메뉴 건너뛰기




Volumn 45, Issue 3, 2004, Pages 579-581

Synthesis and biological evaluation of the first example of an eight-membered iminoalditol

Author keywords

Azocanes; Glycosidase inhibitors; Iminoalditols

Indexed keywords

2 HYDROXYMETHYLAZOCANE 3,4,5 TRIOL; ANTINEOPLASTIC AGENT; CARBOHYDRATE DERIVATIVE; ENZYME INHIBITOR; GLUCOSIDASE; UNCLASSIFIED DRUG;

EID: 0346363691     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.195     Document Type: Article
Times cited : (36)

References (42)
  • 1
    • 0014162475 scopus 로고
    • For selected references see: (a) For selected references see: Paulsen H., Todt K. Chem. Ber. 100:1967;512 (b) Farr R.A., Holland A.K., Huber E.W., Peet N.P., Weintraub P.M. Tetrahedron. 50:1994;1033 (c) Lohray B.B., Jayamma Y., Chatterji M. J. Org. Chem. 60:1995;5958 (d) Morri-Varas F., Qian X.-H., Wong C.-H. J. Am. Chem. Soc. 118:1996;7647 (e) Gauzy L., Le Merrer Y., Depezay J.-C., Clere F., Mignani S. Tetrahedron Lett. 40:1999;6005 (f) Fuentes J., Olano D., Pradera M.A. Tetrahedron Lett. 40:1999;4063 (g) Andersen S.M., Ekhart C., Lundt I., Stütz A.E. Carbohydr. Res. 326:2000;22 (h) Painter G.F., Falshaw A. J. Chem. Soc., Perkin Trans. 1. 2000;1157 (i) Tezuka K., Compain P., Martin O.R. Synlett. 2000;1837 (j) Gallos J.K., Demeroudi S.C., Stathopoulou C.C., Dellios C.C. Tetrahedron Lett. 42:2001;7497 (k) Mehta G., Lakshminath S. Tetrahedron Lett. 43:2002;331 (l) Tilekar J.N., Patil N.T., Jadhav H.S., Dhavale D.D. Tetrahedron. 59:2003;1873.
    • (1967) Chem. Ber. , vol.100 , pp. 512
    • Paulsen, H.1    Todt, K.2
  • 2
    • 0027979680 scopus 로고
    • For selected references see: (a) For selected references see: Paulsen H., Todt K. Chem. Ber. 100:1967;512 (b) Farr R.A., Holland A.K., Huber E.W., Peet N.P., Weintraub P.M. Tetrahedron. 50:1994;1033 (c) Lohray B.B., Jayamma Y., Chatterji M. J. Org. Chem. 60:1995;5958 (d) Morri-Varas F., Qian X.-H., Wong C.-H. J. Am. Chem. Soc. 118:1996;7647 (e) Gauzy L., Le Merrer Y., Depezay J.-C., Clere F., Mignani S. Tetrahedron Lett. 40:1999;6005 (f) Fuentes J., Olano D., Pradera M.A. Tetrahedron Lett. 40:1999;4063 (g) Andersen S.M., Ekhart C., Lundt I., Stütz A.E. Carbohydr. Res. 326:2000;22 (h) Painter G.F., Falshaw A. J. Chem. Soc., Perkin Trans. 1. 2000;1157 (i) Tezuka K., Compain P., Martin O.R. Synlett. 2000;1837 (j) Gallos J.K., Demeroudi S.C., Stathopoulou C.C., Dellios C.C. Tetrahedron Lett. 42:2001;7497 (k) Mehta G., Lakshminath S. Tetrahedron Lett. 43:2002;331 (l) Tilekar J.N., Patil N.T., Jadhav H.S., Dhavale D.D. Tetrahedron. 59:2003;1873.
