Synthesis, Characterization, and Antimicrobial Activities of Novel N‐substituted β‐Hydroxy Amines and β‐Hydroxy Ethers that Contained 8‐Methoxy Fluoroquinolones

Abstract

Synthesis of novel N‐substituted β‐hydroxy amines 4a , 4b , 4c , 4d , 4e , 4f , 4g , 4h , 4i , 4j and β‐hydroxy ethers 5a , 5b , 5c that contained 8‐methoxy fluoroquinolones has been described. 8‐Methoxy fluoroquinolone carboxylic acid 1 , reacted with piperizine in acetonitrile in the presence of triethyl amine under reflux, gave 7‐piperazine 8‐methoxyfluoroquinolone 2 . The latter is reacted with epichlorohydrine in the presence of NaOH in acetone to yield the N‐substituted epoxide 3 , which on treatment with aliphatic, aromatic, and cyclic amines gives β‐hydroxy amines 4a , 4b , 4c , 4d , 4e , 4f , 4g , 4h , 4i , 4j . On other hand, 3 on treatment with alcohols in the presence of NaOH afforded the corresponding β‐hydroxy ethers 5a , 5b , 5c . The structures of the synthesized compounds have been established on the basis of spectral and analytical data. Docking analysis was performed using Surflex‐Dock module in Sybyl X 1.0. The antimicrobial activities of newly synthesized compounds were evaluated against bacteria and fungi by using moxifloxacin as the reference. Many of the evaluated compounds exhibited remarkable activities.