SYNTHESIS AND CYTOTOXIC ACTIVITY OF ALKYL 2-AZIDO-2,3-DIDEOXY-α-D-RIBO-HEXOPYRANOSIDE FROM α,β-UNSATURATED SUGAR ENONES AND SODIUM AZIDE

João Rufino Freitas Filho, Juliano Carlo Rufino Freitas, Jucleiton José Rufino de Freitas, Gardênia Carmen Gadelha Militão, Terezinha Gonçalves da Silva, Anderson José Firmino Santos da Silva, Silvia Maria de Souza

Resumo


The synthesis of five new alkyl 2-azido-2,3-dideoxy-α-D-ribo-hexopyranoside (7a-d) from α,β-unsaturated sugar enones and sodium azide in the presence of acetic acid is described. One key intermediate, alkyl 2-azide-dideoxy-α-erythro-hexopyranosid-4-ulose (6a-d), was used to obtain compounds 7a-d. The compounds 7a-d were obtained in moderate yields. The structures of the synthesized compounds were elucidated using IR, 1H and 13C NMR spectroscopy and elemental analysis and their antiproliferative activities was evaluated against four different human cell lines that are also described in this paper.

Palavras-chave


Azide sugar; α,β-Unsaturated carbonyl; Cytotoxic Activity.



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