Copyright (c) 2016 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Characterization of Ethyl 7-Acetyl-2-substituted 3-(substituted benzoyl)indolizine-1-carboxylates for in vitro Anticancer Activity
Corresponding Author(s) : Basavaraj Padmashali
Asian Journal of Chemistry,
Vol. 28 No. 5 (2016): Vol 28 Issue 5
Abstract
Efficient synthesis of a series of novel indolizines (2a-r) has been achieved by reaction between 4-acetyl-1-[2-(substituted phenyl)-2-oxoethyl]pyridin-1-ium bromide and substituted alkynes in presence of anhydrous potassium carbonate in dimethyl formamide medium. The title compounds have been characterized by spectroscopic techniques and elemental analysis. Selected compounds 2b, 2h, 2i, 2q and 2r have been screened for in vitro anticancer activity using adriamycin as positive control and it was found that compounds 2b, 2q and 2r have shown significant anticancer activity.
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- M.W. Edwards, J.W. Daly and C.W. Myers, J. Nat. Prod., 51, 1188 (1988); doi:10.1021/np50060a023.
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- P.S. Liu, R.S. Rogers, M.S. Kang and P.S. Sunkara, Tetrahedron Lett., 32, 5853 (1991); doi:10.1016/S0040-4039(00)79409-3.
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- D.J. Vocadlo, E.J. McEachern and K. Stubbs, Selective Glycosidase Inhibitors and Uses Thereof, WO2010012106A1 (2010).
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- A. Hazra, S. Mondal, A. Maity, S. Naskar, P. Saha, R. Paira, K.B. Sahu, P. Paira, S. Ghosh, C. Sinha, A. Samanta, S. Banerjee and N.B. Mondal, Eur. J. Med. Chem., 46, 2132 (2011); doi:10.1016/j.ejmech.2011.02.066.
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- M.L. Bode and P.T. Kaye, J. Chem. Soc., Perkin Trans. 1, 2612 (1990); doi:10.1039/p19900002612.
- V. Boekelheide and R.J. Windgassen Jr., J. Am. Chem. Soc., 81, 1456 (1959); doi:10.1021/ja01515a044.
- J. Hurst, T. Melton and D.G. Wibberley, J. Chem. Soc., 46, 2948 (1965); doi:10.1039/jr9650002948.
- G. Jones and J. Stanyer, J. Chem. Soc. C: Organic, 901 (1969); doi:10.1039/j39690000901.
- E. Pohjala, Tetrahedron Lett., 13, 2585 (1972); doi:10.1016/S0040-4039(01)84880-2.
- R.M. Acheson and D.A. Robinson, J. Chem. Soc. C: Organic, 1629 (1968); doi:10.1039/j39680001629.
- C. Sandeep, B. Padmashali and R.S. Kulkarni, Tetrahedron Lett., 54, 6411 (2013); doi:10.1016/j.tetlet.2013.09.033.
- A. Padwa, D.J. Austin, L. Precedo and L. Zhi, J. Org. Chem., 58, 1144 (1993); doi:10.1021/jo00057a029.
- Y. Miki, H. Hachiken, S. Takemura and M. Ikeda, Heterocycles, 22, 701 (1984); doi:10.3987/R-1984-04-0701.
- O. Tsuge, S. Kanemasa, S. Kuraoka and S. Takenaka, Chem. Lett., 13, 279 (1984); doi:10.1246/cl.1984.279.
- X. Wei, Y. Hu, T. Li and H. Hu, J. Chem. Soc., Perkin Trans. 1, 2487 (1993); doi:10.1039/p19930002487.
- K.N. Venugopala, R. Govender, M.A. Khedr, R. Venugopala, B.E. Aldhubiab, S. Harsha and B. Odhav, Drug Design Develop. Therapy, 9, 911 (2015); doi:10.2147/DDDT.S73890.
- K.N. Venugopala, M. Krishnappa, S.K. Nayak, B.K. Subrahmanya, J.P. Vaderapura, R.K. Chalannavar, R.M. Gleiser and B. Odhav, Eur. J. Med. Chem., 65, 295 (2013); doi:10.1016/j.ejmech.2013.04.061.
- P. Panini, K.N. Venugopala, B. Odhav and D. Chopra, Acta Crystallogr. B, 70, 681 (2014); doi:10.1107/S2052520614006209.
- P. Munshi, K.N. Venugopala, B.S. Jayashree and T.N. Guru Row, Cryst. Growth Des., 4, 1105 (2004); doi:10.1021/cg049948l.
- V. Vichai and K. Kirtikara, Nat. Protoc., 1, 1112 (2006); doi:10.1038/nprot.2006.179.
