26172-03-2Relevant articles and documents
Studies on quinones. Part 47. Synthesis of novel phenylaminophenanthridinequinones as potential antitumor agents
Valderrama, Jaime A.,Ibacache, Andrea,Rodriguez, Jaime A.,Theoduloz, Cristina,Benites, Julio
scheme or table, p. 3398 - 3409 (2011/08/03)
In our search for potential anticancer agents, a series of 8- and 9-phenylamino-3,4-tetrahydro-phenanthridine-1,7,10(2H)-triones with substituent variations at 6-, 8- and 9-positions were prepared using a highly efficient sequence involving: a) solar photoacylation reactions of benzoquinone with arylaldehydes, b) one-pot procedure for the synthesis of 3,4- dihydrophenanthridine-1,7,10(2H)-trione intermediates from acylhydroquinones and c) highly regiocontrolled acid-induced amination reaction of phenanthridinequinones with phenylamines. The members of this series were in vitro evaluated using the MTT colorimetric method against one normal cell line and three human cancer cell lines. The SAR analysis indicates that the location of nitrogen substituents on the quinone nucleus, the presence of methyl, phenyl, furyl and thienyl groups at the 6-position and the aromatization of the angular cycloaliphatic ring of the phenylamino-3,4-tetrahydrophenanthridine-1,7,10(2H)- trione pharmacophore play key roles in the antitumor activity.
A new synthetic access to furo[3,2-f]chromene analogues of an antimycobacterial
Alvey, Luke,Prado, Soizic,Huteau, Valerie,Saint-Joanis, Brigitte,Michel, Sylvie,Koch, Michel,Cole, Stewart T.,Tillequin, Francois,Janin, Yves L.
experimental part, p. 8264 - 8272 (2009/04/11)
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.
Studies on quinones. Part 39: Synthesis and leishmanicidal activity of acylchloroquinones and hydroquinones
Valderrama, Jaime A.,Zamorano, Carlos,Gonzalez, M. Florencia,Prina, Eric,Fournet, Alain
, p. 4153 - 4159 (2007/10/03)
Acylhydroquinone-based compounds are attractive targets for the design of new leishmanicidal drugs. We have previously described sesquiterpene quinones and hydroquinones series, which exhibit different degree of potency against Leishmania amazonensis. The present study details the preparation of acylchloroquinones and hydroquinones possessing lipophilic substituents and examines their in vitro activity against intracellular L. amazonensis amastigotes. The quinone or hydroquinone nucleus is essential for the activity of the members of the series. The lipophilicity of the cycloaliphatic systems in these members seems to attenuate the cytotoxical effect and increases the selectivity of those compounds containing the norbornene system.
