Synthesis and antiproliferative activity of indolizine derivatives incorporating a cyclopropylcarbonyl group against Hep-G2 cancer cell line

European Journal of Medicinal Chemistry

Volumn 45, Issue 7, 2010, Pages 3184-3190

  Shen, Yong Miao ^a,b   Lv, Peng Cheng ^a   Chen, Wu ^a   Liu, Peng Gang ^a   Zhang, Ming Zhu ^b   Zhu, Hai Liang ^a  

^a NANJING UNIVERSITY   (China)

^b SHAOXING UNIVERSITY   (China)

Author keywords

Antiproliferative activities; Docking simulations; EGFR; Hep G2 cell line; Indolizine derivatives; Structure activity relationship

Indexed keywords

1 CYCLOPROPYLCARBONYLPYRROLO[1,2A]QUINOLINE 3 CARBONITRILE; 3 CYCLOPROPYLCARBONYL 1 INDOLIZINECARBONITRILE; 3 CYCLOPROPYLCARBONYL 7 METHYL 1 INDOLIZINECARBOXAMIDE; 3 CYCLOPROPYLCARBONYL N PHENYL 1 INDOLIZINECARBOXAMIDE; 3 CYCLOPROPYLCARBONYLPYRROLO[1,2A]QUINOLINE 3 CARBONITRILE; 4 CYCLOPROPYLCARBONYL 2 METHYL 1,3 DIOXO 1H PYRROLO[3,4A] INDOLIZINE; 5 BROMO CYCLOPROPYLCARBONYL 1 INDOLIZINECARBONITRILE; 6 CYCLOPROPYLCARBONYL IMIDAZO[2,1F]PYRROLO[1,2B]PYRIDAZINE 8 CARBOXYLATE 3 CARBONITRILE; 8 BROMO 3 CYCLOPROPYLCARBONYL 5 METHYL 1 INDOLIZINECARBONITRILE; DIETHYL 3 CYCLOPROPYLCARBONY 7 METHYL INDOLIZINE 1,2 DICARBOXYLATE; DIETHYL 3 CYCLOPROPYLCARBONYLINDOLIZINE 1,2 DICARBOXYLATE; DIMETHYL 3 CYCLOPROPYLCARBONYLPYRROLO[1,2A]QUINOLINE 3 CARBOXYLATE; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE INHIBITOR; INDOLIZINE DERIVATIVE; METHYL 1 CYCLOPROPYLCARBONYLPYRROLO[1,2A]QUINOLINE 3 CARBOXYLATE; METHYL 3 CYCLOPROPYLCARBONY 7 METHYLLINDOLIZINE 1 CARBOXYLATE; METHYL 3 CYCLOPROPYLCARBONYLINDOLIZINE 1 CARBOXYLATE; METHYL 3 CYCLOPROPYLCARBONYLPYRROLO[1,2A]QUINOLINE 3 CARBOXYLATE; METHYL 5 BROMO 3 CYCLOPROPYLCARBONY INDOLIZINE 1 CARBOXYLATE; METHYL 6 CYCLOPROPYLCARBONYL IMIDAZO[2,1F]PYRROLO[1,2B]PYRIDAZINE 8 CARBOXYLATE 3 CARBONITRILE; METHYL 8 BROMO 3 CYCLOPROPYLCARBONYL 5 METHYL INDOLIZINE 1 CARBOXYLATE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CANCER INHIBITION; CANCER THERAPY; CYCLOADDITION; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; LIVER CELL CARCINOMA; MOLECULAR DOCKING; ONE POT SYNTHESIS;

EID: 77954348728     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.02.056     Document Type: Article

References (29)

