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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anti-Bacterial Agents / chemical synthesis*
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / pharmacology*
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Benzofurans / chemical synthesis*
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Benzofurans / chemistry
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Benzofurans / pharmacology*
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Benzopyrans / chemical synthesis*
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Benzopyrans / chemistry
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Benzopyrans / pharmacology*
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Dose-Response Relationship, Drug
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Drug Evaluation, Preclinical
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Magnetic Resonance Spectroscopy / methods
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Microbial Sensitivity Tests
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Molecular Structure
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Mycobacterium smegmatis / drug effects*
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Mycobacterium smegmatis / growth & development
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Mycobacterium tuberculosis / drug effects*
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Mycobacterium tuberculosis / growth & development
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Stereoisomerism
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Structure-Activity Relationship
Substances
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Anti-Bacterial Agents
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Benzofurans
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Benzopyrans