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Synthesis and anti-HIV studies of 2- and 3-adamantyl-substituted thiazolidin-4-ones.

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 (EC(50)=0.67 microM). 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 (EC(50)=1.0-11 microM) but also pronounced cytostatic activity. For example 24, 26 and 29 showed an EC(50) of 1.0-2.0 microM, while the 50% effective concentrations for 23 and 28 were 7.8 and 11.0 microM, 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.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Balzarini J,Orzeszko-Krzesińska B,Maurin JK,Orzeszko A

doi

10.1016/j.ejmech.2008.02.039

subject

Has Abstract

pub_date

2009-01-01 00:00:00

pages

303-11

issue

1

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(08)00111-6

journal_volume

44

pub_type

杂志文章

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