Synthesis of RGD analogues containing α-Tfm-arginine as potential fibrinogen receptor antagonists

被引：27

作者：

Dal Pozzo, A

Muzi, L

Moroni, M

Rondanin, R

de Castiglione, R

Bravo, P

Zanda, M

机构：

[1] Ist Ric Chim & Biochim G Ronzoni, I-20133 Milan, Italy

[2] CNR, Politecn Milan, Dipartimento Chim, I-20131 Milan, Italy

来源：

TETRAHEDRON | 1998年 / 54卷 / 22期

关键词：

D O I：

10.1016/S0040-4020(98)00282-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of two peptide mimetics of RGD, alpha-Tfm-Arg-Gly-Asp-Phe-NH2 9 and alpha-Tfm-Arg-Gly-Asp-NH-(CH2)(2)-C6H5 13, is described. The precursor of alpha-Tfm-ornithine was obtained in two synthetic steps from 2-N-Cbz-2-Tfm-hexanediacid-1-alkyl ester and introduced into the peptide chain by alpha-carboxy-group activation via oxazolone. The introduction of the guanidine residue led to the final peptides as mixtures of the two diastereomers. Configurationally pure peptides were obtained in good yields by RP-HPLC. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：6019 / 6028

页数：10

共 17 条

[1] CONFORMATIONALLY CONSTRAINED PEPTIDES AND SEMIPEPTIDES DERIVED FROM RGD AS POTENT INHIBITORS OF THE PLATELET FIBRINOGEN RECEPTOR AND PLATELET-AGGREGATION [J].

ALI, FE ;

BENNETT, DB ;

CALVO, RR ;

ELLIOTT, JD ;

HWANG, SM ;

KU, TW ;

LAGO, MA ;

NICHOLS, AJ ;

ROMOFF, TT ;

SHAH, DH ;

VASKO, JA ;

WONG, AS ;

YELLIN, TO ;

YUAN, CK ;

SAMANEN, JM .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (06) :769-780

[2] LOW-MOLECULAR-WEIGHT, NONPEPTIDE FIBRINOGEN RECEPTOR ANTAGONISTS [J].

ALIG, L ;

EDENHOFER, A ;

HADVARY, P ;

HURZELER, M ;

KNOPP, D ;

MULLER, M ;

STEINER, B ;

TRZECIAK, A ;

WELLER, T .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (23) :4393-4407

[3] 1H-PYRAZOLE-1-CARBOXAMIDINE HYDROCHLORIDE - AN ATTRACTIVE REAGENT FOR GUANYLATION OF AMINES AND ITS APPLICATION TO PEPTIDE-SYNTHESIS [J].

BERNATOWICZ, MS ;

WU, YL ;

MATSUEDA, GR .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2497-2502

[4]

BURGER K, 1990, CHEM ZTG, V114, P101

[5] PROTEASE-CATALYZED AND CHEMICAL PEPTIDE-BOND FORMATION WITH ALPHA-TRIFLUOROMETHYL SUBSTITUTED ALPHA-AMINO-ACIDS [J].

BURGER, K ;

MUTZE, K ;

HOLLWECK, W ;

KOKSCH, B ;

KUHL, P ;

JAKUBKE, HD ;

RIEDE, J ;

SCHIER, A .

JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1993, 335 (04) :321-331

[6]

Koksch B, 1996, ACS SYM SER, V639, P42

[7]

Koksch B, 1997, J PEPT SCI, V3, P157, DOI 10.1002/(SICI)1099-1387(199705)3:3<157::AID-PSC94>3.0.CO

[8]

2-W

[9]

KOKSCH B, 1994, P 23 EUR PEPT S BRAG, P323

[10]

KRICHELDORF HR, 1972, SYNTHESIS-STUTTGART, P695

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