Bimane cyclic esters, possible stereologues of trypanothione as antitrypanosomal agents. Bimanes 29

Add time:08/06/2019    Source:sciencedirect.com

SummaryTricyclic esters derived from bimanes have been synthesized with ring sizes near or equal to that of trypanothione disulfide (T(S)2), a bis-glutathionylspermidine that is involved in regulating the thiol status of Leishmania and other trypanosomatids. Modest activity for many of the compounds against Leishmania donovani with a maximum at the T(S)2 ring size suggests that the esters act as T(S)2 surrogates. However, no inhibition of T(S)2-reductase is observed for a number of the compounds. A series of tricyclic bimane amides with structures more closely analogous to T(S)2 are inactive in biological tests. New approaches were developed for the synthesis of the amides. The surprising effectiveness of the cyclic ester synthesis is explained. Acid chloride formation catalyzed by sulfides is briefly described.

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