Title:Z-Acrylonitrile Derivatives: Improved Synthesis, X-ray Structure, and Interaction with Human Serum Albumin
Volume: 16
Issue: 8
Author(s): Mehtab Parveen*, Afroz Aslam, Shahab A.A. Nami and Musheer Ahmad
Affiliation:
- Division of Organic Synthesis, Department of Chemistry, Aligarh Muslim University, Aligarh 202002,India
Keywords:
Acrylonitrile, zinc chloride, knoevenagel condensation, human serum albumin studies, Z-acrylonitrile, organic synthesis.
Abstract: Aims 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 the 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 the 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 acrylonitrile derivatives can be synthesized by an efficient method via the
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 include excellent yields (90-95%), short reaction
period (30 min.), moderate reaction environment, easy workup procedure and managing of the catalyst. This
method may find a wide significance in organic synthesis for the synthesis of the Z-acrylonitrile.
