Premium
Quinazolines. VII. Synthesis of 1,3‐Diamino‐5,6‐dihydrobenzo[ f ]quinazolines
Author(s) -
Rosowsky Andre,
Chen Katherine K. N.,
Papathanasopoulos Nickolas,
Modest Edward J.
Publication year - 1972
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.5570090214
Subject(s) - chemistry , tetralones , pyrimethamine , dihydrofolate reductase , stereochemistry , condensation , combinatorial chemistry , medicinal chemistry , organic chemistry , plasmodium falciparum , enzyme , malaria , immunology , biology , physics , thermodynamics
Eighteen new 1,3‐diamino‐5,6‐dihydrobenzo[ f ] quinazolines ( 6 , R. = alkyl, Cl, MeO) were synthesized via the condensation of appropriate 2‐tetralones with cyanoguanidine under fusion conditions. Methods were developed for the preparation of a number of heretofore undescribed 2‐tetralones as precursors. The final products can be viewed as conformationally rigid analogs of pyrimethamine ( 2 ), and are of interest as inhibitors of dihydrofolate reductase and as potential antimalarial and antitumor agents.