A β-carboline-1-one mimic of the anticancer Amaryllidaceae constituent pancratistatin:: Synthesis and biological evaluation

被引：69

作者：

Rinner, U

Hudlicky, T

Gordon, H

Pettit, GR

机构：

[1] Brock Univ, Dept Chem, St Catharines, ON L2S 3A1, Canada

[2] Arizona State Univ, Dept Chem & Biochem, Tempe, AZ 85287 USA

[3] Arizona State Univ, Canc Res Inst, Tempe, AZ 85287 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 40期

关键词：

antitumor agents; asymmetric synthesis; natural products; pancratistatin; synthetic methods;

D O I：

10.1002/anie.200460218

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

New drug design possibilities are suggested by the results of a biological evaluation of the indole derivative 1 of pancratistatin, a known anticancer agent, in a panel of cancer cell lines. Enzymatic dihydroxylation was one of the key steps in the short, enantioselective synthesis of 1.

引用

页码：5342 / 5346

页数：5

共 51 条

[1] *ACC INC, 2001, CHARMM
[2] Banerjee AK, 2001, USP KHIM+, V70, P1094
[3] CHARMM - A PROGRAM FOR MACROMOLECULAR ENERGY, MINIMIZATION, AND DYNAMICS CALCULATIONS
BROOKS, BR
BRUCCOLERI, RE
OLAFSON, BD
STATES, DJ
SWAMINATHAN, S
KARPLUS, M
[J]. JOURNAL OF COMPUTATIONAL CHEMISTRY, 1983, 4 (02) : 187 - 217
[4] NARCICLASINE - ANTITUMOR ALKALOID WHICH BLOCKS PEPTIDE-BOND FORMATION BY EUKARYOTIC RIBOSOMES
CARRASCO, L
FRESNO, M
VAZQUEZ, D
[J]. FEBS LETTERS, 1975, 52 (02) : 236 - 239
[5] NARCICLASINE - AN ANTIMITOTIC SUBSTANCE FROM NARCISSUS BULBS
CERIOTTI, G
[J]. NATURE, 1967, 213 (5076) : 595 - &
[6] Total synthesis of (+)-7-deoxypancratistatin and (+)-7-deoxy-trans-dihydronarciclasine
Chida, N
Jitsuoka, M
Yamamoto, Y
Ohtsuka, M
Ogawa, S
[J]. HETEROCYCLES, 1996, 43 (07) : 1385 - 1390
[7] TOTAL SYNTHESIS OF (+/-)-PANCRATISTATIN
DANISHEFSKY, S
LEE, JY
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (13) : 4829 - 4837
[8] A convergent synthesis of (+)-pancratistatin based on intramolecular electrophilic aromatic substitution
Doyle, TJ
Hendrix, M
VanDerveer, D
Javanmard, S
Haseltine, J
[J]. TETRAHEDRON, 1997, 53 (32) : 11153 - 11170
[9] A short synthesis of (+)-narciclasine via a strategy derived from stereocontrolled epoxide formation and SnCl4-catalyzed arene-epoxide coupling
Elango, S
Yan, TH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) : 6954 - 6959
[10] SELECTIVITY OF STERICALLY FIXED TRYPTAMINE AND 5-METHOXYTRYPTAMINE DERIVATIVES FOR SEROTONIN RECEPTOR SUBTYPES .2. STRUCTURE-ACTIVITY-RELATIONSHIPS AND IN-VITRO PHARMACOLOGY OF N-ALKYL- AND N,N-DIALKYL-3-INDOLYLBICYCLO-[2.2.1]-HEPTANE-2-AMINES
ELZ, S
ZIMMERMANN, H
REHSE, K
[J]. ARCHIV DER PHARMAZIE, 1993, 326 (11) : 893 - 899

← 1 2 3 4 5 6 →