Folate antagonists.  14 . Synthesis of pyrazino[2,3‐ f ]quinazoline‐8,10‐diamines and related heterocycles as potential antimalarial agents (1,2) | Zendy

Johnson Judith | Zendy; Elslager Edward F. | Zendy; Werbel Leslie M. | Zendy

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Folate antagonists. 14 . Synthesis of pyrazino[2,3‐ f ]quinazoline‐8,10‐diamines and related heterocycles as potential antimalarial agents (1,2)

Author(s) -

Johnson Judith,

Elslager Edward F.,

Werbel Leslie M.

Publication year - 1979

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.5570160604

Subject(s) - chemistry , quinazoline , amination , nitro , formamide , phenazine , in vitro , amine gas treating , ammonia , medicinal chemistry , stereochemistry , organic chemistry , biochemistry , catalysis , alkyl

Amination of 5‐chloro‐6‐nitro‐2,4‐quinazolinediamine ( 2 ) afforded 6‐nitro‐2,4,5‐quinazolinetriamine ( 3 ) which was hydrogenated catalytically to produce 2,4,5,6‐quinazolinetetraamine ( 5 ). Condensation of 5 with the requisite diketones afforded 8,9,10,11‐tetrahydropyrimido[5,4‐ a ]‐phenazine‐1,3‐diamine ( 6 ), several pyrazino[2,3‐ f ]quinazoline‐8,10‐diamines ( 7–10,13 ) as well as two pyrimido[4,5‐ f ]phenazinediamines ( 11,12 ). Amination of 2 in the presence of formamide at 120° led to the formation of 9‐nitro‐1 H ‐pyrimido[4,5,6‐ de ]quinazolin‐5‐amine ( 4 ). None of these compounds showed suppressive activity when tested parenterally against lethal Plasmodium berghei infections in mice. When tested against various bacteria in vitro , 7 and 10 exhibited activity against Streptococcus faecalis at a concentration below 2.5 μg./ml.

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