321162-53-2Relevant academic research and scientific papers
Synthesis of 2- and 4-oxo-1H-1-azaanthracene-9,10-diones from 2-amino-1,4-naphthoquinone
Marcos, Alicia,Pedregal, Carmen,Avendano, Carmen
, p. 12941 - 12952 (1994)
In spite of the poor nucleophilicity of its amino group, which is considered to have an "amide like" character, 2-amino-1,4-naphthoquinone reacts with β-dielectrophiles to give 2-oxo- or 4-oxo-1H-1-azaanthracene-9,10-diones.
Synthesis and cytotoxic evaluation of certain tricyclic benzo[g]quinolin-4(1H)-one and benzo[g]quinoline-4,9,10-trione derivatives
Hsu, Shu-Lin,Chen, Yeh-Long,Tzeng, Cherng-Chyi
, p. 529 - 537 (2007/10/03)
The present report describes the synthesis and evaluation of tricyclic benzo[g]quinoline-4(1H)-one derivatives (CAB type) in which an additional aromatic ring is linearly fused on the antibacterial quinolone-3-carboxylic acid to maintain a free carboxylic acid (increase water-solubility) and a coplanar tricyclic DNA-intercalating chromophore (improve antitumor activity). 1H-Benzo[g]quinoline-4,5,10-trione, 1-methyl-1H-benzo[g]quinoline-4,5,10-trione, and ethyl 1-methylbenzo[g]quinoline-4,5,10-trione-3-carboxylate exhibited significant cytotoxicity against all 60 cancer cells with mean GI50 values of 5.92, 7.75, and 2.52 μM respectively while 1-methylbenzo[g]quinoline-4,5,10-trione-3-carboxylic acid and 5-hydroxy-10-methoxy-1-methylbenzo[g]quinolin-4(1H)-one-3-carboxylic acid were inactive, indicated free carboxylic acid at C-3 position is unfavorable. The results have also implied the importance of carbonyl moieties at C-5 and C-10 due to the inactiveness of reduced products, ethyl 5-hydroxy-10-methoxy-1-methylbenzo[g]quinolin-4(1H)-one-3-carboxylate and ethyl 10-benzyloxy-5-hydroxybenzo[g]quinolin-4(1H)-one-3-carboxylate.
