Title:Synthesis, Characterization, Antimicrobial Activity of Novel N-Substituted β-Hydroxy Amines and βHydroxy Ethers Contained Chiral Benzoxazine Fluoroquinolones
Volume: 10
Issue: 1
Author(s): B. Guruswamy and R. Arul
Affiliation:
Keywords:
Antimicrobial activity, Chiral benzoxazine fluoroquinolones, Epichlorohydrine, 7-Piperazinyl chiral benzoxazine
fluoroquinolones, spectrum antibiotics, FDA, piperazinyl fluoroquinolones, pharmacophore, Gram-positive, piperazine ring
Abstract: Synthesis of novel N-substituted β-hydroxy amines 4(a-j) and β-hydroxyethers 5(a-c) with chiral benzoxazine
fluoroquinolones has been described. Benzoxazinefluoroquinolone carboxylic acid 1, on reaction with piperizine in
acetonitrile in presence of triethylamine under reflux gives 7- piperazinyl benzoxazine fluoroquinolone 2. The latter is
reacted with epichlrohydrine in presence of NaOH in acetone to yield respective N-substituted epoxide 3 with retained
chirality, the 3 on treatment with different amines gives respective β-hydroxy amines 4(a-j). On other hand, 3 on
treatment with alcohols in presence of NaOH afforded the corresponding β-hydroxy ethers 5(a-c). The structures of the
synthesized compounds have been established on the basis of its spectral and analytical data. The antimicrobial activity of
newly synthesized compounds ware evaluated against different microorganisms comparing with levofloxacin and found
all the compounds exhibited remarkable activity.
