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Synfacts 2019; 15(11): 1215
DOI: 10.1055/s-0039-1691017
DOI: 10.1055/s-0039-1691017
Synthesis of Natural Products and Potential Drugs
Nanomolar Inhibitor of Trypanosoma brucei Trypanothione Reductase
Further Information
Publication History
Publication Date:
18 October 2019 (online)
Key words
trypanothione reductase inhibitor - benzotriazole - N,N-acetal - tertiary amine - Suzuki–Miyaura coupling - Sonogashira couplingSignificance
The parasitic protozoa responsible for trypanosomiasis, Chagas’ disease, and leishmaniasis require the reduction of trypanothione disulfide to trypanothione, which the parasites use in several essential processes. Target molecule N is the strongest competitive inhibitor in vitro of trypanothione reductase from Trypanosoma cruzi reported to date.
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Comment
Note the construction of highly hindered amine E by nucleophilic substitution of benzotriazole from N,N-acetal B by the organomagnesium reagent D.
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Review
For a Review on properties and synthetic utility of N-substituted benzotriazoles, see A. R. Katritzky, X. Lan, J. Z. Yang Chem. Rev. 1998, 98, 409–548.
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