Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 16, Issue 3, Pages 1328-1336Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2007.10.055
Keywords
phloroglucinol; robustadial A and B; euglobals; S-euglobals; antileishmanial; antimalarial; antimicrobial
Ask authors/readers for more resources
Several new euglobal analogues (named as S-euglobals) were synthesized from phloroglucinol via a biomimetic three-component reaction involving Knoevenagel condensation followed by [4+2]-Diels-Alder cycloaddition with monoterpene. Newly synthesized euglobal analogues involve monoterpenes that have not yet been encountered in natural euglobals. S-Euglobals along with previously synthesized robustadial A and B were evaluated for in vitro antileishmanial, antimalarial, antimicrobial, and cytotoxic activities. Out of 16, nine analogues were found to exhibit antileishmanial activity against Leishmania donovani promastigotes. Analogue 7 was the most potent with IC50 of 2.4 mu g/mL and IC90 of 8 mu g/mL, followed by analogues 8 and 11 (IC50 5.5 and 9.5 mu g/mL). Antilelshmanial activity of robustadial A (5) and B (6) was moderate with IC50 of 20 and 16 mu g/mL, respectively. Robustadial A and B and S-euglobal 8 exhibited weak antimalarial activity against Plasmodium falciparum (IC50 of 2.7-4.76 mu g/mL). Few of the eualobal analogues showed antibacterial activity against methicillin-resistant Staphylococcus aureus. Amongst these, analogue I I was the most potent with IC50 of 1.0 mu g/mL and MIC of 5.0 mu g/mL. Most of the compounds were not cytotoxic up to 25 mu g/mL in a panel of cell lines consisting of both cancer (SK-MEL, KB, BT-549, and SK-OV-3) as well as non-cancer kidney (Vero and LLC-PK11) cells. (C) 2007 Elsevier Ltd. All rights reserved.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available