A biomimetic approach for polyfunctional secocholanes: Tuning flexibility and functionality on peptidic and macrocyclic scaffolds derived from bile acids

Journal of Organic Chemistry

Volumn 73, Issue 16, 2008, Pages 6229-6238

  Rivera, Daniel G ^a,b   Pando, Orlando ^a   Bosch, Rayser ^a   Wessjohann, Ludger A ^b  

^a UNIVERSITY OF HAVANA   (Cuba)

^b LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ARTIFICIAL RECEPTORS; BILE ACIDS; BIO-MIMETIC; BIOLOGICALLY ACTIVE LIGANDS; BUILDING BLOCKS; CHEMICAL EQUATIONS; FUNCTIONAL INFORMATION; MACRO-CYCLIC; MACRO-CYCLIZATION; MACROCYCLE; MACROCYCLES; MACROLACTAMIZATION; MACROLACTONIZATION; MULTI COMPONENTS; NOVEL STRUCTURES; PEPTIDE CONJUGATES; STRUCTURAL ELEMENTS;

AMINES; AMINO ACIDS; BIOMIMETICS; BODY FLUIDS; CHELATION; CHEMICAL REACTIONS; CHEMISTRY; CHLORINE COMPOUNDS; COMPLEXATION; ORGANIC ACIDS; SCAFFOLDS; SUPRAMOLECULAR CHEMISTRY;

ACIDS;

ALPHA AMINO ACID; BILE ACID; CHOLANE DERIVATIVE; SECOCHOLANE DERIVATIVE;

ARTICLE; BIOMIMETICS; CHEMICAL STRUCTURE; CYCLIZATION; MACROLACTONIZATION; STEREOCHEMISTRY;

BILE ACIDS AND SALTS; BIOMIMETIC MATERIALS; CHOLANES; LACTAMS, MACROCYCLIC; MACROCYCLIC COMPOUNDS; PEPTIDES;

EID: 50149085736     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800708m     Document Type: Article

References (68)

