ABSTRACT
Five oxypropanol amine derivatives that four of them are novel have been synthesized with high yields and practical methods. in vitro antibacterial susceptibility of Acinetobacter baumannii, Pseudomonas aeruginosa, Escherichia coli and Staphylococcus aureus strains to synthesized substances were evaluated with agar well-diffusion method by comparison with commercially available drugs. Most of the bacteria were multidrug resistant. It was concluded that these compounds are much more effective than reference drugs. These eugenol bearing oxypropanolamine derivatives were also effective inhibitors against α-glycosidase, cytosolic carbonic anhydrase I and II isoforms (hCA I and II), and acetylcholinesterase (AChE) enzymes with Ki values in the range of 0.80⯱â¯0.24-3.52⯱â¯1.01⯵M for hCA I, 1.08⯱â¯0.15-3.64⯱â¯0.92⯵M for hCA II, 5.18⯱â¯0.84-12.46⯱â¯2.08⯵M for α-glycosidase, and 11.33⯱â¯2.83-32.81⯱â¯9.73⯵M for AChE, respectively.
Subject(s)
Anti-Bacterial Agents/pharmacology , Cholinergic Antagonists/pharmacology , Enzyme Inhibitors/pharmacology , Eugenol/pharmacology , Hypoglycemic Agents/pharmacology , Propanolamines/pharmacology , Acetylcholinesterase/metabolism , Acinetobacter baumannii/drug effects , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Carbonic Anhydrase I/antagonists & inhibitors , Carbonic Anhydrase I/metabolism , Carbonic Anhydrase II/antagonists & inhibitors , Carbonic Anhydrase II/metabolism , Cholinergic Antagonists/chemical synthesis , Cholinergic Antagonists/chemistry , Dose-Response Relationship, Drug , Enzyme Inhibitors/chemical synthesis , Enzyme Inhibitors/chemistry , Escherichia coli/drug effects , Eugenol/chemical synthesis , Eugenol/chemistry , Glycoside Hydrolases/antagonists & inhibitors , Glycoside Hydrolases/metabolism , Hypoglycemic Agents/chemical synthesis , Hypoglycemic Agents/chemistry , Microbial Sensitivity Tests , Molecular Structure , Propanolamines/chemical synthesis , Propanolamines/chemistry , Pseudomonas aeruginosa/drug effects , Staphylococcus aureus/drug effects , Structure-Activity RelationshipABSTRACT
A series of classical and newly synthesized thymol bearing oxypropanolamine compounds were synthesized and characterized. Their in vitro antibacterial activity on A. baumannii, P. aeruginosa, E. coli and S. aureus strains were investigated with agar well diffusion method. The results were compared with commercially available drug active compounds. As well as 3a, 3b and 3c have the most significant antibacterial effect among all the tested compounds; approximately all of them have more antibacterial activity than the reference drugs. These novel thymol bearing oxypropanolamine derivatives were effective inhibitors of the α-glycosidase, cytosolic carbonic anhydrase I and II isoforms (hCA I and II), and acetylcholinesterase enzymes (AChE) with Ki values in the range of 463.85-851.05⯵M for α-glycosidase, 1.11-17.34⯵M for hCA I, 2.97-17.83⯵M for hCA II, and 13.58-31.45⯵M for AChE, respectively.
