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Facile Synthesis and Biological Evaluation of Substituted 5-(1H-Indol-3-ylmethylene) pyrimidine-2,4,6-trione Derivatives Using L-Tyrosine in Aqueous Medium
Corresponding Author(s) : G. Thirupathi
Asian Journal of Chemistry,
Vol. 25 No. 15 (2013): Vol 25 Issue 15
Abstract
L-Tyrosine as an efficient catalyst for the Knoevenagel condensation of substituted indole-3-aldehydes 1(a-d), N-methyl indole-3-aldehydes 4(a-d), N-ethyl indole-3-aldehydes 6(a-d) with barbituric acid (2) containing cyclic active methylene group to produce 3(a-d), 5(a-d) and 7(a-d), respectively in water at room temperature for 10 min. The antimicrobial activities of 3(a-d), 5(a-d) and 7(a-d) have been studied.
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- G. Jones, The Knovenagel Condensation Reaction in Organic Reactions, Wiley New York, Vol. 15, p. 204 (1967).
- E. Knoevenagel, Ber., 31, 2585 (1898).
- L.F. Tietze and U. Beifuss, In eds.: B.M. Trost, I. Fleming and C.H. Heathcock, Comprehensive Organic Synthesis, Pergamon: Oxford, Vol. 2, p. 341 (1991).
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- N. Zidar, T. Tomasic and R. Sink, J. Med. Chem., 53, 6584 (2010).
- M. Ibrahim, A.M. Abdel-Hamed and M. El-Gohary, J. Braz. Chem. Soc., 22, 1130 (2011).
- M. Oguchi, K. Wada and H. Honma, J. Med. Chem., 43, 3052 (2000).
- M.S. Malamas, J. Sredy and J.I. Gunawan, J. Med. Chem., 43, 995 (2000).
- R. Murugan, S. Anbazhagan and S.S. Narayanan, Eur. J. Med. Chem., 44, 3272 (2009).
- U.V. Desai, D.M. Pore, R.B. Mane, S.B. Solabanavar and P.P. Wadgaonkar, Synth. Commun., 34, 25 (2004).
- D. Fildes, V. Caignaert, D. Villemin and P. Jaffres, Green Chem., 3, 52 (2001).
- F. Texier-Boullet and A. Foucod, Tetrahedron Lett., 23, 4927 (1982).
- J.A. Cabello, J.M. Campelo,A. Garcia, D. Luna and J.M. Marians, J. Org. Chem., 49, 5195 (1984).
- J.S. Yadav, B.V.S. Reddy, A.K. Basak, B. Visali, A.V. Narsaiah and K. Nagaiah, Eur. J. Med.Chem., 67, 546 (2004).
- D.H. Yang, B.H. Yang, B.C. Chen and S.Y. Chen, Org. Prep. Proced. Int., 38, 81 (2006).
- A.V. Narsaiah,A.K. Basak, B. Visali and K. Nagaiah, Synth. Commun., 34, 2893 (2004).
- I. Rodriguez, S. Iborra, A. Corma, F. Rey and J.L. Jorda, Chem. Commun., 35, 593 (1999).
- D. Prajapati, K.C. Lekhok, J.S. Sandhu and A.C. Ghosh, J. Chem. Soc. Perkin Trans. I, 9, 959 (1996).
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- A.V. Narsaiah and K. Nagaiah, Synth. Commun., 33, 3819 (2003).
- L. Martins, K.M. Vieira, L.M. Rios and D. Cardoso, Cat. Today, 133, 706 (2008).
- U.P.N. Tran, K.K.A. Le and N.T.S. Phan, ACS Catal., 1, 120 (2011).
- T.I. Reddy and R.S. Verma, Tetrahedron Lett., 38, 1721 (1997).
- P. Formentin, H. Garcia and A. Leyva, J. Mol. Catal., 214, 137 (2004).
- Y. Hu, Z.C. Chen, Z.C. Le and Q.G. Zheng, Synth. Commun., 34, 3801 (2004).
- F. Santamarta, P. Verdia and E. Tojo, Catal. Commun., 9, 1779 (2008).
- H. McNab, Chem. Soc. Rev., 7, 345 (1978).
- G.A. Kraus and M.E. Krolski, J. Org. Chem., 51, 3347 (1986).
- X. Huang and L. Xie, Synth. Commun., 16, 1701 (1986).
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- M.T. Thorat, M.H. Jagdale, R.B. Mane, M.M. Salunkhe and P.P. Wadgaonkar, Curr. Sci., 56, 771 (1987).
- P.S. Rao and R.V. Venkataratnam, Indian J. Chem., 32B, 484 (1993).
- S. Miroslav, P. Daniel, A. Marta, F.Andres, C. Carmen, A. Fernando and A. Mercedes, J. Med. Chem., 52, 6217 (2009).
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- V. Ravichandran, R. Harish, K.S. Kumar and A.R. Kishore, Lett. Drug Design Discov., 8, 82 (2011).
