Abstract
A new class of antimicrobial and antioxidant agents, based on thiourea and urea derivatives of 6-fluoro-3-(piperidin-4-yl)benzo[d] isoxazole were synthesized by adopting a simple and efficient method. Synthesized compounds were characterized by spectral data of IR, 1H, 13C NMR and mass spectra. The compounds were evaluated for their efficacy as antimicrobial and antioxidant agents. A few compounds showed good antibacterial, antifungal and antioxidant activity when compared to standard drugs and thus represent a new class of promising lead compounds.
A new series of thiourea and urea derivatives of 6-fluoro-3-(piperidin-4-yl)benzo[d] isoxazole were synthesized in a convenient way. The in vitro antimicrobial activity of the title compounds were screened against selected organisms by disc diffusion technique and the antioxidant activity were evaluated by H2O2 and DPPH Methods.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Sadashiva M P, Mallesha H, Karunakara Murthy K and Rangappa K S 2005 Biorg. Med. Chem. 15 1811
(a) Baraldi P G, Barco A, Benetti S, Pollini G P and Simoni D 1987 Synthesis857; (b) Kotyatkina A I, Zhabinsky V N and Khripach V A 2001 Russ. Chem. Rev. 70 641
(a) Batra S, Roy A K, Patra A, Bhaduri A P, Surin W R, Raghavan S A V, Sharma P, Kapoor K and Dikshit M 2004 Biorg. Med. Chem. 12 2059; (b) Agirbas H, Guner S, Budak F, Keceli S, Kandemirli F, Shvets N, Kovalishyn V and Dimoglo A 2007 Biorg. Med. Chem. 15 2322
Pinho EM and Teresa M V D 2005 Curr. Org. Chem. 9 925
Sobieszek G, Borowicz K K, Kimber-trojnar, Malek R, Piskorska B and Czuczwar S J 2003 Pol. J. Pharmacol. 55 683
Stiff D D and Zemaitis M A 1990 Drug Metab. Dispos. 18 888
Nicholas J H, John G J, Kendra L B, Paul G C, Harold B H, Lisa L K, Joachim E R and Ann T W1994 J. Med. Chem. 37 2308
Jain M and Kwon C H 2003 J. Med. Chem. 46 5428
Scobie M and Threadgill M D 1994 J. Org. Chem. 59 7008
Priya B S, Basappa Nanjunda Swamy S and Rangappa K S 2005 Biorg. Med. Chem. 13 2623
Nuhrich A, Varache-Lembege M, Renard P and Devaux G 1994 Eur. J. Med. Chem.29 75
Jacob J P, Anthony K L F, James A P, Richard J P, Steven R C, Andre G P, Paul R B and Patrick W D 1984 J. Med. Chem. 27 1016
Rajeev J, Agarwal D D and Damodharan 1995 J. Indian Chem. Soc. 72 825
Saunder J C and Williamson W R N 1979 J. Med. Chem. 22 1554
Khedekar P B, Bahekar R H, Chopade R S, Umathe S N, Rao A R and Bhusari K P 2003 Drug Res. 53 640
Strupczewski J T, Allen R C, Gardener B A, Schmid B L, Stache U, Glamkowski E J, Jones M C, Ellis D B, Huger F P and Dunn R W 1985 J. Med. Chem. 28 761
Del Corona L, Signorelli G, Faini D, Pinzetta A and Coppi G 1989 Boll. Chim. Farm. 128 177
Anabella V, James F B, Kelly B, Todd W B, Douglas S C, Yuhpyng L C, Jeffrey L I, Shawn B J, Dane R L, Arthur A N, Deane M N, Jann A N, Ismail A S and Frost White W 1994 J. Med. Chem. 37 2721
Pavankumar V S, Sekhar Babu U, Bhushan S P and Vijayavitthal T M 2013 ACS Sustainable Chem. Eng. 1 243
(a) Jean-Pierre Band Bonnet-Delpon D 2006 J. Fluorine Chem. 12 7 992; (b) Park B K and Kitteringham N R 1994 Drug Metab. Rev. 26 605
Suhas R, Chandrashekar S and Channe Gowda D 2011 Eur. J. Med. Chem. 46 704
Benaka Prasad S B, Vinaya K, Ananda Kumar C S, Sanjay Swarup and Rangappa K S 2009 Invest. New Drugs 27 534
(a) Lemriss S, Marquet B, Ginestet H, Lefeuvre L, Fassouane A and Boiron P 2003 J. Mycol. Med 13 189; (b) Drew W L, Barry A L, O’Toole R and Sherris J C 1972 Appl. Microbiol. 24 240; (c) Srdjan S, Natasa A, Ivana D and Milena S V 2003 Microbiol. Res. 158 353
(a) Collins A H 1976 In Microbiological Methods 2nd Edition (London: Butterworth:)11 24; (b) Skaggs B A A, Motley M, Warnock D W and Morrison C J 2000 J. Clin. Microbiol 38 2254; (c) Shaik T B, Chennamsetty S, Devineni S R, Shaik N R, Mundla N D, Rajkumari J P and Chamarthi N R 2014 Bulg. Chem. Commun. 46 724
(a) Awad S M and Mohamed M S 2005 Arch. Pharm. Res. 28 1205; (b) Faidallah H M, Khan K A and Asiri A M 2011 J. Fluorine Chem. 132 131
(a) Eun-Kyung K Seung-Jae L Sang-Ho M Byong-Tae J Chang-Bum A Bokyun K, Beong-Ou L and Pyo-Jam P 2009 Food Chem. 11 7 232; (b) Mansouri M, Movahedian A, Rostami M and Fassihi A 2012 Res. Pharm Sci. 72 57
(a) Ruch R J, Cheng S J and Klaunig J E 1989 Carcinogenesis. 10 1003; (b) Thaslim Basha S K, Rasheed S, Chandra Sekhar K, Naga Raju C, Subhan Ali Md and Appa Rao Ch 2014 Phosphorus, Sulfur Silicon Relat. Elem. 189 1546
(a) Gamez E J C, Luyengi L, Lee S K, Zhu L F, Zhou B N, Fong H H S, Pezzuto J M and Kinghorn A D 1998 J. Nat. Prod. 61 706; (b) Brand-Williams W, Cuvelier M E and Berset C 1995 LWT Food Sci. Technol 28 25
(a) Gulcin I 2006 Life Sci. 78 803; (b) Ismaili L Nadaradjane A Nicod L Guyon C Xicluna A Robert J F and Refouvelet B 2008 Eur. J. Med. Chem. 43 1270
Acknowledgement
The authors are thankful to Department of Science and Technology (DST) Innovation in Science pursuit for inspired research (INSPIRE), New Delhi for financial support.
Author information
Authors and Affiliations
Corresponding author
Additional information
Supplementary Information
Experimental details and tables of results of antibacterial, antifungal and antioxidant (DPPH and H 2 O 2 methods) activities, numbering of the title compound and scanned spectra of 1H and 13C of 8c and 9d compounds are given in the Supplementary Information which is available at www.ias.ac.in/chemsci.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
SUDHAMANI, H., BASHA, S.T., VENKATESWARLU, N. et al. Synthesis and characterization of new thiourea and urea derivatives of 6-fluoro-3-(piperidin-4-yl)benzo[d] isoxazole: In vitro Antimicrobial and Antioxidant activity. J Chem Sci 127, 1739–1746 (2015). https://doi.org/10.1007/s12039-015-0935-6
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12039-015-0935-6