THE ZARAGOZIC ACIDS - STRUCTURE ELUCIDATION OF A NEW CLASS OF SQUALENE SYNTHASE INHIBITORS

被引:61
作者
HENSENS, OD
DUFRESNE, C
LIESCH, JM
ZINK, DL
REAMER, RA
VANMIDDLESWORTH, F
机构
[1] Merck Research Laboratories, Rahway, NJ 07065-0900
[2] Glaxo Research Laboratories, Research Triangle Park
关键词
ZARAGOZIC ACID-A AND ACID-B; SQUALENE SYNTHASE INHIBITORS; 2D NMR; SPOROMIELLA-INTERMEDIA; LEPTODONTIIUM-ELATIUS;
D O I
10.1016/0040-4039(93)85086-C
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Structures of two novel fungal metabolites, zaragozic acids A (1) and B (2), characterized by a novel 2,8-dioxobicyclo[3.2.1]octane-4,6,7-trihydroxy-3,4,5-tricarboxylic acid core, are proposed predominantly on the basis of 2D NMR.
引用
收藏
页码:399 / 402
页数:4
相关论文
共 10 条
  • [1] BARTIZAL KF, 1991, Patent No. 5026554
  • [2] LONG-RANGE PROTON C-13 NMR SPIN COUPLING-CONSTANTS
    BAX, A
    FREEMAN, R
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (04) : 1099 - 1100
  • [3] BERGSTROM JD, UNPUB P NAT ACAD SCI
  • [4] REGRESSION OF CORONARY-ARTERY DISEASE AS A RESULT OF INTENSIVE LIPID-LOWERING THERAPY IN MEN WITH HIGH-LEVELS OF APOLIPOPROTEIN-B
    BROWN, G
    ALBERS, JJ
    FISHER, LD
    SCHAEFER, SM
    LIN, JT
    KAPLAN, C
    ZHAO, XQ
    BISSON, BD
    FITZPATRICK, VF
    DODGE, HT
    [J]. NEW ENGLAND JOURNAL OF MEDICINE, 1990, 323 (19) : 1289 - 1298
  • [5] GRUNDY SM, 1988, NEW ENGL J MED, V319, P24
  • [6] KALINOWSKI E, 1988, CARBON 13 NMR SPECTR, P132
  • [7] 1,6-ANHYDROFURANOSES .19. H-1 NMR-SPECTRA AND C-13 NMR-SPECTRA OF 1,6-ANHYDROHEXOFURANOSES
    KOLL, P
    ANGYAL, SJ
    [J]. CARBOHYDRATE RESEARCH, 1988, 179 : 1 - 5
  • [8] CONFIGURATIONAL EFFECTS ON C-13 CHEMICAL-SHIFTS OF 1,6-ANHYDROHEXOPYRANOSES AND RELATED COMPOUNDS - UTILITY OF C-13-H-1 COUPLING PATTERNS FOR SIGNAL ASSIGNMENTS
    RITCHIE, RGS
    CYR, N
    PERLIN, AS
    [J]. CANADIAN JOURNAL OF CHEMISTRY, 1976, 54 (14) : 2301 - 2309
  • [9] THE SQUALESTATINS, NOVEL INHIBITORS OF SQUALENE SYNTHASE PRODUCED BY A SPECIES OF PHOMA .2. STRUCTURE ELUCIDATION
    SIDEBOTTOM, PJ
    HIGHCOCK, RM
    LANE, SJ
    PROCOPIOU, PA
    WATSON, NS
    [J]. JOURNAL OF ANTIBIOTICS, 1992, 45 (05) : 648 - 658
  • [10] WILSON K, IN PRESS J ORG CHEM