Solid-phase synthesis of 1,2,3,4-tetrahydro-β-carboline-containing peptidomimetics

被引：34

作者：

Li, XF

Zhang, LS ^{[1
]}

Zhang, W

Hall, SE

Tam, JP

机构：

[1] Sphinx Pharmaceut, Cambridge, MA 02139 USA

[2] Vanderbilt Univ, Dept Microbiol & Immunol, Nashville, TN 37232 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 20期

关键词：

D O I：

10.1021/ol006209z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A solid-phase method for the synthesis of 1,2,3,4-tetrahydro-beta-carboline-containing peptidomimetics has been developed. The key step in the strategy is the Pictet-Spengler condensation of a resin-bound tryptophan-containing fragment with an Fmoc-amino aldehyde.

引用

收藏

页码：3075 / 3078

页数：4

相关论文

共 43 条

[1] Multiple-component condensation strategies for combinatorial library synthesis [J].

Armstrong, RW ;

Combs, AP ;

Tempest, PA ;

Brown, SD ;

Keating, TA .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :123-131

[2]

Asche G, 1998, J PEPT RES, V51, P323

[3] Potent, selective tetrahydro-beta-carboline antagonists of the serotonin 2B (5HT(2B)) contractile receptor in the rat stomach fundus [J].

Audia, JE ;

Evrard, DA ;

Murdoch, GR ;

Droste, JJ ;

Nissen, JS ;

Schenck, KW ;

Fludzinski, P ;

Lucaites, VL ;

Nelson, DL ;

Cohen, ML .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (14) :2773-2780

[4]

Barany G., 1979, PEPTIDES A, V2, P1

[5] The use of topographical constraints in receptor mapping: Investigation of the topographical requirements of the Tryptophan 30 residue for receptor binding of Asp-Tyr-D-Phe-Gly-Trp-(N-Me)Nle-Asp-Phe-NH2 (SNF 9007), a cholecystokinin (26-33) analogue that binds to both CCK-B and delta-opioid receptors [J].

Boteju, LW ;

Nikiforovich, GV ;

HaskellLuevano, C ;

Fang, SN ;

Zalewska, T ;

Stropova, D ;

Yamamura, HI ;

Hruby, VJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (20) :4120-4124

[6] THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].

COX, ED ;

COOK, JM .

CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842

[7] Solid-phase synthesis of pyridones and pyridopyrazines as peptidomimetic scaffolds [J].

Creighton, CJ ;

Zapf, CW ;

Bu, JH ;

Goodman, M .

ORGANIC LETTERS, 1999, 1 (09) :1407-1409

[8] Comprehensive survey of combinatorial library synthesis: 1998 [J].

Dolle, RE ;

Nelson, KH .

JOURNAL OF COMBINATORIAL CHEMISTRY, 1999, 1 (04) :235-282

[9] Synthesis of N-protected α-amino aldehydes from their morpholine amide derivatives [J].

Douat, C ;

Heitz, A ;

Martinez, J ;

Fehrentz, JA .

TETRAHEDRON LETTERS, 2000, 41 (01) :37-40

[10] Synthesis of diverse tetrahydro-β-carboline-3-carboxamides and -2,3-bis-lactams on a versatile 4-hydroxythiophenol-linked solid support [J].

Fantauzzi, PP ;

Yager, KM .

TETRAHEDRON LETTERS, 1998, 39 (11) :1291-1294

← 1 2 3 4 5 →