NOVEL ANGIOTENSIN-CONVERTING ENZYME-INHIBITORS CONTAINING ALPHA-HYDROXY KETOMETHYLENE DIPEPTIDE ISOSTERES

被引：11

作者：

KIM, BH

RYU, EJ

CHUNG, YJ

机构：

[1] Department of Chemistry, Center for Biofunctional Molecules, Pohang University of Science and Technology, Pohang

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1994年 / 4卷 / 23期

关键词：

D O I：

10.1016/S0960-894X(01)80597-7

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Synthesis of novel angiotensin converting enzyme inhibitors has been accomplished using the alpha-hydroxy ketomethylene dipeptide isostere as a key constituent. (2R, 5S)-2-hydroxy-5-benzamido-4-oxo-6-phenyl hexanoyl (S)-(-)-indoline-2-carboxylic acid (7) showed potent inhibitory activity against angiotensin converting enzyme, IC50 = 0.09 mu M.

引用

页码：2799 / 2804

页数：6

共 24 条

[1] SOLID-PHASE SYNTHESIS OF HYDROXYETHYLAMINE PEPTIDE-BOND ISOSTERES - SYNTHESIS OF THE POTENT-HIV-1 PROTEASE INHIBITOR JG365 [J].

ALEWOOD, PF ;

BRINKWORTH, RI ;

DANCER, RJ ;

GARNHAM, B ;

JONES, A ;

KENT, SBH .

TETRAHEDRON LETTERS, 1992, 33 (07) :977-980

[2] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF A KETOMETHYLENE ANALOG OF A TRIPEPTIDE INHIBITOR OF ANGIOTENSIN CONVERTING ENZYME [J].

ALMQUIST, RG ;

CHAO, WR ;

ELLIS, ME ;

JOHNSON, HL .

JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (12) :1392-1398

[3] DERIVATIVES OF THE POTENT ANGIOTENSIN CONVERTING ENZYME-INHIBITOR 5(S)-BENZAMIDO-4-OXO-6-PHENYLHEXANOYL-L-PROLINE - EFFECT OF CHANGES AT POSITION-2 AND POSITION-5 OF THE HEXANOIC ACID PORTION [J].

ALMQUIST, RG ;

CRASE, J ;

JENNINGSWHITE, C ;

MEYER, RF ;

HOEFLE, ML ;

SMITH, RD ;

ESSENBURG, AD ;

KAPLAN, HR .

JOURNAL OF MEDICINAL CHEMISTRY, 1982, 25 (11) :1292-1299

[4] HIGHLY DIASTEREOSELECTIVE ALKYLATIONS OF CHIRAL AMIDE ENOLATES - NEW ROUTES TO HYDROXYETHYLENE DIPEPTIDE ISOSTERE INHIBITORS OF HIV-1 PROTEASE [J].

ASKIN, D ;

WALLACE, MA ;

VACCA, JP ;

REAMER, RA ;

VOLANTE, RP ;

SHINKAI, I .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) :2771-2773

[5] (R)-2-(3-MERCAPTO-2(S)-METHYL-1-OXO-PROPOXY)-3-(METHYLTHIO)PROPANOIC ACID, THE 1ST ULTRA-SHORT-ACTING ANGIOTENSIN CONVERTING-ENZYME-INHIBITOR [J].

BAXTER, AJG ;

CARR, RD ;

EYLEY, SC ;

FRASERRAE, L ;

HALLAM, C ;

HARPER, ST ;

HURVED, PA ;

KING, SJ ;

MEGHANI, P .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (20) :3718-3720

[6] REDUCTION OF DELTA-2-ISOXAZOLINES .3. RANEY-NICKEL CATALYZED FORMATION OF BETA-HYDROXY KETONES [J].

CURRAN, DP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (18) :5826-5833

[7] SPECTROPHOTOMETRIC ASSAY AND PROPERTIES OF ANGIOTENSIN-CONVERTING ENZYME OF RABBIT LUNG [J].

CUSHMAN, DW ;

CHEUNG, HS .

BIOCHEMICAL PHARMACOLOGY, 1971, 20 (07) :1637-+

[8] ANGIOTENSIN CONVERTING ENZYME . METHOD OF ASSAY AND PARTIAL PURIFICATION [J].

DORER, FE ;

SKEGGS, LT ;

KAHN, JR ;

LENTZ, KE ;

LEVINE, M .

ANALYTICAL BIOCHEMISTRY, 1970, 33 (01) :102-+

[9] DEHYDRO KETO METHYLENE AND KETO METHYLENE ANALOGS OF SUBSTANCE-P - SYNTHESIS AND BIOLOGICAL-ACTIVITY [J].

EWENSON, A ;

LAUFER, R ;

CHOREV, M ;

SELINGER, Z ;

GILON, C .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (02) :416-421

[10] POTENT HIV-1 PROTEASE INHIBITORS - STEREOSELECTIVE SYNTHESIS OF A DIPEPTIDE MIMIC [J].

GHOSH, AK ;

MCKEE, SP ;

THOMPSON, WJ ;

DARKE, PL ;

ZUGAY, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1025-1029

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