Synthesis, Characterization, and Antimicrobial Activities of Novel N‐substituted β‐Hydroxy Amines and β‐Hydroxy Ethers that Contained 8‐Methoxy Fluoroquinolones. (31st March 2015)

• Record Type: Journal Article
• Authors: Guruswamy, B.; Arul, R.
• Is Part Of: Journal of heterocyclic chemistry. Volume 53:Number 1(2016:Jan.)
• Page Start: 284
• Page End: 293
• Publication Date: 2015-03-31
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.1927
• Languages: English
• ISSNs: 0022-152X

Abstract

Abstract : Synthesis of novel N‐substituted β‐hydroxy amines4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j and β‐hydroxy ethers5a, 5b, 5c that contained 8‐methoxy fluoroquinolones has been described. 8‐Methoxy fluoroquinolone carboxylic acid1, reacted with piperizine in acetonitrile in the presence of triethyl amine under reflux, gave 7‐piperazine 8‐methoxyfluoroquinolone2 . The latter is reacted with epichlorohydrine in the presence of NaOH in acetone to yield the N‐substituted epoxide3, which on treatment with aliphatic, aromatic, and cyclic amines gives β‐hydroxy amines4a, 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 ethers5a, 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. Abstract :