Asymmetric synthesis of mercaptoalcohols - Matrix metalloproteinase inhibitors

Synlett

Volumn , Issue 9, 1999, Pages 1371-1374

  Paulvannan, K ^a   Chen, Tao ^a  

^a AFFYMAX RESEARCH INSTITUTE   (United States)

Author keywords

Decarboxylation; Epoxide opening; Malonate alkylation; Mercaptoalcohol; MMP inhibitor

Indexed keywords

ALCOHOL DERIVATIVE; EPOXIDE; HYDROXYL GROUP; MATRIX METALLOPROTEINASE INHIBITOR; MERCAPTOETHANOL;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032824110     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2858     Document Type: Article

References (14)

1. Reviews: (a) Spurlino, J. C. Structural implications in the design of matrix-metalloproteinase inhibitors. In Structure-Based Drug Design; Veerapandian, P., Ed.; Marcel Dekker, Inc: New York, 1997; pp 171-189. (b) Matrix Metalloproteinases; Parks, W. C.; Mecham, R. P., Eds.; Academic Press; New York, 1998.
2. Reviews: (a) Spurlino, J. C. Structural implications in the design of matrix-metalloproteinase inhibitors. In Structure-Based Drug Design; Veerapandian, P., Ed.; Marcel Dekker, Inc: New York, 1997; pp 171-189. (b) Matrix Metalloproteinases; Parks, W. C.; Mecham, R. P., Eds.; Academic Press; New York, 1998.
3. (c) Shuttleworth, S. J. An the identification of matrix metalloproteinase inhibitors (MMPIs). In Advances in Drug Discovery Technique; Harvey, A. L., Ed.; Wiley: New York, 1998; pp 115-141.
4. (d) Coussens, L. M.; Werb, Z. Chemistry & Biology 1996, 3, 895.
5. (e) Beckett, R. P.; Davidson, A. H.; Drummond, A. H.; Huxley, P.; Whittaker, M. Drug Discovery Today 1996, 1, 16.
6. (f) Morphy, J. R.; Millican, T. A.; Porter, J. R. Curr. Med. Chem. 1995, 2, 743.
7. (a) Levin, J. I.; DiJoseph, J. F.; Killar, L. M.; Sharr, M. A.; Skotnicki, J. S.; Patel, D. V.; Xiao, X.; Shi, L.; Navre, M.; Campbell, D. A. Bioorg. Med. Chem. Lett. 1998, 8, 1163.
8. (b) Campbell, D. A.; Xiao, X.; Harris, D.; Ida, S.; Mortezaei, R.; Ngu, K.; Shi, L.; Tien, D.; Wang, Y.; Navre, M.; Patel, D. V.; Sharr, M. A.; DiJoseph, J. F.; Killar, L. M.; Leone, C. L.; Levine, J. L.; Skotnicki, J. S. Bioorg. Med. Chem. Lett. 1998, 8, 1157.
9. (c) Baxter, A. D.; Bird, J.; Bhogal, R.; Massil, T.; Minton, K. J.; Montana, J.; Owen, D. A. Bioorg. Med. Chem. Lett. 1997, 7, 897.
10. (d) Baxter, A. D.; Bhogal, R.; Bird, J. B.; Buckley, G. M.; Gregory, D. S.; Hedger, P. C.; Manallack, D. T.; Massil, T.; Minton, K. J.; Montana, J. G.; Neidle, S.; Owen, D. A.; Watson, R. J. Bioorg. Med. Chem. Lett. 1997, 7, 2765.
11. (a) Gowravaram, M. R.; Tomczuk, B. E.; Johnson, J. S.; Delecki, D.; Cook, E. R.; Ghose, A. K.; Mathiowetz, A. M.; Spurlino, J. C.; Rubin, B.; Smith, D. L.; Pulvino, T.; Wahl, R.C. J. Med. Chem. 1995, 38, 2570.
12. (a) Xue, C.-B.; He, X.; Roderick, J.; DeGrado, W. F.; Decicco, C.; Copeland, R. A. Bioorg. Med. Chem. Lett. 1996, 6, 379.
13. (b) Sahoo, S. P.; Caldwell, C. G.; Chapman, K. T.; Durette, P. L.; Esser, C. K.; Kopka, I. E.; Polo, S. A.; Sperow, K. M.; Niedzwiecki, L. M.; Izquierdo-Martin, M.; Chang, B. C.; Harrison, R. K.; Stein, R. L.; MacCoss, M.; Hagmann, W. K. Bioorg. Med. Chem. Lett. 1995, 5, 2441.
14. -1. Retention times: compound 3 = 23.8 min and compound 16 = 19.9 min.