Synthesis and biological evaluation of novel β-hydroxy benzimidazolyl sulfone fluoroquinolones by selective oxidation using ammonium molybdate catalysed H2O2

Batthini Guruswamy, Rama Krishnan Arul, Muggu Venkata Satya Rama Krishna Chaitan, Sai Subrahmanya Praveen Kumar Darsi

Abstract


Synthesis of new β-hydroxy benzimidazolyl sulfides (4a-e) and β-hydroxy benzimidazolyl sulfones (5a-e) containing 7-piperazine fluoroquinolones have been described and evaluated for their antimicrobial activity. Benzoxazine fluoroquinolone carboxylic acid, 1, on reaction with piperazine in presence of triethylamine in acetonitrile under reflux resulted 7-piperazine bezoxazole fluoroquinolone, 2. The latter is reacted with epichlorohydrine in presence of NaOH in acetone yielded corresponding N-substituted epoxide, 3, with retained chirality, which on treatment with 5-substituted-2-mercaptobenzimidazoles given the corresponding β-hydroxy bezimidazolyl sulfides (4a-e). Further compounds 4a-e on treatment with H2O2 and ammonium molybdate in dichloromethane yielded the β-hydroxy bezimidazolyl sulfones, 5a-e. The antimicrobial activity of newly synthesized compounds along with levofloxacin (reference drug) were evaluated against different microorganisms and found many of the evaluated compounds have been exhibited remarkable activity.

4_4_329_335

Keyword(s)


Levofloxacin; Epichlorohydrine; Antimicrobial activity; Ammonium molybdate; β-Hydroxy benzimidazolyl sulfones; Chiral benzoxazole fluoroquinolones

European Journal of Chemistry, 4 (4), (2013), 329-335

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DOI: http://dx.doi.org/10.5155/eurjchem.4.4.329-335.792


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