FACILE ROUTES TO 1-HALO-1-ALKYL BORONIC ESTERS AS PRECURSORS FOR NOVEL THROMBIN INHIBITORS

被引：25

作者：

ELGENDY, S

CLAESON, G

KAKKAR, VV

GREEN, D

PATEL, G

GOODWIN, CA

BABAN, JA

SCULLY, MF

DEADMAN, J

机构：

[1] Thrombosis Research Institute, Chelsea London, SW3 6LR, Emmanuel Kaye Building, Manresa Road

来源：

TETRAHEDRON | 1994年 / 50卷 / 12期

关键词：

D O I：

10.1016/S0040-4020(01)90400-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methods of synthesis are described of alpha-haloboronic esters by hydroboration of 1-halo-1-alkenes with catecholborane and by reaction of pinanediol dichloromethylboronate with organometallic reagents. The resulting alpha-haloboronic esters are synthetically useful, especially for the synthesis of peptides containing alpha-aminoboronic acids. The inhibitory activities of these peptides have been studied with thrombin.

引用

收藏

页码：3803 / 3812

页数：10

相关论文

共 13 条

[1] N-15 NMR-SPECTROSCOPY OF THE CATALYTIC-TRIAD HISTIDINE OF A SERINE PROTEASE IN PEPTIDE BORONIC ACID INHIBITOR COMPLEXES [J].

BACHOVCHIN, WW ;

WONG, WYL ;

FARRJONES, S ;

SHENVI, AB ;

KETTNER, CA .

BIOCHEMISTRY, 1988, 27 (20) :7689-7697

[2]

BODE R, 1987, BIOCHEMISTRY-US, V26, P7609

[3] HYDROBORATION .27. HYDROBORATION OF 1-BUTENYL AND RELATED VINYL DERIVATIVES CONTAINING REPRESENTATIVE SUBSTITUENTS . AN UNUSUALLY POWERFUL DIRECTIVE INFLUENCE OF ETHOXY SUBSTITUENT [J].

BROWN, HC ;

SHARP, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (11) :2915-+

[4]

BROWN HC, 1975, ORGANIC SYNTHESES VI

[5] BENZYLOXYCARBONYL-D-PHE-PRO-METHOXYPROPYLBOROGLYCINE - A NOVEL INHIBITOR OF THROMBIN WITH HIGH SELECTIVITY CONTAINING A NEUTRAL SIDE-CHAIN AT THE P1 POSITION [J].

CLAESON, G ;

PHILIPP, M ;

AGNER, E ;

SCULLY, MF ;

METTERNICH, R ;

KAKKAR, VV ;

DESOYZA, T ;

NIU, LH .

BIOCHEMICAL JOURNAL, 1993, 290 :309-312

[6] NEW PEPTIDE BORONIC ACID INHIBITORS OF THROMBIN [J].

ELGENDY, S ;

DEADMAN, J ;

PATEL, G ;

GREEN, D ;

CHINO, N ;

GOODWIN, CA ;

SCULLY, MF ;

KAKKAR, VV ;

CLAESON, G .

TETRAHEDRON LETTERS, 1992, 33 (29) :4209-4212

[7]

KAKKAR VV, 1992, Patent No. 7869

[8]

KETTNER C, 1990, J BIOL CHEM, V265, P18289

[9] ALPHA-HALO BORONIC ESTERS - INTERMEDIATES FOR STEREODIRECTED SYNTHESIS [J].

MATTESON, DS .

CHEMICAL REVIEWS, 1989, 89 (07) :1535-1551

[10] SYNTHESIS AND PROPERTIES OF PINANEDIOL ALPHA-AMIDO BORONIC ESTERS [J].

MATTESON, DS ;

JESTHI, PK ;

SADHU, KM .

ORGANOMETALLICS, 1984, 3 (08) :1284-1288