SYNTHETIC ANTHRACYCLINES - REGIOSPECIFIC TOTAL SYNTHESIS OF A D-RING INDOLE ANALOG OF DAUNOMYCIN

被引：12
|
作者：
KITA, Y [1 ]
KIRIHARA, M [1 ]
SASHO, M [1 ]
FUJII, Y [1 ]
SEKIHACHI, J [1 ]
OKUNAKA, R [1 ]
TAMURA, Y [1 ]
SHIMOOKA, K [1 ]
机构：
[1] PFIZER PHARMACEUT INC LTD, CTR NEW PROD DEV, AICHI 47023, JAPAN
来源：
CHEMICAL & PHARMACEUTICAL BULLETIN | 1990年 / 38卷 / 03期
关键词：
antitumor agent; cycloaddition; D-ring indole analogue; daunomycin analogue; heteroanthracycline;
D O I：
10.1248/cpb.38.585
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
The 4-methoxy-5-methylpyrano[4, 3-£]indole-1, 3(4H, 5H)-dione (9), prepared from methyl 3-methoxycarbony1-1-acetate (6), underwent a strong base-induced cycloaddition reaction with 2-chloro-6, 6-ethylenedioxy-5, 6, 7, 8-tetrahydro-1, 4-naphthoquinone (11) to give the tetrahydronaphtho[2, 3-b]carbazole-7, 12-dione (10), regioselectively. The cycloadduct (10) was successfully converted to a D-ring indole analogue of daunomycin (la). © 1990, The Pharmaceutical Society of Japan. All rights reserved.
引用
收藏
页码：585 / 589
页数：5
相关论文
共 50 条
  • [41] BIOMIMETIC SYNTHESES OF PRETETRAMIDES .2. A SYNTHETIC ROUTE BASED ON A PREFORMED D-RING
    HARRIS, TM
    HARRIS, CM
    OSTER, TA
    BROWN, LE
    LEE, JYC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (18) : 6180 - 6186
  • [42] SYNTHETIC APPROACH TO INDOLE ALKALOID APPARICINE - SYNTHESIS OF RING SKELETON
    SCOPES, DIC
    ALLEN, MS
    HIGNETT, GJ
    WILSON, NDV
    HARRIS, M
    JOULE, JA
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (21): : 2376 - 2385
  • [43] Synthesis, photophysical and anticancer study of D-ring extended estrone analogues
    Maurya, Hardesh K.
    Hasanain, Mohammad
    Kumar, Ch Pavan
    Vasudeva, Prema G.
    Sarkar, Jayanta
    Chandrasekharam, M.
    Gupta, Atul
    RSC ADVANCES, 2015, 5 (84): : 68843 - 68851
  • [44] A SYNTHESIS OF (+/-)-2-HYDROXYHOMOAPORPHINES BEARING A HYDROXYL GROUP ON THE D-RING
    HOSHINO, O
    OGOSE, H
    INOUE, M
    UMEZAWA, B
    HETEROCYCLES, 1984, 21 : 699 - 699
  • [45] Synthesis and biological activity of some D-ring modified estrone derivatives
    Gupta, R
    Jindal, DP
    Borras, M
    Legros, N
    Leclercq, G
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1999, 38 (05): : 563 - 571
  • [46] NEW SYNTHESIS OF PHOSPHASTEROIDS EMPLOYING MCCORMACK CYCLOADDITION FOR CONSTRUCTION OF D-RING
    SYMMES, C
    MORRIS, J
    QUIN, LD
    TETRAHEDRON LETTERS, 1977, (04) : 335 - 338
  • [47] Synthesis and insecticidal activity of new deoxypodophyllotoxin derivatives modified in the D-ring
    Wang, Juanjuan
    Yu, Xiang
    Zhi, Xiaoyan
    Xu, Hui
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (18) : 4542 - 4545
  • [48] Total Synthesis of Indole Alkaloid Alsmaphorazine D
    Zhu, Chenlong
    Liu, Zhaobo
    Chen, Guanyu
    Zhang, Kai
    Ding, Hanfeng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (03) : 879 - 882
  • [49] Synthetic studies on the tetrasubstituted D-ring of cystobactamids lead to potent terephthalic acid antibiotics
    Stappert, Moritz
    Kohnhaeuser, Daniel
    Seedorf, Tim
    Coetzee, Janetta
    Rox, Katharina
    Fuchs, Hazel L. S.
    Cirnski, Katarina
    Leitner, Christian
    Herrmann, Jennifer
    Kirschning, Andreas
    Mueller, Rolf
    Broenstrup, Mark
    COMMUNICATIONS CHEMISTRY, 2024, 7 (01):
  • [50] Studies on the synthesis of croomine: Synthesis of the tricyclic B,C,D-ring core structure
    Lindsay, KB
    Pyne, SG
    SYNLETT, 2004, (05) : 779 - 782
12345