- Substituted benzoquinazolinones. Part 2: Synthesis of amino-, and sulfanyl-derivatives of benzo[f]- and benzo[h]quinazolinones
-
Amino- and sulfanyl-derivatives of benzoquinazolinones 16a-c, 20a-c and 21a-c were prepared under palladium-catalyzed Buchwald-Hartwig coupling reaction using bromobenzoquinazolinones 15, 19a, 19b and 1-substituted piperazines or mercaptans. The combination of Pd(OAc)2 with XantPhos proved to be the best for these conversions in the presence of KOt-Bu, in 1,4-dioxane as a solvent, at 90-100 °C. The 8-bromobenzo[f]quinazolin-1(2H)-one 15 was synthesized via condensation of the ethyl or tert-butyl 2-amino-8-bromonaphthalene-1-carboxylate 6, 10 with formamide, followed by reaction with 3,4-dimethoxybenzyl bromide. However, the 6-bromobenzo[h]quinazolin-4(3H)-ones 19a, 19b were prepared from ethyl 4-bromo-1-[(tert-butoxycarbonyl)amino]naphthalene-2-carboxylate (17). Biological screening of the potential cytotoxicity of compounds 16a, 20a, 20c on HT29 and HCT116 cell lines, has shown that compound 20a has a significant anticancer activity.
- Nowak, Monika,Malinowski, Zbigniew,Fornal, Emilia,Jó?wiak, Andrzej,Parfieniuk, Ewa,Gajek, Gabriela,Kontek, Renata
-
p. 9463 - 9473
(2015/11/18)
-
- Benzoquinazoline derivatives as new agents affecting DNA processing
-
A new series of benzo[h]quinazoline and benzo[f]quinazoline derivatives was prepared and studied for the biological activity. The compounds carrying a dimethylaminoethyl side chain (6c, 8c and 12) inhibit cell growth. The ability to form a molecular compl
- Marzaro, Giovanni,Via, Lisa Dalla,Toninello, Antonio,Guiotto, Adriano,Chilin, Adriana
-
experimental part
p. 1197 - 1204
(2011/03/23)
-