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

Abstract : 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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https://hal-pasteur.archives-ouvertes.fr/pasteur-00315963
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Submitted on : Tuesday, September 2, 2008 - 9:37:44 AM
Last modification on : Monday, July 20, 2020 - 9:34:05 AM

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Luke Alvey, Soizic Prado, Valérie Huteau, Brigitte Saint-Joanis, Sylvie Michel, et al.. A new synthetic access to furo[3,2-f]chromene analogues of an antimycobacterial.. Bioorganic and Medicinal Chemistry, Elsevier, 2008, 16, pp.8264-8272. ⟨10.1016/j.bmc.2008.06.057⟩. ⟨pasteur-00315963⟩

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