当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY期刊下所有文献 > Endoperoxide polyketides from a Chinese Plakortis simplex: further evidence of the impact of stereochemistry on antimalarial activity of simple 1,2-dioxanes.

Endoperoxide polyketides from a Chinese Plakortis simplex: further evidence of the impact of stereochemistry on antimalarial activity of simple 1,2-dioxanes.

Abstract：

:Chemical investigation of the organic extract obtained from the sponge Plakortis simplex collected in the South China Sea afforded five new polyketide endoperoxides (2 and 4-7), along with two known analogues (1 and 3). The stereostructures of these metabolites have been deduced on the basis of spectroscopic analysis and chemical conversion. The isolated endoperoxide derivatives have been tested for their in vitro antimalarial activity against Plasmodium falciparum strains, showing IC50 values in the low micromolar range. The structure-activity relationships were analyzed by means of a detailed computational investigation and rationalized in the light of the mechanism of action proposed for this class of simple antimalarials. The relative orientation of the atoms involved in the putative radical generation and transfer reaction was demonstrated to have a great impact on the antimalarial activity. The resulting 3D pharmacophoric model can be a useful guide to design simple and effective antimalarial lead compounds belonging to the class of 1,2-dioxanes.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Chianese G,Persico M,Yang F,Lin HW,Guo YW,Basilico N,Parapini S,Taramelli D,Taglialatela-Scafati O,Fattorusso C

doi

10.1016/j.bmc.2014.07.034

subject

Has Abstract

pub_date

2014-09-01 00:00:00

pages

4572-80

issue

17

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(14)00550-1

journal_volume

22

pub_type

杂志文章

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