European Journal of Chemistry 2013, 4(4), 329-335. doi:https://doi.org/10.5155/eurjchem.4.4.329-335.792

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


Batthini Guruswamy (1,*) , Rama Krishnan Arul (2) , Muggu Venkata Satya Rama Krishna Chaitan (3) , Sai Subrahmanya Praveen Kumar Darsi (4)

(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

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

Keywords


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

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DOI: 10.5155/eurjchem.4.4.329-335.792

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[1]. I. V. Ledenyova, P. A. Kartavtsev, Kh. S. Shikhaliev, A. Yu. Egorova
4-Aryl-3-(methanesulfonyl)pyrazolo[5,1-c][1,2,4]triazines and their transformations
Russian Journal of Organic Chemistry  52(9), 1316, 2016
DOI: 10.1134/S1070428016090116
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[2]. Mahdi Jamshidi, Davood Nematollahi, Mehdi Bayat, Eslam Salahifar
Unsymmetrical Diaryl Sulfones through Electrochemical Oxidation of Fast Violet B in the Presence of Aryl Sulfinic Acids
Journal of The Electrochemical Society  163(14), G211, 2016
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How to cite


Guruswamy, B.; Arul, R.; Chaitan, M.; Darsi, S. Eur. J. Chem. 2013, 4(4), 329-335. doi:https://doi.org/10.5155/eurjchem.4.4.329-335.792
Guruswamy, B.; Arul, R.; Chaitan, M.; Darsi, S. Eur. J. Chem. Synthesis and biological evaluation of novel β-hydroxy benzimidazolyl sulfone fluoroquinolones by selective oxidation using ammonium molybdate catalysed H2O2. 2013, 4(4), 329-335. doi:https://doi.org/10.5155/eurjchem.4.4.329-335.792
Guruswamy, B., Arul, R., Chaitan, M., & Darsi, S. (2013). Synthesis and biological evaluation of novel β-hydroxy benzimidazolyl sulfone fluoroquinolones by selective oxidation using ammonium molybdate catalysed H2O2. European Journal of Chemistry, 4(4), 329-335. doi:https://doi.org/10.5155/eurjchem.4.4.329-335.792
Guruswamy, Batthini, Rama Krishnan Arul, Muggu Venkata Satya Rama Krishna Chaitan, & Sai Subrahmanya Praveen Kumar Darsi. "Synthesis and biological evaluation of novel β-hydroxy benzimidazolyl sulfone fluoroquinolones by selective oxidation using ammonium molybdate catalysed H2O2." European Journal of Chemistry [Online], 4.4 (2013): 329-335. Web. 21 Apr. 2018
Guruswamy, Batthini, Arul, Rama, Chaitan, Muggu, AND Darsi, Sai. "Synthesis and biological evaluation of novel β-hydroxy benzimidazolyl sulfone fluoroquinolones by selective oxidation using ammonium molybdate catalysed H2O2" European Journal of Chemistry [Online], Volume 4 Number 4 (31 December 2013)

DOI: https://doi.org/10.5155/eurjchem.4.4.329-335.792

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