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References
M.W. Edwards, J.W. Daly and C.W. Myers, J. Nat. Prod., 51, 1188 (1988); doi:10.1021/np50060a023.
J.W. Daly, T.F. Spande, N. Whittaker, R.J. Highet, D. Feigl, N. Nishimori, T. Tokuyama and C.W. Myers, J. Nat. Prod., 49, 265 (1986);doi:10.1021/np50044a012.
T.H. Jones, A. Laddago, A.W. Don and M.S. Blum, J. Nat. Prod., 53, 375 (1990); doi:10.1021/np50068a016.
B. Lüning, C. Lundin, P.J. Garegg, A. Haug and G. Hagen, Acta Chem. Scand., 21, 2136 (1967); doi:10.3891/acta.chem.scand.21-2136.
Y.Z. Lee, C.W. Huang, C.W. Yang, H.Y. Hsu, I.J. Kang, Y.S. Chao, I.S. Chen, H.Y. Chang and S.J. Lee, Planta Med., 77, 1932 (2011); doi:10.1055/s-0030-1271199.
P.S. Liu, R.S. Rogers, M.S. Kang and P.S. Sunkara, Tetrahedron Lett., 32, 5853 (1991); doi:10.1016/S0040-4039(00)79409-3.
Y. Cheng, X. Jiang, G. Shi and Z. Kang, Polyhydroxy Substituted Octahydroindolizidine and Synthesis Method Thereof, CN101215285A (2008).
D.J. Vocadlo, E.J. McEachern and K. Stubbs, Selective Glycosidase Inhibitors and Uses Thereof, WO2010012106A1 (2010).
W. Huang, T. Zuo, X. Luo, H. Jin, Z. Liu, Z. Yang, X. Yu, L. Zhang and L. Zhang, Chem. Biol. Drug Des., 81, 730 (2013); doi:10.1111/cbdd.12119.
L. Zhang, X. Yu, W. Huang, T. Zuo, Z. Yang and L. Zhang, Substituted Purrocoline Compound and Preparation Method and Application Thereof, China Patent CN103087061A (2013).
A. Hazra, S. Mondal, A. Maity, S. Naskar, P. Saha, R. Paira, K.B. Sahu, P. Paira, S. Ghosh, C. Sinha, A. Samanta, S. Banerjee and N.B. Mondal, Eur. J. Med. Chem., 46, 2132 (2011); doi:10.1016/j.ejmech.2011.02.066.
D. Basavaiah and A. Jaganmohan Rao, Chem. Commun., 604 (2003); doi:10.1039/b211349j.
M. Nakanishi and M. Mori, Angew. Chem. Int. Ed., 41, 1934 (2002); doi:10.1002/1521-3773(20020603)41:11<1934::AID-ANIE1934>3.0.CO;2-F.
S. Yokoshima, T. Ueda, S. Kobayashi, A. Sato, T. Kuboyama, H. Tokuyama and T. Fukuyama, J. Am. Chem. Soc., 124, 2137 (2002); doi:10.1021/ja0177049.
G. Solladié and G.-H. Chu, Tetrahedron Lett., 37, 111 (1996); doi:10.1016/0040-4039(95)02086-1.
J. Royer and H.-P. Husson, Tetrahedron Lett., 26, 1515 (1985); doi:10.1016/S0040-4039(00)98540-X.
J. Gubin, H. de Vogelaer, H.I nion, C. Houben, J. Lucchetti, J. Mahaux, G. Rosseels, M. Peiren and M. Clinet, J. Med. Chem., 36, 1425 (1993); doi:10.1021/jm00062a015.
S. Hagishita, M. Yamada, K. Shirahase, T. Okada, Y. Murakami, Y. Ito, T. Matsuura, M. Wada, T. Kato, M. Ueno, Y. Chikazawa, K. Yamada, T. Ono, I. Teshirogi and M. Ohtani, J. Med. Chem., 39, 3636 (1996); doi:10.1021/jm960395q.
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J. Bermudez, C.S. Fake, G.F. Joiner, K.A. Joiner, F.D. King, W.D. Miner and G.J. Sanger, J. Med. Chem., 33, 1924 (1990); doi:10.1021/jm00169a016.
H. Ulbrich, B. Fiebich and G. Dannhardt, Eur. J. Med. Chem., 37, 953 (2002); doi:10.1016/S0223-5234(02)01418-6.
B. Portevin, C. Tordjman, P. Pastoureau, J. Bonnet and G. De Nanteuil, J. Med. Chem., 43, 4582 (2000); doi:10.1021/jm990965x.
M. Artico, S. Massa, G. Stefancich, R. Silvestri, R. Di Santo and F. Corelli, J. Heterocycl. Chem., 26, 503 (1989); doi:10.1002/jhet.5570260246.
