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Current Organic Synthesis

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ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

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Research Article

Synthesis, Characterization and Biological Activity of Benzimidazoleacrylonitrile Derivatives

Author(s): Mehtab Parveen*, Mohammad Azeem, Afroz Aslam, Mohammad Haris, Amir Khan and Mahboob Alam

Volume 20, Issue 4, 2023

Published on: 12 October, 2022

Page: [458 - 469] Pages: 12

DOI: 10.2174/1570179419666220912090458

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Abstract

Background: 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.

Methods: 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).

Results: 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.

Conclusion: 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.

Keywords: Knoevenagel condensation, 2-benzimidazolylacrylonitriles, X-ray crystallographic study, nematicidal activity, vitamin B12, anti-tumor/anti-proliferative activity.

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