Inhibition of naringinase (L-rhamnosidase) by piperidine analogues of L-rhamnose: Scaffolds for libraries incorporating trihydroxypipecolic acids

Tetrahedron Letters

Volumn 37, Issue 47, 1996, Pages 8569-8572

  Shilvock, John P ^a   Wheatley, Joseph R ^a   Davis, Benjamin ^a   Nash, Robert J ^b   Griffiths, Rhodri C ^c   Jones, M George ^c   Müller, Matthias ^a   Crook, Sarah ^a   Watkin, David J ^a   Smith, Colin ^d,e   Besra, Gurdyal S ^f   Brennan, Patrick J ^f   Fleet, George W J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b ABERYSTWYTH UNIVERSITY   (United Kingdom)

^c ABERYSTWYTH UNIVERSITY   (United Kingdom)

^d GLAXOSMITHKLINE   (United Kingdom)

^e Immunology and Pathology   (United States)

^f Colorado State University ^*

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDASE; GLYCOSIDASE INHIBITOR; PIPERIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENZYME INHIBITION; STRUCTURE ACTIVITY RELATION;

EID: 16144363956     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01958-2     Document Type: Article

References (26)

1. 1. preceding paper.
2. 2. Winchester, B., Al-Daher, S., Carpenter, N. M., Cenci di Bello, I., Choi, S. S., Fairbanks, A. J., Fleet, G. W. J., Biochem. J., 1993, 290, 743.
3. 3. Fairbanks, A. J., Carpenter, N. M., Fleet, G. W. J., Ramsden, N. G., Cenci di Bello, I., Winchester, B. G., Al-Daher, S. S., Nagahashi, G., Tetrahderon, 1992, 48, 3365.
4. 4. Zhou, P., Salleh, H. M., Chan, P. C., Lajoie, G., Honek, J. F., Nambiar, P, Ward, O.P., Carbohydr. Res., 1993, 239, 155.
5. 5. Provencher, L., Steensma, D. H., Wong, C.-H., Biorg. Med. Chem., 1994, 2, 1179.
6. 6. Brandstetter, T., Davis, B., Hyett, D., Smith, C., Hackett, L., Winchester, B., Fleet. G., Tetrahedron Lett., 1995, 36, 7511.
7. 7. Kite, G. C., Fellows, L. E., Liu, P. S., Scofield, A. M., Fleet, G. W. J., Smith, N. G., Tetrahedron Lett., 1988, 29, 6483.
8. 8. Myerscough, P. M., Fairbanks, A. J., Jones, A. H., Choi, S.-S., Fleet, G. W. J., Al-Daher, S. S., Cenci di Bello, I., Winchester, B., Tetrahedron, 1992, 48, 10177; Bruce, I., Fleet, G. W. J., Cenci di Bello, I., Winchester, B., Tetrahedron, 1992, 48, 10191; Lundt, I., Madsen, R., Lundt, I., Madsen, R., Synthesis, 1995, 787; Wong, C. H., Provencher, L., Porco, J. A., Jung, S. H., Wang, Y. F., Chen, L. R., Wang, R., J. Org. Chem., 1995, 60, 1492.
9. 8. Myerscough, P. M., Fairbanks, A. J., Jones, A. H., Choi, S.-S., Fleet, G. W. J., Al-Daher, S. S., Cenci di Bello, I., Winchester, B., Tetrahedron, 1992, 48, 10177; Bruce, I., Fleet, G. W. J., Cenci di Bello, I., Winchester, B., Tetrahedron, 1992, 48, 10191; Lundt, I., Madsen, R., Lundt, I., Madsen, R., Synthesis, 1995, 787; Wong, C. H., Provencher, L., Porco, J. A., Jung, S. H., Wang, Y. F., Chen, L. R., Wang, R., J. Org. Chem., 1995, 60, 1492.
