Synthesis of some new 4-thiazolidinone derivatives and their activity as anticancer agents / Doha Samir Mohamed Okpy ; Supervised Mohamed Ahmed Badawy , Nadia Hanafy Metwally

Thesis (Ph.D.) - Cairo University - Faculty of Science - Department of Organic Chemistry

The original work studies the reactions of 2-thioxo-4-thiazolidinone with 2-hydroxy-5-(substituted-diazenyl)benzaldehydes and 2,4-dihydroxy-5-(substituted-diazenyl)benzaldehydes to afford 5-arylmethylene-2-thioxo-4-thiazolidinones derivatives. Also, the reaction of 2-substituted-4-((2-(methylthio)-4-oxothiazol-5(4H)-ylidene)methyl)phenyl benzoate with different amino acids afforded products 22a-f and 23a-f. Moreover, 5-(ethoxymethylene)-2-thioxo-4-thiazolidinone reacted with different amines to yield 5-(substituted-methylene)-2-thioxo-4-thiazolidinones derivatives. Also, it reacted with each of ammonium bicarbonate and hydrazine hydrate to give 5-(aminomethylene)-2-thioxo-4-thiazolidinone and 5-(hydrazineylmethylene)-2-thioxo-4-thiazolidinone, respectively. The latter product reacted with some different compounds such as 4,4,4-trifluoro-1-(thiophen-3-yl)butane-1,3-dione, malononitrile dimer and benzylidenemalononitrile derivatives to give pyrazole derivative 37, pyrazolo[3,4-b]pyridine 39 and aminopyrazole 40, respectively. 3-Phenyl-2,4-thiazolidinediones reacted with 4-hydroxybenzaldehyde and 4-hydroxy-3-methoxy benzaldehyde via Knövenagel condensation. The [4+2]cycloaddition of 5-arylmethylene derivatives of 2-thioxo-4-thiazolidinone, 2,4-thiazolidinedion3es or 3-phenyl-4-thioxo-2-thiazolidinone with dienophiles such as N-arylmaleimides, acrylonitrile and ethyl acrylate are also investigated. Some of the newly synthesized compounds were investigated against three cell lines and confirmed by Molecular Docking

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