A practical and expeditious method for the preparation of the potential anticancer agent 5,6,11,12,17,18,23,24-octahydrocyclododeca[1,2-b:4,5-b′: 7,8-b″:10,11-b‴]tetraindole (CTet)

Tetrahedron Letters

Volumn 52, Issue 22, 2011, Pages 2812-2814

  Lucarini, Simone ^a   Antonietti, Francesca ^a   Tontini, Andrea ^a   Mestichelli, Paola ^a   Magnani, Mauro ^a   Duranti, Andrea ^a  

^a UNIVERSITY OF URBINO   (Italy)

Author keywords

Breast cancer; Indole cyclic tetramer; Indole 3 carbinol; One pot reaction

Indexed keywords

5,6,11,12,17,18,23,24 OCTAHYDROCYCLODODECA[1,2 B:4,5 B':7,8 B'':10,11 B'' ']TETRAINDOLE; ANTINEOPLASTIC AGENT; INDOLE; SULFANILAMIDE; UNCLASSIFIED DRUG;

ARTICLE; SYNTHESIS;

EID: 79955558845     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.03.117     Document Type: Article

References (23)

1. K.R. Grose, and L.F. Bjeldanes Chem. Res. Toxicol. 5 1992 188 193
2. A.I. Virtanen Phytochemistry 4 1965 207 228
3. L.W. Wattenberg, and W.D. Loub Cancer Res. 38 1978 1410 1413
4. J.-R. Weng, C.-H. Tsai, S.K. Kulp, and C.-S. Chen Cancer Lett. 269 2008 153 163
5. G. Brandi, M. Paiardini, B. Cervasi, C. Fiorucci, P. Filippone, C. De Marco, N. Zaffaroni, and M. Magnani Cancer Res. 63 2003 4028 4036
6. S. Lucarini, M. De Santi, F. Antonietti, G. Brandi, G. Diamantini, A. Fraternale, M.F. Paoletti, A. Tontini, M. Magnani, and A. Duranti Molecules 15 2010 4085 4093
7. J. Bergman, S. Högberg, and J.-O. Lindström Tetrahedron 26 1970 3347 3352
8. R.E. Staub, and L.F. Bjeldanes J. Org. Chem. 68 2003 167 169
9. C.A. De Kruif, J.W. Marsman, J.C. Venekamp, H.E. Falke, J. Noordhoek, B.J. Blaauboer, and H.M. Wortelboer Chem. Biol. Interact. 80 1991 303 315
10. C.-H. Lee, and H. Kohn J. Org. Chem. 55 1990 6098 6104
11. F. Gaedke, R. Knorr, and F. Zymalkowski Arch. Pharm. 313 1980 166 173
12. G.E. Stokker, A.A. Deana, S.J. deSolms, E.M. Schultz, R.L. Smith, R.L. Cragoe, J.E. Baer, H.F. Russo, and L.S. Watson J. Med. Chem. 25 1982 735 742
13. 6
14. 1H NMR are according to those reported by Wang, F.; Liu, H.; Fu, H.; Jiang, Y.; Zhao, Y. Adv. Synth. Cat. 2009, 351, 246-252] and unidentified by-products.
15. 6) δ: 112.6, 113.2, 113.3, 122.1, 123.0, 124.4, 124.7, 124.8, 129.5, 138.0, 141.2, 153.6, 162.8 ppm.
16. 6) δ: 38.8, 111.0, 111.8, 113.1, 119.0, 119.1, 121.6, 124.4, 126.0, 126.9, 129.0, 136.7, 152.9 ppm.
17. 2 (0.09 g) was added. The mixture was hydrogenated at 5 atm and 60 °C for 6 h, cooled and filtered on Celite, and the filtrate was concentrated. Purification was conducted as described in note 13 (cyclohexane/EtOAc 1:1, CTet/CTr 25:75). Yield 27% (0.09 g).
18. 4), and concentrated. Purification was conducted as described in note 13 (cyclohexane/EtOAc 7:3, CTet/CTr 15:85). Yield 42% (0.09 g).
19. 2 (0.07 g) was added and the mixture was hydrogenated at 5 atm and 60 °C for 5 h. A TLC analysis of the mixture showed that, apart from a consistent amount of unreacted 2, only traces of unidentifiable products are present.
20. 2 (0.1 g) in AcOH (100 mL) was hydrogenated at 5 atm and 60 °C for 16 h, cooled and filtered upon Celite. Work-up and purification were conducted as described in note 13 (cyclohexane/EtOAc 7:3, CTet/CTr 1:9). Yield 35% (0.45 g).
21. 2CO, yield 15% (0.068 g).
22. 6) d: 2.26 (s, 3H), 4.11 (s, 2H), 6.86-7.49 (m, 9H), 10.60 (br s, 1H), 10.85 (br s, 1H).
23. T. Hino, T. Nakamura, and M. Nakagawa Chem. Pharm. Bull. 23 1975 2990 2997