Journal of Medicinal Chemistry p. 763 - 768 (1988)
Update date:2022-08-04
Topics: Aminopterin Methotrexate Analogues Meta and Ortho Isomers Double Bond in the Side Chain Novel Analogue Modified at the α-Carbon In Vitro Biological Studies
Rosowsky, Andre
Bader, Henry
Forsch, Ronald A.
Moran, Richard G.
Freisheim, James H.
Five heretofore undescribed analogues of methotrexate (MTX) and aminopterin (AMT) were synthesized and tested as dihydrofolate reductase (DHFR) inhibitors and tumor cell growth inhibitors.The meta isomer of AMT was obtained from 2,4-diamino-6-(bromomethyl)pteridine and m-(aminobenzoyl)-L-glutamic acid, while the ortho isomer was obtained via the same route by using α-methyl γ-tert-butyl o-(aminobenzoyl)-L-glutamate instead of the free acid.Analogues of MTX and AMT containing a double bond in the side chain were prepared from dimethyl D,L-2-amino-4-hexenedioate and 4-amino-4-deoxy-N10-methylpteroic acid and 4-amino-4-deoxy-N10-formylpteroic acid, respectively.Finally, a positional isomer of MTX with the CH2CH2COOH moiety moved from the α-carbon to the adjacent carboxamide nitrogen was synthesized from 3-
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