Monocyclic pteridine analogues. A pyrazine analogue of methotrexate | Zendy

Lever O. William | Zendy; Vestal B. Randall | Zendy

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Monocyclic pteridine analogues. A pyrazine analogue of methotrexate

Author(s) -

Lever O. William,

Vestal B. Randall

Publication year - 1985

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.5570220102

Subject(s) - chemistry , pteridine , pyrazine , methotrexate , deoxygenation , dihydrofolate reductase , stereochemistry , hydrolysis , condensation , pyrimidine , medicinal chemistry , organic chemistry , enzyme , immunology , catalysis , physics , thermodynamics , biology

Reaction of aminocyanoacetamide with bromomethylpyruvaldoxime provided 3‐amino‐6‐bromomethyl‐2‐carbamoylpyrazine 4‐oxide (7) , which was converted to a pyrazine analogue (3) of methotrexate by subsequent condensation with diethyl N ‐[4‐(methylamino)benzoyl]‐L‐glutamate, deoxygenation, and hydrolysis. The methotrexate analogue 3 was a poor inhibitor (I 50 > 150 μM) of bacterial or mammalian dihydrofolate reductase.

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