Efficient Conversion of N-Terminal of L-Tyrosine, DL-Phenyl Alanine, and Glycine to Substituted 2-Thioxo-thiazolidine-4-ones: A Stereospecific Synthesis

Abstract

We report facile and efficient conversion of the amino functional group of amino acids such a s L-tyrosine, DL-phenylalanine, and glycine to the corresponding (±)-2-thioxo-thiazolidine-4-ones (rhodanines). Stereospecific synthesis of amino acid–incorporated rhodanine is achieved in the case of L-tyrosine. Knoevenagel condensation over the active methylene group at the fifth position of the corresponding rhodanines is also described. The substituted rhodanine incorporated with tyrosine in the form of a dimer connected via two-carbon linker possesses significant anticancer activity against A549 cells (human lung cancer cells).

GRAPHICAL ABSTRACT

Keywords:

• A549 cells
• anticancer activity
• Knoevenagel condensation
• rhodanine
• stereospecific synthesis
• 2-thioxo-thiazolidine-4-one

Notes

^a CTC₅₀: Concentration that inhibited 50% growth of A549 cells.