1. (a) Aiello, A.; Fattorusso, E.; Menna, M. Steroids 1999, 64, 687-714.
2. (b) Morris, L. A.; Christie, E. M.; Jaspars, M.; van Ofwegen, L. P. J. Nat. Prod. 1998, 61, 538-541.
3. (c) Seo, Y.; Cho, K. W.; Chung, H.; Lee, H. S.; Shin, J. J. Nat. Prod. 1998, 61, 1441-1443.
4. (d) Rueda, A.; Zubia, E.; Ortega, M. J.; Carballo, J. L.; Salva, J. J. Nat. Prod. 1998, 61, 258-261.
5. (e) Pika, J.; Andersen, R. J. Tetrahedron 1993, 49, 8757-8760.
6. (f) Dopeso, J.; Quinoa, E.; Riguera, R.; Debitus, C.; Berquist, P. R. Tetrahedron 1994, 50, 3813-3828.
7. (g) Kirson, I.; Zaretskii, V. I. J. Chem. Soc., Perkin Trans. 1 1976, 1244-1247.
8. (a) Feldman, D.; Glorieux, F. H.; Pike, J. W. Vitamin D; Academic Press: New York, 1997.
9. (b) Norman, A. W.; Bouillon, R.; Thomasset, M. Vitamin D, a Pluripotent Steroid Hormone: Structural Studies, Molecular Endocrinology and Clinical Applications; Walter de Gruyter: Berlin, 1994.
10. (a) Arve, L.; Voigt, T.; Waldmann, H. QSAR Comb. Sci. 2006, 25, 449-456.
11. (b) Dekker, F. J.; Koch, M. A.; Waldmann, H. Curr. Opin. Chem. Biol. 2005, 9, 232-239.
12. (c) Koch, M. A.; Waldmann, H. Drug Discovery Today 2005, 10, 471-482.
13. (d) Breinbauer, R.; Vetter, I. R.; Waldmann, H. Angew. Chem., Int. Ed. 2002, 41, 2878-2890.
14. (a) Batzold, F. H.; Robinson, C. H. J. Org. Chem. 1976, 41, 313-317.
15. (b) Smith, A. G.; Brooks, C. J. W. Biochem. J. 1977, 167, 121-129.
16. (c) Zerhouni, N. A.; Maes, M.; Sultan, C.; Rothwell, S.; Migeon, C. J. Steroids 1979, 33, 277-285.
17. (d) Penning, T. M.; Covey, D. F.; Talalay, P. J. Biol. Chem. 1981, 256, 6842-6850.
18. (e) Penning, T. M. Steroids 1982, 39, 301-311.
19. (f) Vazquez, M. H.; Tezon, J. G.; Blaquier, J. A. J. Steroid Biochem. 1987, 28, 227-231.
20. (g) Hu, Y.; Covey, D. F. J. Chem. Soc., Perkin Trans. 1 1993, 417-422.
21. (h) Reich, I. L.; Lardy, H.; Wei, Y.; Marwah, P.; Kneer, N.; Powell, D. R.; Reich, H. J. Steroids 1998, 63, 542-553.
22. (a) Bäurle, S.; Blume, T.; Günther, J.; Henschel, D.; Hilling, R. C.; Husemann, M.; Mengel, A.; Parchmann, C.; Schmid, E.; Skuballa, W. Bioorg. Med. Chem. Lett. 2004, 14, 1673-1677.
23. (b) Peng, H.; Xie, W.; Otterness, D. M.; Cogswell, J. P.; McConnell, R. T.; Carter, H. L.; Powis, G.; Abraham, R. T.; Zalkow, L. H. J. Med. Chem. 2001, 44, 834-848.
24. (c) Peng, H.; Otterness, D. M.; Abraham, R. T.; Zalkow, L. H. Tetrahedron 2001, 57, 1891-1896.
25. (d) Peng, H.; Xie, W.; Kim, D.; Zalkow, L. H.; Powis, G.; Otterness, D. M.; Abraham, R. T. Bioorg. Med. Chem. 2000, 8, 299-306.
26. (e) Pesteil, K. E.; Ducruet, A. P.; Wipf, P.; Lazo, J. S. Oncogene 2000, 19, 6607-6612.
27. (f) Peng, H.; Zalkow, L. H.; Abraham, R. T.; Powis, G. J. Med. Chem. 1998, 41, 4677-4680.
28. (a) Bäurle, S.; Blume, T.; Mengel, A.; Parchmann, C.; Skuballa, W.; Basier, S.; Schäfer, M.; Sülzle, D.; Wrona-Metzinger, H.-P. Angew. Chem., Int. Ed. 2003, 42, 3961-3964.
29. (b) Winterfeldt, E. Chimia 1993, 47, 39-45.
30. (c) Prelle, A.; Winterfeldt, E. Heterocycles 1989, 28, 333-346.
31. (d) Chowdhury, P.-K.; Prelle, A.; Schomburg, D.; Thielmann, M.; Winterfeldt, E. Liebigs Ann. Chem. 1987, 1095-1099.
32. (e) Schomburg, D.; Thielmann, M.; Winterfeldt, E. Tetrahedron Lett. 1985, 26, 1705-1706.
33. (a) Lorenc, L.; Bondarenko, L.; Pavlovic, V.; Fuhrer, H.; Rihs, G.; Kalvoda, J.; Mihailovic, M. L. Helv. Chim. Acta 1989, 72, 608-623.
34. (b) Mihailovic, M. L.; Lorenc, L.; Pavlovic, V.; Bondarenko-Gheorghiu, L. J. Serb. Chem. Soc. 1989, 54, 459-464.
