Mild synthetic approach to novel indole-1-carbinols and preliminary evaluation of their cytotoxicity in hepatocarcinoma cells

Archiv der Pharmazie

Volumn 345, Issue 3, 2012, Pages 195-202

  Zedda, Gloria ^a   Simbula, Gabriella ^a   Begala, Michela ^a   Pibiri, Monica ^a   Floris, Costantino ^a   Casu, Mariano ^a   Casu, Laura ^a   Tocco, Graziella ^a  

^a UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

Apoptosis; Cytotoxicity; Hepatocarcinoma; Indole 1 carbinols; Solvent free reaction

Indexed keywords

(1H INDOL 1 YL)METHANOL; (2 METHYL 1H INDOL 1 YL)METHANOL; (3 (2 METHOXYPHENYL) 1H INDOL 1 YL)METHANOL; (3 BROMO 1H INDOL 1 YL)METHANOL; (3 IODO 1H INDOL 1 YL)METHANOL; (3 METHYL 1H INDOL 1 YL)METHANOL; 1 (HYDROXYMETHYL) 1H INDOLE 3 CARBALDEHYDE; 1 (HYDROXYMETHYL) 1H INDOLE 3 CARBONITRILE; 1 [1 (HYDROXYMETHYL) 1H INDOL 3 YL]ETHANONE; [3 (2 BROMOPHENYL) 1H INDOL 1 Y]METHANOL; CALCIUM OXIDE; INDOLE DERIVATIVE; MAGNESIUM OXIDE; METHANOL DERIVATIVE; METHYL 1 (HYDROXYMETHYL) 1H INDOLE 3 CARBOXYLATE; PARAFORMALDEHYDE; SOLVENT; TITANIUM DIOXIDE; UNCLASSIFIED DRUG; ZINC OXIDE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL PROLIFERATION; CHEMICAL REACTION; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; LIVER CELL CARCINOMA; PRIORITY JOURNAL; REACTION TIME; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; CARCINOMA, HEPATOCELLULAR; CELL PROLIFERATION; INDOLES; LIVER NEOPLASMS; METHANOL; RATS; TUMOR CELLS, CULTURED;

EID: 84858012273     PISSN: 03656233     EISSN: 15214184     Source Type: Journal    
DOI: 10.1002/ardp.201100104     Document Type: Article

References (29)

1. R. J. Sundberg, In The Chemistry of Indoles; (Ed. Academic Press, New York), 1996, p 113.
2. J.-R. Weng, C.-H. Tsai, S. K. Kulp, C. S. Chen, Cancer Lett. 2008, 262, 153-163.
3. W. R. Chao, D. Yean, K. Amin, C. Green, L. Jong, J. Med. Chem. 2007, 50, 3412-3415.
4. J.-R. Weng, C.-H. Tsai, S. K. Kulp, D. Wang, C.-H. Lin, H.-C. Yang, Y. Ma, A. Sargeant, C.-F. Chiu, M.-H. Tsai, C.-S. Chen, Cancer Res. 2007, 67, 7815-7824
5. H. A. Omar, A. M. Sargeant, J.-R. Weng, D. Wang, S. K. Kulp, T. Patel, C.-S. Chen, Mol. Pharm. 2009, 76, 957-968.
6. A. R. Katritzky, S. Rachwal, B. J. Rachwal, Chem. Soc. Perkin Trans. 1, 1987, 799-804
7. A. R. Katritzky, K. Manju, S. K. Singh, N. K. Meher, Tetrahedron 2005, 62, 2555-2581
8. G. Deguest, L. Bischoff, C. Fruit, F. Marsais, Org. Lett. 2007, 9, 1165-1167.
9. L. Hong, W. Sun, C. Liu, L. Wang, R. Wang, Chem. Eur. J. 2010, 16, 440-444.
10. Y. Sui, L. Liu, J.-L. Zhao, D. Wang, Y.-J. Chen, Tetrahedron Lett. 2007, 48, 3779-3782
11. Q. Wang, X. Cui, S. Liu, L. Sun, C. Li, Synlett 2008, 11, 1729-1733.
12. J. M. McFarland, N. S. Joshi, M. B. Francis, J. Am. Chem. Soc. 2008, 130, 7639-7644.
13. H.-C. Hsu, D.-R. Hou, Tetrahedron Lett. 2009, 50, 7169-7171.
14. D. Dhanak, C. B. Reese, J. Chem. Soc. Perkin Trans 1, 1986, 2181-2186
15. J.-P. Lio, C.-Y. Wu, H.-P. Hsieh, C.-Y. Chang, C.-M. Che, C.-C. Kuo, J.-Y. Chang, J. Med. Chem. 2007, 50, 4548-4552
16. W. Kemnitzer, J. Drewe, S. Jiang, H. Zhang, C. Crogan-Grundy, D. Labreque, M. Bubenick, G. Attardo, R. Denid, S. Lamothe, H. Gourdeau, B. Tseng, S. Kasibhatla, Xiong S. Cai, J. Med. Chem. 2008, 51, 417-423
17. M. S. Scott, A. C. Lucas, C. A. Luckhurst, J. C. Prodger, D. J. Dixon, Org Biomol. Chem. 2006, 4, 1313-1327.
18. S. Roy, G. W. Gribble, Synth. Commun. 2007, 37, 829-837.
19. Y. Cui, F. Li, Z.-H. Lu, S. Wang, Dalton Trans. 2007, 2634-2643.
20. Predictions on metabolic transformations have been performed by using the MetaSite 3.0.4 (Molecular Discovery LTd) computational procedure
21. G. Cruciani, E. Carosati, B. De Boeck, K. Ethirajulu, C. Mackie, T. Howe, R. Vianello, J. Med. Chem. 2005, 48, 6970-6979.
22. L. Van Gool, R. Meyer, E. Tobiasch, C. Cziepluch, J. C. Jauniaux, A. Mincheva, P. Lichter, G. G. Poirier, A. Burkle, J. H. Kupper, Eur. J. Biochem. 1997, 244, 15-20.
23. C. Nosseri, S. Coppola, L. Ghibelli, Exp. Cell. Res. 1994, 212, 367-373.
24. Y. A. Lazebnik, S. H. Kauffmann, S. Desnoyers, G. G. Poirier, W. C. Earnshaw, Nature 1994, 371, 346-347.
25. J. W. Kim, K. Kim, K. Kang, C. O. Joe, J. Biol. Chem. 2000, 275, 8121-8125.
26. E. Borenfreund, J. A. Puerner, Toxicology 1986, 39, 121.
27. M. M. Bradford, Anal. Biochem. 1976, 72, 248.
28. H.-C. Hsu, D.-R. Hou, Tetrahedron Lett. 2009, 50, 7169-7171.
29. H. Mitsudera, (Sumitomo Chemical Company). EP 1710234 A1. 2006.