A versatile access to calystegine analogues as potential glycosidases inhibitors

Journal of Organic Chemistry

Volumn 74, Issue 16, 2009, Pages 6266-6274

  Kaliappan, Krishna P ^a   Das, Prasanta ^a   Chavan, Sanjay T ^b   Sabharwal, Sushma G ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

^b UNIVERSITY OF PUNE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; OLEFINS;

CHEMICAL EQUATIONS; DEPROTECTION; DIHYDROXYLATION; GLYCOSIDASES; GRIGNARD REAGENT; MANNOSIDASE; NITRONES; NUCLEOPHILIC ADDITIONS; RING CLOSING METATHESIS; STEREO-SELECTIVE; SYNTHETIC STRATEGIES;

SYNTHESIS (CHEMICAL);

8 AZABICYCLO[3.2.1]OCTANE 2,3,4,6,7 PENTAOL; 8 AZABICYCLO[3.2.1]OCTANE 2,6,7 TRIOL; 8 AZABICYCLO[3.2.1]OCTANE 6,7 DIOL; ALKENE DERIVATIVE; ALPHA MANNOSIDASE; GLYCOSIDASE INHIBITOR; GRIGNARD REAGENT; MANNOSE; N ACETYL BETA GLUCOSAMINIDASE; NITRONE DERIVATIVE; NUCLEOPHILE; UNCLASSIFIED DRUG; ENZYME INHIBITOR; GLUCOSIDASE; GLUCOSYLCERAMIDASE; GLYCOSIDASE; NORTROPANE DERIVATIVE;

ARTICLE; CALYSTEGIA; DEPROTECTION REACTION; DIHYDROXYLATION; DRUG SYNTHESIS; HYDROGENATION; RING CLOSING METATHESIS; STEREOCHEMISTRY; ANTAGONISTS AND INHIBITORS; CHEMISTRY; IC50; SYNTHESIS;

ENZYME INHIBITORS; GLUCOSIDASES; GLUCOSYLCERAMIDASE; GLYCOSIDE HYDROLASES; INHIBITORY CONCENTRATION 50; NORTROPANES;

EID: 70349140966     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901342w     Document Type: Article

References (102)