10. 8. Myerscough, P. M., Fairbanks, A. J., Jones, A. H., Choi, S.-S., Fleet, G. W. J., Al-Daher, S. S., Cenci di Bello, I., Winchester, B., Tetrahedron, 1992, 48, 10177; Bruce, I., Fleet, G. W. J., Cenci di Bello, I., Winchester, B., Tetrahedron, 1992, 48, 10191; Lundt, I., Madsen, R., Lundt, I., Madsen, R., Synthesis, 1995, 787; Wong, C. H., Provencher, L., Porco, J. A., Jung, S. H., Wang, Y. F., Chen, L. R., Wang, R., J. Org. Chem., 1995, 60, 1492.
11. 8. Myerscough, P. M., Fairbanks, A. J., Jones, A. H., Choi, S.-S., Fleet, G. W. J., Al-Daher, S. S., Cenci di Bello, I., Winchester, B., Tetrahedron, 1992, 48, 10177; Bruce, I., Fleet, G. W. J., Cenci di Bello, I., Winchester, B., Tetrahedron, 1992, 48, 10191; Lundt, I., Madsen, R., Lundt, I., Madsen, R., Synthesis, 1995, 787; Wong, C. H., Provencher, L., Porco, J. A., Jung, S. H., Wang, Y. F., Chen, L. R., Wang, R., J. Org. Chem., 1995, 60, 1492.
12. 9. Dominguez, J. N., Owen, L. N., Carbohydr. Res., 1979, 75, 101.
13. 10. Unless otherwise stated, all specific rotations were measured in chloroform.
14. 2O, 50MHz) 15.7 (q, C-6), 44.8 (t, C-1), 49.3 (d, C-5), 66.6, 71.3, 72.9 (d × 3, C-2, C-3, C-4).
15. 12. Estevez, J. C., Smith, M. D., Wormald, M. R., Besra, G. S., Brennan, P. J., Nash, R. J., Fleet, G. W. J.,Tetrahedron Asymm., 1996, 7, 391.
16. 13. The structure of lactone 19 was firmly established by X-ray crystallographic analysis of a cyclohexylidene derivative.
17. +, 100%).
18. 15. Details of the X-ray structure of 22 will be provided in the full paper.
19. +, 100%).
20. +, 100%).
21. 18. The details of ring opening of the lactones with amines will be presented in a full paper.
22. m 1.1 mM). The compounds were also assayed for potential inhibition of α-glucosidase (Brewers yeast, rabbit gut), β-glucosidase (almond emulsin, rabbit gut, rabbit liver), α-galactosidase (green coffee bean,), β-galactosidase (E.coli, rabbit gut, rabbit liver), α-mannosidase (Jack Bean), β-N-acetylglucosaminidase (Jack Bean, bovine), xylanase (Trichoderma viride), pectinase (Aspergillus niger), and rabbit gut sucrase, maltase, trehalase and lactase; there was no significant inhibition of any of these enzymes other than where stated in the text. Details of the enzyme assays will be given in a full paper.
23. 20. Estevez, J. C., Sounders, J., Besra, G. S., Brennan, P. J., Nash, R. J., Fleet, G. W. J., Tetrahedron: Asymm., 1996, 7, 383; Estevez, J. C., Smith, M. D., Lane, A. L., Crook, S., Watkin, D. J., Besra, G. S., Brennan, P. J., Nash, R. J., Fleet, G. W. J., Tetrahedron Asymm., 1996, 7, 387.
24. 20. Estevez, J. C., Sounders, J., Besra, G. S., Brennan, P. J., Nash, R. J., Fleet, G. W. J., Tetrahedron: Asymm., 1996, 7, 383; Estevez, J. C., Smith, M. D., Lane, A. L., Crook, S., Watkin, D. J., Besra, G. S., Brennan, P. J., Nash, R. J., Fleet, G. W. J., Tetrahedron Asymm., 1996, 7, 387.
25. 21. Huebner, R. E., Castro, K. G., Annu. Rev. Med., 1995, 46, 47.
26. 22. This work was supported by CASE and graduate studentships from EPSRC and BBSRC, and by NCDDG (NIH, AI-38087).