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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

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Synthesis, structural characterization, and DFT studies of anti-cancer drug

S N Chandana¹, Fares Hezam Al-Ostoot^2,3, Yasser Hussein Eissa Mohammed^2,4

¹Department of Engineering Physics, Adichunchanagiri Institute of Technology, Jyothinagara, Chikkamamagaluru 577102, Karnataka, India.

|April 12, 2021

Summary

Researchers synthesized and characterized a novel compound, N-(2-aminophenyl)-2-(4-bromophenoxy) acetamide, using X-ray diffraction. Intermolecular interactions were analyzed to understand crystal structure stabilization, aiding future drug design.

Area of Science:

Medicinal Chemistry
Crystallography
Computational Chemistry

Background:

Drug design aims to create novel, safe, and tailored therapeutics.
Understanding molecular interactions and physicochemical properties is crucial for effective drug development.

Purpose of the Study:

To synthesize and characterize the compound N-(2-aminophenyl)-2-(4-bromophenoxy) acetamide.
To elucidate the crystal structure and analyze intermolecular interactions.
To computationally investigate molecular properties and interactions.

Main Methods:

Synthesis and characterization using spectroscopic techniques (1H, 13C NMR, LC-MS).
X-ray diffraction (XRD) for crystal structure determination.
Hirshfeld surface analysis, 2D fingerprint plots, and Energy framework analysis using CrystalExplorer17.
Density Functional Theory (DFT) calculations for HOMO/LUMO energies.

Main Results:

The compound N-(2-aminophenyl)-2-(4-bromophenoxy) acetamide was synthesized in good yield.
The crystal structure was confirmed as orthorhombic with space group Pca2(1).
Intermolecular interactions (N-H … O, N-H … Cg) were identified and quantified, stabilizing the crystal structure.
Computational analyses provided insights into interaction energies and electronic properties.

Conclusions:

The study successfully synthesized and structurally characterized a novel compound.
Analysis of intermolecular interactions provides a foundation for understanding structure-activity relationships.
Computational methods complement experimental data, aiding in the rational design of new drug candidates.

Keywords:

3D-interaction energies DFT Docking analysis Hirshfeld surface XRD

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