A short and unequivocal synthesis of 5-aminotetrazolo[1,5-a]quinazoline as a tricyclic analogue of 4-(3-bromoanilino)6,7-dimethoxyquinazoline (PD 153035)

被引:12
作者
Bencteux, E
Houssin, R
Henichart, JP
机构
[1] Institut de Chimie Pharmaceutique, Université de Lille 2, rue du Professeur Laguesse
关键词
D O I
10.1002/jhet.5570340447
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The discovery of 4-(3-bromoanilino)-6,7-dimethoxyquinazoline (PD 153035) as an extremely potent inhibitor of the tyrosine kinase activity of the epidermal growth factor receptor led to the preparation of several fused tricyclic quinazoline analogues. The present paper reports a new tricyclic derivative: 5-(3-bromoanilino)-7,8-dimethoxytetrazolo[1,5-a]quinazoline. This compound was synthesized by two different pathways via a 1,3-dipolar cycloaddition of an azide at carbon 2 of the quinazoline ring.
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收藏
页码:1375 / 1378
页数:4
相关论文
共 17 条
  • [1] BARKER AJ, 1995, Patent No. 0635507
  • [2] BARKER AJ, 1992, Patent No. 520722
  • [3] Bridges AJ, 1996, CURR MED CHEM, V3, P167
  • [4] Tyrosine kinase inhibitors .8. An unusually steep structure-activity relationship for analogues of 4-(3-bromoanilino)-6,7-dimethoxyquinazoline (PD 153035), a potent inhibitor of the epidermal growth factor receptor
    Bridges, AJ
    Zhou, H
    Cody, DR
    Rewcastle, GW
    McMichael, A
    Showalter, HDH
    Fry, DW
    Kraker, AJ
    Denny, WA
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (01) : 267 - 276
  • [5] PROTEIN-TYROSINE KINASES - POTENTIAL TARGETS FOR ANTICANCER DRUG DEVELOPMENT
    BURKE, TR
    [J]. STEM CELLS, 1994, 12 (01) : 1 - 6
  • [6] PROTEIN-TYROSINE KINASE INHIBITION - MECHANISM-BASED DISCOVERY OF ANTITUMOR AGENTS
    CHANG, CJ
    GEAHLEN, RL
    [J]. JOURNAL OF NATURAL PRODUCTS, 1992, 55 (11): : 1529 - 1560
  • [7] SYNTHETIC ANTIMALARIALS .14. SOME 2-ARYLAMINO-4-AMINOALKYLAMINOQUINAZOLINES
    CURD, FHS
    LANDQUIST, JK
    ROSE, FL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1947, (JUN): : 775 - 783
  • [9] A SPECIFIC INHIBITOR OF THE EPIDERMAL GROWTH-FACTOR RECEPTOR TYROSINE KINASE
    FRY, DW
    KRAKER, AJ
    MCMICHAEL, A
    AMBROSO, LA
    NELSON, JM
    LEOPOLD, WR
    CONNERS, RW
    BRIDGES, AJ
    [J]. SCIENCE, 1994, 265 (5175) : 1093 - 1095
  • [10] ANTIHYPERTENSIVE 2-AMINO-4(3H)-QUINAZOLINONES
    HESS, HJ
    CRONIN, TH
    SCRIABINE, A
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1968, 11 (01) : 130 - +