Synthesis of tetrahydro-β-carboline-3-carbohydrazide derivatives based on Pictet-Spengler reaction and their bioactivities

Abstract

According to our previous research on the antiviral activity of β-carboline and tetrahydro-β-carboline derivatives, series of novel tetrahydro-β-carboline derivatives containing acylhydrazone moiety and different substituents at 1 position were designed, synthesized via Pictet-Spengler reaction, and evaluated for their biological activities. Most of these compounds exhibited excellent antiviral activity both in vitro and in vivo. The in vivo inactivation, curative, and protection activities of part of these compounds were much higher than that of ribavirin (36.5%, 35.2%, and 37.1% at 500 μg/mL) and harmine (40.5%, 38.6% and 42.4% at 500 μg/mL). Especially, the in vivo activities of compounds VI-1 (61.4%, 57.2%, and 68.1%) and compound VI-2 (74.5%, 69.0%, and 68.1%) at 500 μg/mL, which were nearly twofold of that of ribavirin at 500 μg/mL. At the same time, the fungicidal results showed that compound IV-2 exhibited more than 60% fungicidal activities against 5 kinds of phytopathogens. Additionally, compound IV-5 exhibited more than 60% larvicidal activity against C. pipiens pallens at 0.25 mg/kg.