R. Chaniyara, S. Tala, C.W. Chen, X. Zang, R. Kakadiya, L.F. Lin, C.H. Chen, S.I. Chien, T.C. Chou, T.H. Tsai, T.C. Lee, A. Shah and T.L. Su, J. Med. Chem., 56, 1544 (2013); doi:10.1021/jm301788a.
A.U. De and B.P. Saha, J. Pharm. Sci., 64, 249 (1975); doi:10.1002/jps.2600640211.
I. Antonini, F. Claudi, U. Gulini, L. Micossi and F. Venturi, J. Pharm. Sci., 68, 321 (1979); doi:10.1002/jps.2600680317.
I. Antonini, M. Cardellini, F. Claudi, P. Franchetti, U. Gulini, G. De Caro and F. Venturi, J. Pharm. Sci., 66, 1692 (1977); doi:10.1002/jps.2600661209.
P. Renaud, C. Ollivier and P. Panchaud, Angew. Chem. Int. Ed., 41, 3460 (2002); doi:10.1002/1521-3773(20020916)41:18<3460::AID-ANIE3460>3.0.CO;2-6.
N. Toyooka, A. Fukutome, H. Nemoto, J.W. Daly, T.F. Spande, H.M. Garraffo and T. Kaneko, Org. Lett., 4, 1715 (2002); doi:10.1021/ol025775m.
K.B. Lindsay and S.G.Pyne, J. Org. Chem., 67, 7774 (2002); doi:10.1021/jo025977w.
M.L. Bode and P.T. Kaye, J. Chem. Soc., Perkin Trans. 1, 1809 (1993); doi:10.1039/p19930001809.
M.L. Bode and P.T. Kaye, J. Chem. Soc., Perkin Trans. 1, 2612 (1990); doi:10.1039/p19900002612.
V. Boekelheide and R.J. Windgassen Jr., J. Am. Chem. Soc., 81, 1456 (1959); doi:10.1021/ja01515a044.
J. Hurst, T. Melton and D.G. Wibberley, J. Chem. Soc., 46, 2948 (1965); doi:10.1039/jr9650002948.
G. Jones and J. Stanyer, J. Chem. Soc. C: Organic, 901 (1969); doi:10.1039/j39690000901.
E. Pohjala, Tetrahedron Lett., 13, 2585 (1972); doi:10.1016/S0040-4039(01)84880-2.
R.M. Acheson and D.A. Robinson, J. Chem. Soc. C: Organic, 1629 (1968); doi:10.1039/j39680001629.
C. Sandeep, B. Padmashali and R.S. Kulkarni, Tetrahedron Lett., 54, 6411 (2013); doi:10.1016/j.tetlet.2013.09.033.
A. Padwa, D.J. Austin, L. Precedo and L. Zhi, J. Org. Chem., 58, 1144 (1993); doi:10.1021/jo00057a029.
Y. Miki, H. Hachiken, S. Takemura and M. Ikeda, Heterocycles, 22, 701 (1984); doi:10.3987/R-1984-04-0701.
O. Tsuge, S. Kanemasa, S. Kuraoka and S. Takenaka, Chem. Lett., 13, 279 (1984); doi:10.1246/cl.1984.279.
X. Wei, Y. Hu, T. Li and H. Hu, J. Chem. Soc., Perkin Trans. 1, 2487 (1993); doi:10.1039/p19930002487.
K.N. Venugopala, R. Govender, M.A. Khedr, R. Venugopala, B.E. Aldhubiab, S. Harsha and B. Odhav, Drug Design Develop. Therapy, 9, 911 (2015); doi:10.2147/DDDT.S73890.
K.N. Venugopala, M. Krishnappa, S.K. Nayak, B.K. Subrahmanya, J.P. Vaderapura, R.K. Chalannavar, R.M. Gleiser and B. Odhav, Eur. J. Med. Chem., 65, 295 (2013); doi:10.1016/j.ejmech.2013.04.061.
P. Panini, K.N. Venugopala, B. Odhav and D. Chopra, Acta Crystallogr. B, 70, 681 (2014); doi:10.1107/S2052520614006209.
P. Munshi, K.N. Venugopala, B.S. Jayashree and T.N. Guru Row, Cryst. Growth Des., 4, 1105 (2004); doi:10.1021/cg049948l.
V. Vichai and K. Kirtikara, Nat. Protoc., 1, 1112 (2006); doi:10.1038/nprot.2006.179.
P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J.T. Warren, H. Bokesch, S. Kenney and M.R. Boyd, J. Natl. Cancer Inst., 82, 1107 (1990); doi:10.1093/jnci/82.13.1107.