Premium
Synthesis of some 1,3,8‐trisubstituted pyrimido[4,5‐ c ][2,7]‐naphthyridin‐6‐ones as potential antitumor agents
Author(s) -
Gangjee Aleem,
O'Donnell John K.,
Bardos Thomas J.,
Kalman Thomas I.
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210347
Subject(s) - chemistry , tricyclic , dehydrogenation , condensation , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , physics , thermodynamics
Condensation of three 2,4‐disubstituted 6‐aminopyrimidines with methyl 1‐benzyl‐4‐oxo‐3‐piperidinecarboxylate afforded, in each case, new tricyclic, angular 1,3,8‐trisubstituted pyrimido[4,5‐ c ][2,7]naphthyridin‐6‐ones. 2,4,6‐Triaminopyrimidine gave the 7,8,9,10‐tetrahydrocyclo condensed product 5 as anticipated. However, the use of 2‐amino‐4‐oxo‐ or 2,4‐dioxo‐6‐aminopyrimidine afforded the dehydrogenated, 9,10‐dihydrotricyclic products 11 and 12 . The growth of leukemia L1210 cells in culture were inhibited 50% by the 1,3‐diamino analog 5 at 2 × 10 −6 M and by the 1,3‐dioxo analog 12 at 10 −5 M .