1. Tepfer, D.; Goldmann, A.; Pamboukdjian, N.; Maille, M.; Lepingle, A.; Chevalier, D.; Dénarié, J.; Rosenberg, C. J. Bacteriol. 1988, 170, 1153-1161.
2. Goldmann, A.; Message, B.; Tepfer, D.; Molineux, R. J.; Duclos, O.; Boyer, F.-D.; Pan, Y. T.; Elbein, A. D. J. Nat. Prod. 1996, 59, 1137-1142.
3. For a specific review, see: Molyneux, R. J.; Nash, R. J.; Asano, N. The Chemistry and Biological Activity of Calystegines and Related Nortropane Alkaloids. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: Oxford, UK, 1996; Vol.11, pp 303-343.
4. Dräger, B. Nat. Prod. Rep. 2004, 21, 211-223 and references cited therein.
5. Nash, R. J.; Rothschild, M.; Porter, E. A.; Watson, A. A.; Waigh, R. D. Phytochemistry 1993, 34, 1281-1283.
6. For recent reviews on alkaloid glycosidase inhibitors, including the calystegines, see: Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645-1680.
7. (a) Asano, N.; Oseki, K.; Tomioka, E.; Kizu, H.; Matsui, K. Carbohydr. Res. 1994, 259, 243-255.
8. (b) Asano, N.; Kato, A.; Oseki, K.; Kizu, H.; Matsui, K. Eur. J. Biochem. 1995, 229, 369-376.
9. (c) Jhonson, C. R.; Bis, S. J. J. Org. Chem. 1995, 60, 615-623.
10. (d) Asano, N.; Kato, A.; Yokoyama, Y.; Miyauchi, M.; Yamamoto, M.; Kizu, H.; Matsui, K. Carbohydr. Res. 1996, 284, 169-178.
11. (e) Asano, N.; Kato, A.; Kizu, H.; Matsui, K.; Watson, A. A.; Nash, R. J. Carbohydr. Res. 1996, 293, 195-204.
12. (f) Asano, N.; Kato, A.; Miyauchi, M.; Kizu, H.; Tomimori, T.; Matsui, K.; Nash, R. J.; Molyneux, R. J. Eur. J. Biochem. 1997, 248, 296-303.
13. (g) Asano, N.; Kato, A.; Kizu, H.; Matsui, K.; Griffiths, R. C.; Jones, M. G.; Watson, A. A.; Nash, R. J. Carbohydr. Res. 1997, 304, 173-178.
14. (h) Fernández, J. M. G.; Mellet, C. O.; Benito, J. M.; Fuentes, J. Synlett 1998, 316-318.
15. (i) van Hooft, P. A. V.; Litjens, R. E. J. N.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom J. H. Org. Lett. 2001, 3, 731-733.
16. (j) García-Moreno, M. I.; Benito, J. M.; Mellet, C. O.; Fernández, J. M. G. J. Org. Chem. 2001, 66, 7604-7614.
17. (k) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2002, 67, 3705-3717.
18. For reviews, see: (a) Asano, N. Glycobiology 2003, 13, 93-104.
19. (b) Nishimura, Y. In Iminosugars, from Synthesis to Therapeutic Applications; Compain, P., Martin, O. R., Eds.; Wiley-VCH: Weinheim, Germany, 2007, pp 269-294.
20. (a) Carlson, G. B.; Butters, T. D.; Dwek, R. A.; Platt, F. M J. Biol. Chem. 1993, 268, 570-576.
21. (b) Greimel, P.; Spreitz, J.; Stütz, A. E.; Wrodnigg, T. M. Curr. Top. Med. Chem. 2003, 3, 513-523.
22. (c) Norton, P. A.; Baohua, G.; Block, T. M. In Iminosugars, From Synthesis to Therapeutic Applications; Compain, P., Martin, O. R., Eds.; Wiley-VCH: Weinheim, Germany, 2007; pp 209-224.
23. (a) Anzeveno, P. B.; Creemer, L. J.; Daniel, J. K.; King, C.-H.; Liu, P. S. J. Org. Chem. 1989, 54, 2539-2542.
24. (b) Platt, F. M.; Neises, G. R.; Reinkensmeier, G.; Townsend, M. J.; Perry, V. H.; Proia, R. L.; Winchester, B.; Dwek, R. A.; Butters, T. D. Science 1997, 276, 428-431.
25. (a) García-Moreno, M. I.; Mellet, C. O.; Fernandez, J. M. G. Eur. J. Org. Chem. 2004, 1803-1819.
