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

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.