A decarboxylative traceless linker approach for the solid phase synthesis of quinazolines

被引：34

作者：

Cobb, JM ^{[1
]}

Fiorini, MT ^{[1
]}

Goddard, CR ^{[1
]}

Theoclitou, ME ^{[1
]}

Abell, C ^{[1
]}

机构：

[1] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 05期

关键词：

D O I：

10.1016/S0040-4039(99)80108-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A decarboxylative traceless linker strategy for the cleavage of resin-bound quinazolines has been developed using hydroxymethylpolystyrene (HMPS) resin derivatised as the ethyl oxalate. Methods for the solid phase synthesis of the linker, quinazoline formation, functionalisation and cleavage are described. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：1045 / 1048

页数：4

相关论文

共 20 条

[1] 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 [J].

Bridges, AJ ;

Zhou, H ;

Cody, DR ;

Rewcastle, GW ;

McMichael, A ;

Showalter, HDH ;

Fry, DW ;

Kraker, AJ ;

Denny, WA .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (01) :267-276

[2]

FRY DW, 1994, EXPERT OPIN INV DRUG, V3, P577

[3] Decarboxylation-based traceless linking with aroyl acrylic acids [J].

Garibay, P ;

Nielsen, J ;

Hoeg-Jensen, T .

TETRAHEDRON LETTERS, 1998, 39 (15) :2207-2210

[4] Traceless linker: Oxidative activation and displacement of a sulfur-based linker [J].

Gayo, LM ;

Suto, MJ .

TETRAHEDRON LETTERS, 1997, 38 (02) :211-214

[5] Epidermal growth factor receptor tyrosine kinase: Structure-activity relationships and antitumour activity of novel quinazolines. [J].

Gibson, KH ;

Grundy, W ;

Godfrey, AA ;

Woodburn, JR ;

Ashton, SE ;

Curry, BJ ;

Scarlett, L ;

Barker, AJ ;

Brown, DS .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (21) :2723-2728

[6] REACTIONS OF HYDROXYGLYCINES - NEW SYNTHETIC ROUTES TO 4-PHENYLQUINAZOLINE DERIVATIVES [J].

HOEFNAGEL, AJ ;

VANKONINGSVELD, H ;

VANMEURS, F ;

PETERS, JA ;

SINNEMA, A ;

VANBEKKUM, H .

TETRAHEDRON, 1993, 49 (31) :6899-6912

[7] Application of polymer-bound phosphonium salts as traceless supports for solid phase synthesis [J].

Hughes, I .

TETRAHEDRON LETTERS, 1996, 37 (42) :7595-7598

[8] PROTEIN-TYROSINE KINASES [J].

HUNTER, T ;

COOPER, JA .

ANNUAL REVIEW OF BIOCHEMISTRY, 1985, 54 :897-930

[9] EGF RECEPTOR IN NEOPLASIA AND METASTASIS [J].

KHAZAIE, K ;

SCHIRRMACHER, V ;

LICHTNER, RB .

CANCER AND METASTASIS REVIEWS, 1993, 12 (3-4) :255-274

[10] Resin-immobilised benzyl and aryl vinyl sulfones: New versatile traceless linkers for solid-phase organic synthesis [J].

Kroll, FEK ;

Morphy, R ;

Rees, D ;

Gani, D .

TETRAHEDRON LETTERS, 1997, 38 (49) :8573-8576