Premium
Folate antagonists. 6. Synthesis and antimalarial effects of fused 2,4‐diaminothieno[2,3‐ d ]pyrimidines
Author(s) -
Elslager Edward F.,
Jacob Patricia,
Werbel Leslie M.
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.5570090403
Subject(s) - chemistry , pyrimidine , stereochemistry , staphylococcus aureus , plasmodium berghei , bacteria , malaria , biology , genetics , immunology
2,4‐Diamino‐5,7‐dihydro‐6 H ‐thiopyrano[4′,3′:4,5]thieno[2,3‐ d ]pyrirnidine, 2,4‐diamino‐9 H ‐mdeno[1′,2′:4,5]thieno[2,3‐ d ]pyrimidine, 2,4‐diamino‐5 H ‐indeno[2′,1′:4,5]thieno[2,3‐ d ]pyrimidine, 9,11‐diamino‐5,6‐dihydronaphtho[1′,2′:4,5]thieno[2,3‐ d ]pyrimidine, 7,9‐diamino‐5,6‐dihydronaphtho[2′,1′:4,5]thieno[2,3‐ d ]pyrimidine, 2,4‐diamino‐7‐benzy]‐5,6,7,8‐tetrahydropyrido[4′,3′:4,5]thieno[2,3‐ d ]pyrimidine, and various 2,4‐diamino‐5,6,7,8‐tetrahydro‐[1]benzothieno[2,3‐ d ]pyrimidines were synthesized by cyclization of the requisite fused 2‐aminothio‐phenene‐3‐carbonitriles utilizing chloroformamidine hydrochloride in diglyme. Several compounds exhibited strong inhibitory effects against Streptococcus faecalis (MGH‐2), Staphylococcus aureus (UC‐76), Streptococcus faecium (ATCC 8043), Lactobacillus casei (ATCC 7469), and Pediococcus cerevisiae (ATCC 8081) in vitro , and three compounds displayed antimalarial activity against Plasmodium berghei in mice and P. falciparum (Uganda I) in vitro .