Organolithium mediated synthesis of prenylchalcones as potential inhibitors of chemoresistance

被引：75

作者：

Daskiewicz, JB

Comte, G

Barron, D

Di Pietro, A

Thomasson, F

机构：

[1] Univ Lyon 1, Lab Produits Nat, F-69622 Villeurbanne, France

[2] CNRS, Inst Biol Chim Prot, F-69367 Lyon 07, France

[3] Univ Grenoble 1, Fac Pharm, Lab Pharmacognosie, F-38706 La Tronche, France

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 39期

关键词：

aldol reaction; biologically active compounds; chalcones; protecting groups;

D O I：

10.1016/S0040-4039(99)01461-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A number of substituted chalcones have been prepared by a novel LiHMDS-mediated aldol condensation, the first method consistent with the use of alkali-labile protecting groups such as tert-butyldiphenylsilyl or tert-butyldimethylsilyl. Chalcone substitution by prenylation increases their binding affinity to P-glycoprotein responsible for cancer cells chemoresistance. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：7095 / 7098

页数：4

共 15 条

[1] Altenbach H.-J., 1984, ANGEW CHEM, V96, P991
[2] Isoprenylated flavonoids from hairy root cultures of Glycyrrhiza glabra
Asada, Y
Li, W
Yoshikawa, T
[J]. PHYTOCHEMISTRY, 1998, 47 (03) : 389 - 392
[3] Isoprenylated flavonoids - A survey
Barron, D
Ibrahim, RK
[J]. PHYTOCHEMISTRY, 1996, 43 (05) : 921 - 982
[4] Synthesis of exiguaflavanone K and (+/-)-leachianone G
Bu, XY
Li, YL
[J]. JOURNAL OF NATURAL PRODUCTS, 1996, 59 (10): : 968 - 969
[5] Bu XY, 1997, SYNTHESIS-STUTTGART, P1246
[6] Flavonoids: A class of modulators with bifunctional interactions at vicinal ATP- and steroid-binding sites on mouse P-glycoprotein
Conseil, G
Baubichon-Cortay, H
Dayan, G
Jault, JM
Barron, D
Di Pietro, A
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (17) : 9831 - 9836
[7] FUJIMOTO T, 1984, HETEROCYCLES, V22, P997
[8] HANO Y, 1995, HETEROCYCLES, V41, P2313
[9] AN IMPROVED PROCEDURE FOR CYCLIZATION OF CHALCONES TO FLAVANONES USING CELITE SUPPORTED POTASSIUM FLUORIDE IN METHANOL - TOTAL SYNTHESIS OF BAVACHININ
HARWOOD, LM
LOFTUS, GC
OXFORD, A
THOMSON, C
[J]. SYNTHETIC COMMUNICATIONS, 1990, 20 (05) : 649 - 657
[10] THE PREPARATION OF SUBSTITUTED 3,4-DIHYDRO-1H-2-BENZOPYRAN-1-ONES FROM THE DIANIONS OF ORTHO-TOLUIC ACIDS
HILDEBRAN, KC
CORDRAY, TL
CHAN, KW
BEAM, CF
[J]. SYNTHETIC COMMUNICATIONS, 1994, 24 (06) : 779 - 788

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