Synthesis of a phostone glycomimetic of the endothelin converting enzyme inhibitor phosphoramidon

被引：25

作者：

Hanessian, S ^{[1
]}

Rogel, O ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1999年 / 9卷 / 16期

关键词：

D O I：

10.1016/S0960-894X(99)00401-1

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The phostone analog of phosphoramidon, an inhibitor of endothelin converting enzyme, was synthesized from L-rhamnose. Coupling of the cyclic phosphonic acid with the dipeptide H-Leu-Trp-OMe gave, after deprotection and purification by reverse-phase HPLC, the desired phostone which exhibited an IC50 of 5.05 +/- 2.7 mu M. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2441 / 2446

页数：6

共 35 条

[1]

ABRAMOV VS, 1952, ZH OBSHCH KHIM+, V22, P647

[2] Novel selective quinazoline inhibitors of endothelin converting enzyme-1 [J].

Ahn, K ;

Sisneros, AM ;

Herman, SB ;

Pan, SM ;

Hupe, D ;

Lee, C ;

Nikam, S ;

Cheng, XM ;

Doherty, AM ;

Schroeder, RL ;

Haleen, SJ ;

Kaw, S ;

Emoto, N ;

Yanagisawa, M .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1998, 243 (01) :184-190

[3] Ready access to fluorinated phosphonate mimics of secondary phosphates. Synthesis of the (alpha,alpha-difluoroalkyl) phosphonate analogues of L-phosphoserine, L-phosphoallothreonine, and L-phosphothreonine [J].

Berkowitz, DB ;

Eggen, M ;

Shen, QR ;

Shoemaker, RK .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) :4666-4675

[4] HYDROXAMIC ACIDS AS POTENT INHIBITORS OF ENDOTHELIN-CONVERTING ENZYME FROM HUMAN BRONCHIOLAR SMOOTH-MUSCLE [J].

BIHOVSKY, R ;

LEVINSON, BL ;

LOEWI, RC ;

ERHARDT, PW ;

POLOKOFF, MA .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (12) :2119-2129

[5]

Brel VK, 1998, SYNTHESIS-STUTTGART, P710

[6] SYNTHESIS, CHARACTERIZATION, AND REACTIONS OF MONO AND BICYCLIC PHOSTONES [J].

CREMER, SE ;

SOMMESE, AG ;

RODRIGUEZ, O .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1993, 75 (1-4) :107-110

[7] CYCLIC PHOSPHONATE ANALOGS OF HEXOPYRANOSES [J].

DARROW, JW ;

DRUECKHAMMER, DG .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :2976-2985

[8]

DENANTEUIL G, 1995, TETRAHEDRON LETT, V36, P1435

[9] N-BENZYLOXYAMINO PHOSPHINYL PEPTIDES [J].

ELHADDADI, M ;

JACQUIER, R ;

PETRUS, C ;

PETRUS, F .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1991, 63 (3-4) :255-259

[10] SYNTHESIS OF 2,6-DIDEOXY-ALPHA-L-LYXO-HEXOPYRANOSYL HALIDES AND 2,6-DIDEOXY-ALPHA-L-ARABINO-HEXOPYRANOSYL HALIDES [J].

ELKHADEM, HS ;

SWARTZ, DL ;

NELSON, JK ;

BERRY, LA .

CARBOHYDRATE RESEARCH, 1977, 58 (01) :230-234

← 1 2 3 4 →