    • (1994) Tetrahedron , vol.50 , pp. 1033
    • Farr, R.A.1    Holland, A.K.2    Huber, E.W.3    Peet, N.P.4    Weintraub, P.M.5
  • 3
    • 0029088080 scopus 로고
    • For selected references see: (a) For selected references see: Paulsen H., Todt K. Chem. Ber. 100:1967;512 (b) Farr R.A., Holland A.K., Huber E.W., Peet N.P., Weintraub P.M. Tetrahedron. 50:1994;1033 (c) Lohray B.B., Jayamma Y., Chatterji M. J. Org. Chem. 60:1995;5958 (d) Morri-Varas F., Qian X.-H., Wong C.-H. J. Am. Chem. Soc. 118:1996;7647 (e) Gauzy L., Le Merrer Y., Depezay J.-C., Clere F., Mignani S. Tetrahedron Lett. 40:1999;6005 (f) Fuentes J., Olano D., Pradera M.A. Tetrahedron Lett. 40:1999;4063 (g) Andersen S.M., Ekhart C., Lundt I., Stütz A.E. Carbohydr. Res. 326:2000;22 (h) Painter G.F., Falshaw A. J. Chem. Soc., Perkin Trans. 1. 2000;1157 (i) Tezuka K., Compain P., Martin O.R. Synlett. 2000;1837 (j) Gallos J.K., Demeroudi S.C., Stathopoulou C.C., Dellios C.C. Tetrahedron Lett. 42:2001;7497 (k) Mehta G., Lakshminath S. Tetrahedron Lett. 43:2002;331 (l) Tilekar J.N., Patil N.T., Jadhav H.S., Dhavale D.D. Tetrahedron. 59:2003;1873.
    • (1995) J. Org. Chem. , vol.60 , pp. 5958
    • Lohray, B.B.1    Jayamma, Y.2    Chatterji, M.3
  • 4
    • 0029840739 scopus 로고    scopus 로고
    • For selected references see: (a) For selected references see: Paulsen H., Todt K. Chem. Ber. 100:1967;512 (b) Farr R.A., Holland A.K., Huber E.W., Peet N.P., Weintraub P.M. Tetrahedron. 50:1994;1033 (c) Lohray B.B., Jayamma Y., Chatterji M. J. Org. Chem. 60:1995;5958 (d) Morri-Varas F., Qian X.-H., Wong C.-H. J. Am. Chem. Soc. 118:1996;7647 (e) Gauzy L., Le Merrer Y., Depezay J.-C., Clere F., Mignani S. Tetrahedron Lett. 40:1999;6005 (f) Fuentes J., Olano D., Pradera M.A. Tetrahedron Lett. 40:1999;4063 (g) Andersen S.M., Ekhart C., Lundt I., Stütz A.E. Carbohydr. Res. 326:2000;22 (h) Painter G.F., Falshaw A. J. Chem. Soc., Perkin Trans. 1. 2000;1157 (i) Tezuka K., Compain P., Martin O.R. Synlett. 2000;1837 (j) Gallos J.K., Demeroudi S.C., Stathopoulou C.C., Dellios C.C. Tetrahedron Lett. 42:2001;7497 (k) Mehta G., Lakshminath S. Tetrahedron Lett. 43:2002;331 (l) Tilekar J.N., Patil N.T., Jadhav H.S., Dhavale D.D. Tetrahedron. 59:2003;1873.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 7647
    • Morri-Varas, F.1    Qian, X.-H.2    Wong, C.-H.3
  • 5
    • 0033551756 scopus 로고    scopus 로고
