Síntese de tiossemicarbazonas aldeídicas e cetônicas derivadas do (-)-cafeno

Abstract

The thiosemicarbazones are molecules that present large shape of biological activities, the changing with alkyl or aryl group is common in position N-1, but are rare cases of terpene substituents on nitrogen terminal N-4. Before these facts, our research group has begun the synthesis of new thiosemicarbazones with terpene unities in N-4. In continuing to the synthesis of thiosemicarbazones derived from menoterpene (-) ? camphene, the present paper describes the synthesis` conclusion from new thiosemicarbazones aldehydic range (m-metoxi-p-hidroxi (32a), p-fluor (32b), ohidroxi (32c) benzaldehyde thiosemicarbazone) and benzene thiosemicarbazone (34)), and an unprecedented range of thiosemicarbazone derived from heterocyclic aldehyde (2-phurane (33a), 2-pyrrole (33b), 2- thiophene (33c) carboxaldehyde thiosemicarbazone), and beyond the synthesis of thiosemicarbazone derived from cinnamaldehyde, menthone and ethyl pyruvate (cinnamal thiosemicarbazone (35), menthene thiosemicarbazone (36) and ethyl thiosemicarbazone (37) The achievement of thiosemicarbazone was done trough the condensation of thiosemicarbazone derived of (-)-camphene, with various carbonyl compound using methodology adapted from literature and a new methodology using gel of silica catalyst with H2SO4 . Before the difference in the reactions time to the achievement of thiosemicarbazone derived of (-)- camphene, R-(+)-limonene and of N-bisabolol were done computational theoretical calculation to analyze the reaction intermediate from the addition of hydrazine to the different isothiocyanate ((-)-camphene, R-(+)-limonene and of N-bisabolol). The thiosemicarbazone sinthetyze (31a-37) were submitted to an initial choice to the evaluation of antitumor activity before the cells of melanoma SKMEL-37, which the thiosemicarbazone (31a, 31c, 31e, 32a-c, 33a, 33c e 37) that induced to the higher mortality of cancer cells were separated to the continuing of studies.