Title: Synthesis and anti-HIV studies of 2-and 3-adamantyl-substituted thiazolidin-4-ones
Authors: Balzarini, Jan ×
Orzeszko-Krzesinska, Barbara
Maurin, Jan K
Orzeszko, Andrzej #
Issue Date: Jan-2009
Series Title: European Journal of Medicinal Chemistry vol:44 issue:1 pages:303-311
Abstract: A series of novel thiazolidin-4-ones bearing a lipophilic adamantyl substituent at position 2 or 3 were synthesized. A majority of them showed a modest anti-HIV-1 activity, whereas 2-adamantan-1-yl-3-(4,6-dimethylpyrimidin-2-yl)-thiazolidin-4-one (8) was endowed with a remarkable antiviral potency (EC50 = 0.67 mu M). The new series of compounds (22-29) with an adamantyl moiety at the 3-position of the thiazolidinone ring showed good to modest anti-HIV-1 activity (EC50 = 1.0-11 mu M) but also pronounced cytostatic activity. For example 24, 26 and 29 showed an EC50 of 1.0-2.0 mu M, while the 50% effective concentrations for 23 and 28 were 7.8 and 11.0 mu M, respectively. X-ray studies and quantum chemical calculations revealed that the anti-HIV activity of the compounds strongly depends on their dipole moments and conformation of the thiazolidinones. (C) 2008 Elsevier Masson SAS. All rights reserved.
ISSN: 0223-5234
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Laboratory of Virology and Chemotherapy (Rega Institute)
× corresponding author
# (joint) last author

Files in This Item:

There are no files associated with this item.

Request a copy


All items in Lirias are protected by copyright, with all rights reserved.

© Web of science