Synthesis of novel 4-hydroxycarbazole derivatives and evaluation of their in vitro anti-inflammatory, anti-oxidant activities and molecular docking

Abstract

Synthesis of novel 4-hydroxycarbazole derivatives 4a–q has been reported in good yields. The reaction involves O-alkylation of 4-hydroxycarbazole using methyl 5-bromovalerate results in 2, which on hydrolysis followed by coupling reaction with different primary and secondary amines leads to the formation of 4a–q. All the synthesized compounds 4a–q were characterized using IR, NMR and mass spectral analysis. The synthesized compounds 4a–q was screened for their in vitro anti-inflammatory and total anti-oxidant activity using albumin denaturation and phosphomolybdenum methods, respectively. Among the synthesized compounds, compounds 4h, 4j and 4q were found to show good anti-inflammatory activities against the standard drug diclofenac sodium. Similarly, compounds 4j, 4q and 4p showed very good anti-oxidant activities when compared with the standard drug ascorbic acid. Free energy of binding for all the synthesized compounds was calculated using AutoDock 1.5.4 against corticosteroid-binding globulin (PDB ID: 2V95) receptor. Among the synthesized compounds, compound 4j has shown a high binding energy value of −8.36 kcal/mol.