Abstract
A series of new boron-containing benzoxaborole compounds was designed and synthesized for a continuing structure-activity relationship (SAR) investigation to assess the antimalarial activity changes derived from side-chain structural variation, substituent modification on the benzene ring and removal of boron from five-membered oxaborole ring. This SAR study demonstrated that boron is required for the antimalarial activity, and discovered that three fluoro-substituted 7-(2-carboxyethyl)-1,3-dihydro-1-hydroxy-2,1-benzoxaboroles (9, 14 and 20) have excellent potencies (IC(50) 0.026-0.209 μM) against Plasmodium falciparum.
Copyright © 2011 Elsevier Ltd. All rights reserved.
MeSH terms
-
Antimalarials / chemical synthesis*
-
Antimalarials / chemistry
-
Antimalarials / pharmacology*
-
Antimalarials / toxicity
-
Boron Compounds / chemical synthesis*
-
Boron Compounds / chemistry
-
Boron Compounds / pharmacology*
-
Boron Compounds / toxicity
-
Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
-
Bridged Bicyclo Compounds, Heterocyclic / chemistry
-
Bridged Bicyclo Compounds, Heterocyclic / pharmacology*
-
Bridged Bicyclo Compounds, Heterocyclic / toxicity
-
Cell Survival / drug effects
-
Fluorine / chemistry*
-
HeLa Cells
-
Humans
-
Inhibitory Concentration 50
-
Jurkat Cells
-
Molecular Structure
-
Plasmodium falciparum / drug effects*
-
Structure-Activity Relationship
Substances
-
Antimalarials
-
Boron Compounds
-
Bridged Bicyclo Compounds, Heterocyclic
-
Fluorine
-
tavaborole