Synthesis of some 1,3,8-trisubstituted pyrimido[4,5-c][2,7]-naphthyridin-6-ones as potential antitumor agents |
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| Authors: | Aleem Gangjee John K O'Donnell Thomas J Bardos Thomas I Kalman |
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| Institution: | 1. Department of Pharmaceutical Chemistry and Pharmaceutics, School of Pharmacy, Duquesne University, Pittsburgh, Pennsylvania 15282;2. Department of Medicinal Chemistry, School of Pharmacy, State University of New York at Buffalo, Buffalo, New York 14260 |
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| Abstract: | 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 pyrimido4,5-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 × 10−6M and by the 1,3-dioxo analog 12 at 10−5M. |
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