Synthesis, Docking Study and β-Adrenoceptor Activity of Some New Oxime Ether Derivatives

Abstract

Abstract:A new series of oxime ethers 4a-z was designed and synthesized to test the blocking activity against β 1 and β 2 -adrenergic receptors. Docking of these ether derivatives into the active site of the identified 3D structures of β 1 and β 2 -adrenergic receptors showed MolDock scores comparable to those of reference compounds. Biological results revealed that the inhibition effects on the heart rate and contractility are less than those of propranolol. Nevertheless, the two compounds 4p and 4q that displayed the highest negative MolDock score with β 2 -adrenergic receptors showed β 2 -antagonistic activity by decreasing salbutamol relaxation of precontracted tracheal strips, which indicates the importance of a chlorothiophene moiety in the hydrophobic region for best complementarity with β 2 receptors. On other hand, the presence of a homoveratryl moiety increases the MolDock score of the tested compounds with the β 1 receptor.

Screening of β1- and β2-Adrenergic Receptor Modulators through Advanced Pharmacoinformatics and Machine Learning Approaches

“…Ghabbour et al [ 31 ] synthesized some new oxime ether derivative compounds and performed their molecular docking study against β1-AR. According to the findings of the mentioned study, the key amino acids Phe201, Tyr207, Ser211, Phe216, and Phe307 of β1-AR interacted with the oxime ether derivatives.…”

Crystal structure of 3-(((cyclohexyl(phenyl)methylidene)amino)oxy)-2-hydroxy-N-(propan-2-yl)propan-1-aminium chloride, C19H31ClN2O2

“…The O-alkylation of oximes is vital in drug design since O-oxime ether derivatives are famous structural motifs, which are present in many pharmacologically active compounds [1][2]. In our previous research, we studied the O-alkylation of structurally diverse oximes with epichlorohydrin to access various potential bioactive compounds as betaadrenoceptore blocking agent analogs [1].…”

“…In our previous research, we studied the O-alkylation of structurally diverse oximes with epichlorohydrin to access various potential bioactive compounds as betaadrenoceptore blocking agent analogs [1]. In continues of our work we report here the crystal structure of title compound elucidated by crystallographic analysis (see the gure).…”

“…synthesis of the title compound was carried out according to procedure reported by Ghabbour et al [1]. The title compound was obtained as colorless plate crystals from ethanol.…”

Design, Synthesis, and Bioassay of Novel Compounds of Isolongifolenone Oxime Derivatives

“…Oxime ether derivatives, known as important precursors and intermediates for natural products and various drugs , have been the hot topic for research workers due to their bioactivity against antibacterial , antifungal , larvicidal , antiretroviral , antineoplastic , BK channel‐opening , and acaricidal activities. In addition, oxime ether derivatives have also been reported as potent anti‐inflammatory agents and inhibitors of monocyte‐to‐macrophage transformation , β ‐adrenergic blocking , anticancer agents , sugar surfactants , and ethylene inhibitor . Recently, isolongifolenone, obtained through the oxidation of isolongifolene which was isomerized by natural product of longifolene , has been found to exert potent against tyrosinase and breast cancer .…”