Total synthesis and reassessment of the phosphatase-inhibitory activity of the antitumor agent TMC-69-6H

被引：41

作者：

Fürstner, A

Feyen, F

Prinz, H

Waldmann, H

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

[2] Max Planck Inst Mol Physiol, D-44227 Dortmund, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 43期

关键词：

heterocycles; natural products; palladium; phosphatases; structure-activity relationships;

D O I：

10.1002/anie.200352268

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The unexpected selectivity proflie of I (17R)-and (17S)-TMC-69-6H (see formula) suggests that N-hydroxypyridone derivatives constitute a promising new lead structure in the search for selective phosphatase inhibitors. An unprecedented Pd-catalyzed C-C bond formation to a pyranone derivative was a key step in the synthesis of enantiopure (17R)-and (17S)-TMC-69-6H.

引用

收藏

页码：5361 / 5364

页数：4

相关论文

共 57 条

[11] STRUCTURE AND BIOSYNTHESIS OF HARZIANOPYRIDONE, AN ANTIFUNGAL METABOLITE OF TRICHODERMA-HARZIANUM [J].

DICKINSON, JM ;

HANSON, JR ;

HITCHCOCK, PB ;

CLAYDON, N .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (11) :1885-1887

[12] Elevated expression of the cdc25A protein phosphatase in colon cancer [J].

Dixon, D ;

Moyana, T ;

King, MJ .

EXPERIMENTAL CELL RESEARCH, 1998, 240 (02) :236-243

[13] Cdc25 protein phosphatases in cell proliferation [J].

Draetta, G ;

Eckstein, J .

BIOCHIMICA ET BIOPHYSICA ACTA-REVIEWS ON CANCER, 1997, 1332 (02) :M53-M63

[14]

ElBasyouni SH, 1968, CAN J BOT, V46, P441, DOI [DOI 10.1139/B68-067, 10.1139/b68-067]

[15] Design and synthesis of a pyridone-based phosphotyrosine mimetic [J].

Fu, JM ;

Castelhano, AL .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (19) :2813-2816

[16] STRUCTURE OF FISCHERIN, A NEW TOXIC METABOLITE FROM AN ASCOMYCETE, NEOSARTORYA-FISCHERI VAR FISCHERI [J].

FUJIMOTO, H ;

IKEDA, M ;

YAMAMOTO, K ;

YAMAZAKI, M .

JOURNAL OF NATURAL PRODUCTS, 1993, 56 (08) :1268-1275

[17] Total synthesis of the antiviral glycolipid cycloviracin B1 [J].

Fürstner, A ;

Mlynarski, J ;

Albert, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (35) :10274-10275

[18] CDC25 PHOSPHATASES AS POTENTIAL HUMAN ONCOGENES [J].

GALAKTIONOV, K ;

LEE, AK ;

ECKSTEIN, J ;

DRAETTA, G ;

MECKLER, J ;

LODA, M ;

BEACH, D .

SCIENCE, 1995, 269 (5230) :1575-1577

[19]

Gasparotto D, 1997, CANCER RES, V57, P2366

[20]

GRYNKIEWICZ G, 1980, Z NATURFORSCH B, V35, P1024

← 1 2 3 4 5 6 →