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1,5‐naphthyridines. Synthesis of 7‐chloro‐4‐(4‐diethylamino‐1‐methylbutylamino)‐2‐methoxy‐1,5‐naphthyridine and related compounds
Author(s) -
Mccaustland Daniel J.,
Cheng C. C.
Publication year - 1970
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.5570070301
Subject(s) - chemistry , plasmodium berghei , chloroquine , antimalarial agent , drug , combinatorial chemistry , stereochemistry , pharmacology , malaria , medicine , immunology , biology
Abstract The synthesis of 7‐chloro‐4‐(4‐diethylamino‐1‐methylbutylamino)‐2‐methoxy‐1,5‐naphthyridine, a compound which incorporates the structure of both chloroquine (a schizontocidal drug) and pamaquine (a gametocytocidal drug), has been carried out. In addition, two structurally related derivatives, the, “5‐azachloroquine” and the “5‐azapamaquine,” have also been obtained by multi‐step syntheses. “5‐Azachloroquine” possesses good antimalarial activity against Plasmodium berghei. The compound was also found to be less toxic than the known 4‐aminoquinoline and 8‐aminoquinoline antimalarial drugs.