Synthesis of poly-O-sulfated glycosides of 2,5-anhydro-D-mannitol

被引:7
|
作者
Kuszmann, J [1 ]
Medgyes, G [1 ]
Boros, S [1 ]
机构
[1] IVAX Drug Res Inst, H-1325 Budapest, Hungary
关键词
2.5-anhydro-D-mannitol derivatives; mono-; di-; tri-; tetra- and pentasaccharides; poly-O-sulfated saccharides; antiasthmatic compounds;
D O I
10.1016/j.carres.2005.05.006
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
2,5-Anhydro-3-O-beta-D-glucopyranosyl-; -3-O-alpha-D-idopyranosyl-; -3-O-alpha-D-arabinopyranosyl-; -3-O-alpha-L-arabinopyranosyl--; -3-0-beta-D-maltopyranosyl-; -3-O-beta-D-gentiobiopyranosyl-; -1,6-di-O-beta-D-glucopyranosyl-; -1,6-di-O-alpha-L-idopyranosyl,-; -1-O-beta-D-maltopyranosyl-.- -1,3,.6-tri-O-beta-D-glucopyranosyl-; -1,6-di-O-beta-maltopyranosyl- and -1,6-di-O-beta-D-gentiobiopyranosyl-2,5-anhydro-D-mannitol as well as their poly-O-sulfated derivatives were synthesized. The IP3-IC50 values of their sodium and/or potassium salts were determined for structure-activity studies aiming at the synthesis of new, orally active antiasthmatic compounds. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1739 / 1749
页数:11
相关论文
共 50 条
  • [31] PHOSPHATE LOADING PREVENTS THE DECREASE IN ATP AND INCREASE IN FOOD-INTAKE PRODUCED BY 2,5-ANHYDRO-D-MANNITOL
    RAWSON, NE
    FRIEDMAN, MI
    AMERICAN JOURNAL OF PHYSIOLOGY, 1994, 266 (06): : R1792 - R1796
  • [32] MECHANISM OF ACTION OF 2,5-ANHYDRO-D-MANNITOL IN HEPATOCYTES - EFFECTS OF PHOSPHORYLATED METABOLITES ON ENZYMES OF CARBOHYDRATE-METABOLISM
    RIQUELME, PT
    WERNETTEHAMMOND, ME
    KNEER, NM
    LARDY, HA
    JOURNAL OF BIOLOGICAL CHEMISTRY, 1984, 259 (08) : 5115 - 5123
  • [33] 2,5-anhydro-D-mannitol induces Fos-like immunoreactivity in hindbrain and forebrain: relationship to eating behavior
    Horn, CC
    Friedman, MI
    BRAIN RESEARCH, 1998, 779 (1-2) : 17 - 25
  • [34] Synthesis of 3-deoxy-3-nucleobase-2,5-anhydro-D-mannitol: a novel class of hydroxymethyl-branched isonucleosides
    Lei, Z
    Min, JM
    Zhang, LH
    TETRAHEDRON-ASYMMETRY, 2000, 11 (14) : 2899 - 2906
  • [35] THE PREPARATION OF 1,5-ANHYDRO-D-MANNITOL (STYRACITOL) FROM D-MANNITOL
    FLETCHER, HG
    DIEHL, HW
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (12) : 3175 - 3176
  • [36] Brain Fos-like immunoreactivity in chronic decerebrate and neurologically intact rats given 2,5-anhydro-D-mannitol
    Horn, CC
    Kaplan, JM
    Grill, HJ
    Friedman, MI
    BRAIN RESEARCH, 1998, 801 (1-2) : 107 - 115
  • [37] 2,5-ANHYDRO-D-MANNITOL - ITS UNIQUE CENTRAL ACTION ON FOOD-INTAKE AND BLOOD-GLUCOSE IN RATS
    KUROKAWA, M
    SAKATA, T
    YOSHIMATSU, H
    MACHIDORI, H
    BRAIN RESEARCH, 1991, 566 (1-2) : 270 - 275
  • [38] 2,5-ANHYDRO-1-DEOXY-D-LYXITOL, 2,5-ANHYDRO-1-DEOXY-D-MANNITOL, AND 2,5-ANHYDRO-1-DEOXY-D-TALITOL - SYNTHESIS AND ENZYMIC STUDIES
    DILLS, WL
    COVEY, TR
    SINGER, P
    NEAL, S
    RAPPAPORT, MS
    CARBOHYDRATE RESEARCH, 1982, 99 (01) : 23 - 31
  • [39] EFFECTS OF GLP-1 AND 2,5-ANHYDRO-D-MANNITOL ON INSULIN-SECRETION AND PLASMA-GLUCOSE IN MICE
    AHREN, B
    LINDSKOG, S
    VANDIJK, G
    SCHEURINK, AJW
    STEFFENS, AB
    ENDOCRINE RESEARCH, 1995, 21 (03) : 583 - 594
  • [40] Ornithine decarboxylase activity in rat intestinal mucosa and liver is stimulated by central administration of 2-deoxy-D-glucose but not of 2,5-anhydro-D-mannitol
    Morita, H
    Fujimoto, K
    Sakata, T
    Kurokawa, M
    Yoshimatsu, H
    Noda, T
    Iwakiri, R
    Sakai, T
    BRAIN RESEARCH, 1996, 719 (1-2) : 112 - 116