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.
Studies on quinones. Part 42: Synthesis of furylquinone and hydroquinones with antiproliferative activity against human tumor cell lines
Benites, Julio,Valderrama, Jaime A.,Rivera, Felipe,Rojo, Leonel,Campos, Nair,Pedro, Madalena,Jose Nascimento, Maria Saeo
, p. 862 - 868 (2008/09/17)
The preparation of furyl-1,4-quinone and hydroquinones by reaction of 2-furaldehyde N,N-dimethylhydrazone with benzo- and naphthoquinones is reported. Access to furylnaphthoquinones from unactivated quinones requires acid-induced conditions, however oxidative coupling reactions of activated quinones proceed under neutral conditions. The in vitro cytotoxic activity of the prepared compounds against a panel of three human cancer cell lines has been studied. Most of the furyl-1,4-quinones exhibited good antiproliferative activity (GI50 = 6.5-33.5 μm) against the MCF-7, NCI-H460, and SF-268 (CNS cancer) cell lines chosen for testing.
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.
Design and synthesis of angucyclinone 5-aza analogues
Valderrama, Jaime A.,González, M. Florencia,Colonelli, Pamela,Vásquez, David
, p. 2777 - 2780 (2008/02/11)
A highly efficient one-pot procedure for the synthesis of phenanthridine-1,7,10-triones from acylbenzoquinones and cyclic enaminones is reported. The cycloaddition reactions of these quinones with 1-trimethylsilyloxybutadiene followed by hydrolysis and oxidative processes provide entry to a variety of angucyclinone 5-aza analogues. Georg Thieme Verlag Stuttgart.
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.
Studies on quinones. Part 35: Access to antiprotozoal active euryfurylquinones and hydroquinones
Valderrama, Jaime A.,Benites, Julio,Cortés, Manuel,Pessoa-Mahana, David,Prina, Eric,Fournet, Alain
, p. 881 - 886 (2007/10/03)
(+)-Euryfuran adds regiospecifically to activated monosubstituted 1,4-benzoquinones under mild conditions to give the corresponding Michael adducts which, depending on the quinone substituent, undergo in situ redox reactions to the respective euryfurylbenzoquinones. One of these Michael adducts undergoes a facile stereoselective cyclisation under oxidant conditions to afford a naphthofuro[4,3-c]benzopyran derivative. The in vitro activities of the obtained euryfurylquinones and hydroquinones against Leishmania amazonensis are described.
Synthesis of phenanthrenes from formylbenzoquinone
Kraus, George A,Hoover, Kim,Zhang, Ning
, p. 5319 - 5321 (2007/10/03)
Phenanthrenes are synthesized by condensation of formylbenzoquinone with a substituted toluene followed by O-methylation and cyclization using the phosphazine base P4-tBu.
Regiospecific Michael reaction of (+)-euryfuran with activated 1,4- benzoquinones
Valderrama, Jaime A.,Cortés, Manuel,Pessoa-Mahana, David,Preite, Marcelo,Benites, Julio
, p. 3563 - 3566 (2007/10/03)
(+)-Euryfuran cycloadds regiospecifically to activated monosubstituted 1,4-benzoquinones under mild conditions to give the corresponding Michael adducts which, depending on the quinone substituent, undergo in situ redox reactions to the respective euryfurylbenzoquinones. One of the reported Michael adducts undergoes a facile stereoselective cyclisation under oxidant conditions to afford a naphthofuro[4,3-c]benzopyran derivative. The regiospecificity of the Michael and cyclisation reactions are discussed. (C) 2000 Elsevier Science Ltd.
STUDIES ON QUINONES XVII. THE REACTION OF ACYLBENZOQUINONES WITH HYDRAZOIC ACID: A ROUTE TO THE PREPARATION OF 2,1-BENZISOXAZOL-4,7-QUINONES
Cassis, Raul,Fernandez, Monica,Tapia, Ricardo,Valderrama, Jaime A.
, p. 1077 - 1088 (2007/10/02)
A straightforward route to 2,1-benzisoxazol-4,7-quinones by oxidation of acylazido hydroquinones, obtained through reaction of acylbenzoquinones with hydrazoic acid, is described.
Studies on Quinones. VII(1). Synthesis of Some Benzothiophene-4,7-diones
Ruiz, V. M.,Tapia, R.,Valderrama, J.,Vega, J. C.
, p. 1161 - 1164 (2007/10/02)
The synthesis of methyl 4,7-dihydro-4,7-dioxobenzothiophene-2-carboxylate (20) based on the reaction of methyl mercaptoacetate with activated 1,4-benzoquinones is described.Methyl 4,7-dihydro-4,7-dioxo-5-hydroxybenzothiophene-2-carboxylate (24) and its corresponding methyl ether 26 were obtained through a Thiele-Winter acetoxylation on 20.On the basis of the properties of methyl 4,7-dihydro-4,7-dioxo-6-methoxybenzothiophene-2-carboxylate (21) obtained from 2,4,5-trimethoxybenzaldehyde (32), the structures of the products 24 and 26 are proposed.
