Submit Manuscript  

Article Details


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

[ Vol. 16 , Issue. 3 ]

Author(s):

Mohammad S.T. Makki, Reda M. Abdel-Rahman and Nawaa A.H. Alshammari*   Pages 413 - 422 ( 10 )

Abstract:


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.

Keywords:

Synthesis, fluorine substituted rhodanine, cellobiase activity of fungi, CDK2 inhibitors, bioactive probes, tumor cells.

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

Graphical Abstract:



Read Full-Text article