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One Pot Multicomponent Synthesis of Anti-inflammatory Active Tetrahydrofuro[3,2-c]pyridinone-2-carboxylate Derivatives
Corresponding Author(s) : Venkata Swamy Tangeti
Asian Journal of Chemistry,
Vol. 30 No. 2 (2018): Vol 30 Issue 2
Abstract
A novel, one-pot method has been developed for the synthesis of tetrahydrofuro[3,2-c]pyridine-2-carboxylate derivatives via cascade four-component condensation of 6-methyl, 4-hydroxy pyranone, aryl amines, aromatic aldehydes and pyridinium ylide, in presence of triethylamine as a catalyst under ethanol reflux conditions. It affords the corresponding product in high yield (78-92 %) with short reaction time (15-25 min).The anti-inflammatory activity of these compounds was determined. Out of the 17 synthesized compounds, compounds 5j, 5k, 5l, 5m and 5n were excellent inhibitors of TNF-a and IL-6, COX-2, b-glucuronidase.
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- H.S.P. Rao and V.S. Tangeti, Proc. Natl. Acad. Sci. India Sect. A: Phys. Sci., 85, 41 (2015); https://doi.org/10.1007/s40010-014-0179-8.
- N.S. Topno, H.S.P. Rao, V.S. Tangeti and R. Krishna, Acta Crystallogr., E69, o284 (2013); https://doi.org/10.1107/S1600536812051872.
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References
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Y. Sugie, S.J. Truesdell, J.W. Wong, N. Yoshikawa and A. Sugiura, Furopyridine Antibacterials and Production Thereof, EP 999212 A1 (2000).
T. Fukuda, Y. Yamaguchi, R. Masuma, H. Tomoda and S.J. Omura, Antibiot., 58, 309 (2005); https://doi.org/10.1038/ja.2005.38.
B. Wolters and U. Eilert, Planta Med., 43, 166 (1981); https://doi.org/10.1055/s-2007-971494.
G. Petit-Pali, M. Rideau and J.C. Chenieux, Planta Med. Phytother., 16, 55 (1982).
G.H. Svoboda, G.A. Poore, P.J. Simpson and G.B. Boder, J. Pharm. Sci., 55, 758 (1966); https://doi.org/10.1002/jps.2600550803.
L.K. Basco, S. Mitaku,A.L. Skaltsounis, N. Ravelomanantsoa, F. Tillequin, M. Koch and J. Le Bras, Antimicrob. Agents Chemother., 38, 1169 (1994); https://doi.org/10.1128/AAC.38.5.1169.
D.L.J. Clive and X. Huang, J. Org. Chem., 69, 1872 (2004); https://doi.org/10.1021/jo030284g.
Y. Rok Lee, B.S. Kim and H. Il Kweon, Tetrahedron, 56, 3867 (2000); https://doi.org/10.1016/S0040-4020(00)00307-0.
H. Senboku, M. Takashima, M. Suzuki, K. Kobayashi and H. Suginome, Tetrahedron, 52, 6125 (1996); https://doi.org/10.1016/0040-4020(96)00210-4.
H. Suginome, K. Kobayashi, M. Itoh, S. Seko and A. Furusaki, J. Org. Chem., 55, 4933 (1990); https://doi.org/10.1021/jo00303a034.
B.B. Snider and Q. Che, Org. Lett., 6, 2877 (2004); https://doi.org/10.1021/ol049130t.
D. Conreaux, T. Delaunay, P. Desbordes, N. Monteiro and G. Balme, Tetrahedron Lett., 50, 3299 (2009); https://doi.org/10.1016/j.tetlet.2009.02.073.
M.C. Pirrung and F. Blume, J. Org. Chem., 64, 3642 (1999); https://doi.org/10.1021/jo982503h.
J. Su, J. Xiong, S. Liang, G. Qiu, X. Feng, H. Teng, L. Wu and X. Hu, Synth. Commun., 36, 693 (2006); https://doi.org/10.1080/00397910500446530.
R. Zhang, Y. Liang, G. Zhou, K. Wang and D. Dong, J. Org. Chem., 73, 8089 (2008); https://doi.org/10.1021/jo801289p.
F. Liang, S. Lin and Y. Wei, J. Am. Chem. Soc., 133, 1781 (2011); https://doi.org/10.1021/ja110870f.
S. Tangeti, G.V. Siva Prasad, J. Panda and K.R. Varma, Synth. Commun., 46, 878 (2016); https://doi.org/10.1080/00397911.2016.1174781.
H.S.P. Rao and V.S. Tangeti, J. Chem. Sci., 125, 777 (2013); https://doi.org/10.1007/s12039-013-0458-y.
H.S.P. Rao, V.S. Tangeti and L.N. Adigopula, Res. Chem. Intermed., 42, 7285 (2016); https://doi.org/10.1007/s11164-016-2536-5.
V.S. Tangeti, R. Varma K, G.V. Siva Prasad and K.V.V.V. Satyanarayana, Synth. Commun., 46, 613 (2016); https://doi.org/10.1080/00397911.2016.1159696.
H. S.P. Rao and V. S. Tangeti, Lett. Org. Chem., 9, 218 (2012); https://doi.org/10.2174/157017812800167501.
H.S.P. Rao and V.S. Tangeti, Proc. Natl. Acad. Sci. India Sect. A: Phys. Sci., 85, 41 (2015); https://doi.org/10.1007/s40010-014-0179-8.
N.S. Topno, H.S.P. Rao, V.S. Tangeti and R. Krishna, Acta Crystallogr., E69, o284 (2013); https://doi.org/10.1107/S1600536812051872.
V.S. Tangeti, D. Vasundhara, K.V.V.V. Satyanarayana and K.S.P. Kumar, Asian J. Chem., 29, 1525 (2017); https://doi.org/10.14233/ajchem.2017.20550.
S.M. Rajesh, S. Perumal, J.C. Menéndez, S. Pandian and R. Murugesan, Tetrahedron, 68, 5631 (2012); https://doi.org/10.1016/j.tet.2012.04.058.
C. Hwang, M. Catanaga, A. Gale and T. Gatanaga, J. Immunol., 151, 5631 (1993).
M. Tandon, P. Tandon, J.P. Barthwal, T.N. Bhalla and K.P. Bhargava, Drug Res., 32, 1233 (1982).
B.P. Bandgar, B.S. Hote, S.S. Jalde and R.N. Gacche, Med. Chem. Res., 21, 3006 (2012); https://doi.org/10.1007/s00044-011-9834-7.
T. Bilfinger and G. Stefano, Curr. Pharm. Des., 8, 505 (2002); https://doi.org/10.2174/1381612023395763.