NOVEL-APPROACH FOR SYNTHESIS OF (+/-)-CALANOLIDE-A AND ITS ANTI-HIV ACTIVITY

被引:0
|
作者
KUCHERENKO, A [1 ]
FLAVIN, MT [1 ]
BOULANGER, WA [1 ]
KHILEVICH, A [1 ]
SHONE, RL [1 ]
RIZZO, JD [1 ]
SHEINKMAN, AK [1 ]
XU, ZQ [1 ]
机构
[1] MEDICHEM RES INC,LEMONT,IL 60439
关键词
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Anti-HIV agent (+/-)-calanolide A (1) has been synthesized. The key intermediate, chromene 5, was synthesized by the sequence of Pechmann reaction, acylation and chromenylation by 4,4-dimethoxy-2-methylbutan-2-ol. The anti-HN activity for synthetic (+/-)-1 has been determined and compared with the natural product.
引用
收藏
页码:5475 / 5478
页数:4
相关论文
共 50 条
  • [1] BIOLOGICAL CHARACTERIZATION OF THE ANTI-HIV ACTIVITY OF CALANOLIDE-A
    CURRENS, MJ
    GULAKOWSKI, RJ
    MORAN, RA
    MCMAHON, JB
    BOYD, MR
    FASEB JOURNAL, 1993, 7 (04): : A691 - A691
  • [2] Total Synthesis of (±)-Calanolide A and Its Anti-HIV Activity
    Chun Mei ZHOU
    Lin WANG
    Ming Long ZHANG
    Zhi Zhong ZHAO
    (Institute of Materia Medica
    Xiang Hong CHEN
    Hong Shan CHEN (Institute of Medicinal Biotechno
    Chinese Chemical Letters, 1998, (05) : 433 - 434
  • [3] Total synthesis of (±)-calanolide A and its anti-HIV activity
    Zhou, CM
    Wang, L
    Zhang, ML
    Zhao, ZZ
    Zhang, XQ
    Chen, XH
    Chen, HS
    CHINESE CHEMICAL LETTERS, 1998, 9 (05) : 433 - 434
  • [4] RESOLUTION AND COMPARATIVE ANTI-HIV EVALUATION OF THE ENANTIOMERS OF CALANOLIDE-A AND CALANOLIDE-B
    CARDELLINA, JH
    BOKESCH, HR
    MCKEE, TC
    BOYD, MR
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (09) : 1011 - 1014
  • [5] In vivo anti-HIV activity of (+)-calanolide A in the hollow fiber mouse model
    Xu, ZQ
    Hollingshead, MG
    Borgel, S
    Elder, C
    Khilevich, A
    Flavin, MT
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (02) : 133 - 138
  • [6] A CONCISE SYNTHESIS OF CHIRAL 2-METHYL CHROMAN-4-ONES - STEREO SELECTIVE BUILDUP OF THE CHROMANOL MOIETY OF ANTI-HIV AGENT, CALANOLIDE-A
    RAO, AVR
    GAITONDE, AS
    PRAKASH, KRC
    RAO, SP
    TETRAHEDRON LETTERS, 1994, 35 (34) : 6347 - 6350
  • [7] Total synthesis of(±)-cordatolide A and its anti-HIV activity
    Gao, Q
    Wang, L
    Liang, XT
    CHINESE CHEMICAL LETTERS, 1999, 10 (08) : 653 - 656
  • [8] Total Synthesis of (±)-Cordatolide A and its Anti-HIV Activity
    Qi GAO
    Lin WANG
    Xiao Tian LIANG (Institute of Materia Medica
    Chinese Chemical Letters, 1999, (08) : 653 - 656
  • [9] Design, synthesis, and anti-HIV activity of some novel NNRTIs
    Singh, Ramendra K.
    Kumari, Garima
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [10] Synthesis and anti-HIV activity of novel oligo and polyribonucleotides.
    Torpe, RM
    Buckheit, RW
    Broom, AD
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U272 - U272