Microwave-Assisted Expeditious Synthesis of 2-Alkyl-2-(<i>N</i>-arylsulfonylindol-3-yl)-3-<i>N</i>-acyl-5-aryl-1,3,4-oxadiazolines Catalyzed by HgCl₂ under Solvent-Free Conditions as Potential Anti-HIV-1 Agents

Abstract

A series of 2-alkyl-2-(N-arylsulfonylindol-3-yl)-3-N-acyl-5-aryl-1,3,4-oxadiazolines were expeditious prepared under microwave-assisted, catalyzed by HgCl2 and solvent-free conditions. This method has the advantage of low catalyst loading and recovering catalyst, ease reaction and repaid reaction times, easy separation products and excellent yields, and more conducive to the large-scale synthesis products. Furthermore, compounds 3s, 3y, 3a′, 3b′, 3f′, 3i′, 3q′, and 3r′ exhibited more potent anti-HIV-1 activity with EC50 values of 3.35, 6.12, 3.63, 9.54, 1.79, 0.51, 3.00, and 4.01 μg/mL, and TI values of 32.66, >32.68, 31.22, 13.94, 24.27, 39.59, 26.01, and 24.51, respectively. Especially compound 3i′ displayed the highest anti-HIV-1 activity with TI values of 39.59.

Keywords

• 1,3,4-oxadiazolines
• microwave irradiation
• HgCl₂ catalyst
• anti-HIV-1 activity