Structure-activity relationships for antiplasmodial activity among 7-substituted 4-aminoquinolines.

doi:10.1021/JM980146X

Paper

Structure-activity relationships for antiplasmodial activity among 7-substituted 4-aminoquinolines.

Published Nov 13, 1998 · D. De, Frances M. Krogstad, L. Byers

Journal of medicinal chemistry

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178

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2

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Abstract

Aminoquinolines (AQs) with diaminoalkane side chains (-HNRNEt2) shorter or longer than the isopentyl side chain [-HNCHMe(CH2)3NEt2] of chloroquine are active against both chloroquine-susceptible and -resistant Plasmodium falciparum. (De, D.; et al. Am. J. Trop. Med. Hyg. 1996, 55, 579-583). In the studies reported here, we examined structure-activity relationships (SARs) among AQs with different N, N-diethyldiaminoalkane side chains and different substituents at the 7-position occupied by Cl in chloroquine. 7-Iodo- and 7-bromo-AQs with diaminoalkane side chains [-HN(CH2)2NEt2, -HN(CH2)3NEt2, or -HNCHMeCH2NEt2] were as active as the corresponding 7-chloro-AQs against both chloroquine-susceptible and -resistant P. falciparum (IC50s of 3-12 nM). In contrast, with one exception, 7-fluoro-AQs and 7-trifluoromethyl-AQs were less active against chloroquine-susceptible P. falciparum (IC50s of 15-50 nM) and substantially less active against chloroquine-resistant P. falciparum (IC50s of 18-500 nM). Furthermore, most 7-OMe-AQs were inactive against both chloroquine-susceptible (IC50s of 17-150 nM) and -resistant P. falciparum (IC50s of 90-3000 nM).

In Vitro Study

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7-iodo- and 7-bromo-aminoquinolines with diaminoalkane side chains are as active as chloroquine against both chloroquine-susceptible and chloroquine-resistant Plasmodium falciparum, while 7-fluoro

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Structure-activity relationships for antiplasmodial activity among 7-substituted 4-aminoquinolines.

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References

Citations

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Novel 1,2,4-trioxanes, 17a1 and 17a2, show 100% protection against multidrug-resistant Plasmodium yoelii nigeriensis in mice when administered orally, twice as potent as artemisinin.

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