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

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Author(s): Mohammad S.T. Makki, Reda M. Abdel-Rahman, Nawaa A. H. Alshammari*.

Journal Name: Current Organic Synthesis

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Aim and Objective: It is known that the rhodanine drug has various biocidal activity. The aims of this work are attempts to improve the structure of rhodanine drug via alkylation at N, S, and O- centers in additional, the introduction of fluorine atoms. The new fluorinated modified rhodanines 2-16 evaluated as enzymatic probes for cellobiase activity produced by fungi and as CDK2 inhibition of tumor cells.

Material and Methods: Novel fluorine substituted N-alkyl, S-alkyl and substituted amino-rhodanines obtained via Hydroxy methylation, Mannich reactions, chlorination and amination of 5-(4'-fluorophenylene)-2-thioxo-thiazolidin-4-one, then evaluated as enzymatic affects cellobiase produced by fungi and /or CDK2 inhibition of tumor cells.

Results: Most of the targets, obtained with high yield and very pure crystals with characteristic colors. Only the compounds 5, 8, 10, 13, and 14 exhibited a higher activity as cellobiase while the compounds 2 & 5 showed a highly enzymatic effect towards tumor cells, in addition, the compounds 2 & 10 can be used as Olomoucine (standard referees).

Conclusion: A various N, S and O-alkyl derivatives of fluorine-substituted rhodanines prepared via a simple method and use as enzymatic probes towards 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 transformation in the future.

Keywords: Synthesis, Fluorine substituted rhodanine, Cellobiase activity of fungi, CDK2 inhibitors.

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(E-pub Ahead of Print)
DOI: 10.2174/1570179416666190312150046
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