Synthesis and Characterization of Novel Atazanavir Analogs

Abstract

In this work, we report the synthesis of diverse atazanavir analogues as possible potential novel drugs for human immunodeficiency virus (HIV-1). The synthesis was carried as follows: First, condensation of 4-oxiranylmethoxy-9H-carbazole (1) with N-1-(tert-butyloxycarbonyl)-N-2-(4-(pyridine-2-yl)-benzyl) hydrazine (2) in presence of isopropyl alcohol at 70-75 °C followed by deprotection with
mineral acid yielded intermediate 4 which was subsequently coupled with carbamate amino acid (5a-o) in the presence of EDAC.HCl and HOBt at room temperature to produce atazanavir analogues containing the carbazole moiety (6a10c). These compounds were characterized by the following analytical methods: IR, 1H NMR, 13C NMR and mass spectroscopy.