Synthesis and biological evaluation of (-)-laulimalide analogues

被引:45
作者
Wender, PA [1 ]
Hegde, SG
Hubbard, RD
Zhang, L
Mooberry, SL
机构
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
[2] SW Fdn Biomed Res, Dept Physiol & Med, San Antonio, TX 78245 USA
关键词
D O I
10.1021/ol035339f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The syntheses of five laulimalide analogues are described, incorporating modifications at the C-16-C-17-epoxide, the C-20-alcohol, as well as the C-1-C-3-enoate of the parent natural product. The resultant analogues are active in drug-sensitive HeLa and MDA-MB-435 cell lines. Significantly, like laulimalide, these analogues are poor substrates for the drug transport protein P-glycoprotein (Pgp) and are thus effective against Taxol-resistant cell lines.
引用
收藏
页码:3507 / 3509
页数:3
相关论文
共 22 条
  • [1] Total synthesis of the microtubule stabilizing antitumor agent laulimalide and some nonnatural analogues:: The power of sharpless' asymmetric epoxidation
    Ahmed, A
    Hoegenauer, EK
    Enev, VAS
    Hanbauer, M
    Kaehlig, H
    Öhler, E
    Mulzer, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (08) : 3026 - 3042
  • [2] LAULIMALIDES - NEW POTENT CYTO-TOXIC MACROLIDES FROM A MARINE SPONGE AND A NUDIBRANCH PREDATOR
    CORLEY, DG
    HERB, R
    MOORE, RE
    SCHEUER, PJ
    PAUL, VJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) : 3644 - 3646
  • [3] Crimmins MT, 2002, CURR OPIN DRUG DISC, V5, P944
  • [4] Asymmetric total synthesis of (-)-laulimalide: Exploiting the asymmetric glycolate alkylation reaction
    Crimmins, MT
    Stanton, MG
    Allwein, SP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) : 5958 - 5959
  • [5] TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC LONOMYCIN-A (EMERICID)
    EVANS, DA
    RATZ, AM
    HUFF, BE
    SHEPPARD, GS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (12) : 3448 - 3467
  • [6] EVEV VS, 2001, J AM CHEM SOC, V123, P10764
  • [7] Total synthesis of microtubule-stabilizing agent (-)-laulimalide
    Ghosh, AK
    Wang, Y
    Kim, JT
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) : 8973 - 8982
  • [8] Total synthesis of (-)-laulimalide
    Ghosh, AK
    Wang, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (44) : 11027 - 11028
  • [9] REGIOCONTROLLED OPENING OF CYCLIC ETHERS USING DIMETHYLBORON BROMIDE
    GUINDON, Y
    THERIEN, M
    GIRARD, Y
    YOAKIM, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (09) : 1680 - 1686
  • [10] SEMIHYDROGENATION OF TRIPLE BONDS IN 1-ALKENE SOLUTIONS
    HO, TL
    LIU, SH
    [J]. SYNTHETIC COMMUNICATIONS, 1987, 17 (08) : 969 - 973