Generation of libraries of pharmacophoric structures with increased complexity and diversity by employing polymorphic scaffolds

Angewandte Chemie - International Edition

Volumn 41, Issue 19, 2002, Pages 3677-3680

  Couladouros, Elias A ^a,b   Strongilos, Alexandros T ^a,b  

^a AGRICULTURAL UNIVERSITY OF ATHENS   (Greece)

^b INSTITUTE OF NANOSCIENCE AND NANOTECHNOLOGY   (Greece)

Author keywords

Combinatorial chemistry; Drug design; Heterocycles; Solid phase synthesis

Indexed keywords

DRUG PRODUCTS; ORGANIC COMPOUNDS;

PHARMACOPHORIC STRUCTURES;

HERBICIDES;

ACLACINOMYCIN; ACTINOBOLIN; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; ASPERLIN; BENZODIAZEPINE DERIVATIVE; BUTENOLIDE; COCCIDIOSTATIC AGENT; FORSKOLIN; FRONTALIN; HERBICIDE; LACTONE DERIVATIVE; MACROLIDE; MONOCROTALINE; NOGALAMYCIN; OXAZOLE DERIVATIVE; PENICILLIC ACID; PESTICIDE; PSEUDOMONIC ACID; PYRANOSIDE; PYRONE DERIVATIVE; SPIRONOLACTONE; STEROID; THIAZEPINE DERIVATIVE; TIRANDAMYCIN;

ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; COMPLEX FORMATION; DIRECTED MOLECULAR EVOLUTION; DRUG DESIGN; DRUG STRUCTURE; GENETIC POLYMORPHISM; METHODOLOGY; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION;

BINDING SITES; COMBINATORIAL CHEMISTRY TECHNIQUES; DIRECTED MOLECULAR EVOLUTION; DRUG DESIGN; MOLECULAR STRUCTURE; PYRONES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037020336     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021004)41:19<3677::AID-ANIE3677>3.0.CO;2-Y     Document Type: Article

References (39)

