当前位置： SCI文献检索 > EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY期刊下所有文献 > Further optimization of plakortin pharmacophore: structurally simple 4-oxymethyl-1,2-dioxanes with promising antimalarial activity.

Further optimization of plakortin pharmacophore: structurally simple 4-oxymethyl-1,2-dioxanes with promising antimalarial activity.

Abstract：

:For the optimization of the plakortin pharmacophore, we recently proposed a straightforward synthesis of 4-carbomethoxy-3-methoxy-1,2-dioxanes as potential antimalarial drug candidates. Herein we report the chemoselective reduction of the 4-carbomethoxy group which has allowed us to prepare in good yields twenty-four new endoperoxides carrying either the hydroxymethyl or the methoxymethyl group on C4 in various stereochemical arrangements with respect to the alkyl groups on C3 and C6 (the endoperoxide carbons). Some of these compounds showed promising in vitro antimalarial activities, both against chloroquine-resistant (CQ-R) and susceptible (CQ-S) strains of Plasmodium falciparum, with IC₅₀ values in the range of 0.5-1.0 μM. Compound 8g showed activity against the CQ-R strain comparable to that of the structurally more demanding plakortin.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Persico M,Parapini S,Chianese G,Fattorusso C,Lombardo M,Petrizza L,Quintavalla A,Rondinelli F,Basilico N,Taramelli D,Trombini C,Fattorusso E,Taglialatela-Scafati O

doi

10.1016/j.ejmech.2013.10.050

subject

Has Abstract

pub_date

2013-01-01 00:00:00

pages

875-86

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(13)00691-0

journal_volume

70

pub_type

杂志文章

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