Copyright (c) 2013 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Biological Activity of Some 3-[(4-Amino-5-thioxo-1,2,4-triazol-3-yl)methyl]benzothiazol-2(3H)-one Derivatives
Corresponding Author(s) : Tijen Önkol
Asian Journal of Chemistry,
Vol. 25 No. 1 (2013): Vol 25 Issue 1
Abstract
Fourteen new 3-[(4-amino-5-thioxo-1,2,4-triazol-3-yl)methyl]benzothiazol-2(3H)-one derivatives have been synthesized. The structures of these compounds were confirmed by IR, 1H NMR, mass spectrum and elemental analysis. The synthesized compounds were evaluated for their antibacterial activity against various gram-positive and gram-negative strains of bacteria and their clinical isolates, for their antifungal activity against Candida albicans and C. krusei and for their antimycobacterial activity against M. tuberculosis H37Rv and its clinical isolate. Some of the compounds showed promising activity.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- E. Rubinstein, Science, 264, 360 (1994).
- W. Brumfitt and J.M.T. Hamilton-Miller, Drugs Exp. Clin. Res., 20, 215 (1994).
- H.C. Neu, Science, 257, 1064 (1992).
- M. Shiradkar, G.V.S. Kumar, V. Dasari, S. Tatikonda, K.C. Akula and R. Shah, Eur. J. Med. Chem., 42, 807 (2007).
- I. Chopra, J. Hodgson, B. Metcalf and G. Poste, Antimicrob. Agents Chemother., 41, 497 (1997).
- L. Ballell, R.A. Field, K. Duncan and R.J. Young, Antimicrob. Agents Chemother., 49, 2153 (2005).
- S.G.V. Kumar, Y. Rajendraprasad, B.P. Mallikarjuna, S.M. Chandrashekar and C. Kistayya, Eur. J. Med. Chem., 45, 2063 (2010).
- T. Onkol, B. Çakir, S. Ito, B. Ozçelik and M.F. Sahin, Turk. J. Pharm. Sci., 6, 195 (2009).
- B. Cakir, E. Yildirim, T. Ercanli, K. Erol and M.F. Sahin, Farmaco, 54, 842 (1999).
- D.S. Dogruer, S. Unlu, M.F. Sahin and E. Yesilada, Farmaco, 53, 80 (1998).
- Y. Dundar, B. Cakir and E. Kupeli, Turk. J. Chem., 31, 301 (2007).
- T. Onkol, B. Cakir, M.F. Sahin, E. Yildirim and K. Erol, Turk. J. Chem., 28, 461 (2004).
- T. Onkol, S. Ito, E. Yildirim, K. Erol and M.F. Sahin, Arch. Pharm. Pharm. Med. Chem., 334, 17 (2001).
- B. Cakir, A. Ulucay, D.S. Dogruer, A. Isimer and M.F. Sahin, Farmaco, 54, 846 (1999).
- M. Gokce, B. Cakir, K. Erol and M.F. Sahin, Arch. Pharm. Pharm. Med. Chem., 334, 279 (2001).
- B.A. Nadkarni, V.R. Kamat and B.G. Khadse, Arzneim Forsch, 51, 569 (2001).
- M.S. Karthikeyan, B.S. Holla, B. Kalluraya and N.S. Kumari, Monatsh. Chem., 138, 1309 (2007).
- B.S. Holla, P.M. Akberali and M.K. Shivananda, Farmaco, 56, 919 (2001).
- M. Sakata, Y. Shirakawa, N. Kamata,Y.S. Hiroshino and O.Y. Jie, J. Heterocycl. Chem., 37, 269 (2000).
- X.P. Hui, Y. Zhang, P.F. Xu, Q. Wang, Q. Zhang and Z.Y. Zhang, Chin. J. Org. Chem., 25, 700 (2005).
- B.S. Holla, B.S. Rao, B.K. Sarojini, P.M. Akberali and N.S. Kumari, Eur. J. Med. Chem., 41, 657 (2006).
- M.S. Karthikeyan, D.J. Prasad, B. Poojary, K.S. Bhat, B.S. Holla and N.S. Kumari, Bioorg. Med. Chem., 14, 7482 (2006).
