Synthesis of Novel Sulfonamide Incorporated Azo Compounds as a PotentSolvatochromic and Antimycobacterial Agents

• Published in: ChemistrySelect (Weinheim) Vol. 7; no. 10
• Main Authors: Manjunatha, B., Bodke, Yadav D., Venkatesh, Talavara, Pasha, K M. Mussuvir, Jain, R. Sandeep Kumar
• Format: Journal Article
• Language: English
• Published: 15-03-2022
• Subjects: Azo compounds; Biological potency; Density functional calculations; Sulfonamide; UV-Vis absorption
• ISSN: 2365-6549; 2365-6549
• DOI: 10.1002/slct.202200036

In search of potent solvatochromic and biological agents, here we reported the synthesis of four azo dyes (S1–S4) owing sulfonamide functionality by diazo coupling reaction and their spectroscopic properties were investigated through UV, DRS, IR, NMR and mass spectrometry. Quantum chemical parameters of the synthesised colourants were assessed through DFT studies. The solvatochromic behaviour of sulfonamide incorporated azo compounds was investigated in ten different solvents owing different polarity and proticity and they exhibited remarkable positive solvatochromic behaviour and they exhibited λmax in the range 395–464 nm. Antituberculosis efficacy was evaluated using MABA assay against M. Tuberculosis,among the synthesised colourants compound S3furnished good activity viz MIC=3.85 μM and the remaining compounds showed moderate activity with the MIC values in the range 14.84–32.38 μM.
In this work, four novel azo dyes (S1–S4) were synthesised and characterized through various spectroscopic techniques. The optical band gap (Eg) was calculated using diffuse reflectance (DR) study. Quantum chemical parameters and solvatochromic behaviour of the titled compounds were examined. The synthesised azo dyes were tested for antimycobacterial activity using MABA assay against M. Tuberculosis and they exhibited significant antituberculosis activity.