26. (b) Groetzl, B.; Handa, S.; Malpass, J. R. Tetrahedron Lett. 2006, 47, 9147-9150.
27. (c) García-Moreno, M. I.; Ortiz Mellet, C.; García Fernández, J. M. Tetrahedron 2007, 63, 7879-7884.
28. (d) Singh, T. K. M.; Wong, W. F.; Ikeno, T.; Yamada, T. Org. Lett. 2007, 9, 207-209.
29. (e) Chagnault, V.; Compain, P.; Lewinski, K.; Ikeda, K.; Asano, N.; Martin, O. R. J. Org. Chem. 2009, 74, 3179-3182.
30. (a) Kaliappan, K. P.; Kumar, N. Tetrahedron Lett. 2003, 44, 379-381.
31. (b) Kaliappan, K. P.; Gowrisankar, P. Tetrahedron Lett. 2004, 45, 8207-8209.
32. (c) Kaliappan, K. P.; Ravikumar, V. J. Org. Chem. 2007, 72, 6116-6226.
33. (d) Kaliappan, K. P.; Ravikumar, V. Org. Lett. 2007, 9, 2417-2419.
34. (a) Kaliappan, K. P.; Nandurdikar, R. S. Chem. Commum. 2004, 2506-2507.
35. (b) Kaliappan, K. P.; Ravikumar, V. Org. Biomol. Chem. 2005, 3, 848-851.
36. (c) Kaliappan, K. P.; Das, P.; Kumar, N. Tetrahedron Lett. 2005, 46, 3037-3040.
37. (d) Kaliappan, K. P.; Nandurdikar, R. S.; Mobin, S. M. Tetrahedron 2006, 62, 5064-5073.
38. (e) Kaliappan, K. P.; Subrhamanyam, A. V. Org. Lett. 2007, 9, 1121-1124.
39. (f) Kaliappan, K. P.; Das, P. Synlett 2008, 841-844.
40. For selected reviews on metathetic reactions see: (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2055.
41. (b) Grubbs R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
42. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388.
43. (d) Randall, M. L.; Snapper M. L. Strem Chem. 1998, 17, 1-9.
44. (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077.
45. (f) Yet, L. Chem. Rev. 2000, 100, 2963-3007.
46. (g) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
47. (h) Trnka T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
48. (i) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073-2077.
49. (j) Kotha, S.; Sreenivasachary, N. Indian J. Chem. 2001, 40B, 763-780.
50. (k) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900-1923.
51. (l) Walters, M. A. Prog. Heterocycl. Chem. 2003, 15, 1-36.
52. (m) Grubbs, R. H. Tetrahedron 2004, 60, 7117-7140.
53. (n) Schmidt, B. Eur. J. Org. Chem. 2004, 1865-1880.
54. (o) Schmidt, B.; Hermanns, J. Top. Organomet. Chem. 2004, 7, 223-267.
55. (p) Connon, S. J.; Blechert, S. Top. Organomet. Chem. 2004, 7, 93-124.
56. (q) Connon, S. J.; Blechert, S. Top. Organomet. Chem. 2004, 11, 93.
57. (r) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490-4527.
58. (s) Kaliappan, K. P. Lett. Org. Chem. 2005, 2, 678-686.
59. (t) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490-4527.
60. (u) Gradillas, A.; Pérez-Castells, J. Angew. Chem., Int. Ed. 2006, 45, 6086-6101.
61. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
62. (b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
63. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
64. Hoveyda, A. H.; Gillingham, D. G.; Van Veldhuizen, J. J.; Kataoka, O.; Garber, S. B.; Kingsbury, J. S.; Harrity, J. P. A. Org. Biomol. Chem. 2004, 2, 8-23.
65. (a) White, J. D.; Hrnciar, P. J. Org. Chem. 2000, 65, 9129-9142.
66. (b) Rambaud, L.; Compain, P.; Martin, O. R. Tetrahedron: Asymmetry 2001, 12, 1807-1809.
