Solid-phase synthesis of phenolic steroids: Towards combinatorial libraries of estradiol derivatives

被引：20

作者：

Tremblay, MR ^{[1
]}

Poirier, D ^{[1
]}

机构：

[1] Univ Laval, Med Res Ctr, Div Med Chem, Mol Endocrinol Lab, Quebec City, PQ G1V 4G2, Canada

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 07期

关键词：

D O I：

10.1016/S0040-4039(98)02640-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 16 beta-(azidopropyl) derivative of estradiol (7) was synthesized and coupled to aminomethyl resin via a photolabile o-nitrobenzyl linker. Condensation of the corresponding iminophosphorane with activated acids successfully gave amides. Photocleavage resulted in good yield recovery of estradiol derivatives 15 and 16 in acceptable purities for biological screening. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1277 / 1280

页数：4

共 25 条

[1] SYNTHESIS, REACTIONS, AND C-13 FT NMR-SPECTROSCOPY OF POLYMER-BOUND STEROIDS [J].

BLOSSEY, EC ;

CANNON, RG ;

FORD, WT ;

PERIYASAMY, M ;

MOHANRAJ, S .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4664-4668

[2] ALTERNATIVE PROCEDURES FOR THE MACROLACTAMIZATION OF OMEGA-AZIDO ACIDS [J].

BOSCH, I ;

ROMEA, P ;

URPI, F ;

VILARRASA, J .

TETRAHEDRON LETTERS, 1993, 34 (29) :4671-4674

[3] PEPTIDOSTEROIDAL RECEPTORS FOR OPIOID-PEPTIDES - SEQUENCE-SELECTIVE BINDING USING A SYNTHETIC RECEPTOR LIBRARY [J].

BOYCE, R ;

LI, G ;

NESTLER, HP ;

SUENAGA, T ;

STILL, WC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (17) :7955-7956

[4] Solid-phase synthesis of 1,3-dialkyl quinazoline-2,4-diones [J].

Buckman, BO ;

Mohan, R .

TETRAHEDRON LETTERS, 1996, 37 (26) :4439-4442

[5] A GENERAL AND EXPEDIENT METHOD FOR THE SOLID-PHASE SYNTHESIS OF 1,4-BENZODIAZEPINE DERIVATIVES [J].

BUNIN, BA ;

ELLMAN, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) :10997-10998

[6] A PARADIGM FOR DRUG DISCOVERY EMPLOYING ENCODED COMBINATORIAL LIBRARIES [J].

BURBAUM, JJ ;

OHLMEYER, MHJ ;

READER, JC ;

HENDERSON, I ;

DILLARD, LW ;

LI, G ;

RANDLE, TL ;

SIGAL, NH ;

CHELSKY, D ;

BALDWIN, JJ .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (13) :6027-6031

[7]

CHABALA JC, 1994, PERSPECT DRUG DISCOV, V2, P305

[8] POLYMER-ANCHORED ORGANOSILYL PROTECTING GROUP IN ORGANIC-SYNTHESIS [J].

CHAN, TH ;

HUANG, WO .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (13) :909-911

[9] Sequence-selective peptide binding with a peptido-A,B-trans-steroidal receptor selected from an encoded combinatorial receptor library [J].

Cheng, YA ;

Suenaga, T ;

Still, WC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (07) :1813-1814

[10] Solid-phase synthesis of proline analogs via a three component 1,3-dipolar cycloaddition [J].

Hamper, BC ;

Dukesherer, DR ;

South, MS .

TETRAHEDRON LETTERS, 1996, 37 (21) :3671-3674

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