Efficient synthesis from d-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-l-arabinitol LABNAc, a potent pyrrolidine inhibitor of hexosaminidases

Tetrahedron Letters

Volumn 48, Issue 24, 2007, Pages 4287-4291

  Rountree, J S Shane ^a,b   Butters, Terry D ^a   Wormald, Mark R ^a   Dwek, Raymond A ^a   Asano, Naoki ^c   Ikeda, Kyoko ^c   Evinson, Emma L ^d   Nash, Robert J ^d   Fleet, George W J ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF OXFORD   (United Kingdom)

^c HOKURIKU UNIVERSITY   (Japan)

^d ABERYSTWYTH UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 ACETAMIDO 1,4 IMINO 1,2,4 TRIDEOXY DEXTRO ARABINITOL; 2 ACETAMIDO 1,4 IMINO 1,2,4 TRIDEOXY LEVO ARABINITOL; ALCOHOL DERIVATIVE; ALPHA GALACTOSIDASE; ALPHA GLUCOSIDASE; ALPHA LEVO FUCOSIDASE; BETA GALACTOSIDASE; BETA GLUCOSIDASE; GLUCAN 1,4 ALPHA GLUCOSIDASE; IMINOSUGAR; UNCLASSIFIED DRUG;

ARTICLE; DRUG INHIBITION; DRUG SYNTHESIS; ENANTIOMER; HYPOTHESIS;

EID: 34248578636     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.04.041     Document Type: Article

References (56)