- Z.A. Kaplancikli, G. Turan-Zitouni, A. Ozdemir and G. Revial, Eur. J. Med. Chem., 43, 155 (2008).
- B.S. Holla, M. Mahalinga, M.S. Karthikeyan, B. Poojary, P.M. Akberali and N.S. Kumari, Eur. J. Med. Chem., 40, 1173 (2005).
- H. Bayrak, A. Demirbas, N. Demirbas and S.A. Karaoglu, Eur. J. Med. Chem., 44, 4362 (2009).
- M. Shiradkar, G.V.S. Kumar, V. Dasari, S. Tatikonda, K.C. Akula and R.R. Shah, Eur. J. Med. Chem., 42, 807 (2007).
- C.O. Kappe, A. Stadler, R. Mannhold, H. Kubinyi, G. Folkers, Microwaves in Organic and Medicinal Chemistry, 25, Wiley-VCH Verlag GmbH (2005).
- L. Uzun, M.Sc. Thesis, Institute of Health Sciences, Gazi University (2007).
- T. Onkol, Y. Dündar, B. Sirmagul, K. Erol and M.F. Sahin, J. Fac. Pharm. Gazi., 19, 15 (2002).
- Clinical and Laboratory Standards Institute (CLSI) (formerly NCCLS), Performance Standards for Antimicrobial Disk Susceptibility Tests Approved Standard, M2-A9, Clinical and Laboratory Standards Institute, 940 West Valley Road, Wayne, Pennsylvania, USA (2006).
- Clinical and Laboratory Standards Institute (CLSI) (Formerly NCCLS), Performance Standards for Antimicrobial Susceptibility Testing 18th Informational Supplement. CLSI M100-S18, Clinical and Laboratory Standards Institute, 940 West Valley Road, Wayne, Pennsylvania, USA (2008).
- Clinical and Laboratory Standards Institute (CLSI) (formerly NCCLS): Reference Method for Broth Dilution Antifungal Susceptibility Testing yeast; Approved Standard, M27-A3. Clinical and Laboratory Standarts Institute, 940 West Valley Road, Wayne, Pennsylvania, USA (2008).
- S.G.F. Franzblau, R.S. Witzig, J.C. Mclaughlin, P. Torres, G. Madico, A. Hernandez, M.T. Degnan, M.B. Cook, V.K. Quenzer, R.M. Ferguson and R.H. Gilman, J. Clin. Microbiol., 362 (1998).
- X.H. Sun, Y. Tao, Y.F. Liu and B. Chen, Chin. J. Chem., 25, 1573 (2007).
References
E. Rubinstein, Science, 264, 360 (1994).
W. Brumfitt and J.M.T. Hamilton-Miller, Drugs Exp. Clin. Res., 20, 215 (1994).
H.C. Neu, Science, 257, 1064 (1992).
M. Shiradkar, G.V.S. Kumar, V. Dasari, S. Tatikonda, K.C. Akula and R. Shah, Eur. J. Med. Chem., 42, 807 (2007).
I. Chopra, J. Hodgson, B. Metcalf and G. Poste, Antimicrob. Agents Chemother., 41, 497 (1997).
L. Ballell, R.A. Field, K. Duncan and R.J. Young, Antimicrob. Agents Chemother., 49, 2153 (2005).
S.G.V. Kumar, Y. Rajendraprasad, B.P. Mallikarjuna, S.M. Chandrashekar and C. Kistayya, Eur. J. Med. Chem., 45, 2063 (2010).
T. Onkol, B. Çakir, S. Ito, B. Ozçelik and M.F. Sahin, Turk. J. Pharm. Sci., 6, 195 (2009).
B. Cakir, E. Yildirim, T. Ercanli, K. Erol and M.F. Sahin, Farmaco, 54, 842 (1999).
D.S. Dogruer, S. Unlu, M.F. Sahin and E. Yesilada, Farmaco, 53, 80 (1998).