35. (c) Lorenc, L.; Bondarenko-Gheorghiu, L.; Pavlovic, V.; Fuhrer, H.; Kalvoda, J.; Mihailovic, M. L. Helv. Chim. Acta 1992, 75, 203-209.
36. For recent reviews, see: (a) Davis, A. P. Molecules 2007, 12, 2106-2122.
37. (b) Davis, A. P. Coord. Chem. Rev. 2006, 250, 2939-2951.
38. (c) Virtanen, E.; Kolehmainen, E. Eur. J. Org. Chem. 2004, 3385-3399.
39. (d) Davis, A. P.; Joss, J.-B. Coord. Chem. Rev. 2003, 240, 143-156.
40. For recent examples, see: (a) Rivera, D. G.; Wessjohann, L. A. Molecules 2007, 12, 1890-1899.
41. (b) Feigel, M.; Ladeberg, R.; Engels, S.; Herbst-Irmer, R.; Fróhlich, R. Angew. Chew., Int. Ed. 2006, 45, 5698-5702.
42. (c) Feigel, M.; Landberg, R.; Winter, M.; Bláaser, D.; Boese, R. Eur. J. Org. Chem. 2006, 371-377.
43. (d) Sisson, A. L.; Clare, A. P. Chem. Commun. 2005, 5263-5265.
44. (e) Averin, A. D.; Ranyuk, E. R.; Beletskaya, I. P. Chem. Eur. J. 2005, 11, 7030-7039.
45. For examples, see: (a) Ding, B.; Taotofa, U.; Orsak, T.; Chadwell, M.; Savage, P. B. Org. Lett. 2004, 6, 3433-3436.
46. (b) Madder, A.; Li, L.; De Muynck, H.; Van Haver, D.; Fant, F.; Vanhoenacker, G.; Sandra, P.; Davis, A. P.; De Clercq, P. J. J. Comb. Chem. 2002, 4, 552-562.
47. (c) De Muynck, H.; Madder, A.; Farcy, N.; De Clercq, P. J.; Pérez-Payń, M. N.; Oḧberg, L. M.; Davis, A. P. Angew. Chew., Int. Ed. 2000, 39, 145-148.
48. (d) Li, H.; Wang, L.-X. Org. Biol. Chem. 2003, 1, 3507-3513.
49. (e) Cheng, Y.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1996, 118, 1813-1814.
50. (f) Boyce, R.; Li, G.; Nestler, H. P.; Suenaga, T.; Still, W. J. Am. Chem. Soc. 1994, 116, 7955-7956.
51. Wessjohann, L. A.; Voigt, B.; Rivera, D. G. Angew. Chem., Int. Ed. 2005, 44, 4785-4790.
52. (a) Sakurai, A.; Yokota, T.; Clouse, S. D. Brassinosteroids. Steroidal Plant Hormones; Springer-Verlag: Tokyo, 1999.
53. (b) Khripach, V. A.; Zhabinskii, V. N.; de Groot, A. E. Brassinosteroids. A New Class of Plant Hormones; Academic Press: San Diego, 1999.
54. (a) Takatsuto, S.; Ikekawa, N. Tetrahedron Lett. 1983, 24, 917-920.
55. (b) Rivera, D. G.; Pando, O.; Suardiaz, R.; Coll, F. Steroids 2007, 72, 467-473, and references therein.
56. (a) Dommerholt, F. J.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 1991, 32, 1499-1502.
57. (b) Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
58. Grießer, H.; Kroner, M.; Schmidt, U. Synthesis 1991, 294-300.
59. For examples of multiple multicomponent macrocyclizations, see: (a) Wessjohann, L. A.; Ruijter, E. Mol. Diversity 2005, 9, 159-169.
60. (b) León, F.; Rivera, D. G.; Wessjohann, L. A. J. Org. Chem. 2008, 73, 1162-1161.
61. (c) Wessjohann, L. A.; Rivera, D. G.; Coll, F. J. Org. Chem. 2006, 71, 7521-7526.
62. (d) Rivera, D. G.; Vercillo, O. E.; Wessjohann, L. A. Synlett 2007, 308-312.
63. (e) Michalik, D.; Schaks, A.; Wessjohann, L. A. Eur. J. Org. Chem. 2007, 149-157.
64. (f) Rivera, D. G.; Wessjohann, L. A. J. Am. Chem. Soc. 2006, 128, 7122-7123.
65. The diacid/dialdehyde combination was not considered because of the poor availability and stability of dialdehydes. Also, due to the nonselective nature of the Ugi-4CR, mixtures of diastereoisomeric macrocycles are produced, thereby making the characterization process very difficult. For example, see: Wessjohann, L. A.; Rivera, D. G.; Leon, F. Org. Lett. 2007, 9, 4733-4336.
66. Wessjohann, L. A.; Andrade, C. K. Z.; Vercillo, O. E.; Rivera, D. G. Targets Heterocycl. Syst. 2006, 10, 24-53.
67. (a) Sui, Q.; Borchardt, D. L. J. Am. Chem. Soc. 2007, 129, 12042-12048.
68. (b) Fischer, G. Chem. Soc. Rev. 2000, 29, 119-127.