1. A.R. Katrtzky, C.W. Rees (Eds.), Comprehensive Heterocyclic Chemistry, vol.4, Pergamon, Oxford, 1984, pp. 476-80.
2. P. Michael, Nat. Prod. Rep. 21 (2004) 625-649.
3. D. Sriram, P. Yogeeswari, R. Thirumurugan, T.R. Bal, Nat. Prod. Res. 19 (2005) 393-412.
4. E. Valencia, J. Freyer, M. Shamma, V. Fajardo, Tetrahedron Lett. 25 (1984) 599-602.
5. R. Alonso, L. Castedo, D. Dominguez, Tetrahedron Lett. 26 (1985) 2925-2928.
6. H. Malonne, J. Hanuise, J. Fontaine, Pharm. Pharmacol. Commun. 4 (1998) 241-242.
7. K. Kitadokoro, S. Hagishita, T. Sato, M. Ohtani, K. Miki, J. Biochem. 123 (1998) 619-623.
8. L.D. Bolle, G. Andrei, R. Snoeck, Y. Zhang, A.V. Lommel, M. Otto, A. Bousseau, C. Roy, E.D. Clercq, L. Naesens, Biochem. Pharmacol. 67 (2004) 325-336.
9. P. Sonnet, P. Dallemagne, J. Guillon, C. Engueard, S. Stiebing, J. Tangue, B. Bureau, S. Rault, P. Auvray, S. Moslemi, P. Sourdaine, G.-E. Seralini, Bioorg. Med. Chem. 8 (2000) 945-955.
10. F. Campagna, A. Carotti, G. Casini, M. Macripo Heterocycles 31 (1990) 97-107.
11. M. Bols, V.H. Lillelund, H.H. Jensen, X. Liang, Chem. Rev. 102 (2002) 515-553.
12. N. Asano, R.J. Nash, R.J. Molyneux, G.W. Fleet, J. Tetrahedron Asymmetry 11 (2000) 1645-1680.
13. O.B. ∅stby, B. Dalhus, L.-L. Gundersen, F. Rise, A. Bast, G.R.M.M. Haenen, Eur. J. Org. Chem. 9 (2000) 3763-3770.
14. L.L. Gundersen, K.E. Malterud, A.H. Negussie, F. Rise, S. Teklu, O.B. Ostby, Bioorg. Med. Chem. 11 (2003) 5409-5419.
15. S. Teklu, L.-L. Gundersen, T. Larsen, K.E. Malterud, F. Rise, Bioorg. Med. Chem. 13 (2005) 3127-3139.
16. D.L.J. Clive, D.M. Coltart, Y. Zhou, J. Org. Chem. 64 (1999) 1447-1454.
17. R.A. Gruters, J.J. Neefjes, M. Tersmette, R.E.Y. De Goede, A. Tulp, H.G. Huisman, F. Miedema, H.L. Ploegh, Nature 330 (1987) 74-77.
18. A. Kaspas, G.W. Fleet, R.A. Dwek, S. Petursson, S.K. Namgoong, N.G. Ramsden, G.S. Jacob, T.W. Radamacher, Proc. Natl. Acad. Sci. U.S.A. 85 (1988) 9229-9233.
19. J. Pietruszka, Chem. Rev. 103 (2003) 1051-1070.
20. L.A. Wessjohann, W. Brandt, T. Thiemann, Chem. Rev. 103 (2003) 1625-1648.
21. J. Salaün, Top. Curr. Chem. 207 (2000) 1-67.
22. C. Zorn, A. God, A. Brandi, K. Johnson, S.I. Kozhushkov, A. de Meijere, Chem. Con. (1998) 903-904.
23. S.X. Cai, John A. Drewe, S. Jiang, S. Kasibhatla, J.D. Kuemmerle, N.S. Sirisoma, H.-Z. Zhang, WO 2004055163, A2, 20040701, 2004.
24. S.P. Dourakis, Curr. Canc. Ther. Rev. 4 (2008) 219-226.
25. P.-C. Lv, C.-F. Zhou, J. Chen, P.-G. Liu,W.-J. Mao, J. Xiong, H.-L. Zhu, Bioorg. Med. Chem. 18 (2010) 314-319.
26. P.-C. Lv, K.-R. Wang, J. Chen, J. Sun, Q.-S. Li, H.-L. Zhu, Bioorg. Med. Chem. (2009). doi:10.1016/j.bmc.2009.12.048.
27. B.X. Wang, X.C. Zhang, Y.F. Hu, H.H. Hu, J. Chem. Soc. Perkin Trans. 1 (1999) 1571-1575.
28. D.H. Ess, K.N. Houk, J. Am. Chem. Soc. 130 (2008) 10187-10198.
29. S. Som, A.K. Das, Orient J. Chem. 22 (2006) 415-420.