Abstract
<p>A series of novel thiazolidinedione analogues (TZD) were designed and synthesized potent inhibitors of HBV capsid assembly. The synthesis of thiazolidine-2,4-dione derivatives (4a–4o), starting from the condensation of 5-(ethoxymethylene)thiazolidine-2,4-dione (1) with various secondary amines (3) derived from biologically active compounds. The newly synthesized TZD analogues 4a-4o were characterized by <sup>1</sup>H NMR, <sup>13</sup>C NMR, and MS and evaluated for their anti-HBV activity. Most of the compounds inhibited the expression of viral antigens at low concentration. Six compounds, 4g, 4h, 4l, 4m, 4n, and 4o, demonstrated potent inhibition of HBV DNA replication at submicromolar range. Of these five initial hits, compound 4o was the most active when compared with lamivudine.</p><p> </p><p> </p>
Highlights
Worldwide more than two billion people were seriously affected by hepatitis B virus (HBV), which can cause Liver cirrhosis and hepatocellular carcinoma in humans
Thin-layer chromatography (TLC) was performed on Merck silica gel 60 F254 plates and visualized under UV light. 1H NMR spectra were recorded with a Varian Mercury Plus 400 MHz instrument. 13C NMR spectra were recorded on a Varian Gemini 100 MHz instrument
Thiazolidine-2,4-dione 1 was reacted with triethyl orthoformate in the presence of Ac2O at reflux temperature afforded 5-(ethoxymethylene)thiazolidine-2,4-dione 2 as a pale yellow crystalline solid (Lo et al, 1954)
Summary
Worldwide more than two billion people were seriously affected by hepatitis B virus (HBV), which can cause Liver cirrhosis and hepatocellular carcinoma in humans.
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