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BAZI N-(BENZOTİYAZOL-2-İL)-2-(4H-[1,2,4]TRİAZOL-3- İLSÜLFANİL)ASETAMİDLERİN SENTEZİ VE BUNLARIN ANTİMİKROBİYAL AKTİVİTELERİ

Year 2011, Volume: 1 Issue: 2, 145 - 151, 29.07.2011

Abstract

Bu çalışmanın amacı, yeni benzotiyazolil-amid türevlerini sentezlemek ve bunların antimikrobiyal aktivitelerini araştırmaktır. N-(benzotiyazol-2-il)-2-kloroasetamidler ile uygun 4H-[1,2,4]triazol-2tiyonların reaksiyona sokulmasıyla N-(Benzotiyazol-2-il)-2-(4H-[1,2,4]triazol-3-ilsülfanil) asetamid türevleri hazırlanmıştır. Sentezlenen bileşiklerin kimyasal yapıları elemental analiz, IR, 1H-NMR, 13CNMR ve FAB+-MS spektral verileri ile aydınlatılmıştır. Bunların antimikrobiyal aktiviteleri Escherichia coli (NRRL B-3008), Staphylococcus aureus (ATCC 6538), Pseudomonas aeruginosa (ATCC 27853), Proteus vulgaris (NRRL B-123), Salmonella typhimurium (ATCC 13311), Methicillin-resistant Staphylococcus aureus (MRSA) (clinic isolate), Candida albicans (NRRL Y-12983) ve Candida parapsilosis’e (NRRL Y-12696) karşı araştırılmıştır. Sonuçlar test edilen tüm bileşiklerin, test organizmalarına karşı inaktif olduğunu gösterdi

References

  • Ali, A., Taylor, G.E. and Graham, D.W. (2001). PCT Int. Appl. WO 2001028561.
  • Bayrak, H., Demirbas, A., Demirbas, N. and Karaoglu, S.A. (2009). Synthesis of some new 1,2,4-triazoles starting from isonicotinic acid hydrazide and evaluation of their antimicrobial activities. Eur. J. Med. Chem. 44, 4362-4366.
  • Bhargava, P.N. and Ram, P. (1965). Synthesis of local anesthetics. Bull. Chem. Soc. Japan 38, 339-341.
  • Black, C., Deschenes, D., Gagnon, M., Lachance, N., Leblanc, Y., Leger, S., Li, C.S. and Oballa, R.M. (2006). PCT Int. Appl. WO 2006122200 A1 20061116.
  • Blackman, A.J. and Polya, J.B. (1970). Triazoles. Part XI. Synthesis of 1,2,4-Triazole-3-sulphonic Acids by Oxidation of 1,2,4-Triazoline-3-thiones. J. Chem. Soc. (C) 2403-2409.
  • Bose, D.S. and Idrees, M. (2010). Intramolecular Cascade C-S Bond Formation: Regioselective Synthesis of Substituted Benzothiazoles, Synthesis 12, 1983-1988.
  • Koneman, E.W., Allen, S.D. and Winn, W.C. (1997). Colour Atlas and Textbook of Diagnostic Microbiology. Lippincott Raven Publishers, Philadelphia, USA, pp. 86-856.
  • Henriksen, G., Hauser, A.I., Westwell, A.D., Yousefi, B.H., Schwaiger, M., Drzezga, A. and Wester, H.J. (2007). Metabolically stabilized benzothiazoles for imaging of amyloid plaques. J. Med. Chem. 50, 10871089.
  • Hutchinson, I., Chua, M.S., Browne, H.L., Trapani, V., Bradshaw, T.D., Westwell, A.D. and Stewens, M.F.G. (2001). Antitumor benzothiazoles. 14. Synthesis and in vitro biological properties of fluorinated 2-(4aminophenyl)benzothiazoles. J. Med. Chem. 44, 1446-1455.
  • NCCLS (2002). Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts. Approved Standard-Second Edition, NCCLS document M27-A2, ISBN 1-56238-469-4.
  • Palmer, P.J., Trigg, R.B. and Warrington, J.V. (1971). Benzothiazolines as antituberculous agents. J. Med. Chem. 14, 248-251.
  • Saadeh, H.A., Mosleh, I.M., Al-Bakri, A.G. and Mubarak, M.S. (2010). Synthesis and antimicrobial activity of new 1,2,4-triazole-3-thiol metronidazole derivatives. Monatsh. Chem. 141, 471-478.
  • Shaker, R.M. (2006). The chemistry of mercapto-and thione- substituted 1,2,4-triazoles and their utility in heterocyclic synthesis. Arkivoc ix, 59-112.
  • Swamy, S.N., Basappa Priya, B.S., Prabhuswamy, B., Doreswamy, B.H., Prasad, J.S. and Rangappa, K.S. (2006). Synthesis of pharmaceutically important condensed heterocyclic 4,6-disubstituted-1,2,4-triazolo-1,3,4-thiadiazole derivatives as antimicrobials. Eur. J. Med. Chem. 41, 531-538.