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References
G. Jones, The Knovenagel Condensation Reaction in Organic Reactions, Wiley New York, Vol. 15, p. 204 (1967).
E. Knoevenagel, Ber., 31, 2585 (1898).
L.F. Tietze and U. Beifuss, In eds.: B.M. Trost, I. Fleming and C.H. Heathcock, Comprehensive Organic Synthesis, Pergamon: Oxford, Vol. 2, p. 341 (1991).
F. Freeman, Chem. Rev., 80, 329 (1980).
N. Zidar, T. Tomasic and R. Sink, J. Med. Chem., 53, 6584 (2010).
M. Ibrahim, A.M. Abdel-Hamed and M. El-Gohary, J. Braz. Chem. Soc., 22, 1130 (2011).
M. Oguchi, K. Wada and H. Honma, J. Med. Chem., 43, 3052 (2000).
M.S. Malamas, J. Sredy and J.I. Gunawan, J. Med. Chem., 43, 995 (2000).
R. Murugan, S. Anbazhagan and S.S. Narayanan, Eur. J. Med. Chem., 44, 3272 (2009).
U.V. Desai, D.M. Pore, R.B. Mane, S.B. Solabanavar and P.P. Wadgaonkar, Synth. Commun., 34, 25 (2004).
D. Fildes, V. Caignaert, D. Villemin and P. Jaffres, Green Chem., 3, 52 (2001).
F. Texier-Boullet and A. Foucod, Tetrahedron Lett., 23, 4927 (1982).
J.A. Cabello, J.M. Campelo,A. Garcia, D. Luna and J.M. Marians, J. Org. Chem., 49, 5195 (1984).
J.S. Yadav, B.V.S. Reddy, A.K. Basak, B. Visali, A.V. Narsaiah and K. Nagaiah, Eur. J. Med.Chem., 67, 546 (2004).
D.H. Yang, B.H. Yang, B.C. Chen and S.Y. Chen, Org. Prep. Proced. Int., 38, 81 (2006).
A.V. Narsaiah,A.K. Basak, B. Visali and K. Nagaiah, Synth. Commun., 34, 2893 (2004).
I. Rodriguez, S. Iborra, A. Corma, F. Rey and J.L. Jorda, Chem. Commun., 35, 593 (1999).
D. Prajapati, K.C. Lekhok, J.S. Sandhu and A.C. Ghosh, J. Chem. Soc. Perkin Trans. I, 9, 959 (1996).
P.S. Rao and R.V. Ratnam, Tetrahedron Lett., 32, 5821 (1991).
A.V. Narsaiah and K. Nagaiah, Synth. Commun., 33, 3819 (2003).
L. Martins, K.M. Vieira, L.M. Rios and D. Cardoso, Cat. Today, 133, 706 (2008).
U.P.N. Tran, K.K.A. Le and N.T.S. Phan, ACS Catal., 1, 120 (2011).
T.I. Reddy and R.S. Verma, Tetrahedron Lett., 38, 1721 (1997).
P. Formentin, H. Garcia and A. Leyva, J. Mol. Catal., 214, 137 (2004).
Y. Hu, Z.C. Chen, Z.C. Le and Q.G. Zheng, Synth. Commun., 34, 3801 (2004).
F. Santamarta, P. Verdia and E. Tojo, Catal. Commun., 9, 1779 (2008).
H. McNab, Chem. Soc. Rev., 7, 345 (1978).
G.A. Kraus and M.E. Krolski, J. Org. Chem., 51, 3347 (1986).
X. Huang and L. Xie, Synth. Commun., 16, 1701 (1986).
S. Nakamura, H. Rao and T. Ohwada, J. Org. Chem., 69, 4309 (2004).
M.T. Thorat, M.H. Jagdale, R.B. Mane, M.M. Salunkhe and P.P. Wadgaonkar, Curr. Sci., 56, 771 (1987).
P.S. Rao and R.V. Venkataratnam, Indian J. Chem., 32B, 484 (1993).
S. Miroslav, P. Daniel, A. Marta, F.Andres, C. Carmen, A. Fernando and A. Mercedes, J. Med. Chem., 52, 6217 (2009).
L.S.K. Tara and W.G. Gordon, Tetrahedron Lett., 42, 4783 (2001).
V. Ravichandran, R. Harish, K.S. Kumar and A.R. Kishore, Lett. Drug Design Discov., 8, 82 (2011).
Md. Kaspady, V.K. Narayanaswamy, M. Raju and G.K. Rao, Lett. Drug Design Discov., 6, 21 (2010).
S. Frankel, S. Reitman and A.C. Sonnenwirth, Gradwohl’s Clinical Laboratory Methods and Diagnosis, Textbook on a Laboratory Procedure and their Interpretation, edn. 7, Vol. 2, p. 1406 (1970).
Ch. Navneet, K. Pawan, S. Chetan, R. Kamal,Aneja and K.S. Pawan, Lett. Drug Design Discov., 9, 63 (2012).