Spectroscopic and Structural Investigations on Novel 6-Amino-3-Phenyl-4-(Pyridin-4-yl)-2,4-Dihydropyrano[2,3-c] Pyrazole-5-Carbonitrile by FT-IR, NMR, Docking, and DFT Methods

Abstract

The present work deals with a comparative experimental and theoretical study on a synthetic analog of biologically relevant 4H-pyran motif. We have performed spectral and structural properties of 6-amino-3-phenyl-4-(pyridin-4-yl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile. This compound was synthesized in 89% yield by following a simple, straightforward, and highly efficient multicomponent one-pot protocol under the excellent catalytic influence of nontoxic trisodium citrate dihydrate at ambient conditions. The quantum chemical computations of the vibrational frequencies were carried out using the Gaussian 09 program followed by the full optimizations done using density functional theory (DFT) at B3LYP/6-311 + G(d,p) level. The optimized structure, vibrational, and NMR spectra are in good agreement with the experimental data. The combined use of experimental and computational work allowed a firm assignment of the majority of observed bands for the compound. The molecular docking study has been utilized to explore the binding modes of the compound to the target enzyme multidrug resistance protein. This result suggests the pharmaceutical importance of the titled compound in the field of drug discovery.

Keywords:

• Density functional theory
• FT-IR
• green synthesis
• molecular docking
• NMR
• pyrazole

Disclosure statement

There are no conflicts of interest.

Additional information

Funding

Ratnesh Kumar acknowledges University Grand Commission (UGC), New Delhi, India for providing a research fellowship [grant number 34009/(NET-DEC.2014)]. Dr Ambrish Kumar Srivastava acknowledges UGC, New Delhi, India for Start Up Grant [30-466/2019(BSR)].