Design and Synthesis of 1-(2-amino-1-(4-methoxyphenyl)ethyl) cyclohexanol Analogs as Potential Microbial Agents

Abstract

1-(2-amino-1-(4-methoxyphenyl)ethyl)cyclohexanol (1), on condensation with chloroacetyl chloride yielded 2-chloro-N-(2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl)acetamide (2), which on amination with hydrazine hydrate yielded in turn 2-hydrazinyl-N-(2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl)acetamide (3). Compound 3, on condensation with various aromatic aldehydes afforded a series of 2-(2-benzylidenehydrazinyl)-N-(2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl)acetamides 4a-n, which upon dehydrative annulation in the presence of chloroacetyl chloride and triethylamine yielded 2-(3-chloro-2-oxo-4-phenylazetidin-1-ylamino)-N-(2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl) acetamides 5a-n. The synthesized compounds 4a-g and 5a-g were screened for their antibacterial activity against four microorganisms: Staphylococcus aureus (Gram positive), Bacillus subtilis (Gram positive), Pseudomonas aeruginosa (Gram negative) and Escherichia coli (Gram negative). They were found to exhibit good to moderate antibacterial activity. The antifungal activities of these compounds were also tested against three different fungal species. None of them were active against the species tested.