In silico and in vitro anti-inflammatory evaluation of 2,6-bis-(3'-ethoxy, 4'-hydroxybenzylidene)-cyclohexanone, 2,6-bis-(3'-Bromo,4'-methoxybenzylidene)-cyclohexanone, and 2,6-bis- (3',4'-dimethoxybenzylidene)-cyclohexanone

Abstract

The aim of this research is to design the new mono-carbonyl analogs of curcumin, synthesize the molecules, and determine its activity in cyclooxygenase inhibition in vitro and in silico. New design MACs were performed by the Quantitative Structure-Activity Relationship (QSAR) study using the BuildQSAR program. 2,6-bis-(3ʹ-ethoxy, 4ʹ-hydroxybenzylidene)-cyclohexanone, 2,6-bis-(3ʹ-Bromo, 4ʹ-methoxybenzylidene)-cyclohexanone, and 2,6-bis-(3ʹ,4ʹ-dimethoxybenzylidene)-cyclohexanone had been synthesized using aldol condensation reaction. The anti-inflammatory assay was performed to measure the level of malondialdehyde. In silico studies were carried out to evaluate the activity of cyclooxygenase inhibition in cyclooxygenase-1 and cyclooxygenase-2 specific proteins. Molecular operating environment program was used for protocol docking. The results of the QSAR study reveal the good relationship of anti-inflammatory activities. The in vitro anti-inflammatory activities of 6-bis-(3ʹ-ethoxy, 4ʹ-hydroxybenzylidene)cyclohexanone, 2,6-bis-(3ʹ-Bromo, 4ʹ-methoxybenzylidene)-cyclohexanone, and 2,6-bis-(3ʹ,4ʹ-dimethoxybenzylidene)cyclohexanone indicate the promising potential to inhibit cyclooxygenase enzyme with IC 50 13.53 μM, 11.56 μM, and 20.52 μM, respectively. The in silico evaluation showing that O atoms (47, from ketones) of 2,6-bis-(3ʹ-Bromo, 4ʹ-methoxybenzylidene)-cyclohexanone interact with ARG120 and TYR355 through H acceptor.

Docking studies for screening antibacterial compounds of Red Jeringau (Acorus calamus L.) using Shigella flexneri protein as a model system

“…The validation results obtained an RMSD value of 0.7624 Å (figure 1). The RMSD validation value below 2 A indicates that the selected protein is valid and can use for the next step [15,16].…”

“…A molecular docking study with is a branch of science that uses a computational approach to predict a relationship between a drug compound and a receptor [14][15][16]. One of the docking programs in the AutoDock Suite, Vina is undoubtedly one of the more popular ones due to its open-source nature, relative simplicity, and speed compared to other docking programs inside and outside the suite.…”

Photocrosslinking Property of Certain Synthesized Bis(arylidene)cycloalkanone based Random Copolyesters with Computational Support and their Anticancer Study

“…They also display photocrosslinking property [8][9][10], electrical properties [11], crystallinity [12], photo and halochromic responsiveness [13]. Copolyesters containing arylidene-ketones in the main chain were reported to exhibit antibacterial activity [14], antioxidant [15] and antiinflammatory [16] activities.…”