Submit Manuscript  

Article Details


Z-Acrylonitrile Derivatives: Improved Synthesis, X-ray Structure, and Interaction with Human Serum Albumin

Author(s):

Mehtab Parveen*, Afroz Aslam, Shahab A. A. Nami and Musheer Ahmad   Pages 1 - 12 ( 12 )

Abstract:


Aim and Objective: In the synthesis of heterocyclic compounds, acrylonitrile derivatives are the most important and appropriate precursors. These compounds are the most important intermediates and subunits for the enhancement of molecules having pharmaceutical or biological interests. Nitrogen-containing compounds have received extensive consideration in the literature over the years.

Materials and Methods: A facile, economic and efficient method has been developed for the synthesis of acrylonitrile derivatives using p-nitrophenylacetonitrile and aromatic/heterocyclic aldehydes in presence of zinc chloride at room temperature. 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 Bruker Avance-II 400 MHz using DMSO-d6 as a solvent containing TMS as the internal standard.

Results: To continue our ongoing studies to synthesize heterocyclic and pharmaceutical compounds by mild, facile and efficient protocols, herein we wish to report our experimental results on the synthesis of acrylonitrile derivatives, using various aromatic/heterocyclic aldehydes and p-nitrophenylacetonitrile in the presence of zinc chloride in ethanolic media at room temperature. Some of new compounds were tested for their human serum albumin activity (HSA) while a study of interaction with HSA protein was performed for compounds 3a and 3b. The results show that compound 3b binds tightly to HSA as compared to compound 3a.

Conclusion: It can be concluded that we have synthesized the acrylonitrile derivatives by an efficient method to a reaction of p-nitrophenylacetonitrile with aromatic/heterocyclic aldehydes by the use of zinc chloride as an effective solid catalyst. The remarkable features of this procedure are excellent yields (90-95%), small reaction period (30 min.), moderate reaction environment, easy workup procedure, and managing of the catalyst. This method may find wide significance in organic synthesis for the synthesis of the Z-acrylonitrile.

Keywords:

(Z)-acrylonitrile, crystallography, human serum albumin, acrylonitrile derivatives, Knoevenagel condensation, X-ray structure.

Affiliation:

Division of Organic Synthesis, Department of Chemistry, Aligarh Muslim University, Aligarh, 202002, Division of Organic Synthesis, Department of Chemistry, Aligarh Muslim University, Aligarh, 202002, Department of Kulliyat, Faculty of Unani Medicine, Aligarh Muslim University, Aligarh, 202002, Department of Applied Chemistry, Aligarh Muslim University, Aligarh, 202002



Read Full-Text article