A convenient parallel synthesis of low molecular weight hydroxamic acids using polymer-supported 1-hydroxybenzotriazole

Organic and Biomolecular Chemistry

Volumn 1, Issue 5, 2003, Pages 850-853

  Devocelle, Marc ^a   McLoughlin, Brian M ^a   Sharkey, Caroline T ^a   Fitzgerald, Desmond J ^a   Nolan, Kevin B ^a  

^a ROYAL COLLEGE OF SURGEONS IN IRELAND   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; ESTERS; EVAPORATION; MOLECULAR PHYSICS; MOLECULAR WEIGHT; SOLVENTS; SYNTHESIS (CHEMICAL);

HYDROXAMATES; HYDROXAMIC ACIDS; HYDROXYBENZOTRIAZOLE; PARALLEL SYNTHESIS;

ORGANIC ACIDS;

EID: 0041318844     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b211526c     Document Type: Article

References (35)

1. M. J. Miller, Chem. Rev., 1989, 89, 1563-1579.
2. (a) S. S. C. Tam, D. H. S. Lee, E. Y. Wang, D. G. Munroe and C. Y. Lau, J. Biol. Chem., 1995, 270, 13948-13955
3. (b) B. De, M. G. Natchus, M. Cheng, S. Pikul, N. G. Almstead, Y. O. Taiwo, C. E. Snider, L. Chin, B. Barnett, F. Gu and M. Dowty, Ann. N. Y. Acad. Sci., 1999, 878, 40-60
4. (c) A. J. Stemmler, J. W. Kampf, M. L. Kirk and V. L. Pecoraro, J. Am. Chem. Soc., 1995, 117, 6368-6369.
5. R. Zamora, A. Grzesiok, H. Weber and M. Feelisch, Biochem. J., 1995, 312, 333-339.
6. C. J. Marmion, T. Murphy, J. R. Docherty and K. B. Nolan, Chem. Commun., 2000, 13, 1153-1154.
7. (a) P. J. Loll, C. T. Sharkey, S. J. O'Connor, C. M. Dooley, E. O'Brien, M. Devocelle, K. B. Nolan, B. S. Selinsky and D. J. Fitzgerald, Mol. Pharmacol., 2001, 60, 1407-1413
8. (b) C. M. Dooley, M. Devocelle, B. M. McLoughlin, K. B. Nolan, D. J. Fitzgerald and C. T. Sharkey, Mol. Pharmacol., 2003, 63, 450-455.
9. (a) B. Kurzak, H. Kozlowski and E. Farkas, Coord. Chem. Rev., 1992, 114, 169
10. (b) D. Gaynor, Z. A. Starikova, S. Ostrovsky, W. Haase and K. B. Nolan, Chem. Commun., 2002, 506-507.
11. For synthesis on Wang resin: (a) C. D. Floyd, C. N. Lewis, S. R. Patel and M. Whittaker, Tetrahedron Lett., 1996, 37, 8045-8048
12. (b) L. S. Richter and M. C. Desai, Tetrahedron Lett., 1997, 38, 321-322
13. (c) J. M. Salvino, M. Mervic, H. J. Mason, T. Kiesow, D. Teager, J. Airey and R. Labaudiniere, J. Org. Chem., 1999, 64, 1823-1830
14. For synthesis on Sasrin resin: (d) B. Barlaam, P. Koza and J. Berriot, Tetrahedron, 1999, 55, 7221-7232
15. For synthesis on chlorotrityl derivatised resins, crowns: (e) S. L. Mellor, C. McGuire and W. C. Chan, Tetrahedron Lett., 1997, 38, 3311-3314
16. (f) U. Bauer, W.-B. Ho and A. M. P. Koskinen, Tetrahedron Lett., 1997, 38, 7233-7236
17. (g) N. J. Ede, I. W. James, B. M. Krywult, R. M. Griffiths, S. N. Eagle, B. Gubbins, J. A. Leitch, W. R. Sampson and A. M. Bray, Lett. Pept. Sci., 1999, 6, 157-163
18. For synthesis of N-alkylhydroxamic acids on 4-[2,4-dimethoxyphenyl (hdroxy)methyl]-phenoxymethyl PS derivatised-resin: (h) S. L. Mellor and W. C. Chan, Chem. Commun., 1997, 2005-2006.
19. K. Ngu and D. V. Patel, J. Org. Chem., 1997, 62, 7088-7089.
20. For synthesis on ArgoGel-OH: (a) S. M. Dankwardt, Synlett, 1998, 761
21. For synthesis on oxime resin: (b) A. Golebiowski and S. Klopfenstein, Tetrahedron Lett., 1998, 39, 3397-3400
22. (c) E. Thouin and W. D. Lubell, Tetrahedron Lett., 2000, 41, 457-460.
23. (a) J. A. Camarero, A. Adeva and T. W. Muir, Lett. Pept. Sci., 2000, 7, 17-21
24. (b) W. Zhang, L. Zhang, X. Li, J. A. Weigel, S. E. Hall and J. P. Mayer, J. Comb. Chem., 2001, 3, 151-153.
25. M. Caldarelli, J. Habermann and S. V. Ley, Bioorg. Med. Chem. Lett., 1999, 9, 2049-2052.
26. (a) R. Kalir, A. Warshawsky, M. Fridkin and A. Patchornik, Eur. J. Biochem., 1975, 59, 55-61
27. (b) M. Mokotoff, M. Zhao, S. M. Roth, J. A. Shelley, J. N. Slavoski and N. M. Kouttab, J. Med. Chem., 1990, 33, 354-360.
28. (a) I. E. Pop, B. P. Déprez and A. L. Tartar, J. Org. Chem., 1997, 62, 2594-2603
29. (b) K. Dendrinos, J. Jeong, W. Huang and A. G. Kalivretenos, Chem. Commun., 1998, 499-500
30. (c) W. Huang and A. G. Kalivretenos, Tetrahedron Lett., 1995, 36, 9113-9116.
31. K. G. Dendrinos and A. G. Kalivretenos, Tetrahedron Lett., 1998, 39, 1321-1324.
32. Argonaut Technical Documentation, http://www.argotech.com/PDF/resins/pshobttech.pdf.
33. K. G. Dendrinos and A. G. Kalivretenos, J. Chem. Soc., Perkin Trans. 1, 1998, 1463-1464.
34. S. V. Ley and I. R. Baxendale, Nat. Rev. Drug Discovery, 2002, 1, 573-586.
35. A.-M. Chollet, T. Le Diguarher, N. Kucharczyk, A. Loynel, M. Bertrand, G. Tucker, N. Guilbaud, M. Burbridge, P. Pastoureau, A. Fradin, M. Sabatini, J.-L. Fauchère and P. Casara, Bioorg. Med. Chem., 2002, 10, 531-544.