Benzofuro[3,2-f][1]benzopyrans: a new class of antitubercular agents |
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Authors: | Prado Soizic Ledeit Hervé Michel Sylvie Koch Michel Darbord Jacques Christian Cole Stewart T Tillequin François Brodin Priscille |
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Institution: | Laboratoire de Pharmacognosie, UMR/CNRS 8638, 4 avenue de l'Observatoire, 75006 Paris, France. |
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Abstract: | Alkylation of 2-hydroxydibenzofuran with 3-chloro-3-methyl-1-butyne, followed by Claisen rearrangement, gave access to 3,3-dimethyl-3Hbenzofuro3,2-f]1]-benzopyran. Several derivatives modified at the pyran 1,2-double bond were prepared, including the corresponding dihydro compound and (+/-)-cis-diol, which was converted into diacetate and cyclic carbonate upon acylation. Both 3,3-dimethyl-3Hbenzofuro3,2-f]1]benzopyran and 1,2-dihydro-3,3-dimethyl-3Hbenzofuro3,2-f]1]benzopyran displayed significant activities when tested against Mycobacterium tuberculosis H37Rv and Beijing strains, with MIC99 in the range of 1-10 microg/ml. Further biological studies demonstrated good activities against drug-resistant mycobacterial strains. These compounds appear as promising specific antitubercular agents, since they exhibited neither significant cytotoxicity against mammal cells, nor effect on the growth of various bacteria and fungi. |
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