•  
  •  
 

Abstract

The current research deals with 2-carboxyindole, with emphasizing their biological activities. Indole derivatives that well-known for their wide biological characteristics like anticancer, antiviral, and antibacterial activities, were modified by adding Schiff base and beta-lactam frameworks in order to boost their therapeutics prospective. The compounds have been synthesized in a series of steps, which involved Mannich reactions, aldehyde condensation, as well as beta-lactam formation with chloroacetyl chloride. TLC, FTIR, 1H-NMR, and 13C-NMR spectroscopy have been employed to identify the structural details. Schiff base derivatives containing nitro (-NO2) as well as chlorine (-Cl) substituents exhibited high antibacterial as well as antifungal activities, leading to improved lipophilicity and bacterial targeting. Compound C4 exhibited the maximal activity owing to reactive nitrogen species formed by the nitro group. On the other hand, beta-lactam derivatives have revealed poor antibacterial efficacy but substantial antifungal impacts; compounds C7 & C10 revealed the highest inhibition zones against C. albicans. The greater efficacy of Schiff bases can be attributed to their diverse modes of action, which involve metal chelation and covalent contacts with the macromolecules of bacterial spp., unlike the more inflexible core structure of beta-lactams. Our research underscores the possibilities of Schiff base derivatives as promising candidates for combating resistant bacterial strains, as well as the significance of further structural improvements to enhance treatment efficacy. These outcomes contribute to the development of novel antimicrobial drugs that combine both antibacterial and antifungal properties.

Keywords

Antibacterial activity, Beta-lactam, 2-carboxy indole, Mannich reaction, Schiff base derivatives

Subject Area

Chemistry

Article Type

Article

First Page

3184

Last Page

3195

Creative Commons License

Creative Commons Attribution 4.0 International License
This work is licensed under a Creative Commons Attribution 4.0 International License.

Download

Share

 
COinS