Macrocyclic chiral receptors toward enantioselective recognition of naproxen

被引：33

作者：

Gonzalez, Silvia

Pelaez, Rafael

Sanz, Francisca

Jimenez, Ma Belen

Moran, Joaquin R.

Caballero, Ma Cruz

机构：

[1] Univ Salamanca, Dept Quim Organ, E-37008 Salamanca, Spain

[2] Univ Salamanca, Dept Quim Farmaceut, E-37008 Salamanca, Spain

[3] Univ Salamanca, Serv Gen Difracc Rayos 10, E-37008 Salamanca, Spain

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 21期

关键词：

D O I：

10.1021/ol061505i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A macrocyclic receptor based on a bischromenylurea and an alpha,alpha '-(o,o '-dialkyl)diphenyl-p-xylylenediamine spacer provides a C-2 chiral cavity to associate carboxylates by H-bonds. The extent of the selectivity obtained for the racemic receptor 2 and enantiomerically pure (S)-naproxen is 7.2:1. Steric repulsions close to the cavity are decisive for the chiral selectivity.

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页码：4679 / 4682

页数：4

相关论文

共 24 条

[1] Putting chirality to work: The strategy of chiral switches [J].

Agranat, I ;

Caner, H ;

Caldwell, A .

NATURE REVIEWS DRUG DISCOVERY, 2002, 1 (10) :753-768

[2] CYANOHYDRIDOBORATE ANION AS A SELECTIVE REDUCING AGENT [J].

BORCH, RF ;

BERNSTEIN, MD ;

DURST, HD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (12) :2897-+

[3] (4S,8S)-4,8-BIS(DIPHENYLMETHYL)-1,5,7-TRIAZABICYCLO[4,4,0]DEC-5-ENE - A HINDERED, CHIRAL, BICYCLIC GUANIDINE BASE WITH EFFECTIVE C-2-SYMMETRY [J].

BOYLE, PH ;

DAVIS, AP ;

DEMPSEY, KJ ;

HOSKEN, GD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (16) :1875-1876

[4] OPTICALLY-ACTIVE MONO AND BIS(1,1'-BINAPHTHYL)-CYCLOPHANES - LARGE DIFFERENCES IN THE COMPLEXATION OF NAPROXEN DERIVATIVES IN AQUEOUS-SOLUTION [J].

CASTRO, PP ;

DIEDERICH, F .

TETRAHEDRON LETTERS, 1991, 32 (44) :6277-6280

[5] CHIRAL RECOGNITION IN CLEFTS AND CYCLOPHANE CAVITIES SHAPED BY THE 1,1'-BINAPHTHYL MAJOR GROOVE [J].

CASTRO, PP ;

GEORGIADIS, TM ;

DIEDERICH, F .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) :5835-5838

[6] Macrocyclic anion receptors based on directed hydrogen bonding interactions [J].

Choi, KH ;

Hamilton, AD .

COORDINATION CHEMISTRY REVIEWS, 2003, 240 (1-2) :101-110

[7] SYNTHESIS AND INVESTIGATION OF A HINDERED, CHIRAL, BICYCLIC GUANIDINE [J].

DAVIS, AP ;

DEMPSEY, KJ .

TETRAHEDRON-ASYMMETRY, 1995, 6 (11) :2829-2840

[8] Binding properties of an abiotic receptor for complexing carboxylates of α-heterocyclic and α-keto acids [J].

de la Torre, MF ;

Campos, EG ;

González, S ;

Morán, JR ;

Caballero, MC .

TETRAHEDRON, 2001, 57 (18) :3945-3950

[9] Receptors for carboxylates derived from 2-furoic and fusaric acids [J].

delaTorre, MF ;

Gonzalez, S ;

Campos, EG ;

Mussons, ML ;

Moran, JR ;

Caballero, MC .

TETRAHEDRON LETTERS, 1997, 38 (49) :8591-8594

[10] DIASTEREOMERIC COMPLEX-FORMATION BETWEEN A NOVEL OPTICALLY-ACTIVE HOST AND NAPROXEN IN AQUEOUS-SOLUTION [J].

DHARANIPRAGADA, R ;

DIEDERICH, F .

TETRAHEDRON LETTERS, 1987, 28 (22) :2443-2446