Sulfonamide hybrid schiff bases of anthranilic acid: Synthesis, characterization and their biological potential

• Published in: Journal of molecular structure 2019-06, Vol.1185, p.8-20
• Main Authors: Kausar, Naghmana, Muratza, Shahzad, Raza, Muhammad Asam, Rafique, Hummera, Arshad, Muhammad Nadeem, Altaf, Ataf Ali, Asiri, Abdullah M., Shafqat, Syed Salman, Shafqat, Syed Rizwan
• Format: Article
• Language: English
• Subjects: Docking studies; DPPH; Hydrazine; Mental disorders; Methyl anthranilate; Sulfonamide
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2019.02.056

In the present work, the novel Schiff bases (03–20) of 4-chloro-N-[2-(hydrazinocarbonyl) phenyl]benzenesulfonamide (02) were synthesized by reacting it with various aldehydes. 4-Chloro-N-[2-(hydrazinocarbonyl) phenyl]benzenesulfonamide (02) was synthesized by reacting methyl 2-{[(4-chlorophenyl)sulfonyl]amino}benzoate (01) with hydrazine. All synthesized compounds (01–20) were characterized by using FTIR, NMR and Mass spectrometry and by single crystal X-ray diffraction (XRD) analysis techniques. The synthesized compounds were screened for their enzyme inhibition potential against AChE and BChE enzymes. Molecular docking studies were carried out to demonstrate putative binding modes. Antioxidant potential of the synthesized compounds was also determined. Enzyme inhibition assay revealed that compounds 02 and 12 showed maximum inhibition against AChE enzyme with percentage inhibition of 91% and 83% respectively, while compounds 12 and 07 showed highest inhibition against BChE with percentage inhibition of 92% and 81% respectively. Molecular docking studies supported the results of enzyme inhibition assay with binding energy values of −8.49 kcal mol−1 against AChE and −8.39 kcal mol−1 against BChE for compound 12. Antioxidant studies also showed good results with percentage scavenging of 96% for both compounds 02 and 19 investigated by DPPH scavenging method. [Display omitted] •Synthesis of new sulfonamide hybrid Schiff bases of anthranilic acid.•The sulfonamides bearing hydrogen donating groups showed good Antioxidant activities.•Compounds showed moderate to good enzyme inhibition activity against AChE and BChE.•In-silico molecular docking studies supported the experimental results for enzyme inhibition.