A convenient procedure for the synthesis of novel organoselenium compounds was developed from simple aniline selenocyanate 1 and its corresponding diselenide 2. Their chemical reactivity was investigated towards azo coupling type reactions and their corresponding diazo derivatives 3a,b and 5a,b were sequentially obtained. Besides, heterocyclic selenocyanates 7-9 and diselenocyanate 10 were obtained by the subsequent reaction of hydrazines diazo 3a,b and 5b compounds, respectively. Furthermore, condensation of 1 and 2 with phthalic anhydride afforded the phthalimide selenocyanates 4a,b and 6, alternately. Moreover, some representatives of the new synthesized compounds were evaluated for their antitumor activity and were found to be more cytotoxic compared to their corresponding analogues without selenium. It is worth mentioning that the dying characteristic of these compounds was also evaluated and found to exhibit good dying properties.
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