Judith L. Johnson, E. Elslager, L. M. Werbel
Sep 1, 1979
Citations
0
Influential Citations
9
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
Amination of 5-chloro-6-nitro-2,4-quinazolinediamine (2) afforded 6-nitro-2,4,5-quinazolinetriamine (3) which was hydrogenated catalytically to produce 2,4,5,6-quinazolinetetraamine (5). Condensation of 5 with the requisite diketones afforded 8,9,10,11-tetrahydropyrimido[5,4-a]-phenazine-1,3-diamine (6), several pyrazino[2,3-f]quinazoline-8,10-diamines (7–10,13) as well as two pyrimido[4,5-f]phenazinediamines (11,12). Amination of 2 in the presence of formamide at 120° led to the formation of 9-nitro-1H-pyrimido[4,5,6-de]quinazolin-5-amine (4). None of these compounds showed suppressive activity when tested parenterally against lethal Plasmodium berghei infections in mice. When tested against various bacteria in vitro, 7 and 10 exhibited activity against Streptococcus faecalis at a concentration below 2.5 μg./ml.