67. (c) Tang, M.; Pyne, S. G. Tetrahedron 2004, 60, 5759-5767.
68. (d) Ceccon, J.; Greene, A. E.; Poisson, J.-F. Org. Lett. 2006, 8, 4739-4742.
69. (e) Au, C. W. G.; Pyne, S. G. J. Org. Chem. 2006, 71, 7097-7099.
70. (f) Dewi-Wülfing, P.; Blechert, S. Eur. J. Org. Chem. 2006, 1852-1856.
71. (a) Tufariello, J. J. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: New York, 1984.
72. (b) Iida, H.; Watanabe, Y.; Kibayashi, C. J. Org. Chem. 1985, 50, 1818-1825.
73. (c) Torssell, K. B. G. In Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; Feuer, H., Ed.; VCH Publishers: New York, 1988.
74. (d) Takahashi, T.; Fuji, A.; Sugita, J.; Hagi, T.; Kitano, K.; Arai, Y.; Koizumi, T. Tetrahedron: Asymmetry 1991, 2, 1379-1390.
75. (e) Jung, M.; Longmei, Z.; Tangsheng, P.; Huiyan, Z.; Yan, L. J. Org. Chem. 1992, 57, 3528-3530.
76. (f) Pham, V. C.; Charlton, J. L. J. Org. Chem. 1995, 60, 8051-8055.
77. (g) Pham, V. C.; Charlton, J. L. J. Org. Chem. 1995, 60, 8051-8055.
78. (h) Rumbo, A.; Mourino, A.; Castedo, L.; Mascarenas, J. L. J. Org. Chem. 1996, 61, 6114-6120.
79. (i) Rumbo, A.; Mourino, A.; Castedo, L.; Mascarenas, J. L. J. Org. Chem. 1996, 61, 6114-6120.
80. (j) Kozikowski, A. P.; Araldi, G. L.; Ball, R. G. J. Org. Chem. 1997, 62, 503-509.
81. (k) Kozikowski, A. P.; Araldi, G. L.; Ball, R. G. J. Org. Chem. 1997, 62, 503-509.
82. (l) Gothelf, K. V.; Joergensen, K. A. Chem. Rev. 1998, 98, 863-910.
83. (m) Smith, M. P.; George, C.; Kozikowski, A. P. Tetrahedron Lett. 1998, 39, 197-200.
84. (a) Lombardo, M.; Trombini, C. Synthesis 2000, 759-774.
85. (b) Merino, P. In Science of Synthesis; Padwa, A., Ed.; Thieme: Stuttgart, Germany, 2004; Vol.27, pp 511-580.
86. (a) Masson, G.; Py, S.; Vallée, Y. Angew. Chem., Int. Ed. 2002, 41, 1772-1775.
87. (b) Riber, D.; Skrydstrup, D. Org. Lett. 2003, 5, 229-231.
88. (c) Zhong, Y.-W.; Xu, M.-H.; Lin, G.-Q. Org. Lett. 2004, 6, 3953-3956.
89. (d) Cardona, F.; Goti, A. Angew. Chem., Int. Ed. 2005, 44, 7832-7835.
90. (a) Goti, A.; Cicchi, S.; Cacciarini, M.; Cardona, F.; Fedi, V.; Brandi, A. Eur. J. Org. Chem. 2000, 3633-3645 and references cited therein.
91. (b) Cardona, F.; Goti, A.; Brandi, A. Org. Lett. 2003, 5, 1475-1478.
92. (c) Cardona, F.; Moreno, G.; Guarna, F.; Vogel, P.; Schuetz, C.; Merino, P.; Goti, A. J. Org. Chem. 2005, 70, 6552-6555.
93. Tamura, O.; Toyao, A.; Ishibashi, H. Synlett 2002, 1344-1346.
94. (a) Fatig, T.; Soulié, J.; Lallemend, J.-Y.; Ricard, L. Tetrahedron: Asymmetry 1999, 10, 2165-2174.
95. (b) Boyer, F.-D.; Hanna, I. Tetrahedron Lett. 2001, 42, 1275-1277.
96. (c) Madsen, R.; Skaanderup, P. R. J. Org. Chem. 2003, 68, 2115-2122.
97. Lombardo, M.; Fabbroni, S.; Trombini, C. J. Org. Chem. 2001, 66, 1264-1268.
98. Cicchi, S.; Bonanni, M.; Cardona, F.; Revuelta, J.; Goti, A. Org. Lett. 2003, 5, 1773-1776.
99. Garegg, P. J.; Samuelsson, B. Synlett 1979, 469-470.
100. For a review on olefin metathesis of amine-containing systems, see: Compain, P. Adv. Synth. Catal. 2007, 349, 1829-1846.
101. Riché, F.; Masri, F.; Lopez, M. Tetrahedron Lett. 2007, 48, 1609-1612.
102. Murray, A. J.; Parsons, P. J. Synlett 2006, 1443-1445.