    • For selected references see: (a) For selected references see: Paulsen H., Todt K. Chem. Ber. 100:1967;512 (b) Farr R.A., Holland A.K., Huber E.W., Peet N.P., Weintraub P.M. Tetrahedron. 50:1994;1033 (c) Lohray B.B., Jayamma Y., Chatterji M. J. Org. Chem. 60:1995;5958 (d) Morri-Varas F., Qian X.-H., Wong C.-H. J. Am. Chem. Soc. 118:1996;7647 (e) Gauzy L., Le Merrer Y., Depezay J.-C., Clere F., Mignani S. Tetrahedron Lett. 40:1999;6005 (f) Fuentes J., Olano D., Pradera M.A. Tetrahedron Lett. 40:1999;4063 (g) Andersen S.M., Ekhart C., Lundt I., Stütz A.E. Carbohydr. Res. 326:2000;22 (h) Painter G.F., Falshaw A. J. Chem. Soc., Perkin Trans. 1. 2000;1157 (i) Tezuka K., Compain P., Martin O.R. Synlett. 2000;1837 (j) Gallos J.K., Demeroudi S.C., Stathopoulou C.C., Dellios C.C. Tetrahedron Lett. 42:2001;7497 (k) Mehta G., Lakshminath S. Tetrahedron Lett. 43:2002;331 (l) Tilekar J.N., Patil N.T., Jadhav H.S., Dhavale D.D. Tetrahedron. 59:2003;1873.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 6005
    • Gauzy, L.1    Le Merrer, Y.2    Depezay, J.-C.3    Clere, F.4    Mignani, S.5
  • 6
    • 0033591172 scopus 로고    scopus 로고
    • For selected references see: (a) For selected references see: Paulsen H., Todt K. Chem. Ber. 100:1967;512 (b) Farr R.A., Holland A.K., Huber E.W., Peet N.P., Weintraub P.M. Tetrahedron. 50:1994;1033 (c) Lohray B.B., Jayamma Y., Chatterji M. J. Org. Chem. 60:1995;5958 (d) Morri-Varas F., Qian X.-H., Wong C.-H. J. Am. Chem. Soc. 118:1996;7647 (e) Gauzy L., Le Merrer Y., Depezay J.-C., Clere F., Mignani S. Tetrahedron Lett. 40:1999;6005 (f) Fuentes J., Olano D., Pradera M.A. Tetrahedron Lett. 40:1999;4063 (g) Andersen S.M., Ekhart C., Lundt I., Stütz A.E. Carbohydr. Res. 326:2000;22 (h) Painter G.F., Falshaw A. J. Chem. Soc., Perkin Trans. 1. 2000;1157 (i) Tezuka K., Compain P., Martin O.R. Synlett. 2000;1837 (j) Gallos J.K., Demeroudi S.C., Stathopoulou C.C., Dellios C.C. Tetrahedron Lett. 42:2001;7497 (k) Mehta G., Lakshminath S. Tetrahedron Lett. 43:2002;331 (l) Tilekar J.N., Patil N.T., Jadhav H.S., Dhavale D.D. Tetrahedron. 59:2003;1873.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 4063
    • Fuentes, J.1    Olano, D.2    Pradera, M.A.3
  • 7
    • 0034685674 scopus 로고    scopus 로고
    • For selected references see: (a) For selected references see: Paulsen H., Todt K. Chem. Ber. 100:1967;512 (b) Farr R.A., Holland A.K., Huber E.W., Peet N.P., Weintraub P.M. Tetrahedron. 50:1994;1033 (c) Lohray B.B., Jayamma Y., Chatterji M. J. Org. Chem. 60:1995;5958 (d) Morri-Varas F., Qian X.-H., Wong C.-H. J. Am. Chem. Soc. 118:1996;7647 (e) Gauzy L., Le Merrer Y., Depezay J.-C., Clere F., Mignani S. Tetrahedron Lett. 40:1999;6005 (f) Fuentes J., Olano D., Pradera M.A. Tetrahedron Lett. 40:1999;4063 (g) Andersen S.M., Ekhart C., Lundt I., Stütz A.E. Carbohydr. Res. 326:2000;22 (h) Painter G.F., Falshaw A. J. Chem. Soc., Perkin Trans. 1. 2000;1157 (i) Tezuka K., Compain P., Martin O.R. Synlett. 2000;1837 (j) Gallos J.K., Demeroudi S.C., Stathopoulou C.C., Dellios C.C. Tetrahedron Lett. 42:2001;7497 (k) Mehta G., Lakshminath S. Tetrahedron Lett. 43:2002;331 (l) Tilekar J.N., Patil N.T., Jadhav H.S., Dhavale D.D. Tetrahedron. 59:2003;1873.
