Solid-phase synthesis and structural study of substituted 1,4,5,6-tetrahydro-6-oxopyridine-3-carboxylic acids

QSAR and Combinatorial Science

Volumn 25, Issue 10, 2006, Pages 921-927

  Rodríguez, Hortensia ^a   Martín, Osnieski ^a   Ochoa, Estael ^a   Suárez, Margarita ^a   Reyes, Osvaldo ^b   Garay, Hilda ^b   Albericio, Fernando ^c   Martín, Nazario ^d  

^a UNIVERSITY OF HAVANA   (Cuba)

^b CENTER FOR GENETIC ENGINEERING AND BIOTECHNOLOGY   (Cuba)

^c UNIVERSITY OF BARCELONA   (Spain)

^d UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

1,4,5,6 Tetrahydro 6 oxopyridine 3 carboxylic acids; B3LYP 6 31G* theoretical calculations; Solid phase synthesis; Wang resin

Indexed keywords

CYCLIZATION; SPECTROSCOPIC ANALYSIS; SYNTHESIS (CHEMICAL);

1,4,5,6-TETRAHYDRO-6-OXOPYRIDINE-3-CARBOXYLIC ACID; B3LYP/6-31G; B3LYP/6-31G* THEORETICAL CALCULATION; ENAMINES; SOLID PHASE SYNTHESIS; SOLID PHASIS; SOLID-PHASE; STRUCTURAL STUDIES; THEORETICAL CALCULATIONS; WANG RESIN;

RESINS;

1,4,5,6 TETRAHYDRO 2 METHYL 4 (2 NITROPHENYL) 6 OXOPYRIDINE 3 CARBOXYLIC ACID; 1,4,5,6 TETRAHYDRO 2 METHYL 4 (3 NITROPHENYL) 6 OXOPYRIDINE 3 CARBOXYLIC ACID; 1,4,5,6 TETRAHYDRO 2 METHYL 4 (4 NITROPHENYL) 6 OXOPYRIDINE 3 CARBOXYLIC ACID; 1,4,5,6 TETRAHYDRO 2 METHYL 6 OXO 4 PHENYLPYRIDINE 3 CARBOXYLIC ACID; 1,4,5,6 TETRAHYDRO 4 (4'METHOXYPHENYL) 2 METHYL 6 OXOPYRIDINE 3 CARBOXYLIC ACID; 1,4,5,6 TETRAHYDRO 6 OXOPYRIDINE 3 CARBOXYLIC ACID DERIVATIVE; 4 (2 CHLOROPHENOL)1,4,5,6 TETRAHYDRO 2 METHYL 6 OXOPYRIDINE 3 CARBOXYLIC ACID; 4 (2',4' DIMETHOXYPHENYL) 1,4,5,6 TETRAHYDRO 2 METHYL 6 OXOPYRIDINE 3 CARBOXYLIC ACID; 4 (2',4' DIMETHYLPHENYL) 1,4,5,6 TETRAHYDRO 2 METHYL 6 OXOPYRIDINE 3 CARBOXYLIC ACID; 4 (2,4 DICHLOROPHENOL)1,4,5,6 TETRAHYDRO 2 METHYL 6 OXOPYRIDINE 3 CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; ENAMINE; POLYSTYRENE; RESIN; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ACETYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; DRUG CONFORMATION; DRUG PURITY; DRUG STRUCTURE; DRUG SYNTHESIS; IMMOBILIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID PHASE SYNTHESIS;

EID: 33750316969     PISSN: 1611020X     EISSN: 16110218     Source Type: Journal    
DOI: 10.1002/qsar.200620017     Document Type: Article

References (51)

