Folate antagonists. 6. Synthesis and antimalarial effects of fused 2,4‐diaminothieno[2,3‐d]pyrimidines
- 1 August 1972
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 9 (4) , 775-782
- https://doi.org/10.1002/jhet.5570090403
Abstract
2,4‐Diamino‐5,7‐dihydro‐6H‐thiopyrano[4′,3′:4,5]thieno[2,3‐d]pyrirnidine, 2,4‐diamino‐9H‐mdeno[1′,2′:4,5]thieno[2,3‐d]pyrimidine, 2,4‐diamino‐5H‐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 againstStreptococcus faecalis(MGH‐2),Staphylococcus aureus(UC‐76),Streptococcus faecium(ATCC 8043),Lactobacillus casei(ATCC 7469), andPediococcus cerevisiae(ATCC 8081)in vitro, and three compounds displayed antimalarial activity againstPlasmodium bergheiin mice andP. falciparum(Uganda I)in vitro.Keywords
This publication has 24 references indexed in Scilit:
- DISCUSSION PAPER: SYNTHESIS AND BIOLOGICAL ACTIVITY OF TRICYCLIC ANTIFOLATE COMPOUNDS WITH FIXED GEOMETRYAnnals of the New York Academy of Sciences, 1971
- Thieno[2,3‐d]pyrimidines. I. A new method for the preparation of esters and amides of thieno[2,3‐d] pyrimidine‐6‐carboxylic acidsJournal of Heterocyclic Chemistry, 1971
- Antiradiation Compounds XIV:Dithiocarbamates of AminothiophenesJournal of Pharmaceutical Sciences, 1970
- Heterocyclisierungen, V. Synthese von Thieno‐, Tetrahydrobenzothieno‐, Pyrazolo‐Triazolo‐ und Pyrido‐pyrimidinen sowie Naphth‐ und ThienoxazinenEuropean Journal of Inorganic Chemistry, 1969
- 2,4-Diaminopyrimidines. Cyclization of 6-(phenacylthio) and related derivatives to thieno[2,3-d]pyrimidines and thiazolo[3,2-c]pyrimidinesJournal of Medicinal Chemistry, 1969
- Eine neue Synthese 5-substituierter PyrimidineAngewandte Chemie, 1966
- Heterocyclen aus CH‐aciden Nitrilen, VIII. 2‐Amino‐thiophene aus methylenaktiven Nitrilen, Carbonylverbindungen und SchwefelEuropean Journal of Inorganic Chemistry, 1966
- Inhibition of Folate Biosynthesis and Function as a Basis for ChemotherapyPublished by Wiley ,1965
- The Course of the Willgerodt‐Kindler Reaction of Alkyl Aryl KetonesAngewandte Chemie International Edition in English, 1964
- The Knoevenagel Condensation of Aryl Alkyl Ketones with MalononitrileJournal of the American Chemical Society, 1945