1. Woynarowska B., Wilkiel H., Sharma M., Carpenter N., Fleet G.W.J., and Bernacki R.J. Anticancer Res. 12 (1992) 161-166
2. Mohamad S.B., Nagasawa H., Uto Y., and Hori H. Comp. Biochem. Physiol. A Mol. Integr. Physiol 132 (2002) 1-8
3. Reddi A.L., Sankaranarayanan K., Arulraj H.S., Devaraj N., and Devaraj H. Cancer Lett. 158 (2000) 61-64
4. Liu J.J., Numa M.M.D., Liu H.T., Huang S.J., Sears P., Shikhman A.R., and Wong C.H. J. Org. Chem. 69 (2004) 6273-6283
5. Liu J.J., Shikhman A.R., Lotz M.K., and Wong C.H. Chem. Biol. 8 (2001) 701-711
6. Tropak M.B., Reid S.P., Guiral M., Withers S.G., and Mahuran D. J. Biol. Chem. 279 (2004) 13478-13487
7. Horsch M., Mayer C., Sennhauser U., and Rast D.M. Pharmacol. Ther. 76 (1997) 187-218
8. Horsch M., Hoesch L., Fleet G.W.J., and Rast D.M. J. Enzyme Inhib. 7 (1993) 47-53
9. Nagahashi G., Tu S.I., Fleet G., and Namgoong S.K. Plant Physiol. 92 (1990) 413-418
10. Kato M., Uno T., Hiratake J., and Sakat K. Bioorg. Med. Chem. 13 (2005) 1563-1571
11. Asano N., Nash R.J., Molyneux R.J., and Fleet G.W.J. Tetrahedron: Asymmetry 11 (2000) 1645-1680
12. Watson A.A., Fleet G.W.J., Asano N., Molyneux R.J., and Nash R.J. Phytochemistry 56 (2001) 265-295
13. Asano N. Glycobiology 13 (2003) 93R-104R
14. Stutz A.E. Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond (1999), Wiley-VCH, Weinheim
15. Mitrakou A., Tountas N., Raptis A.E., Bauer R.J., Schulz H., and Raptis S.A. Diabet. Med. 15 (1998) 657-660
16. Butters T.D., Dwek R.A., and Platt F.M. Glycobiology 15 (2005) R43-R52
17. Elstein D., Hollak C., Aerts J.M.F.G., van Weely S., Maas M., Cox T.M., Lachmann R.H., Hrebicek M., Platt F.M., Butters T.D., Dwek R.A., and Zimran A. J. Inherit. Metab. Dis. 27 (2004) 757-766
18. Karpas A., Fleet G.W.J., Dwek R.A., Petursson S., Namgoong S.K., Jacob G.S., and Rademacher T.W. Proc. Natl. Acad. Sci. U.S.A. 85 (1988) 9229-9233
19. Fleet G.W.J., Karpas A., Dwek R.A., Fellows L.E., Tyms A.S., Petursson S., Namgoong S.K., Ramsden N.G., Smith P.W., Son J.C., Wilson F.X., Witty D.R., Jacob G.S., and Rademacher T.W. FEBS Lett. 237 (1988) 128-132
20. Fleet G.W.J., and Son J.C. Tetrahedron 44 (1988) 2637-2648
21. Legler G., and Pohl S. Carbohydr. Res. 155 (1986) 119-129
22. Nash R.J., Bell E.A., and Williams J.M. Phytochemistry 24 (1985) 1620
23. Jones D.W.C., Nash R.J., Bell E.A., and Williams J.M. Tetrahedron Lett. 26 (1985) 3127
24. Oikonomakos N.G., Tiraidis C., Leonidas D.D., Zographos S.E., Kristiansen M., Jessen C.U., Norskov-Lauritsen L., and Agius L. J. Med. Chem. 49 (2006) 5687-5701
25. Henke B.R., and Sparks S.M. Mini-Rev. Med. Chem. 6 (2006) 845-857
26. Scofield A.M., Fellows L.E., Nash R.J., and Fleet G.W.J. Life Sci. 39 (1986) 645-651
27. Behling J.R., Campbell A.L., Babiak K.A., Ng J.S., Medich J., Farid P., and Fleet G.W.J. Tetrahedron 49 (1993) 3359-3368
28. Fleet G.W.J., and Smith P.W. Tetrahedron 42 (1986) 5685-5691
29. Fleet G.W.J., Nicholas S.J., Smith P.W., Evans S.V., Fellows L.E., and Nash R.J. Tetrahedron Lett. 26 (1985) 3127-3130
30. Fleet G.W.J., Smith P.W., Nash R.J., Fellows L.E., Parekh R.B., and Rademacher T.W. Chem. Lett. (1986) 1051-1054
31. Boshagen H., Heiker F., and Schuller A. Carbohydr. Res. 164 (1987) 141-148
32. Fleet G.W.J., Fellows L.E., and Smith P.W. Tetrahedron 43 (1987) 979-988
33. Knapp S., Vocadlo D., Gao Z., Kirk B., Lou J., and Withers S.G. J. Am. Chem. Soc. 118 (1996) 6804-6805
34. Terinek T., and Vasella A. Helv. Chim. Acta 88 (2005) 10-22
35. van den Berg R.J.B.N., Donker-Koopman W., van Boom J.H., Aerts H.M.F.G., and Noort D. Bioorg. Med. Chem. 12 (2004) 891-902
36. Dorfmueller H.C., Borodkin V.S., Schimpl M., Shepherd S.M., Shpiro N.A., and van Aalten D.M.F. J. Am. Chem. Soc. 128 (2006) 16484-16485
37. Tatsuta K., Miura S., Ohta S., and Gunji H. J. Antibiot. 48 (1995) 286-288
38. Croucher P.D., Furneaux R.H., and Lynch G.P. Tetrahedron 50 (1994) 13299-13312
39. Liessem B., Giannis A., Sandhoff K., and Nieger M. Carbohydr. Res. 250 (1993) 19-30
40. Batra H., Moriarty R.M., Penmasta R., Sharma V., Stanciuc G., Staszewski J.P., Tuladhar S.M., and Walsh D.A. Org. Process Res. Dev. 10 (2006) 484-486
41. Humphlett W.J. Carbohydr. Res 4 (1967) 157-164
42. Zinner H., Voigt H., and Voigt J. Carbohydr. Res. 7 (1968) 38-55
43. Behling J.R., Campbell A.L., Babiak K.A., Ng J.S., Medich J., Farid P., and Fleet G.W.J. Tetrahedron 49 (1993) 3359-3368
44. Extra care must be taken in the handling of triflate 12D since a co-worker has experienced a strong allergic response to this compound or its decomposition products.
45. 3): 63.2 (C-2), 66.0 (C-5), 73.1 (C-3), 75.6 (C-4), 99.5 (CHPh), 126.1, 128.4, 129.6 (CH(Ar)), 136.4 (C(Ar)), 171.1 (C-1).
46. 2CO, 50.3 MHz): 66.8 (t, C-5), 62.8, 72.3, 75.7 (3 × d, C-2, C-3, C-4), 99.5 (CHPh), 126.9, 128.9, 129.8 (3 × d, CH(Ar)), 138.5 (s, C(Ar)), 172.8 (C{double bond, long}O).
47. Fleet G.W.J., Bruce I., Girdhar A., Haraldsson M., Peach J.M., and Watkin D.J. Tetrahedron 46 (1990) 19-32
48. Krülle T.M., Davis B., Ardron H., Long D.D., Hindle N.A., Smith C., Brown D., Lane A.L., Watkin D.J., Marquess D.G., and Fleet G.W.J. J. Chem. Soc., Chem. Commun (1996) 1271-1272
49. van Ameijde J., Horne G., Wormald M.R., Dwek R.A., Nash R.J., Jones P.W., Evinson E.L., and Fleet G.W.J. Tetrahedron: Asymmetry 17 (2006) 2702-2713
50. 2Ph), 59.4 (C-5), 65.4 (C-2), 71.6 (C-4), 78.4 (C-3), 127.5, 128.5, 128.6 (CH(Ar)), 137.7 (C(Ar)).
51. 2Ph), 60.3 (C-5), 71.1 (C-4), 77.9 (C-3), 128.1, 128.9, 130.2 (CH(Ar)), 137.3 (C(Ar)), 174.2 (C{double bond, long}O).
52. 3), 48.3 (C-1), 57.5 (C-2), 61.4 (C-5), 64.7 (C-4), 77.1 (C-3), 174.7 (C{double bond, long}O).
53. Harding C.C., Rountree J.S.S., Watkin D.J., Cowley A.R., Butters T.D., Wormald M.R., Dwek R.A., and Fleet G.W.J. Acta Cryst. E61 (2005) o1683-o1685
54. Kato A., Kato N., Kano E., Adachi I., Ikeda K., Yu L., Okamoto T., Banba Y., Ouchi H., Takahata H., and Asano N. J. Med. Chem. 48 (2005) 2036-2044
55. Asano N., Ikeda K., Yu L., Kato A., Takebayashi K., Adachi I., Kato I., Ouchi H., Takahata H., and Fleet G.W.J. Tetrahedron: Asymmetry 16 (2005) 223-229
56. Yu C.Y., Asano N., Ikeda K., Wang M.X., Butters T.D., Wormald M.R., Dwek R.A., Winters A.L., Nash R.J., and Fleet G.W.J. Chem. Commun. (2004) 1936-1937