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Synthesis of Substituted 2-Phenyl-1H-indoles and their Fungicidal Activity
Corresponding Author(s) : Geetika Arora
Asian Journal of Chemistry,
Vol. 29 No. 8 (2017): Vol 29 Issue 8
Abstract
Different substituted acetophenones were condensed with phenyl hydrazine to yield different phenyl hydrazones which were subjected to thermal ring closure under strong acidic conditions to afford substituted 2-phenyl-1H-indoles (1-5). The products were identified and characterized by their elemental analysis, UV, IR, 1H NMR and 13C NMR spectra. All the synthesized compounds were screened for their antifungal activity against two phytopathogenic fungi namely Rhizoctonia solani and Fusarium monilliforme isolated from maize. None of the synthesized 2-phenyl-1H-indoles was as effective as bavistin.
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- A. Goyal, S. Sharma, J. Gaba and H. Kaur, Asian J. Chem., 28, 2169 (2016); https://doi.org/10.14233/ajchem.2016.19900.
- P. Singh, M. Kaur and P. Verma, Bioorg. Med. Chem. Lett., 19, 3054 (2009); https://doi.org/10.1016/j.bmcl.2009.04.014.
- I.A. Leneva, R.J. Russell, Y.S. Boriskin and A.J. Hay, Antiviral Res., 81, 132 (2009); https://doi.org/10.1016/j.antiviral.2008.10.009.
- J. Gaba, S. Sharma, G. Arora, S. Joshi and A. Goyal, J. Indian Chem. Soc., 92, 1587 (2015).
- A. Baeyer and A. Emmerling, Ber. Dtsch. Chem. Ges., 2, 679 (1869); https://doi.org/10.1002/cber.186900201268.
- R. D. Clark and D. B. Repke, Heterocycles, 22, 195 (1984); https://doi.org/10.3987/R-1984-01-0195.
- A. Bischler and P. Fireman, Ber. Dtsch. Chem. Ges., 26, 1336 (1893); https://doi.org/10.1002/cber.18930260232.
- R. Möhlau, Ber. Dtsch. Chem. Ges., 14, 171 (1881); https://doi.org/10.1002/cber.18810140146.
- L.S. Hegedus, G.F. Allen and E.L. Waterman, J. Am. Chem. Soc., 98, 2674 (1976); https://doi.org/10.1021/ja00425a051.
- C. Rossy, E. Fouquet and F.X. Felpin, Beilstein J. Org. Chem., 9, 1426 (2013); https://doi.org/10.3762/bjoc.9.160.
- E. Fischer and F. Jourdan, Ber. Dtsch. Chem. Ges., 16, 2241 (1883); https://doi.org/10.1002/cber.188301602141.
- O. Algul, A. Kaessler, Y. Apcin, A. Yilmaz and J. Jose, Molecules, 13, 736 (2008); https://doi.org/10.3390/molecules13040736.
- J.H. Lee and J. Lee, FEMS Microbiol. Rev., 34, 426 (2010); https://doi.org/10.1111/j.1574-6976.2009.00204.x.
- B. Bertinetti, M. Scandiani and G. Cabrera, Am. J. Plant Sci., 2, 245 (2011); https://doi.org/10.4236/ajps.2011.22026.
- A. Kumar, D. Kumar, M. Akram and H. Kaur, Int. J. Pharm. Biol. Arch., 2, 744 (2011).
- J. Badiger, K. Manjulatha, M. Girish, A. Sharif and M.G. Purohit, ARKIVOC, 217 (2009); https://doi.org/10.3998/ark.5550190.0010.c19.
- R.K. Grover and J.D. Moore, Phytopathology, 52, 876 (1962).
References
A. Goyal, S. Sharma, J. Gaba and H. Kaur, Asian J. Chem., 28, 2169 (2016); https://doi.org/10.14233/ajchem.2016.19900.
P. Singh, M. Kaur and P. Verma, Bioorg. Med. Chem. Lett., 19, 3054 (2009); https://doi.org/10.1016/j.bmcl.2009.04.014.
I.A. Leneva, R.J. Russell, Y.S. Boriskin and A.J. Hay, Antiviral Res., 81, 132 (2009); https://doi.org/10.1016/j.antiviral.2008.10.009.
J. Gaba, S. Sharma, G. Arora, S. Joshi and A. Goyal, J. Indian Chem. Soc., 92, 1587 (2015).
A. Baeyer and A. Emmerling, Ber. Dtsch. Chem. Ges., 2, 679 (1869); https://doi.org/10.1002/cber.186900201268.
R. D. Clark and D. B. Repke, Heterocycles, 22, 195 (1984); https://doi.org/10.3987/R-1984-01-0195.
A. Bischler and P. Fireman, Ber. Dtsch. Chem. Ges., 26, 1336 (1893); https://doi.org/10.1002/cber.18930260232.
R. Möhlau, Ber. Dtsch. Chem. Ges., 14, 171 (1881); https://doi.org/10.1002/cber.18810140146.
L.S. Hegedus, G.F. Allen and E.L. Waterman, J. Am. Chem. Soc., 98, 2674 (1976); https://doi.org/10.1021/ja00425a051.
C. Rossy, E. Fouquet and F.X. Felpin, Beilstein J. Org. Chem., 9, 1426 (2013); https://doi.org/10.3762/bjoc.9.160.
E. Fischer and F. Jourdan, Ber. Dtsch. Chem. Ges., 16, 2241 (1883); https://doi.org/10.1002/cber.188301602141.
O. Algul, A. Kaessler, Y. Apcin, A. Yilmaz and J. Jose, Molecules, 13, 736 (2008); https://doi.org/10.3390/molecules13040736.
J.H. Lee and J. Lee, FEMS Microbiol. Rev., 34, 426 (2010); https://doi.org/10.1111/j.1574-6976.2009.00204.x.
B. Bertinetti, M. Scandiani and G. Cabrera, Am. J. Plant Sci., 2, 245 (2011); https://doi.org/10.4236/ajps.2011.22026.
A. Kumar, D. Kumar, M. Akram and H. Kaur, Int. J. Pharm. Biol. Arch., 2, 744 (2011).
J. Badiger, K. Manjulatha, M. Girish, A. Sharif and M.G. Purohit, ARKIVOC, 217 (2009); https://doi.org/10.3998/ark.5550190.0010.c19.
R.K. Grover and J.D. Moore, Phytopathology, 52, 876 (1962).