1. a) I. Sucholeiki, High-throughput Synthesis. Principles and Practices; Marcel Dekker, New York, 2001;
2. b) K. C. Nicolaou, R. Hanko, W. Hartwig (Eds.), Handbook of Combinatorial Chemistry, Wiley-VCH Verlag, Weinheim, Germany, 2002;
3. c) R. E. Dolle, J. Comb. Chem. 2005, 7, 739-798.
4. a) V. Krchnak, M. W. Holladay, Chem. Rev. 2002, 102, 61-91;
5. b) B. Kundu, Curr. Opin. Drug Discov. Devel. 2003, 6, 815-826.
6. D. A. Horton, G. T. Bourne, M. L. Smythe, Chem. Rev. 2003, 103, 893-930.
7. R. G. Franzen, J. Comb. Chem. 2000, 2, 195-214.
8. P. Grosche, A. Höltzel, T. Walk, A. W. Trautwein, G. Jung, Synthesis 1999, 1961-1970.
9. S. M. Hutchnis, K. T. Chapman, Tetrahedron Lett. 1996, 37, 4865-4868.
10. C. Weber, A. Bielik, A. Remeter, I. Borza, G. I. Szendrei, G. M. Keseru, I. Greiner, Tetrahedron 2005, 61, 9375-9380.
11. R. Pérez, O. Reyes, M. Suárez, H. E. Garay, L. J. Cruz, H. Rodríguez, M. D. Molero-Vilchez, C. Ochoa, Tetrahedron Lett. 2000, 41, 613-616.
12. a) W. G. Mayler, Calcium Antagonist, Academic Press, London, 1989;
13. b) R. A. Janis, P. J. Silver, D. J. Triggle, Adv. Drug Res. 1987, 16, 309-391;
14. c) F. Bossert, W. Vater, Med. Res. Rev. 1989, 9, 291-324;
15. d) N. Martín, C. Seoane, Quím. Ind. 1990, 36, 115-127;
16. e) R. Peri, S. Padmanabhan, A. Rutledge, S. Singh, D. J. Triggle, J. Med. Chem. 2000, 43, 2906-2914;
17. f) S. Tasaka, H. Ohmori, N. Gomi, M. Iino, T. Machida, A. Kiue, S. Naito, M. Kuwano, Bioorg. Med. Chem. Lett. 2001, 11, 275-277;
18. g) J. L. Harper, C. S. Camerini-Otero, A. Li, S. Kim, K. A. Jacobson, J. W. Daly, Biochem. Pharmacol. 2003, 65, 329-338;
19. h) A. A. S. Fernandes, M. S. Santos, J. A. F. Vicente, A. J. M. Moreno, A. Velena, G. Duburs, C. R. Oliveira, Mitochondrion 2003, 3, 47-59;
20. i) T. Okamura, T. Kikuchi, A. Nagamine, K. Fukushi, T. Sekine, Y. Arano, T. Irie, Free Radic. Biol. Med. 2005, 38, 1197-1205.
21. a) S. Goldmann, J. Stoltefuss, Angew. Chem. Int. Ed. 1991, 30, 1559-1578;
22. b) D. J. Triggle, D. A. Langs, R. A. Jamis, Med. Res. Rev. 1989, 9, 123-128;
23. c) S. Mehdi, K. Ravikumar, Acta Cryst. 1992, C48, 1627-1630;
24. d) K. R. Rowan, M. E. Holt, Acta Cryst. 1996, C52, 2207-2212;
25. e) B. B. Hemmateenejad, R. Miri, M. A. Safarpour, M. Khoshneviszadeh, N. Edraki, J. Mol. Struct.: THEOCHEM 2002, 717, 139-152.
26. a) M. F. Gordeev, D. V. Patel, E. M. Gordon, E. M. Gordon, J. Org. Chem. 1996, 61, 924-928;
27. b) J. G. Breitenbucher, G. Figliozzi, Tetrahedron Lett. 2000, 22, 1-4;
28. c) J. Breitenbucher, G. Filiozzi Tetrahedron Lett. 2000, 41, 4311-4315.
29. M. F. Gordeev, D. V. Patel, E. M. Wu, J. Gordon, E. M. Gordon, Tetrahedron Lett. 1996, 37, 4643-4646.