    • (2000) Carbohydr. Res. , vol.326 , pp. 22
    • Andersen, S.M.1    Ekhart, C.2    Lundt, I.3    Stütz, A.E.4
  • 8
    • 0034615803 scopus 로고    scopus 로고
    • For selected references see: (a) For selected references see: Paulsen H., Todt K. Chem. Ber. 100:1967;512 (b) Farr R.A., Holland A.K., Huber E.W., Peet N.P., Weintraub P.M. Tetrahedron. 50:1994;1033 (c) Lohray B.B., Jayamma Y., Chatterji M. J. Org. Chem. 60:1995;5958 (d) Morri-Varas F., Qian X.-H., Wong C.-H. J. Am. Chem. Soc. 118:1996;7647 (e) Gauzy L., Le Merrer Y., Depezay J.-C., Clere F., Mignani S. Tetrahedron Lett. 40:1999;6005 (f) Fuentes J., Olano D., Pradera M.A. Tetrahedron Lett. 40:1999;4063 (g) Andersen S.M., Ekhart C., Lundt I., Stütz A.E. Carbohydr. Res. 326:2000;22 (h) Painter G.F., Falshaw A. J. Chem. Soc., Perkin Trans. 1. 2000;1157 (i) Tezuka K., Compain P., Martin O.R. Synlett. 2000;1837 (j) Gallos J.K., Demeroudi S.C., Stathopoulou C.C., Dellios C.C. Tetrahedron Lett. 42:2001;7497 (k) Mehta G., Lakshminath S. Tetrahedron Lett. 43:2002;331 (l) Tilekar J.N., Patil N.T., Jadhav H.S., Dhavale D.D. Tetrahedron. 59:2003;1873.
    • (2000) J. Chem. Soc., Perkin Trans. 1 , pp. 1157
    • Painter, G.F.1    Falshaw, A.2
  • 9
    • 0034533598 scopus 로고    scopus 로고
    • For selected references see: (a) For selected references see: Paulsen H., Todt K. Chem. Ber. 100:1967;512 (b) Farr R.A., Holland A.K., Huber E.W., Peet N.P., Weintraub P.M. Tetrahedron. 50:1994;1033 (c) Lohray B.B., Jayamma Y., Chatterji M. J. Org. Chem. 60:1995;5958 (d) Morri-Varas F., Qian X.-H., Wong C.-H. J. Am. Chem. Soc. 118:1996;7647 (e) Gauzy L., Le Merrer Y., Depezay J.-C., Clere F., Mignani S. Tetrahedron Lett. 40:1999;6005 (f) Fuentes J., Olano D., Pradera M.A. Tetrahedron Lett. 40:1999;4063 (g) Andersen S.M., Ekhart C., Lundt I., Stütz A.E. Carbohydr. Res. 326:2000;22 (h) Painter G.F., Falshaw A. J. Chem. Soc., Perkin Trans. 1. 2000;1157 (i) Tezuka K., Compain P., Martin O.R. Synlett. 2000;1837 (j) Gallos J.K., Demeroudi S.C., Stathopoulou C.C., Dellios C.C. Tetrahedron Lett. 42:2001;7497 (k) Mehta G., Lakshminath S. Tetrahedron Lett. 43:2002;331 (l) Tilekar J.N., Patil N.T., Jadhav H.S., Dhavale D.D. Tetrahedron. 59:2003;1873.
    • (2000) Synlett , pp. 1837
    • Tezuka, K.1    Compain, P.2    Martin, O.R.3
  • 10
    • 0035888314 scopus 로고    scopus 로고
    • For selected references see: (a) For selected references see: Paulsen H., Todt K. Chem. Ber. 100:1967;512 (b) Farr R.A., Holland A.K., Huber E.W., Peet N.P., Weintraub P.M. Tetrahedron. 50:1994;1033 (c) Lohray B.B., Jayamma Y., Chatterji M. J. Org. Chem. 60:1995;5958 (d) Morri-Varas F., Qian X.-H., Wong C.-H. J. Am. Chem. Soc. 118:1996;7647 (e) Gauzy L., Le Merrer Y., Depezay J.-C., Clere F., Mignani S. Tetrahedron Lett. 40:1999;6005 (f) Fuentes J., Olano D., Pradera M.A. Tetrahedron Lett. 40:1999;4063 (g) Andersen S.M., Ekhart C., Lundt I., Stütz A.E. Carbohydr. Res. 326:2000;22 (h) Painter G.F., Falshaw A. J. Chem. Soc., Perkin Trans. 1. 2000;1157 (i) Tezuka K., Compain P., Martin O.R. Synlett. 2000;1837 (j) Gallos J.K., Demeroudi S.C., Stathopoulou C.C., Dellios C.C. Tetrahedron Lett. 42:2001;7497 (k) Mehta G., Lakshminath S. Tetrahedron Lett. 43:2002;331 (l) Tilekar J.N., Patil N.T., Jadhav H.S., Dhavale D.D. Tetrahedron. 59:2003;1873.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 7497
