Microwave-assisted ring opening of epoxides: a general route to the synthesis of 1-aminopropan-2-ols with anti malaria parasite activities.
A series of 1-aminopropan-2-ols were synthesized and evaluated against two strains of malaria, Plasmodium falciparum FCR3 (chloroquine-resistant) and 3D7 (chloroquine-sensitive). Microwave-assisted ring opening of epoxides (aryl and alkyl glycidyl ethers, glycidol, epichlorohydrin) with various amines without catalysts generated the desired library of beta-amino alcohols rapidly and efficiently. Most of the compounds showed micromolar potency against malaria, with seven of them having IC50 values between 1 and 10 microM against both Plasmodium falciparum strains.
Manchester Interdisciplinary Biocentre (MIB), The University of Manchester, 131 Princess street, Manchester M1 7ND, UK.
Aélig
A
Robin
Fraser
F
Brown
Noemí
N
Bahamontes-Rosa
Binghua
B
Wu
Eric
E
Beitz
Jürgen F J
JF
Kun
Sabine L
SL
Flitsch
D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D002478:Cells, Cultured; D002738:Chloroquine / Q000494:pharmacology; D004351:Drug Resistance; D004852:Epoxy Compounds / Q000737:chemistry / Q000528:radiation effects*; D004912:Erythrocytes / Q000187:drug effects / Q000469:parasitology; D006801:Humans; D020128:Inhibitory Concentration 50; D008872:Microwaves; D010963:Plasmodium falciparum / Q000187:drug effects*; D011412:Propanolamines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000962:Antimalarials; D004852:Epoxy Compounds; D011412:Propanolamines; D002738:Chloroquine