Solid-phase synthesis of potential protein tyrosine phosphatase inhibitors via the Ugi four-component condensation

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 18, 1998, Pages 2443-2446

  Li, Zhengong ^a   Yeo, Su Ling ^b   Pallen, Catherine J ^a   Ganesan, A ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b NONE

Author keywords

Enzyme inhibitors; Phosphonic acids and derivs; Solid phase synthesis

Indexed keywords

ALDEHYDE DERIVATIVE; ISONITRILE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PROTEIN TYROSINE PHOSPHATASE; PROTEIN TYROSINE PHOSPHATASE INHIBITOR;

ARTICLE; DRUG HYDROLYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

ALDEHYDES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ENZYME INHIBITORS; IODOBENZOATES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; NITRILES; PHOSPHONIC ACIDS; PROTEIN CONFORMATION; PROTEIN-TYROSINE-PHOSPHATASE;

EID: 0032558506     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00408-9     Document Type: Article

References (29)

1. 1. For recent reviews on PTPases, see: a) Neel, B. G.; Tonks, N. K.; Curr. Opin. Cell Biol. 1997, 9, 193-204.
2. b) Neel, B. G. Curr. Opin. Immunol. 1997, 9, 405-420.
3. c) Widlanski, T. S.; Myers, J. K.; Stec, B.; Holtz, K. M.; Kantrowitz, E. R. Chem. Biol. 1997, 4, 489-492.
4. 2. For recent examples, see: a) Akamatsu, M.; Roller, P. P.; Chen, L.; Zhang, Z.-Y.; Ye, B.; Burke, T. R. Bioorg. Med. Chem. 1997, 5, 157-163.
5. b) Frechette, R. F.; Ackerman, C.; Beers, S.; Look, R.; Moore, J. Bioorg. Med. Chem. Lett. 1997, 7, 2169-2172.
6. c) Beers, S. A.; Malloy, E. A.; Wu, W.; Wachter, M. P.; Gunnia, U.; Cavender, D.; Harris, C.; Davis, J.; Brosius, R.; Pellegrino-Gensey, J. L.; Siekierka, J. Bioorg. Med. Chem. 1997, 5, 2203-2211.
7. d) Wang, Q.; Huang, Z.; Ramachandran, C.; Dinaut, A. N.; Taylor, S. D. Bioorg. Med. Chem. Lett. 1998, 8, 345-350.
8. 3. Marseigne, I.; Roques, B. P. J. Org. Chem. 1988, 53, 3621-3624.
9. 4. Burke, T. R.; Ye, B.; Akamatsu, M.; Ford, H.; Yan, X.; Kole, H. K.; Wolf, G.; Shoelson, S. E.; Roller, P. P. J. Med. Chem. 1996, 39, 1021-1027.
10. 5. a) Cao, X.; Moran, E. J.; Siev, D.; Lio, A.; Ohashi, C.; Mjalli, A. M. M. Bioorg. Med. Chem. Lett. 1995, 5, 2953-2958.
11. b) Mjalli, A. M. M.; Cao, X.; Moran, E. J. PCT Int. Appl. WO 1997, 970894.
12. 6. Chen, L.; Wu, L.; Otaka, A.; Smyth, M. S.; Roller, P. P.; Burke, T. R.; den Hertog, J.; Zhang, Z.-Y. Biochem. Biophys. Res. Commun. 1995, 216, 976-984.
13. 7. For a review, see: Shoelson, S. E. Curr. Opin. Chem. Biol. 1997, 1, 227-234.
14. 8. For example, see: Charifson, P. S.; Shewchuk, L. M.; Rocque, W.; Hummel, C. W.; Jordan, S. R.; Mohr, C.; Pacofsky, G. J.; Peel, M. R.; Rodriguez, M.; Sternbach, D. D.; Consler, T. G. Biochemistry 1997, 36, 6283-6293.
15. 9. For recent reviews on solid-phase organic synthesis, see: a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554.
16. b) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678.
17. c) Brown, R. Contemp. Org. Synth. 1997, 4, 216-237.
18. 10. For reviews, see: a) Gokel, G.; Lüdke, G.; Ugi, I. In Isonitrile Chemistry; Ugi, I., Ed.; Academic: New York, 1971; pp. 145-199.
19. b) Ugi, I.; Lohberger, S.; Karl, R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol 2, pp 1083-1109.
20. 2O exchangeable), 1.34 (t, 6H, J = 7.0 Hz).
21. 12. Yokomatsu, T.; Murano, T.; Suemune, K.; Shibuya, S. Tetrahedron 1997, 53, 815-822.
22. 13. For solid-phase Ugi reactions besides ref 5a, see: a) Tempest, P. A.; Brown, S. D.; Armstrong, R. W. Angew. Chem. Int. Ed. Engl. 1996, 35, 640-642.
23. b) Strocker, A. M.; Keating, T. A.; Tempest, P. A.; Armstrong, R. W. Tetrahedron Lett. 1996, 37, 1149-1152.
24. c) Sutherlin, D. P.; Stark, T. M.; Hughes, R.; Armstrong, R. W. J Org. Chem. 1996, 61, 8350-8354.
25. d) Zhang, C.; Moran, E. J.; Woiwode, T. F.; Short, K. M.; Mjalli, A. M. M. Tetrahedron Lett. 1996, 37, 751-754.
26. e) Mjalli, A. M. M.; Sarshar, S.; Baiga, T. J. Tetrahedron Lett. 1996, 37, 2943-2946.
27. f) Short, K. M.; Ching, B. W.; Mjalli, A. M. M. Tetrahedron 1997, 53, 6653-6679.
28. g) Obrecht, D.; Abrecht, C.; Grieder, A.; Villalgordo, J. M. Helv. Chim. Acta 1997, 80, 65-72.
29. +-1).