Chemical variation of natural-product-like scaffolds: Design, synthesis, and biological activity of fused bicyclic acetal derivatives

Angewandte Chemie - International Edition

Volumn 46, Issue 14, 2007, Pages 2493-2496

  Milroy, Lech Gustav ^a   Zinzalla, Giovanna ^a   Prencipe, Giuseppe ^a   Michel, Patrick ^a   Ley, Steven V ^a   Gunaratnam, Mekala ^b   Beltran, Monica ^b   Neidle, Stephen ^b  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

Antitumor agents; Bicyclic acetals; Drug design; Molecular diversity; Natural products

Indexed keywords

ACETAL RESINS; BIOACTIVITY; LEAD COMPOUNDS; SYNTHESIS (CHEMICAL);

ANTITUMOR AGENTS; DRUG DESIGN; MOLECULAR DIVERSITY; NATURAL PRODUCTS;

DERIVATIVES;

ACETAL DERIVATIVE; FUSED HETEROCYCLIC RINGS;

ARTICLE; CHEMISTRY; DRUG DESIGN; SYNTHESIS;

ACETALS; BICYCLO COMPOUNDS, HETEROCYCLIC; DRUG DESIGN;

EID: 34250805407     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200604688     Document Type: Article

References (30)

1. H. Kiyota, Marine Natural Products, Springer, Berlin, 2006, p. 65 (Topics in Heterocyclic Chemistry, No. 5).
2. a) K. Mori, Eur. J. Org. Chem. 1998, 1479;
3. b) W. Francke, W. Schröder, Curr. Org. Chem. 1999, 3, 407.
4. S. S. Mitchell, D. Rhodes, F. D. Bushman, D. J. Faulkner, Org. Lett. 2000, 2, 1605.
5. T. Chou, O. Kamo, D. Uemura, Tetrahedron Lett. 1996, 37, 4023, and references therein.
6. K. Araki, K. Suenaga, T. Sengoku, D. Uemura, Tetrahedron 2002, 58, 1983.
7. E. M. Suh, Y. Kishi, J. Am. Chem. Soc. 1994, 116, 11 205, and references therein.
8. C. Wagner, H. Anke, O. Sterner, J. Nat. Prod. 1998, 61, 501.
9. K. C. Nicolaou, A. Nadin, Angew. Chem. 1996, 108, 1732;
10. Angew. Chem. Int. Ed. Engl. 1996, 35, 1622.
11. G. Koren-Goldshlager, P. Klein, A. Rudi, Y. Benayahu, M. Schleyer, Y. Kashman, J. Nat. Prod. 1996, 59, 262.
12. For the most recent review, see: R. Halim, M. A. Brimble, Org. Biomol. Chem. 2006, 4, 4048.
13. For an example, see: K. C. Nicolaou, J. A. Pfefferkorn, A. J. Roecker, G.-Q. Cao, S. Barluenga, H. J. Mitchell, J. Am. Chem. Soc. 2000, 122, 9939.
14. R. Balamurugan, F. J. Dekker, H. Waldmann, Mol. BioSyst. 2005, 1, 36.
15. a) G. Zinzalla, L.-G. Milroy, S. V. Ley, Org. Biomol. Chem. 2006, 4, 1977;
16. see also: b) A. A. Birkbeck, S. V. Ley, J. C. Prodger, Bioorg. Med. Chem. Lett. 1995, 5, 2637;
17. c) R. Haag, A. G. Leach, S. V. Ley, M. Nettekoven, J. Schnaubelt, Synth. Commun. 2001, 31, 2965;
18. d) O. Barun, K. Kumar, S. Sommer, A. Langerak, T. U. Mayer, O. Muller, H. Waldmann, Eur. J. Org. Chem. 2005, 4773;
19. e) B. A. Kulkarni, G. P. Roth, E. Lobkovsky, J. A. Proco, Jr., J. Comb. Chem. 2002, 4, 56.
20. H. Kiyota, D. J. Dixon, C. K. Luscombe, S. Hettstedt, S. V. Ley, Org. Lett. 2002, 4, 3223.
21. S. V. Ley, D. K. Baeschlin, D. J. Dixon, A. C. Foster, S. J. Ince, H. W. M. Priepke, D. J. Reynolds, Chem. Rev. 2001, 101, 53.
22. For an example, see: M. Schlosser, Angew. Chem. 2006, 118, 5558;
23. Angew. Chem. Int. Ed. 2006, 45, 5432.
24. P. A. Grieco, C. S. Pogonowski, J. Am. Chem. Soc. 1973, 95, 3071.
25. R. S. Dhillon, R. P. Singh, D. Kaur, Tetrahedron Lett. 1995, 36, 1107.
26. 1H NMR spectroscopic analysis of the crude material.
27. S. G. Hegde, D. C. Myles, Tetrahedron 1997, 53, 11 179.
28. The structures of 12a,b, 14a,b, 15a,b, 29, 31, 34a, and 35 were confirmed by NOE enhancements.
29. Predictive pharmacokinetic calculations were made using ACD/Structure Design Suite software (Advanced Chemistry Development, Inc., Toronto, Canada).
30. C. A. Lipinski, F. Lombardo, B. W. Dominy, P. J. Feeney, Adv. Drug Delivery Rev. 1997, 23, 3.