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© Institut Pasteur
Cristaux de cellulase, enzyme purifiée de Clostridium thermocellum permettant la digestion de la cellulose. Image colorisée.
Publication : Bioorganic & medicinal chemistry

A new synthetic access to furo[3,2-f]chromene analogues of an antimycobacterial

Scientific Fields
Diseases
Organisms
Applications
Technique

Published in Bioorganic & medicinal chemistry - 03 Aug 2008

Alvey L, Prado S, Huteau V, Saint-Joanis B, Michel S, Koch M, Cole ST, Tillequin F, Janin YL

Link to Pubmed [PMID] – 18752967

Bioorg. Med. Chem. 2008 Sep;16(17):8264-72

From the structure of 3,3-dimethyl-3H-benzofuro[3,2-f][1]-benzopyran, a selective in vitro inhibitor of mycobacterial growth, we have undertaken a structure-activity relationship investigation. We wish to report here our results on the use of [2+3] cycloadditions between 2-formylbenzoquinone and various enol derivatives to give various 4-formyl-5-hydroxy benzofurans. In the next step, an ytterbium triflate-catalysed reaction with 2-methylpropene allowed the preparation of various original furo[3,2-f]chromenes derivatives. Their biological evaluation on the growth of Mycobacterium smegmatis as well as Mycobacterium tuberculosis pointed out that some analogues were four times more active than the initial hit.

http://www.ncbi.nlm.nih.gov/pubmed/18752967