Solid-phase synthesis of α-(2-(benzylthio)-1,4-dihydro-6-methyl-4-p- tolylpyrimidine-5-carboxamido) acids: A new strategy to create diversity in heterocyclic scaffolds

Journal of Combinatorial Chemistry

Volumn 6, Issue 4, 2004, Pages 457-459

  Zhang, Lei ^a   Rana, Tariq M ^a  

^a UNIVERSITY OF MASSACHUSETTS MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC CARBOXYLIC ACID; PYRIMIDINE DERIVATIVE;

ARTICLE; BIGINELLI REACTION; COMBINATORIAL CHEMISTRY; DRUG CONFORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; KNOEVENAGEL CONDENSATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STRUCTURE ANALYSIS;

ACIDS; AMIDES; BENZENE; CYCLIZATION; DRUG DESIGN; HYDROXYLATION; MAGNETIC RESONANCE SPECTROSCOPY; METHYLATION; MOLECULAR STRUCTURE; PYRIMIDINES; SULFHYDRYL COMPOUNDS;

EID: 4143104561     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc034064s     Document Type: Article

References (38)

1. Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360-413.
2. O'Reilly, B. C.; Atwal, K. S. Heterocycles 1987, 26, 1185-1188.
3. (a) Kappe, C. O. Tetrahedron 1993, 49, 6937-6963.
4. (b) Kappe, C. O. Acc. Chem. Res. 2000, 33, 879-888.
5. (a) Dondoni, A.; Massi, A.; Simona, S.; Bertolasi, V. J. Org. Chem. 2002, 67, 6979-6994.
6. (b) Fu, N. Y.; Yuan, Y. F.; Cao, Z.; Wang, S. W.; Wang, J. T.; Peppe, C. Tetrahedron 2002, 58, 4801-4807.
7. (c) Dondoni, A.; Massi, A.; Sabbatini, S. Tetrahedron Lett. 2001, 42, 4495-4497.
8. (d) Lu, J.; Ma, H. Synlett 2000, 63-64.
9. (e) Ranu, B. C.; Hajra, A.; Jana, U. J. Org. Chem. 2000, 65, 6270-6272.
10. (f) Lu, J.; Bai, Y.; Wang, Z.; Yang, B.; Ma, H. Tetrahedron Lett. 2000, 41, 9075-9078.
11. (g) Bussolari, J. C.; McDonnell, P. A. J. Org. Chem. 2000, 65, 6777-6779.
12. (h) Hu, E. H.; Sidler, D. R.; Dolling, U. J. Org. Chem. 1998, 63, 3454-3457.
13. (a) Peng, J.; Deng, Y. Tetrahedron Lett. 2001, 42, 5917-5919.
14. (b) Ma, Y.; Qian, C.; Wang, L.; Yang, M. J. Org. Chem. 2000, 65, 3864-3868.
15. Studer, A.; Jeger, P.; Wipf, P.; Curran, D. P. J. Org. Chem. 1997, 62, 2917-2924.
16. (a) Wipf, P.; Cunningham, A. Tetrahedron Lett. 1995, 36, 7819-7822.
17. (b) Kappe, C. O. Bioorg. Med. Chem. Lett. 2000, 10, 49-51.
18. (c) Perez, R.; Beryozkina, T.; Zbruyev, O. I.; Haas, W.; Kappe, C. O. J. Comb. Chem. 2002, 4, 501-510.
19. (d) Dondoni, A.; Massi, A. Tetrahedron Lett. 2001, 42, 7975-7978.
20. (a) Stadler, A.; Kappe, C. O. J. Comb. Chem. 2001, 3, 624-630.
21. (b) Kappe, C. O.; Kumar, D.; Varma, R. S. Synthesis 1999, 1799-1803.
22. (a) Kappe, C. O. Molecules 1998, 3, 1-9.
23. (b) Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043-1052.
24. (a) Junk, B.; Pernat, T.; Kappe, C. O. Molecules 2000, 5, 227-239.
25. (b) Atwal, K. S.; Rovnyak, G. C.; Schwartz, J.; Moreland, S.; Hedberg, A.; Gougoutas, J. Z.; Malley, M. F.; Floyd, D. M. J. Med. Chem. 1990, 33, 1510-1515.
26. Rovnyak, G. C.; Atwal, K. S.; Hedberg, A.; Kimball, S. D.; Moreland, S.; Gougoutas, J. Z.; O'Reilly, B. C.; Schwartz, J.; Malley, M. F. J. Med. Chem. 1992, 35, 3254-3263.
27. Sidler, D. R.; Larsen, R. D.; Chartrain, M.; Ikemoto, N.; Roberge, C. M.; Taylor, C. S.; Li, W.; Bills, G. F.; PCT Int. WO 99 07695, February 8, 1999.
28. Bruce, M. A.; Pointdexter, G. S.; Johnson, G. PCT Int. Appl. WO 98 33791, August 6, 1998.
29. Mayer, T. U.; Kapoor, T. M.; Haggarty, S. J.; King, R. W.; Schreiber, S. L., Mitchison, T. J. Science 1999, 286, 971-974.
30. (a) Tamilarasu, N.; Huq, I.; Rana, T. M. J. Am. Chem. Soc. 1999, 121, 1597-1598.
31. (b) Wang, X.; Huq, I.; Rana, T. M. J. Am. Chem. Soc. 1997, 119, 6444-6445.
32. (a) Chiu, Y. L.; Rana, T. M. Mol. Cell 2002, 10, 585-597.
33. (b) Hwang, S.; Tamilarasu, N.; Ryan, K.; Huq, I.; Richter, S.; Still, W. C.; Rana, T. R. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 12997-13002.
34. Hamper, B. C.; Kolodziej, S. A.; Scates, A. M.; Smith, R. G.; Cortez, E. J. Org. Chem. 1998, 63, 708-718.
35. Gordeev, M. F.; Patel, D. V.; Gordon, E. M. Tetrahedron Lett. 1996, 37, 4636-4646.
36. (a) Kleidernigg, O. P.; Kappe, C. O. Tetrahedron: Asymmetry 1997, 8, 2057-2067.
37. (b) Wang, F.; O'Brien, T.; Dowling, T.; Bicker, G.; Wyvratt, J. J. Chromatogr., A 2002, 958, 69-77.
38. (c) Wang, F.; Loughlin, T.; Dowling, T.; Bicker, G.; Wyvratt, J. J. Chromatogr., A 2000, 872, 279-288.