    • Gallos, J.K.1    Demeroudi, S.C.2    Stathopoulou, C.C.3    Dellios, C.C.4
  • 11
    • 0037033216 scopus 로고    scopus 로고
    • For selected references see: (a) For selected references see: Paulsen H., Todt K. Chem. Ber. 100:1967;512 (b) Farr R.A., Holland A.K., Huber E.W., Peet N.P., Weintraub P.M. Tetrahedron. 50:1994;1033 (c) Lohray B.B., Jayamma Y., Chatterji M. J. Org. Chem. 60:1995;5958 (d) Morri-Varas F., Qian X.-H., Wong C.-H. J. Am. Chem. Soc. 118:1996;7647 (e) Gauzy L., Le Merrer Y., Depezay J.-C., Clere F., Mignani S. Tetrahedron Lett. 40:1999;6005 (f) Fuentes J., Olano D., Pradera M.A. Tetrahedron Lett. 40:1999;4063 (g) Andersen S.M., Ekhart C., Lundt I., Stütz A.E. Carbohydr. Res. 326:2000;22 (h) Painter G.F., Falshaw A. J. Chem. Soc., Perkin Trans. 1. 2000;1157 (i) Tezuka K., Compain P., Martin O.R. Synlett. 2000;1837 (j) Gallos J.K., Demeroudi S.C., Stathopoulou C.C., Dellios C.C. Tetrahedron Lett. 42:2001;7497 (k) Mehta G., Lakshminath S. Tetrahedron Lett. 43:2002;331 (l) Tilekar J.N., Patil N.T., Jadhav H.S., Dhavale D.D. Tetrahedron. 59:2003;1873.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 331
    • Mehta, G.1    Lakshminath, S.2
  • 12
    • 0037430441 scopus 로고    scopus 로고
    • For selected references see: (a) For selected references see: Paulsen H., Todt K. Chem. Ber. 100:1967;512 (b) Farr R.A., Holland A.K., Huber E.W., Peet N.P., Weintraub P.M. Tetrahedron. 50:1994;1033 (c) Lohray B.B., Jayamma Y., Chatterji M. J. Org. Chem. 60:1995;5958 (d) Morri-Varas F., Qian X.-H., Wong C.-H. J. Am. Chem. Soc. 118:1996;7647 (e) Gauzy L., Le Merrer Y., Depezay J.-C., Clere F., Mignani S. Tetrahedron Lett. 40:1999;6005 (f) Fuentes J., Olano D., Pradera M.A. Tetrahedron Lett. 40:1999;4063 (g) Andersen S.M., Ekhart C., Lundt I., Stütz A.E. Carbohydr. Res. 326:2000;22 (h) Painter G.F., Falshaw A. J. Chem. Soc., Perkin Trans. 1. 2000;1157 (i) Tezuka K., Compain P., Martin O.R. Synlett. 2000;1837 (j) Gallos J.K., Demeroudi S.C., Stathopoulou C.C., Dellios C.C. Tetrahedron Lett. 42:2001;7497 (k) Mehta G., Lakshminath S. Tetrahedron Lett. 43:2002;331 (l) Tilekar J.N., Patil N.T., Jadhav H.S., Dhavale D.D. Tetrahedron. 59:2003;1873.
    • (2003) Tetrahedron , vol.59 , pp. 1873
    • Tilekar, J.N.1    Patil, N.T.2    Jadhav, H.S.3    Dhavale, D.D.4
  • 21
    • 0141804127 scopus 로고    scopus 로고
    • Iminosugars: Recent Insights into their Bioactivity and Potential as Therapeutic Agents
    • Iminosugars: Recent Insights into their Bioactivity and Potential as Therapeutic Agents; Martin, O. R., Compain, P., Eds.; Curr. Top. Med. Chem. 2003, 3(5).
    • (2003) Curr. Top. Med. Chem. , vol.3 , pp. 5
    • Martin, O.R.1    Compain, P.2
  • 24
    • 0000258096 scopus 로고    scopus 로고
    • Alper J. Science. 291:2001;2338.
    • (2001) Science , vol.291 , pp. 2338
    • Alper, J.1
  • 40
    • 85030915558 scopus 로고    scopus 로고
    • note
    • 4OH elution) gave a sample of pure 3a.
  • 41
    • 85030922200 scopus 로고    scopus 로고
    • note
    • 4 requires 191.1236).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.