Synthesis, Characterization and Biological Activity of Benzimidazoleacrylonitrile Derivatives

Benzimidazoles have a wide range of synthetic applications in medicinal chemistry and biological activities like anti-tumor/anti-proliferative activities etc. Moreover, different heterocyclic moieties attached to the benzimidazole ring improved anticancer activities.

All the chemicals were purchased from Aldrich Chemical Company, are of AR grade and used as received. Microanalytical data (C, H, and N) were analyzed on a Carlo Erba model 1108 analyzer. Melting points were measured by the Kofler apparatus and were uncorrected. Spectroscopic data were obtained using the following instruments: Fourier transform infrared spectra (KBr discs, 4000-400 cm^-1) by Shimadzu IR-408 Perkin Elmer 1800 instrument; ¹H NMR and ¹³C NMR spectra by JEOL Resonance Inc. Tokyo, Japan, JNM-ECZ400S/L1 using DMSO-d₆ as a solvent containing TMS as the internal standard. Chemical shifts (δ) are reported in parts per million (ppm), and coupling constants (J) are reported in Hertz (Hz).

We chose sulfosalicylic acid as a promoter for forming benzimidazole-acrylonitrile derivatives, which is an eco-friendly reaction, and we applied a series of synthesized compounds 3a-g in nematicidal activity. The results indicate that the concentrations of all treatments significantly kill M. incognita.

This model reaction procedure provides a better method for preparing benzimidazoleacrylonitrile, which is superior to other methods. This protocol simplifies handling model reactions with mild reaction conditions, a short time period, a simple set-up, a fast reaction rate, and so on.