Spectroscopic Studies on Structurally Modified Anthraquinone Azo Hydrazone Tautomer: Theoretical and Experimental...

Area of Science:

• Organic Chemistry
• Medicinal Chemistry
• Computational Chemistry

Background:

• Anthraquinone derivatives are explored for diverse applications.
• Developing novel anti-tubercular agents is a global health priority.
• Structure-activity relationships of azo-substituted anthraquinones require further investigation.

Purpose of the Study:

• To synthesize and characterize novel mono-azo substituted anthraquinone analogues.
• To evaluate the photophysical properties of the synthesized compounds.
• To assess the in-vitro anti-tubercular activity and binding interactions of these analogues.

Main Methods:

• Synthesis via diazo-coupling technique.
• Structural confirmation using FT-IR, 1H NMR, and HRMS.
• Photophysical characterization using UV-Vis and photoluminescence spectroscopy.
• Computational analysis using density functional theory (DFT).
• Molecular docking against 3ZXR Protein.

Main Results:

• Four unique mono-azo substituted anthraquinone analogues were successfully synthesized.
• Spectroscopic and computational methods confirmed molecular structures and properties.
• One synthesized compound demonstrated superior anti-tubercular activity compared to Rifampicin.
• Molecular docking revealed significant binding energy (-10.0 kcal/mol) for compound Q1 against the 3ZXR Protein.

Conclusions:

• The synthesized anthraquinone analogues possess promising anti-tubercular properties.
• Compound Q1 is a potential lead candidate for developing new anti-TB drugs.
• Computational and in-vitro results are consistent, highlighting the utility of this approach.