Synthesis and structure of 1,4-dipiperazino benzenes: Chiral terphenyl-type peptide helix mimetics

被引：74

作者：

Maity, Prantik ^{[1
]}

Konig, Burkhard ^{[1
]}

机构：

[1] Univ Regensburg, Inst Organ Chem, D-93040 Regensburg, Germany

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 07期

关键词：

D O I：

10.1021/ol8002749

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The terphenyl structure has been proven to be an ideal scaffold mimicking side-chain functionalities of peptidic alpha-helices. The synthesis of 1,4-dipiperazino benzenes, using stepwise transition metal-catalyzed N-arylation of chiral piperazines to a central benzene core is reported. The structure determination by X-ray crystallography reveals a geometrical arrangement of the hydrophobic side chains resembling the orientation of key i, i + 3, and i + 7 positions in a peptidic alpha-helix or in terphenyl helix mimetics.

引用

页码：1473 / 1476

页数：4

共 65 条

[1] Facile synthesis of benzamides to mimic an α-helix [J].

Ahn, Jung-Mo ;

Han, Sun-Young .

TETRAHEDRON LETTERS, 2007, 48 (20) :3543-3547

[2] Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles [J].

Anderson, Kevin W. ;

Tundel, Rachel E. ;

Ikawa, Takashi ;

Altman, Ryan A. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) :6523-6527

[3] Design and modular parallel synthesis of a MCR derived α-helix mimetic protein-protein interaction inhibitor scaffold [J].

Antuch, W ;

Menon, S ;

Chen, QZ ;

Lu, YC ;

Sakamuri, S ;

Beck, B ;

Schauer-Vukasinovic, V ;

Agarwal, S ;

Hess, S ;

Dömling, A .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (06) :1740-1743

[4] Modulation of protein-protein interactions with small organic molecules [J].

Berg, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (22) :2462-2481

[5] Heterocyclic α-helix mimetics for targeting protein-protein interactions [J].

Biros, Shannon M. ;

Moisan, Lionel ;

Mann, Enrique ;

Carella, Alexandre ;

Zhai, Dayong ;

Reed, John C. ;

Rebek, Julius, Jr. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (16) :4641-4645

[6] Efficient Pd-catalyzed amination of heteroaryl halides [J].

Charles, MD ;

Schultz, P ;

Buchwald, SL .

ORGANIC LETTERS, 2005, 7 (18) :3965-3968

[7] AN UNNATURAL BIOPOLYMER [J].

CHO, CY ;

MORAN, EJ ;

CHERRY, SR ;

STEPHANS, JC ;

FODOR, SPA ;

ADAMS, CL ;

SUNDARAM, A ;

JACOBS, JW ;

SCHULTZ, PG .

SCIENCE, 1993, 261 (5126) :1303-1305

[8] Antagonists of protein-protein interactions [J].

Cochran, AG .

CHEMISTRY & BIOLOGY, 2000, 7 (04) :R85-R94

[9] Substituted 1,4-benzodiazepine-2,5-diones as α-helix mimetic antagonists of the HDM2-p53 protein-protein interaction [J].

Cummings, MD ;

Schubert, C ;

Parks, DJ ;

Calvo, RR ;

LaFrance, LV ;

Lattanze, J ;

Milkiewicz, KL ;

Lu, TB .

CHEMICAL BIOLOGY & DRUG DESIGN, 2006, 67 (03) :201-205

[10]

DAUGAN ACM, Patent No. 0740668

← 1 2 3 4 5 6 7 →