30. P. Schell, M. P. Richards, K. Hanson, S. C. Berk, G. M. Makara, J. Comb. Chem. 2005, 7, 96-98.
31. R. Pérez, T. Beryozkina, O. I. Zbrouyen, W. Haas, C. O. Kappe, J. Comb. Chem. 2002, 4, 501-510.
32. J. A. Linn, S.W. Gerritz, A. Handlon, C. E. Hayman, D. Heyer, Tetrahedron Lett. 1999, 4, 2227-2230.
33. Y. Wang, S. Wilson, Tetrahedron Lett. 1997, 38, 4021-4024.
34. K. Paulvannan, T. Tao Chen, J. Org. Chem. 2000, 65, 6160-6166.
35. A. Morales, E. Ochoa, M. Suárez, Y. Verdecia, L. González, N. Martín, M. Quinteiro, C. Seoane, J. L. Soto, J. Heterocycl. Chem. 1996, 33, 103-107.
36. E. Ochoa, M. Suárez, Y. Verdecia, B. Pita, N. Martin, M. Quinteiro, C. Seoane, J. L. Soto, Tetrahedron 1998, 54, 12409-12420.
37. M. Suárez, E. Ochoa, Y. Verdecia, B. Pita, L. Moran, N. Martín, M. Quinteiro, C. Seoane, J. L. Soto, H. Novoa, R. Blaton, O. Peeters, C. De Ranter, Eur. J. Org. Chem. 2000, 2079-2088.
38. A preliminary communication of part of this work has been previously reported: H. Rodríguez, O. Reyes, M. Suárez, H. Garay, R. Pérez, J. Cruz, Y. Verdecia, N. Martín, C. Seoane, Tetrahedron Lett. 2002, 43, 439-441.
39. H. Rodríguez, M. Suárez, R. Pérez, A. Petit, A. Loupy, Tetrahedron Lett. 2003, 44, 3709-3712.
40. a) Y. Verdecia, M. Suárez, A. Morales, E. Rodríguez, E. Ochoa, L. González, N. Martín, M. Quinteiro, C. Seoane, J. L. Soto, J. Chem. Soc. Perkin Trans. 1 1996, 947-951;
41. b) M. Suárez, E. Ochoa, B. Pita, R. Espinosa, L. González, N. Martín, M. Quinteiro, C. Seoane, J. L. Soto, J. Heterocycl. Chem. 1997, 34, 931-935;
42. c) M. Suárez, H. Novoa, Y. Verdecia, E. Ochoa, A. Alvarez, R. Pérez, R. Martínez-Álvarez, D. Molero, C. Seoane, N. Blaton, O. Peeters, N. Martín, Tetrahedron 2006, 62, 1365-1371.
43. M. Yamashita, S. Sang-Hyeup, G. Lee Koch, J. Zimmermann, B. Clapham, K. D. Janda, Tetrahedron Lett. 2005, 46, 5495-5498.
44. H. Novoa, N. Blaton, O. Peeters, C. De Ranter, M. Suarez, E. Ochoa, Y. Verdecia, E. Salfran, J. Chem. Cryst. 2000, 30, 189-194.
45. a) J. S. Binkley, J. A. Pople, W. J. Hehre, J. Am. Chem. Soc. 1980, 102, 939-947;
46. b) M. S. Gordon, J. S. Binkley, J. A. Pople, W. J. Pietro, W. J. Hehre, J. Am. Chem. Soc. 1982, 104, 2797-2803;
47. c) W. J. Pietro, M. M. Francl, W. J. Hehre, D. J. Defrees, J. A. Pople, J. S. Binkley, J. Am. Chem. Soc. 1982, 104, 5039-5048;
48. d) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652;
49. e) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B, 1988, 37, 785-789;
50. f) P. J. Stephens, F. J. Devlin, C. F. Chabalowski, M. J. Frisch, J. Phys. Chem. 1994, 98, 11623-11627.
51. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, GAUSSIAN 98 (Revision A.37), Gaussian, Inc., Pittsburgh, PA, 1998.