ambeu, Janat Akhanovna Mamyrbekova-Bekro, Camille Déliko Dago, Yves-Alain Bekro, Rémy Le Guével, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Chimie Bioorganique et des Substances Naturelles (LCBOSN), Université Abobo-Adjamé, Université Péléforo Gon Coulibaly, UFR des Sciences Biologiques, Korhogo BP 1328, Côte d’Ivoire, Université Nangui Abrogoua, Plate-forme ImPACcell (ImPACcell), Structure Fédérative de Recherche en Biologie et Santé de Rennes ( Biosit : Biologie - Santé - Innovation Technologique ), Synthèse Caractérisation Analyse de la Matière (ScanMAT), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Benianh International Foundation, ElecBTP, Ministere de l'Enseignement Superieur et de la Recherche de la Cote d'Ivoire, French National Cancer Institute 'Canceropole Grand Ouest', Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Nangui Abrogoua (UNA), and Université de Rennes (UR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
010405 organic chemistry, Cell growth, Chemistry, Stereochemistry, 3-thiazolidin-4-one, Organic Chemistry, Regioselectivity, Tyramine, 010402 general chemistry, 01 natural sciences, Medicinal chemistry, In vitro, 0104 chemical sciences, 3-[4-(arylalkoxy)phenylethyl]-2-thioxo-1, chemistry.chemical_compound, HaCaT, Rhodanine, Caco-2, Cancer cell, rhodanine, [CHIM]Chemical Sciences, tumoral cell lines, microwave irradiation
Abstract

International audience; Herein, we report on the 5-step synthesis of new 3-[4-(arylalkoxy)phenylethyl]-2-thioxo-1,3-thiazolidin-4-ones without 5-arylidene fragments starting from tyramine The construction involved protection with Boc(2)O, regioselective O-alkylation, deprotection with 6 M HCl, neutralization, and finally reaction of bis(carboxymethyl) trithiocarbonate under microwave irradiation. The intermediates and the N-substituted rhodanine have been also evaluated for their in vitro inhibition of cell proliferation (Huh7, Caco 2, MDA-MB231, HCT 116, PC3, NCI-H727, HaCat). Two compounds have shown a selective potent activity against HCT116 cell line.

Published
2017
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