

Synthesis and biological evaluation of novel β-hydroxy benzimidazolyl sulfone fluoroquinolones by selective oxidation using ammonium molybdate catalysed H2O2
Batthini Guruswamy (1,*)




(1) Neuland Laboratories Research and Development Center, Bonthapally, Medak, Andhra Pradesh-500313, India
(2) Neuland Laboratories Research and Development Center, Bonthapally, Medak, Andhra Pradesh-500313, India
(3) Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad College of Engineering, Kukatpally, Hyderabad-500085, India
(4) Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad College of Engineering, Kukatpally, Hyderabad-500085, India
(*) Corresponding Author
Received: 05 Apr 2013 | Accepted: 12 Jul 2013 | Published: 31 Dec 2013 | Issue Date: December 2013
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.

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DOI: 10.5155/eurjchem.4.4.329-335.792
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Neuland Laboratories Limited, Hyderabad (A.P.), India; Indian Institute of Chemical Technology (IICT), Hyderabad; Jawaharlal Nehru Technological University, Kukatpally, Hyderabad (A.P.), India.
Citations
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Russian Journal of Organic Chemistry 52(9), 1316, 2016
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