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

Author(s):

Mohammad S.T. Makki, Reda M. Abdel-Rahman and Nawaa A. H. Alshammari*   Pages 1 - 10 ( 10 )

Abstract:


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.

Affiliation:

Department of Chemistry, Faculty of Science, King Abdul Aziz University, P.O. Box.42805 Jeddah, 21551, Department of Chemistry, Faculty of Science, King Abdul Aziz University, P.O. Box.42805 Jeddah, 21551, Department of Chemistry, Faculty of Science, King Abdul Aziz University, P.O. Box.42805 Jeddah, 21551



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