SYNTHESIS OF SOME N-(BENZOTHIAZOL-2-YL)-2-(4H-[1,2,4]TRIAZOL -3- YLSULFANYL)ACETAMIDES AND THEIR ANTIMICROBIAL ACTIVITY

Year 2011, Volume: 1 Issue: 2, 145 - 151, 29.07.2011

Abstract

The aim of this study is to synthesize novel benzothiazolyl-amide derivatives and investigate their antimicrobial activities. N-(Benzothiazol-2-yl)-2-(4H-[1,2,4]triazol-3-ylsulfanyl) acetamide derivatives were prepared by the reaction of N-(benzothiazol-2-yl)-2-chloroacetamides with appropriate 4H-[1,2,4]triazol-2-thione. The chemical structures of the compounds were elucidated by elemental analyses, IR, 1H-NMR, 13C-NMR and FAB+-MS spectral data. Their antimicrobial activities against Escherichia coli (NRRL B-3008), Staphylococcus aureus (ATCC 6538), Pseudomonas aeruginosa (ATCC 27853), Proteus vulgaris (NRRL B-123), Salmonella typhimurium (ATCC 13311), Methicillin-resistant Staphylococcus aureus (MRSA) (clinic isolate), Candida albicans (NRRL Y-12983) and Candida parapsilosis (NRRL Y-12696)  were investigated. The results showed that all of the tested compounds were inactive against the test organism.

References

  • Ali, A., Taylor, G.E. and Graham, D.W. (2001). PCT Int. Appl. WO 2001028561.
  • Bayrak, H., Demirbas, A., Demirbas, N. and Karaoglu, S.A. (2009). Synthesis of some new 1,2,4-triazoles starting from isonicotinic acid hydrazide and evaluation of their antimicrobial activities. Eur. J. Med. Chem. 44, 4362-4366.
  • Bhargava, P.N. and Ram, P. (1965). Synthesis of local anesthetics. Bull. Chem. Soc. Japan 38, 339-341.
  • Black, C., Deschenes, D., Gagnon, M., Lachance, N., Leblanc, Y., Leger, S., Li, C.S. and Oballa, R.M. (2006). PCT Int. Appl. WO 2006122200 A1 20061116.
  • Blackman, A.J. and Polya, J.B. (1970). Triazoles. Part XI. Synthesis of 1,2,4-Triazole-3-sulphonic Acids by Oxidation of 1,2,4-Triazoline-3-thiones. J. Chem. Soc. (C) 2403-2409.
  • Bose, D.S. and Idrees, M. (2010). Intramolecular Cascade C-S Bond Formation: Regioselective Synthesis of Substituted Benzothiazoles, Synthesis 12, 1983-1988.
  • Koneman, E.W., Allen, S.D. and Winn, W.C. (1997). Colour Atlas and Textbook of Diagnostic Microbiology. Lippincott Raven Publishers, Philadelphia, USA, pp. 86-856.
  • Henriksen, G., Hauser, A.I., Westwell, A.D., Yousefi, B.H., Schwaiger, M., Drzezga, A. and Wester, H.J. (2007). Metabolically stabilized benzothiazoles for imaging of amyloid plaques. J. Med. Chem. 50, 10871089.
  • Hutchinson, I., Chua, M.S., Browne, H.L., Trapani, V., Bradshaw, T.D., Westwell, A.D. and Stewens, M.F.G. (2001). Antitumor benzothiazoles. 14. Synthesis and in vitro biological properties of fluorinated 2-(4aminophenyl)benzothiazoles. J. Med. Chem. 44, 1446-1455.
  • NCCLS (2002). Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts. Approved Standard-Second Edition, NCCLS document M27-A2, ISBN 1-56238-469-4.
  • Palmer, P.J., Trigg, R.B. and Warrington, J.V. (1971). Benzothiazolines as antituberculous agents. J. Med. Chem. 14, 248-251.
  • Saadeh, H.A., Mosleh, I.M., Al-Bakri, A.G. and Mubarak, M.S. (2010). Synthesis and antimicrobial activity of new 1,2,4-triazole-3-thiol metronidazole derivatives. Monatsh. Chem. 141, 471-478.
  • Shaker, R.M. (2006). The chemistry of mercapto-and thione- substituted 1,2,4-triazoles and their utility in heterocyclic synthesis. Arkivoc ix, 59-112.
  • Swamy, S.N., Basappa Priya, B.S., Prabhuswamy, B., Doreswamy, B.H., Prasad, J.S. and Rangappa, K.S. (2006). Synthesis of pharmaceutically important condensed heterocyclic 4,6-disubstituted-1,2,4-triazolo-1,3,4-thiadiazole derivatives as antimicrobials. Eur. J. Med. Chem. 41, 531-538.
There are 14 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Ahmet Özdemir

