PREPARATION OF (+/-)-(ERYTHRO)-2-VINYLCITRIC AND (+/-)-(THREO)-2-VINYLCITRIC ACIDS AS POTENTIAL MECHANISM-BASED INHIBITORS OF ATP-CITRATE LYASE

被引：7

作者：

DOLLE, RE ^{[1
]}

NOVELLI, R ^{[1
]}

SAXTY, BA ^{[1
]}

WELLS, TNC ^{[1
]}

KRUSE, LI ^{[1
]}

CAMILLERI, P ^{[1
]}

EGGLESTON, D ^{[1
]}

机构：

[1] SMITHKLINE BEECHAM PHARMACEUT,DEPT MED CHEM,THE FRYTHE,WELWYN GARDEN CIT AL6 9AR,HERTS,ENGLAND

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 35期

关键词：

D O I：

10.1016/0040-4039(91)80046-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The dianion of diethyl-1,3-acetone dicarboxylate 6 was reacted with a vinyl cation equivalent, 2-bromoethyl phenyl selenide, to give the mono alkylated 3-oxoglutarate 7 in 80% yield. Subsequent four-step elaboration gave the title citric acid analogues. These agents were designed as potential mechanism-based inhibitors of ATP-citrate lyase, an enzyme involved in cholesterol and lipid biosynthesis.

引用

页码：4587 / 4590

页数：4

共 13 条

[1] BEACH RL, 1977, J BIOL CHEM, V252, P2702
[2] PURIFICATION AND SOME KINETIC-PROPERTIES OF RAT-LIVER ATP-CITRATE LYASE
HOUSTON, B
NIMMO, HG
[J]. BIOCHEMICAL JOURNAL, 1984, 224 (02) : 437 - 443
[3] KATAEV EG, 1973, ZH ORG KHIM+, V9, P1983
[4] NUCLEAR MAGNETIC-RESONANCE EXAMINATION OF ORGANIC DIANIONS
LAMBERT, JB
WHARRY, SM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (22) : 5857 - 5862
[5] SYNTHESIS OF ARYL 2-HALOETHYL SELENIDES AND THEIR REACTIONS WITH POTASSIUM SELENOCYANATE
LINDGREN, B
[J]. ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1977, 31 (01): : 1 - 6
[6] LOWENSTEIN JM, 1981, METHOD ENZYMOL, P486
[7] MARLETTA MA, 1981, BIOCHEMISTRY-US, V20, P2719
[8] SILVERMAN RB, 1988, MECHANISM BASED ENZY, V1
[9] SILVERMAN RB, 1988, MECHANISM BASED ENZY, V2
[10] Smith, 1989, DESIGN ENZYME INHIBI

← 1 2 →