Solid-phase synthesis of 1,2,3,4-tetrahydroisoquinoline derivatives employing support-bound tyrosine esters in the pictet-spengler reaction

Journal of Combinatorial Chemistry

Volumn 6, Issue 4, 2004, Pages 564-572

  Kane, Timothy R ^a   Ly, Cuong Q ^a   Kelly, Daphne E ^a   Dener, Jeffrey M ^a,b  

^a Discovery Partners International   (United States)

^b CELERA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2,5 DIFLUOROBENZYL) 7 METHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE 3 CARBOXYLIC ACID (PYRIDIN 2 YLMETHYL)AMIDE; 2 (3 CHLOROBENZENESULFONYL) 7 ETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE 3 CARBOXYLIC ACID [2 (2 FLUOROPHENYL)ETHYL]AMIDE; 2 (4 ACETYLAMINOBENZENESULFONYL) 7 (2 TRIFLUOROMETHYLBENZYLOXY) 1,2,3,4 TETRAHYDROISOQUINOLINE 3 CARBOXYLIC ACID 3,4 DIMETHOXYBENZYLAMIDE; 2 FURAN 3 YLMETHYL 7 (3 PHENYLPROPOXY) 1,2,3,4 TETRAHYDROISOQUINOLINE 3 CARBOXYLIC ACID (2 HYDROETHYL)AMIDE; 7 BUTOXY 2 (5 METHYLTHIOPHEN 2 YLMETHYL) 1,2,3,4 TETRAHYDROISOQUINOLINE 3 CARBOXYLIC ACID (2 PIPERIDIN 1 YLETHYL)AMIDE; 7 METHOXY 2 (3 METHOXYBENZYL) 1,2,3,4 TETRAHYDROISOQUINOLINE 3 CARBOXYLIC ACID BUTYLAMIDE; AMIDE; CARBOXYL GROUP; ESTER DERIVATIVE; REDUCING AGENT; TETRAHYDROISOQUINOLINE DERIVATIVE; TYROSINE; UNCLASSIFIED DRUG;

ACYLATION; AMINATION; ARTICLE; COMBINATORIAL CHEMISTRY; DERIVATIZATION; DRUG SYNTHESIS; ESTERIFICATION; ORGANIC CHEMISTRY; PICTET SPENGLER REACTION; REACTION ANALYSIS; REDUCTION; SOLID STATE;

EID: 4143121319     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc020105t     Document Type: Article

References (26)