Zafer Kaplancıklı

Gülhan Turan-zıtounı This is me

Mehlika Altıntop This is me

Fatih Demirci

Publication Date July 29, 2011
Published in Issue Year 2011 Volume: 1 Issue: 2

Cite

APA Özdemir, A., Kaplancıklı, Z., Turan-zıtounı, G., Altıntop, M., et al. (2011). SYNTHESIS OF SOME N-(BENZOTHIAZOL-2-YL)-2-(4H-[1,2,4]TRIAZOL -3- YLSULFANYL)ACETAMIDES AND THEIR ANTIMICROBIAL ACTIVITY. Anadolu University Journal of Science and Technology C - Life Sciences and Biotechnology, 1(2), 145-151.
AMA Özdemir A, Kaplancıklı Z, Turan-zıtounı G, Altıntop M, Demirci F. SYNTHESIS OF SOME N-(BENZOTHIAZOL-2-YL)-2-(4H-[1,2,4]TRIAZOL -3- YLSULFANYL)ACETAMIDES AND THEIR ANTIMICROBIAL ACTIVITY. Anadolu University Journal of Science and Technology C - Life Sciences and Biotechnology. July 2011;1(2):145-151.
Chicago Özdemir, Ahmet, Zafer Kaplancıklı, Gülhan Turan-zıtounı, Mehlika Altıntop, and Fatih Demirci. “SYNTHESIS OF SOME N-(BENZOTHIAZOL-2-YL)-2-(4H-[1,2,4]TRIAZOL -3- YLSULFANYL)ACETAMIDES AND THEIR ANTIMICROBIAL ACTIVITY”. Anadolu University Journal of Science and Technology C - Life Sciences and Biotechnology 1, no. 2 (July 2011): 145-51.
EndNote Özdemir A, Kaplancıklı Z, Turan-zıtounı G, Altıntop M, Demirci F (July 1, 2011) SYNTHESIS OF SOME N-(BENZOTHIAZOL-2-YL)-2-(4H-[1,2,4]TRIAZOL -3- YLSULFANYL)ACETAMIDES AND THEIR ANTIMICROBIAL ACTIVITY. Anadolu University Journal of Science and Technology C - Life Sciences and Biotechnology 1 2 145–151.
IEEE A. Özdemir, Z. Kaplancıklı, G. Turan-zıtounı, M. Altıntop, and F. Demirci, “SYNTHESIS OF SOME N-(BENZOTHIAZOL-2-YL)-2-(4H-[1,2,4]TRIAZOL -3- YLSULFANYL)ACETAMIDES AND THEIR ANTIMICROBIAL ACTIVITY”, Anadolu University Journal of Science and Technology C - Life Sciences and Biotechnology, vol. 1, no. 2, pp. 145–151, 2011.
ISNAD Özdemir, Ahmet et al. “SYNTHESIS OF SOME N-(BENZOTHIAZOL-2-YL)-2-(4H-[1,2,4]TRIAZOL -3- YLSULFANYL)ACETAMIDES AND THEIR ANTIMICROBIAL ACTIVITY”. Anadolu University Journal of Science and Technology C - Life Sciences and Biotechnology 1/2 (July 2011), 145-151.
JAMA Özdemir A, Kaplancıklı Z, Turan-zıtounı G, Altıntop M, Demirci F. SYNTHESIS OF SOME N-(BENZOTHIAZOL-2-YL)-2-(4H-[1,2,4]TRIAZOL -3- YLSULFANYL)ACETAMIDES AND THEIR ANTIMICROBIAL ACTIVITY. Anadolu University Journal of Science and Technology C - Life Sciences and Biotechnology. 2011;1:145–151.
MLA Özdemir, Ahmet et al. “SYNTHESIS OF SOME N-(BENZOTHIAZOL-2-YL)-2-(4H-[1,2,4]TRIAZOL -3- YLSULFANYL)ACETAMIDES AND THEIR ANTIMICROBIAL ACTIVITY”. Anadolu University Journal of Science and Technology C - Life Sciences and Biotechnology, vol. 1, no. 2, 2011, pp. 145-51.
Vancouver Özdemir A, Kaplancıklı Z, Turan-zıtounı G, Altıntop M, Demirci F. SYNTHESIS OF SOME N-(BENZOTHIAZOL-2-YL)-2-(4H-[1,2,4]TRIAZOL -3- YLSULFANYL)ACETAMIDES AND THEIR ANTIMICROBIAL ACTIVITY. Anadolu University Journal of Science and Technology C - Life Sciences and Biotechnology. 2011;1(2):145-51.