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Journal of Chemical Sciences

, Volume 127, Issue 10, pp 1739–1746 | Cite as

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

  • HASTI SUDHAMANI
  • SK THASLIM BASHA
  • NAGAM VENKATESWARLU
  • TARTTE VIJAYA
  • CHAMARTHI NAGA RAJUEmail author
Article

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.

Graphical Abstract

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.

Keywords

Isothiocyanates Isocyanates 6-Fluoro-3-(piperidin-4-yl)benzo[d] isoxazole Antimicrobial and Antioxidant activity 

Notes

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.

Supplementary material

12039_2015_935_MOESM1_ESM.docx (479 kb)
(DOCX 478 KB)

References

  1. 1.
    Sadashiva M P, Mallesha H, Karunakara Murthy K and Rangappa K S 2005 Biorg. Med. Chem. 15 1811Google Scholar
  2. 2.
    (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 641Google Scholar
  3. 3.
    (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 2322Google Scholar
  4. 4.
    Pinho EM and Teresa M V D 2005 Curr. Org. Chem. 9 925Google Scholar
  5. 5.
    Sobieszek G, Borowicz K K, Kimber-trojnar, Malek R, Piskorska B and Czuczwar S J 2003 Pol. J. Pharmacol. 55 683Google Scholar
  6. 6.
    Stiff D D and Zemaitis M A 1990 Drug Metab. Dispos. 18 888Google Scholar
  7. 7.
    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 2308Google Scholar
  8. 8.
    Jain M and Kwon C H 2003 J. Med. Chem. 46 5428Google Scholar
  9. 9.
    Scobie M and Threadgill M D 1994 J. Org. Chem. 59 7008Google Scholar
  10. 10.
    Priya B S, Basappa Nanjunda Swamy S and Rangappa K S 2005 Biorg. Med. Chem. 13 2623Google Scholar
  11. 11.
    Nuhrich A, Varache-Lembege M, Renard P and Devaux G 1994 Eur. J. Med. Chem.29 75Google Scholar
  12. 12.
    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 1016Google Scholar
  13. 13.
    Rajeev J, Agarwal D D and Damodharan 1995 J. Indian Chem. Soc. 72 825Google Scholar
  14. 14.
    Saunder J C and Williamson W R N 1979 J. Med. Chem. 22 1554Google Scholar
  15. 15.
    Khedekar P B, Bahekar R H, Chopade R S, Umathe S N, Rao A R and Bhusari K P 2003 Drug Res. 53 640Google Scholar
  16. 16.
    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 761Google Scholar
  17. 17.
    Del Corona L, Signorelli G, Faini D, Pinzetta A and Coppi G 1989 Boll. Chim. Farm. 128 177Google Scholar
  18. 18.
    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 2721Google Scholar
  19. 19.
    Pavankumar V S, Sekhar Babu U, Bhushan S P and Vijayavitthal T M 2013 ACS Sustainable Chem. Eng. 1 243Google Scholar
  20. 20.
    (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 605Google Scholar
  21. 21.
    Suhas R, Chandrashekar S and Channe Gowda D 2011 Eur. J. Med. Chem. 46 704Google Scholar
  22. 22.
    Benaka Prasad S B, Vinaya K, Ananda Kumar C S, Sanjay Swarup and Rangappa K S 2009 Invest. New Drugs 27 534Google Scholar
  23. 23.
    (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 353Google Scholar
  24. 24.
    (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 724Google Scholar
  25. 25.
    (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 131Google Scholar
  26. 26.
    (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 57Google Scholar
  27. 27.
    (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 1546Google Scholar
  28. 28.
    (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 25Google Scholar
  29. 29.
    (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 1270Google Scholar

Copyright information

© Indian Academy of Sciences 2015

Authors and Affiliations

  • HASTI SUDHAMANI
    • 1
  • SK THASLIM BASHA
    • 1
  • NAGAM VENKATESWARLU
    • 2
  • TARTTE VIJAYA
    • 2
  • CHAMARTHI NAGA RAJU
    • 1
    Email author
  1. 1.Department of ChemistryS V UniversityTirupatiIndia
  2. 2.Department of BotanyS V UniversityTirupatiIndia

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