1. For reviews, see: (a) Bunin, B. A.; Dener, J. M.; Livingston, D. A. Application of Combinatorial and Parallel Synthesis to Medicinal Chemistry. In Annual Reports in Medicinal Chemistry; Doherty, A. Ed.; Elsevier: New York, 1999; Vol. 34, Chapter 27, pp 267-286. (b) Andres, C. J.; Denhart, D. J.; Deshpande, M. S.; Gillman, K. W. Comb. Chem. High Throughput Screening 1999, 2, 191-210.
2. For reviews, see: (a) Bunin, B. A.; Dener, J. M.; Livingston, D. A. Application of Combinatorial and Parallel Synthesis to Medicinal Chemistry. In Annual Reports in Medicinal Chemistry; Doherty, A. Ed.; Elsevier: New York, 1999; Vol. 34, Chapter 27, pp 267-286. (b) Andres, C. J.; Denhart, D. J.; Deshpande, M. S.; Gillman, K. W. Comb. Chem. High Throughput Screening 1999, 2, 191-210.
3. For reviews of carbon-carbon-forming reactions on the solid phase, see: (a) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549-1581. (b) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 2001, 101, 137-202.
4. For reviews of carbon-carbon-forming reactions on the solid phase, see: (a) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549-1581. (b) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 2001, 101, 137-202.
5. (a) Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449-472.
6. (b) Loughlin, W. A. Aust. J. Chem. 1998, 51, 875-893.
7. (c) Corbett, J. W. Org. Prep. Proc. Int. 1998, 30, 489-550.
8. (d) Franzen, R. G. J. Comb. Chem. 2000, 2, 195-214.
9. For reviews and key references on the Pictet-Spengler reaction, see: (a) Whaley, W. M.; Govindchari, T. R. Org. React. 1951, 6, 151. (b) Bates, H. A.; Bagheri, K.; Vertino, P. M. J. Org. Chem. 1986, 51, 3061-3063.
10. For reviews and key references on the Pictet-Spengler reaction, see: (a) Whaley, W. M.; Govindchari, T. R. Org. React. 1951, 6, 151. (b) Bates, H. A.; Bagheri, K.; Vertino, P. M. J. Org. Chem. 1986, 51, 3061-3063.
11. For references on the formation of tetrahydroisoquinolines on the solid phase, see: (a) Meutermans, W. D. F.; Alewood, P. F. Tetrahedron Lett. 1995, 36, 7709-7712. (b) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4865-4868. (c) Rölfing, K.; Theil, M.; Künzer, H. Synlett 1996, 1036-1038. (c) Sun, Q.; Kyle, D. J. Comb. Chem. High Throughput Screening 2002, 5, 75-81. For a recent review on the solid-phase synthesis of nitrogen heterocycles including tetrahydroisoquinolines, see: Brase, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415-2437.
12. For references on the formation of tetrahydroisoquinolines on the solid phase, see: (a) Meutermans, W. D. F.; Alewood, P. F. Tetrahedron Lett. 1995, 36, 7709-7712. (b) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4865-4868. (c) Rölfing, K.; Theil, M.; Künzer, H. Synlett 1996, 1036-1038. (c) Sun, Q.; Kyle, D. J. Comb. Chem. High Throughput Screening 2002, 5, 75-81. For a recent review on the solid-phase synthesis of nitrogen heterocycles including tetrahydroisoquinolines, see: Brase, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415-2437.
13. For references on the formation of tetrahydroisoquinolines on the solid phase, see: (a) Meutermans, W. D. F.; Alewood, P. F. Tetrahedron Lett. 1995, 36, 7709-7712. (b) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4865-4868. (c) Rölfing, K.; Theil, M.; Künzer, H. Synlett 1996, 1036-1038. (c) Sun, Q.; Kyle, D. J. Comb. Chem. High Throughput Screening 2002, 5, 75-81. For a recent review on the solid-phase synthesis of nitrogen heterocycles including tetrahydroisoquinolines, see: Brase, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415-2437.
14. For references on the formation of tetrahydroisoquinolines on the solid phase, see: (a) Meutermans, W. D. F.; Alewood, P. F. Tetrahedron Lett. 1995, 36, 7709-7712. (b) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4865-4868. (c) Rölfing, K.; Theil, M.; Künzer, H. Synlett 1996, 1036-1038. (c) Sun, Q.; Kyle, D. J. Comb. Chem. High Throughput Screening 2002, 5, 75-81. For a recent review on the solid-phase synthesis of nitrogen heterocycles including tetrahydroisoquinolines, see: Brase, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415-2437.
15. For references on the formation of tetrahydroisoquinolines on the solid phase, see: (a) Meutermans, W. D. F.; Alewood, P. F. Tetrahedron Lett. 1995, 36, 7709-7712. (b) Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 4865-4868. (c) Rölfing, K.; Theil, M.; Künzer, H. Synlett 1996, 1036-1038. (c) Sun, Q.; Kyle, D. J. Comb. Chem. High Throughput Screening 2002, 5, 75-81. For a recent review on the solid-phase synthesis of nitrogen heterocycles including tetrahydroisoquinolines, see: Brase, S.; Gil, C.; Knepper, K. Bioorg. Med. Chem. 2002, 10, 2415-2437.
16. (a) Breitenbucher, J. G.; Hui, H. C. Tetrahedron Lett. 1998, 39, 8207-8210.
17. (b) Breitenbucher, J. G.; Johnson, C. R.; Haight, M.; Phelan, J. C. Tetrahedron Lett. 1998, 39, 1295-1298.
18. (c) Fantauzzi, P. P.; Yager, K. M. Tetrahedron Lett. 1998, 39, 1291-1294.
19. (d) Boldi, A. M.; Dener, J. M.; Hopkins, T. P. J. Comb. Chem. 2001, 3, 367-373.
20. For the original references describing the synthesis and use of resin 6, see: Marshall, D. L.; Liener, I. E. J. Org. Chem. 1970, 35, 867-868. Flanigan, E.; Marshall, G. R. Tetrahedron Lett. 1970, 2403-2406.
21. For the original references describing the synthesis and use of resin 6, see: Marshall, D. L.; Liener, I. E. J. Org. Chem. 1970, 35, 867-868. Flanigan, E.; Marshall, G. R. Tetrahedron Lett. 1970, 2403-2406.
22. Verschueren, K.; Toth, G.; Tourwé, D.; Lebl, M.; Van Binst, G.; Hruby, V. Synthesis 1992, 458-460.
23. Chung, J. Y. L.; Zhao, D.; Hughes, D. L.; Grabowski, E. J. J. Tetrahedron 1993, 49, 5767-5776.
24. Johnson, C. R.; Zhang, B.; Fantauzzi, P.; Hocker, M.; Yager, K. M. Tetrahedron 1998, 54, 4097-4106. Breitenbucher, J. G.; Arienti, K. L. McClure, K. J. J. Comb. Chem. 2001, 3, 528-533
25. Johnson, C. R.; Zhang, B.; Fantauzzi, P.; Hocker, M.; Yager, K. M. Tetrahedron 1998, 54, 4097-4106. Breitenbucher, J. G.; Arienti, K. L. McClure, K. J. J. Comb. Chem. 2001, 3, 528-533
26. Fang, L.; Pan, J.; Yan, B. Biotechnol. Bioeng. 2000, 71, 162-171.