Copyright (c) 2013 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Microbiological Activity of Some Newly Condensed Derivatives of 2-Oxo-2H-chromen-2-one
Asian Journal of Chemistry,
Vol. 25 No. 11 (2013): Vol 25 Issue 11
Abstract
By the action of 2-amino-5-ethylthio-1,3,4-thidiazole, 3-amino-5-methyl isoxazole and 2-amino benzimidazole on 4-hydroxy-2-oxo-2H-chromene-3-sulfonyl chloride, corresponding 4-hydroxy-2-oxo-2H-chromene-3-sulfonic acid (5-ethyl-[1,3,4]thiadiazol-2-yl)-amide, 4-hydroxy-2-oxo-2H-chromene-3-sulfonic acid (5-methyl-isoxazol-3-yl)-amide and 4-hydroxy-2-oxo-2H-chromene-3-sulfonic acid (1H-benzimidazol-2-yl)-amide were formed and they have been isolated in satisfying yields. Based on the biological activity of chromene-2-ones and heterocyclic compounds condensed in position 3 and 4, we also studied microbiological activity of these new compounds (4-6), against Staphylococcus aureus ATCC 25923, Streptococcus pneumoniae, Aeromonas salmonicida, Bacillus spp and some of them exhibited significant activity.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- M. Daci-Ajvazi, S. Govori and Sh. Omeragiq, E.-J. Chem., 8, 1522 (2011).
- S. Govori, V. Rapic, O. Leci, M. Cacic and I. Tabakovic, J. Heterocycl. Chem., 33, 351 (1996).
- S. Govori, V. Kaljaj, V. Rapic, L. Kaljaj and S. Dakovic, Heterocycl. Commun., 8, 129 (2002).
- I. Manolov and N.D. Danchev, Eur. J. Med. Chem. Chim. Ther., 30, 531 (1995).
- R.B. Arora and C.N. Mathur, Br. J. Pharmacol., 20, 29 (1963).
- E. Ziegler and U. Rossmann, Monatsh. Chem., 88, 25 (1957).
- M.A. Al-Haiza, M.S. Mostafa and M.Y. El-Kady, Molecules, 8, 275 (2003).
- C.J. Dutton, J. Sutcliffe and B. Yang, PCT Int. Appl., US1993/006308, (1994).
- A.I. Vogel and A.R. Tatchell, Vogel's Textbook of Practical Organic Chemistry, A.J. Hannaford and P.W.J. Smith, edn. 5, pp. 1191-1192.
- V.V. Mulwad and J.M. Shirodkhar, Indian J. Heterocycl. Chem., 11, 199 (2002).
- C. Spino, M. Dodier and S. Sotheeswaran, Bioorg. Med. Chem. Lett., 8, 3475 (1998).
- S. Thaisrivongs, K.D. Watenpaugh, W.J. Howe, P.K. Tomich, L.A. Dolak, K.T. Chong, C.S.C. Tomich, A.G. Tomasselli, S.R. Turner, J.W. Strohbach, A.M. Mulichak, M.N. Janakiraman, J.B. Moon, J.C. Lynn, M.M. Horng, R.R. Hinshaw, K.A. Curry and D.J. Rothrock, J. Med. Chem., 38, 3624 (1995).
- S. Gaddam, A. Khilevich, C. Filer, J.D. Rizzo, J. Giltner, M.T. Flavin and Z.Q. Xu, J. Label Comp. Radiopharm., 39, 901 (1997).
- H. Zhao, N. Neamati, H. Hong, A. Mazumder, S. Wang, S. Sunder, G.W.A. Milner, Y. Pommier and Jr. T.R. Burke, J. Med. Chem., 40, 242 (1997).
- S. Gummudavelly, S.Y. Ranganathi, S. Bhasker and N. Rajkumar, Asian J. Res. Chem., 2, 46 (2009).
- V.R. Rao, K. Srimanth and P.V. Kumar, Indian J. Heterocycl. Chem., 14, 141 (2004).
- Z.M. Nofal, M.I. El-Zahar and S.S. Abd El-Karim, Molecules, 5, 99 (2000).
- M. Kovac, A. Sabatic and L. Floch, Arkivoc, 100 (2001).
- I. Tabakovic, K. Tabakovic, R. Grujic, N. Trinajstic and Z. Meic, Heterocycles, 23, 2539 (1985).
- N.P. Buu-Hoï, A. Martani, A. Croisy, P. Jacquignon and F. Périn, J. Chem. Soc. C., 1787 (1966).
References
M. Daci-Ajvazi, S. Govori and Sh. Omeragiq, E.-J. Chem., 8, 1522 (2011).
S. Govori, V. Rapic, O. Leci, M. Cacic and I. Tabakovic, J. Heterocycl. Chem., 33, 351 (1996).
S. Govori, V. Kaljaj, V. Rapic, L. Kaljaj and S. Dakovic, Heterocycl. Commun., 8, 129 (2002).
I. Manolov and N.D. Danchev, Eur. J. Med. Chem. Chim. Ther., 30, 531 (1995).
R.B. Arora and C.N. Mathur, Br. J. Pharmacol., 20, 29 (1963).
E. Ziegler and U. Rossmann, Monatsh. Chem., 88, 25 (1957).
M.A. Al-Haiza, M.S. Mostafa and M.Y. El-Kady, Molecules, 8, 275 (2003).
C.J. Dutton, J. Sutcliffe and B. Yang, PCT Int. Appl., US1993/006308, (1994).
A.I. Vogel and A.R. Tatchell, Vogel's Textbook of Practical Organic Chemistry, A.J. Hannaford and P.W.J. Smith, edn. 5, pp. 1191-1192.
V.V. Mulwad and J.M. Shirodkhar, Indian J. Heterocycl. Chem., 11, 199 (2002).
C. Spino, M. Dodier and S. Sotheeswaran, Bioorg. Med. Chem. Lett., 8, 3475 (1998).
S. Thaisrivongs, K.D. Watenpaugh, W.J. Howe, P.K. Tomich, L.A. Dolak, K.T. Chong, C.S.C. Tomich, A.G. Tomasselli, S.R. Turner, J.W. Strohbach, A.M. Mulichak, M.N. Janakiraman, J.B. Moon, J.C. Lynn, M.M. Horng, R.R. Hinshaw, K.A. Curry and D.J. Rothrock, J. Med. Chem., 38, 3624 (1995).
S. Gaddam, A. Khilevich, C. Filer, J.D. Rizzo, J. Giltner, M.T. Flavin and Z.Q. Xu, J. Label Comp. Radiopharm., 39, 901 (1997).
H. Zhao, N. Neamati, H. Hong, A. Mazumder, S. Wang, S. Sunder, G.W.A. Milner, Y. Pommier and Jr. T.R. Burke, J. Med. Chem., 40, 242 (1997).
S. Gummudavelly, S.Y. Ranganathi, S. Bhasker and N. Rajkumar, Asian J. Res. Chem., 2, 46 (2009).
V.R. Rao, K. Srimanth and P.V. Kumar, Indian J. Heterocycl. Chem., 14, 141 (2004).
Z.M. Nofal, M.I. El-Zahar and S.S. Abd El-Karim, Molecules, 5, 99 (2000).
M. Kovac, A. Sabatic and L. Floch, Arkivoc, 100 (2001).
I. Tabakovic, K. Tabakovic, R. Grujic, N. Trinajstic and Z. Meic, Heterocycles, 23, 2539 (1985).
N.P. Buu-Hoï, A. Martani, A. Croisy, P. Jacquignon and F. Périn, J. Chem. Soc. C., 1787 (1966).