Y. Dundar, B. Cakir and E. Kupeli, Turk. J. Chem., 31, 301 (2007).
T. Onkol, B. Cakir, M.F. Sahin, E. Yildirim and K. Erol, Turk. J. Chem., 28, 461 (2004).
T. Onkol, S. Ito, E. Yildirim, K. Erol and M.F. Sahin, Arch. Pharm. Pharm. Med. Chem., 334, 17 (2001).
B. Cakir, A. Ulucay, D.S. Dogruer, A. Isimer and M.F. Sahin, Farmaco, 54, 846 (1999).
M. Gokce, B. Cakir, K. Erol and M.F. Sahin, Arch. Pharm. Pharm. Med. Chem., 334, 279 (2001).
B.A. Nadkarni, V.R. Kamat and B.G. Khadse, Arzneim Forsch, 51, 569 (2001).
M.S. Karthikeyan, B.S. Holla, B. Kalluraya and N.S. Kumari, Monatsh. Chem., 138, 1309 (2007).
B.S. Holla, P.M. Akberali and M.K. Shivananda, Farmaco, 56, 919 (2001).
M. Sakata, Y. Shirakawa, N. Kamata,Y.S. Hiroshino and O.Y. Jie, J. Heterocycl. Chem., 37, 269 (2000).
X.P. Hui, Y. Zhang, P.F. Xu, Q. Wang, Q. Zhang and Z.Y. Zhang, Chin. J. Org. Chem., 25, 700 (2005).
B.S. Holla, B.S. Rao, B.K. Sarojini, P.M. Akberali and N.S. Kumari, Eur. J. Med. Chem., 41, 657 (2006).
M.S. Karthikeyan, D.J. Prasad, B. Poojary, K.S. Bhat, B.S. Holla and N.S. Kumari, Bioorg. Med. Chem., 14, 7482 (2006).
Z.A. Kaplancikli, G. Turan-Zitouni, A. Ozdemir and G. Revial, Eur. J. Med. Chem., 43, 155 (2008).
B.S. Holla, M. Mahalinga, M.S. Karthikeyan, B. Poojary, P.M. Akberali and N.S. Kumari, Eur. J. Med. Chem., 40, 1173 (2005).
H. Bayrak, A. Demirbas, N. Demirbas and S.A. Karaoglu, Eur. J. Med. Chem., 44, 4362 (2009).
M. Shiradkar, G.V.S. Kumar, V. Dasari, S. Tatikonda, K.C. Akula and R.R. Shah, Eur. J. Med. Chem., 42, 807 (2007).
C.O. Kappe, A. Stadler, R. Mannhold, H. Kubinyi, G. Folkers, Microwaves in Organic and Medicinal Chemistry, 25, Wiley-VCH Verlag GmbH (2005).
L. Uzun, M.Sc. Thesis, Institute of Health Sciences, Gazi University (2007).
T. Onkol, Y. Dündar, B. Sirmagul, K. Erol and M.F. Sahin, J. Fac. Pharm. Gazi., 19, 15 (2002).
Clinical and Laboratory Standards Institute (CLSI) (formerly NCCLS), Performance Standards for Antimicrobial Disk Susceptibility Tests Approved Standard, M2-A9, Clinical and Laboratory Standards Institute, 940 West Valley Road, Wayne, Pennsylvania, USA (2006).
Clinical and Laboratory Standards Institute (CLSI) (Formerly NCCLS), Performance Standards for Antimicrobial Susceptibility Testing 18th Informational Supplement. CLSI M100-S18, Clinical and Laboratory Standards Institute, 940 West Valley Road, Wayne, Pennsylvania, USA (2008).
Clinical and Laboratory Standards Institute (CLSI) (formerly NCCLS): Reference Method for Broth Dilution Antifungal Susceptibility Testing yeast; Approved Standard, M27-A3. Clinical and Laboratory Standarts Institute, 940 West Valley Road, Wayne, Pennsylvania, USA (2008).
S.G.F. Franzblau, R.S. Witzig, J.C. Mclaughlin, P. Torres, G. Madico, A. Hernandez, M.T. Degnan, M.B. Cook, V.K. Quenzer, R.M. Ferguson and R.H. Gilman, J. Clin. Microbiol., 362 (1998).
X.H. Sun, Y. Tao, Y.F. Liu and B. Chen, Chin. J. Chem., 25, 1573 (2007).