Synthesis, biological activity, and evaluation of the mode of action of novel antitubercular benzofurobenzopyrans substituted on A ring

…, I Khouri, T Gaslonde, S Prado, B Saint-Joanis…

Index: Termentzi, Aikaterini; Khouri, Inana; Gaslonde, Thomas; Prado, Soizic; Saint-Joanis, Brigitte; Bardou, Fabienne; Amanatiadou, Elsa P.; Vizirianakis, Ioannis S.; Kordulakova, Jana; Jackson, Mary; Brosch, Roland; Janin, Yves L.; Daffe, Mamadou; Tillequin, Franois; Michel, Sylvie European Journal of Medicinal Chemistry, 2010 , vol. 45, # 12 p. 5833 - 5847

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Citation Number: 11

Abstract

The 8-, 9-, 10-, and 11-halo, hydroxy, and methoxy derivatives of the antimycobacterial 3, 3- dimethyl-3H-benzofuro [3, 2-f][1] benzopyran were synthesized by condensation of the diazonium salts of 2-chloroanilines (13–17) with 1, 4-benzoquinone (18), reduction of the intermediate phenylbenzoquinones 19–22 to dihydroxybiphenyls, cyclisation to halo-2- hydroxydibenzofurans 24–27, and construction of the pyran ring by thermal ...