Three new non-polyglutamatable deazaaminopterins

Details Three new non-polyglutamatable deazaaminopterins Three new non-polyglutamatable deazaaminopterins

1990-01-18

1991-02-26

Daus, Donald G.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

544260, C07D47508

Patent

active

049962078

ABSTRACT:
Three new non-polyglutamatable glutamic acid derivatives in the antifolate series are provided as well as procedures for their preparation. These compounds are: 4-amino-4-deoxy-10-deazapteroyl-.tau.-methyleneglutamic acid (1); 4-amino-4-deoxy-10-ethyl-10-deazapteroyl-.tau.-methylene-glutamic acid (2); and 4-amino-4-deoxy-10-deazapteroyl-3-hydroxyglutamic acid (3). None of the compound undergo polyglutamylation as determined by their inability to serve as substrates for folylpolyglutamate synthetase (FPGS). Compounds 1 and 2 are transported more effectively to tumor cells and they are more powerful in inhibiting the growth of human leukemia cells in culture as compared to the standard anticancer drug methotrexate. All three compounds (1, 2, and 3) inhibit human dihydrofolate reductase to the same extent as methotrexate.

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Nair., J. Organic Chemistry, 50, 1879 (1985).
Nair, Nanvati, Kumar, Gaumont and Kisliuk, J. Med. Chem., 31:181 (1988).

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