Synthesis, Pharmacological Evaluation and Molecular Docking Studies of N-[2-(1H-indol-3-yl)Acetyl]Arylsulfonohydrazides

• Published in: Pharmaceutical chemistry journal Vol. 55; no. 7; pp. 665 - 678
• Main Authors: Rubab, K., Abbasi, M. A., Aziz-ur-Rehman, Siddiqui, S. Z., Shah, S. A. A., Ashraf, M., Qurat-ul-Ain, Lodhi, M. A., Khan, F. A., Shahid, M., Fatima, Hina, Ahmad, I.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01.10.2021; Springer
• Subjects: Acetates; Acetic acid; Carbonates; Heterocyclic compounds; Medicine; Organic acids; Organic Chemistry; Pharmacology/Toxicology; Pharmacy; indol-3yl)acetyl]arylsulfonohydrazides; antibacterial activity; molecular docking; enzyme inhibition analysis; indol-3-yl)acetohydrazide; 2-; hemolytic activity
• ISSN: 0091-150X; 1573-9031
• DOI: 10.1007/s11094-021-02476-z

Synthesis of heterocyclic compounds encompassing multiple functionalities and their biological screening is the most adapted strategy in the world for pharmacological evaluation of future drug candidates. The undertaken research was initiated by esterification 2-(1 H -indol-3-yl)acetic acid (1) with catalytic amount of sulfuric acid in ethanol to ethyl 2-(1 H -indol-3-yl)acetate (2) , which was then reacted with hydrazine hydrate in methanol to achieve 2-(1 H -indol-3-yl)acetohydrazide (3). The corresponding hydrazide 3 was reacted with a variety of arylsulfonyl chlorides (4a-j) in sodium carbonate solution (pH 9-10) to afford N -[2-(1 H -indol-3-yl)acetyl]arylsulfonohydrazides (5a-j) . The structural characterization of synthesized compounds was done by 1 H-NMR, 13 C-NMR, IR and EI-MS spectral data. Moreover, these derivatives were evaluated for anti-bacterial potentials along with their % age hemolytic and enzyme inhibitory activities. It was found that compounds 5a , 5b , 5d and 5h revealed good anti-bacterial against all the bacterial strains used in this study, while 5d, 5g and 5h exhibited good enzyme inhibition potentials against BChE which were close to the reference standard eserine. These compounds also revealed low values of % hemolytic activity. Results of computational docking were also found in agreement with the enzyme inhibition data.