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

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Alvey, Luke | Prado, Soizic | Huteau, Valérie | Saint-Joanis, Brigitte | Michel, Sylvie | Koch, Michel | Cole, Stewart T | Tillequin, François | Janin, Yves L

Edité par CCSD ; Elsevier -

International audience. 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.

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