Efficient synthesis of 1,3,7-substituted xanthines by a safety-catch protection strategy

被引：19

作者：

Allwood, Matthew B. ^{[2
]}

Cannan, Boorna ^{[1
]}

van Aalten, Daan M. F. ^{[2
]}

Eggleston, Ian M. ^{[1
]}

机构：

[1] Univ Bath, Dept Pharm & Pharmacol, Wolfson Lab Med Chem, Bath BA2 7AY, Avon, England

[2] Univ Dundee, Coll Life Sci, Div Biol Chem & Drug Discovery, Dundee DD1 5EH, Scotland

来源：

TETRAHEDRON | 2007年 / 63卷 / 50期

关键词：

D O I：

10.1016/j.tet.2007.09.067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of selectively N-substituted xanthine derivatives is described. Cyclocondensation of a suitably protected ammoimidazole with methyl-2-phenylthioethyl carbamate, followed by oxidation of sulfur to the sulfone, provides access to an orthogonally 1,7-protected xanthine, which may then be regioselectively alkylated and deprotected under mild conditions. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：12294 / 12302

页数：9

共 30 条

[21] Imidazo[2,1-i]purin-5-ones and related tricyclic water-soluble purine derivatives:: Potent A2A- and A3-adenosine receptor antagonists [J].

Müller, CE ;

Thorand, M ;

Qurishi, R ;

Diekmann, M ;

Jacobson, KA ;

Padgett, WL ;

Daly, JW .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (16) :3440-3450

[22]

MULLER CE, 1993, J MED CHEM, V36, P3341

[23] Methylxanthine drugs are chitinase inhibitors: Investigation of inhibition and binding modes [J].

Rao, FV ;

Andersen, OA ;

Vora, KA ;

DeMartino, JA ;

van Aalten, DMF .

CHEMISTRY & BIOLOGY, 2005, 12 (09) :973-980

[24] Deazapurine solid-phase synthesis:: Construction of 3-substituted pyrrolo[3,2-d]pyrimidine-6-carboxylates on cross-linked polystyrene bearing a cysteamine linker [J].

Rombouts, FJR ;

Fridkin, G ;

Lubell, WD .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2005, 7 (04) :589-598

[25] Screening-based discovery and structural dissection of a novel family 18 chitinase inhibitor [J].

Schuttelkopf, Alexander W. ;

Andersen, Ole A. ;

Rao, Francesco V. ;

Allwood, Matthew ;

Lloyd, Clare ;

Eggleston, Ian M. ;

Van Aalten, Daan M. F. .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2006, 281 (37) :27278-27285

[26] SYNTHESIS OF 2-HYDROXYETHYLSULFONYLMETHYL-SUBSTITUTED POLYSTYRENES AND THEIR APPLICATION IN SOLID-PHASE PEPTIDE-SYNTHESIS [J].

TESSER, GI ;

BUIS, JTWARM ;

WOLTERS, ETM ;

BOTHEHELMES, EGAM .

TETRAHEDRON, 1976, 32 (09) :1069-1072

[27] The synthetic development of uric acid, xanthin, theobromine, theophylline, caffeine and cyanacetic acid. [J].

Traube, W .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1900, 33 :3035-3056

[28] INHIBITION OF SEPARATED FORMS OF CYCLIC-NUCLEOTIDE PHOSPHODIESTERASE FROM PIG CORONARY-ARTERIES BY 1,3-DISUBSTITUTED AND 1,3,8-TRISUBSTITUTED XANTHINES [J].

WELLS, JN ;

GARST, JE ;

KRAMER, GL .

JOURNAL OF MEDICINAL CHEMISTRY, 1981, 24 (08) :954-958

[29] Versatile, convenient synthesis of pyrimido[1,2,3-cd]purinediones [J].

Weyler, S ;

Hayallah, AM ;

Müller, CE .

TETRAHEDRON, 2003, 59 (01) :47-54

[30] New and practical method for synthesis of 1-and 1,3-substituted xanthines [J].

Zavialov, IA ;

Dahanukar, VH ;

Nguyen, H ;

Orr, C ;

Andrews, DR .

ORGANIC LETTERS, 2004, 6 (13) :2237-2240

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