Synthesis, pharmacophore modeling, and cytotoxic activity of 2-thioxothiazolidin-4-one derivatives

Alegaon, Shankar G.; Alagawadi, K. R.; Devaraji, Vinod; Unger, Banappa S.; Khatib, N. A.

doi:10.1007/s00044-014-1087-9

Cited by 11 publications

(8 citation statements)

References 31 publications

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“…A literature survey reported a new fluorine compound substituted for rhodanine at positions SH, NH 3 , and active CH 2 positions [ 21 ] and is used for detecting Tau pathology in Alzheimer’s Brains [ 22 ] as well as inhibitors of JSP-1 [ 23 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Novel Fluorine Compounds Substituted-4-thiazolidinones Derived from Rhodanine Drug as Highly Bioactive Probes

Makki¹,

Abdel‐Rahman²,

Alshammari³

2019

COS

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Aim and Objective: It is known that rhodanine drug has various biocidal activities. The aim of this work was to improve the structure of rhodanine drug via alkylation at N, S, and O- centers in addition to the introduction of fluorine atoms. The new fluorinated modified rhodanines 2-16 were evaluated as enzymatic probes for cellobiase activity produced by fungi and as CDK2 inhibitors of tumor cells. Materials and Methods: Novel fluorine substituted N-alkyl, S-alkyl and amino-rhodanines were obtained via Hydroxy methylation, Mannich reactions, chlorination and amination of 5-(4'-fluorophenylene)-2-thioxothiazolidin- 4-one, and the enzymatic effects of cellobiase produced by fungi and /or CDK2 inhibition of tumor cells were evaluated. Results: Most of the targets were obtained in high yield and in the form of very pure crystals with characteristic colors. Only compounds 5, 8, 10, 13, and 14 exhibited a higher activity as cellobiase while compounds 2 and 5 showed a highly enzymatic effect on tumor cells. In addition, compounds 2 and 10 can be used as Olomoucine (standard referees). Conclusion: Various N, S and O-alkyl derivatives of fluorine-substituted rhodanines were prepared via a simple method and used as enzymatic probes for cellobiase activity produced by fungi and CDK2 inhibitors for tumor cells. The more bioactive compounds had rich fluorine atoms as p-fluorophenyl and p-fluorobenzoyl bearing N, S, O-alkyl rhodanine. The highly active compounds may be used as enzymatic materials for various biological transformations in the future.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Novel Fluorine Compounds Substituted-4-thiazolidinones Derived from Rhodanine Drug as Highly Bioactive Probes

Makki¹,

Abdel‐Rahman²,

Alshammari³

2019

COS

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“…Compound 9, which is 5-{4-[3-(4-methoxy-phenyl)-3-oxo-propenyl]-benzylidene}-2thioxothiazolidin-4-one (Figure 5), exhibited promising inhibitory activity against the HeLa, HT29 (colorectal adenocarcinomma), A549, and MCF-7 cell lines with the inhibitory concentration (IC 50 ) values of 28.3, 24.5, 26.6, and 28.6 µM, respectively [11]. Moreover, 5-((2-chloro-6,7-dimethoxyquinolin-3-yl)methylene) rhodanine derivative 10 (Figure 5) turned out to be potent against the gastric (HGC), prostate (DU-145), and breast cancer (MCF-7) lines [30].…”

Section: -Substituted Rhodanine Derivativesmentioning

confidence: 99%

“…The rhodanine derivatives are small compounds with a broad spectrum of biological activities; they are used as antimicrobial [5], antiviral [6], antitubercular [7], antiinflammatory [8], antidiabetic [9], and antitumor agents [10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Anticancer Profile of Rhodanines: Structure–Activity Relationship (SAR) and Molecular Targets—A Review

2022

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The rhodanine core is a well-known privileged heterocycle in medicinal chemistry. The rhodanines, as subtypes of thiazolidin-4-ones, show a broad spectrum of biological activity, including anticancer properties. This review aims to analyze the anticancer features of the rhodanines described over the last decade in the scientific literature. The structure–activity relationship of rhodanine derivatives, as well as some of the molecular targets, were discussed. The information contained in this review could be of benefit to the design of new, effective small molecules with anticancer potential among rhodanine derivatives or their related heterocycles.

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“…Moreover, 4-thiazolidinone derivatives were exhibited anticonvulsant [6], hypnotic [7], antitubercular [8], anthelmintic [9] [10], antimicrobial [11], anticancer [12] [13], antihistaminic [14], antifungal [15], anti-inflammatory [16], andantiviral [17], activities. Also, substituted indolones have gained significant attention as a pharma-core unit in the synthesis of more bioactive compounds [18]. On the other hand, spiroindoles, now wish to report the synthesis of some asymmetrical spiroheterobicyclic systems [19] [20] [21] [22].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characteristic and Antimicrobial Activity of Some New Spiro[indol-thiazolidon-2,4-diones] and Bis(5-fluorospiro[indoline-3,2’-thiazolidine]-2,4’-dione) Probes

Al-Romaizan¹

2020

IJOC

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In a search for new antimicrobial agents, some new spiro[indol-thiazolidon-2,4-diones] (6a-c) were synthesized by condensation of 5-substituted isatins 1 with sulfanilamide in MeOH, followed by aroylation with p-nitrobenzoyl chloride in DMF to get compounds 4a-c. Cycloaddition of 4a-c with thioglycolic acid in a dry non-polar solvent (dioxane) gave the targets 6a-c. Also, bis(5-fluorospiro[indoline-3,2'-thiazolidine]-2,4'-dione) (9) was synthesized by condensation of 5-fluoroindoline-2,3-dione with benzene-1,4-diamine (2:1 by mol) in MeOH, which followed by cycloaddition with thioglycolic acid in dioxane gave compound 8. Acylation of the later with 2,2,2-trifluoroacetic anhydride in THF has yielded the target 9. Structures of the products have been deduced from their elemental analysis and spectral data. The in vitro antimicrobial activity of the new systems 6a-c, and 9 was tested.

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Synthesis, pharmacophore modeling, and cytotoxic activity of 2-thioxothiazolidin-4-one derivatives

Cited by 11 publications

References 31 publications

Synthesis of Novel Fluorine Compounds Substituted-4-thiazolidinones Derived from Rhodanine Drug as Highly Bioactive Probes

Synthesis of Novel Fluorine Compounds Substituted-4-thiazolidinones Derived from Rhodanine Drug as Highly Bioactive Probes

Anticancer Profile of Rhodanines: Structure–Activity Relationship (SAR) and Molecular Targets—A Review

Synthesis, Characteristic and Antimicrobial Activity of Some New Spiro[indol-thiazolidon-2,4-diones] and Bis(5-fluorospiro[indoline-3,2’-thiazolidine]-2,4’-dione) Probes

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