1. a) L. A. Thomson, J. A. Ellman, Chem. Rev. 1996, 96, 555-600;
2. b) J. S. Früchtel, G. Jung, Angew. Chem. 1996, 108, 19-46; Angew. Chem. Int. Ed. 1996, 35, 17-42;
3. b) J. S. Früchtel, G. Jung, Angew. Chem. 1996, 108, 19-46; Angew. Chem. Int. Ed. 1996, 35, 17-42;
4. c) S. L. Schreiber, Science 2000, 287, 1964-1969;
5. d) K. C. Nicolaou, R. Hanko, W. Hartwig, Handbook of Combinatorial Chemistry, Wiley-VCH, Weinheim, 2002.
6. a) R. E. Dolle, K. H. Nelson, Jr., J. Comb. Chem. 1999, 1, 235-282;
7. b) R. E. Dolle, J. Comb. Chem. 2000, 2, 383-432.
8. D. S. Tan, M. A. Foley, B. R. Stockwell, M. D. Shair, S. L. Schreiber, J. Am. Chem. Soc. 1999, 121, 9073-9087.
9. a) K. C. Nicolaou, N. Winssinger, J. Pastor, S. Ninkovic, F. Sarabia, Y. He, D. Vourloumis, Z. Yang, T. Li, P. Giannakakou, E. Hamel, Nature 1997, 387, 268-272;
10. b) K. C. Nicolaou, N. Winssinger, R. Hughes, C. Smethurst, Y. S. Cho, Angew. Chem. 2000, 112, 1126-1130; Angew. Chem. Int. Ed. 2000, 39, 1084-1088;
11. b) K. C. Nicolaou, N. Winssinger, R. Hughes, C. Smethurst, Y. S. Cho, Angew. Chem. 2000, 112, 1126-1130; Angew. Chem. Int. Ed. 2000, 39, 1084-1088;
12. c) K. C. Nicolaou, J. Pastor, N. Winssinger, F. Murphy, J. Am. Chem. Soc. 1998, 120, 5132-5133;
13. d) D. Brohm, S. Metzger, A. Bhargava, O. Müller, F. Lieb, H. Waldmann, Angew. Chem. 2002, 114, 319-323; Angew. Chem. Int. Ed. 2002, 41, 307-311.
14. d) D. Brohm, S. Metzger, A. Bhargava, O. Müller, F. Lieb, H. Waldmann, Angew. Chem. 2002, 114, 319-323; Angew. Chem. Int. Ed. 2002, 41, 307-311.
15. a) B. E. Evans, K. E. Rittle, M. G. Bock, R. M. DiPardo, R. M. Freidinger, W. L. Whitter, G. F. Lundell, D. F. Veber, P. S. Anderson, R. S. L. Chang, V. J. Lotti, D. J. Cerino, T. B. Chen, P. J. Kling, K. A. Kunkel, J. P. Springer, J. Hirshfield, J. Med. Chem. 1988, 31, 2235-2246;
16. b) J. S. Mason, I. Morize, P. R. Menard, D. L. Cheney, C. Hulme, R. F. Labaudiniere, J. Med. Chem. 1999, 42, 3251-3264, and references therein.
17. J. M. Ostrech, G. M. Husar, S. E. Blondelle, B. Dörner, P. A. Weber, R. A. Houghten, Proc. Natl. Acad. Sci. USA 1994, 91, 11138-11142.
18. For preparation of 2H-pyran-3(6H)-ones from furyl alcohols see: a) Y. Lefebvre, Tetrahedron Lett. 1972, 133-136; b) O. Achmatowicz, Jr., P. Bukowski, B. Szechner, Z. Swiezchowska, A. Zamojski, Tetrahedron 1971, 1973-1996; c) M. P. Georgiadis, E. A. Couladouros, J. Org. Chem. 1986, 51, 2725-2727.
19. For preparation of 2H-pyran-3(6H)-ones from furyl alcohols see: a) Y. Lefebvre, Tetrahedron Lett. 1972, 133-136; b) O. Achmatowicz, Jr., P. Bukowski, B. Szechner, Z. Swiezchowska, A. Zamojski, Tetrahedron 1971, 1973-1996; c) M. P. Georgiadis, E. A. Couladouros, J. Org. Chem. 1986, 51, 2725-2727.
20. For preparation of 2H-pyran-3(6H)-ones from furyl alcohols see: a) Y. Lefebvre, Tetrahedron Lett. 1972, 133-136; b) O. Achmatowicz, Jr., P. Bukowski, B. Szechner, Z. Swiezchowska, A. Zamojski, Tetrahedron 1971, 1973-1996; c) M. P. Georgiadis, E. A. Couladouros, J. Org. Chem. 1986, 51, 2725-2727.
21. a) R. Laliberte, G. Medawar, Y. Lefebvre, J. Med. Chem. 1973, 16, 1084;
22. b) M. P. Georgiadis, E. A. Couladouros, A. K. Delitheos, J. Pharm. Sci. 1992, 81, 1126-1131;
23. c) R. Tsang, B. Fraser-Reid, J. Org. Chem. 1992, 57, 1065-1067;
24. d) M. A. Bates, P. G. Sammes, G. A. Thomson, J. Chem. Soc. Perkin Trans. 1 1988, 3037;
25. e) J. M. Harris, M. D. Keranen, G. A. O'Doherty, J. Org. Chem. 1999, 64, 2982-2983;
26. f) N. Prevost, F. Rouessac, Tetrahedron Lett. 1997, 38, 4215-4218;
27. g) S. F. Martin, D. E. Guinn, J. Org. Chem. 1987, 52, 5588-5593;
28. h) M. Tsubuki, K. Kanai, H. Nagase, T. Honda, Tetrahedron 1999, 55, 2493-2514;
29. i) M.-R. Brescia, Y. Class Shimshock, P. DeShong, J. Org. Chem. 1997, 62, 1257-1263;
30. j) C. Neukom, D. P. Richardson, J. H. Myerson, P. A. Bartlett, J. Am. Chem. Soc. 1986, 108, 5559-5568;
31. k) D. C. Billington, F. S. Perron, G. Atassi, A. Pierre, M. Burbridge, N. Guilbaud, Fr. Pat. 2733499 1995;
32. l) N. L. Holder, Chem. Rev. 1982, 82, 287-332.
33. a) T. L. Deegan, O. W. Gooding, S. Baudart, J. A. Porco, Jr., Tetrahedron Lett. 1997, 38, 4973-4976;
34. b) K. Fukase, Y. Nakai, K. Egusa, J. A. Porco, Jr., S. Kusumoto, Synthesis 1999, 1074-1078.
35. M. P. Georgiadis, E. A. Couladouros, J. Heterocycl. Chem. 1990, 27, 1757-1760.
36. C. D. Apostolopoulos, M. P. Georgiadis, E. A. Couladouros, J. Heterocycl. Chem. 1996, 33, 703-708.
37. P. Shanmugam, V. Nair, Synth. Commun. 1996, 26, 3007-3008.
38. This transformation has not been well investigated so far, see: a) B. Hoffmann, A. Schonebaum, H. Lacker, Liebigs Ann. Chem. 1993, 333; K. Tatsuta, K. Akimoto, M. Annaka, Y. Ohno, M. Kinoshita, Bull. Chem. Soc. Jpn. 1985, 58, 1699.
39. This transformation has not been well investigated so far, see: a) B.Hoffmann, A. Schonebaum, H. Lacker, Liebigs Ann. Chem. 1993, 333; K. Tatsuta, K. Akimoto, M. Annaka, Y. Ohno, M. Kinoshita, Bull. Chem. Soc. Jpn. 1985, 58, 1699.