THE SYNTHESIS OF PYRANOACRIDINONE INHIBITORS OF PROTEIN-TYROSINE KINASES

被引:23
作者
GROUNDWATER, PW
SOLOMONS, KRH
机构
[1] School of Chemistry and Applied Chemistry, University of Wales, College of Cardiff, Cardiff CF1 3TB
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 02期
关键词
D O I
10.1039/p19940000173
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
7-Oxo-5,6,7,8-tetrahydroflavone 10 reacts with anthranilonitrile and ethyl anthranilate to give the corresponding enamines. 11 and 13. These enamines undergo base-catalysed cyclization to pyrano[2,3-a] acridin-4-ones, 12 and 14. which undergo oxidation to the fully aromatic systems. 4 and 5. Biological testing of some of these fused heterocyclic systems shows them to have potential in cancer chemotherapy as inhibitors of growth factor-mediated cell proliferation.
引用
收藏
页码:173 / 177
页数:5
相关论文
共 11 条
  • [1] RUTACEOUS CONSTITUENTS .13. A BIOMIMETIC SYNTHESIS OF ACRONYCINE
    ADAMS, JH
    BROWN, PM
    GUPTA, P
    KHAN, MS
    LEWIS, JR
    [J]. TETRAHEDRON, 1981, 37 (01) : 209 - 217
  • [2] Molecular rearrangement of some o-acyloxyacetophenones and the mechanism of the production of 3-acylchromones
    Baker, W
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1933, : 1381 - 1389
  • [3] ONCOGENES AND SIGNAL TRANSDUCTION
    CANTLEY, LC
    AUGER, KR
    CARPENTER, C
    DUCKWORTH, B
    GRAZIANI, A
    KAPELLER, R
    SOLTOFF, S
    [J]. CELL, 1991, 64 (02) : 281 - 302
  • [4] GANNON WF, 1960, ORG SYNTH, V40, P41
  • [5] THE EFFECT OF QUERCETIN ON THE PHOSPHORYLATION ACTIVITY OF THE ROUS-SARCOMA VIRUS TRANSFORMING GENE-PRODUCT INVITRO AND INVIVO
    GRAZIANI, Y
    ERIKSON, E
    ERIKSON, RL
    [J]. EUROPEAN JOURNAL OF BIOCHEMISTRY, 1983, 135 (03): : 583 - 589
  • [6] HAGIWARA M, 1988, BIOCHEM PHARMACOL, V37, P2987
  • [7] LEVITZKI A, 1991, METHOD ENZYMOL, V201, P347
  • [8] TYRPHOSTINS AS MOLECULAR TOOLS AND POTENTIAL ANTIPROLIFERATIVE DRUGS
    LEVITZKI, A
    GILON, C
    [J]. TRENDS IN PHARMACOLOGICAL SCIENCES, 1991, 12 (05) : 171 - 174
  • [9] A FACILE SYNTHESIS OF 2-ARYL-SUBSTITUTED AND 2-HETEROARYL-SUBSTITUTED 4-AMINOQUINOLINES
    STREKOWSKI, L
    KONG, SB
    CEGLA, MT
    HARDEN, DB
    [J]. HETEROCYCLES, 1989, 29 (03) : 539 - 545
  • [10] STUDIES ON A NEW EPIDERMAL GROWTH FACTOR-RECEPTOR KINASE INHIBITOR, ERBSTATIN, PRODUCED BY MH435-HF3
    UMEZAWA, H
    IMOTO, M
    SAWA, T
    ISSHIKI, K
    MATSUDA, N
    UCHIDA, T
    IINUMA, H
    HAMADA, M
    TAKEUCHI, T
    [J]. JOURNAL OF ANTIBIOTICS, 1986, 39 (01) : 170 - 173