The synthesis of enantiopure thiosemicarbazone derivatives from chiral amines

This study involves the synthesis of chiral thiosemicarbazone derivatives as enantiopure that gain importance day by day. In literature, thiosemicarbazones are important compounds which have high biological activities as antifungal, antiviral, antiallergic, antitumor etc. properties. In this study, the chiral forms of thiosemicarbazones in consideration of getting new biological activities were synthesized and their chemical structures were characterized by various spectroscopic techniques. To obtain enantiopure and novel thiosemicarbazones, primarily chiral isothiocynates as two enantiomeric forms were formed by (R)-(+)-α-methylbenzylamine and (S)-(-)-α-methylbenzylamine compounds and converted to corresponding thiosemicarbazides. Then, 12 benzenesulfonate derivatives were synthesized by using p-substituted benzenesulfonyl chlorides with 3-hydroxybenzaldehyde and 4-hydroxybenzaldehyde. Finally, 16 original thiosemicarbazones were obtained based on these products. When the importance of chirality in biological events is evaluated, it is estimated that synthesized new thiosemicarbazones will have new biological properties.