Abstract
N-(2-{[2-(1H-Indol-2-ylcarbonyl)hydrazinyl](oxo)acetyl}phenyl)acetamides (5a–h) and N-[2-(2-{[2-(acetylamino)phenyl](oxo)acetyl}hydrazinyl)-2-oxoethyl]-1H-indole-2-carboxamides (5i–l) were synthesized and characterized with different analytical tools. N-Acetylisatines 4a–d were subjected to ring opening at their C2 carbons with the aid of different indole-bearing hydrazides 3a,b and 7 to afford the respective glyoxylamides 5a–l. The antimicrobial activity of the target compounds 5a–l was assessed with the aid of Diameter of the Inhibition Zone (DIZ) and Minimum Inhibitory Concentration (MIC) assays against a panel of Gram-positive and Gram-negative bacteria and certain fungal strains. The antimicrobial screening revealed that Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, and Candida albicans are the most sensitive microorganisms towards the synthesized compounds 5a–l. In addition, compounds 5c and 5h emerged as the most active congeners towards Staphylococcus aureus and Candida albicans, respectively. Molecular docking studies revealed the possible binding mode of compounds 5c and 5h to their target proteins.
Highlights
Indole is a hetero-aromatic bicyclic ring system and indoles represent an important class in drug discovery and development process [1]
5-methoxyindole fragment was incorporated in a number of bioactive melatoninergic ligands [15,16]
4a–d were allowed to react with the appropriate hydrazide 3a,b in acetonitrile, a polar
Summary
Indole is a hetero-aromatic bicyclic ring system and indoles represent an important class in drug discovery and development process [1]. Indole-bearing compounds are commonly identified and isolated from natural resources and are widely used as precursors in fine organic synthesis to develop new pharmacological lead pharmaceuticals across a broad range of therapeutic areas [2,3,4]. Biological activities exhibited by different indole derivatives include anti-inflammatory [5], anticancer [6], antihypertensive [7], antiviral [8], antibacterial [9] and antifungal activities [10]. 5-methoxyindole constitutes the backbone of the natural hormone melatonin, which helps sleep regulation and wake cycles through manipulation of three different melatoninergic receptors (M1 –M3 ) [11,12]. Melatonin exhibits various therapeutic applications like anti-inflammatory, antioxidant [13], and antitumor activities [14]. 5-methoxyindole fragment was incorporated in a number of bioactive melatoninergic ligands [15,16]
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