Intramolecular O-arylation of phenols with phenylboronic acids: Application to the synthesis of macrocyclic metalloproteinase inhibitors

被引：105

作者：

Decicco, CP ^{[1
]}

Song, Y

Evans, DA

机构：

[1] Dupont Pharmaceut Co, Chem & Phys Sci, Expt Stn, Wilmington, DE 19880 USA

[2] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 07期

关键词：

D O I：

10.1021/ol015572i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The copper acetate mediated intramolecular O-arylation of phenols with phenylboronic acid pseudopeptides is the key step in the preparation of macrocyclic biphenyl ether hydroxamic acid inhibitors of collagenase 1 and gelatinases A and B. The intramolecular macrocyclization was found to be mild and tolerant of common chemical functionality. This methodology should provide a general route to macrocyclic biphenyl ethers.

引用

页码：1029 / 1032

页数：4

共 42 条

[1] Hydration changes implicated in the remarkable temperature-dependent membrane permeation of cyclosporin A [J].

Augustijns, PF ;

Brown, SC ;

Willard, DH ;

Consler, TG ;

Annaert, PP ;

Hendren, RW ;

Bradshaw, TP .

BIOCHEMISTRY, 2000, 39 (25) :7621-7630

[2] HYDROGEN-BOND STRENGTH AND BETA-SHEET PROPENSITIES - THE ROLE OF A SIDE-CHAIN BLOCKING EFFECT [J].

BAI, YW ;

ENGLANDER, SW .

PROTEINS-STRUCTURE FUNCTION AND GENETICS, 1994, 18 (03) :262-266

[3]

BECKETT RP, 1993, SYNLETT, P137

[4]

BOREL JF, 1986, CYCLOSPORINE PROG AL, P38

[5] Metalloproteinase inhibitors and the prevention of connective tissue breakdown [J].

Cawston, TE .

PHARMACOLOGY & THERAPEUTICS, 1996, 70 (03) :163-182

[6] New N- and O-arylations with phenylboronic acids and cupric acetate [J].

Chan, DMT ;

Monaco, KL ;

Wang, RP ;

Winters, MP .

TETRAHEDRON LETTERS, 1998, 39 (19) :2933-2936

[7] Synthesis and activity of conformationally-constrained macrocyclic norstatine-based inhibitors of HIV protease [J].

Chen, JJ ;

Coles, PJ ;

Arnold, LD ;

Smith, RA ;

MacDonald, ID ;

Carriere, J ;

Krantz, A .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (04) :435-438

[8] Macrocyclic amino carboxylates as selective MMP-8 inhibitors [J].

Cherney, RJ ;

Wang, L ;

Meyer, DT ;

Xue, CB ;

Wasserman, ZR ;

Hardman, KD ;

Welch, PK ;

Covington, MB ;

Copeland, RA ;

Arner, EC ;

DeGrado, WF ;

Decicco, CP .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (11) :1749-1751

[9] THE INFLUENCE OF PEPTIDE STRUCTURE ON TRANSPORT ACROSS CACO-2 CELLS .2. PEPTIDE-BOND MODIFICATION WHICH RESULTS IN IMPROVED PERMEABILITY [J].

CONRADI, RA ;

HILGERS, AR ;

HO, NFH ;

BURTON, PS .

PHARMACEUTICAL RESEARCH, 1992, 9 (03) :435-439

[10] ESTIMATING K-I VALUES FOR TIGHT-BINDING INHIBITORS FROM DOSE-RESPONSE PLOTS [J].

COPELAND, RA ;

LOMBARDO, D ;

GIANNARAS, J ;

DECICCO, CP .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (17) :1947-1952

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