Synthesis and antitumor activity of novel C-7 paclitaxel ethers: Discovery of BMS-184476

被引：38

作者：

Altstadt, TJ

Fairchild, CR

Golik, J

Johnston, KA

Kadow, JF

Lee, FY

Long, BH

Rose, WC

Vyas, DM

Wong, H

Wu, MJ

Wittman, MD

机构：

[1] Bristol Myers Squibb Co, Pharmaceut Res Inst, Discovery Chem, Wallingford, CT 06492 USA

[2] Bristol Myers Squibb Co, Pharmaceut Res Inst, Oncol Drug Discovery, Princeton, NJ 08543 USA

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 2001年 / 44卷 / 26期

关键词：

D O I：

10.1021/jm0102607

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The preparation of C-7 paclitaxel ethers is described. Various substituted ethers were prepared via activation of the corresponding methylthiomethyl ether followed by alcohol addition. Variation of the C-7 ether group as well the 3' side chain position led to the discovery of a novel taxane, BMS-184476 (4), with preclinical antitumor activity superior to paclitaxel.

引用

页码：4577 / 4583

页数：7

共 22 条

[1]

[Anonymous], 1999, ADV MED CH

[2] Reinvestigation to the C-7 epimerization of paclitaxel and related taxoids under basic conditions [J].

Fang, WS ;

Fang, QC ;

Liang, XT .

SYNTHETIC COMMUNICATIONS, 1997, 27 (13) :2305-2310

[3]

FARINA V, 1995, CHEM PHARM TAXOL

[4]

GEORGE CI, 1995, ACS S SERIES, V583

[5] Synthesis and antitumor evaluation of paclitaxel phosphonooxymethyl ethers: A novel class of water soluble paclitaxel pro-drugs [J].

Golik, J ;

Wong, HSL ;

Chen, SH ;

Doyle, TW ;

Wright, JJK ;

Knipe, J ;

Rose, WC ;

Casazza, AM ;

Vyas, DM .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (15) :1837-1842

[6]

GOLIK J, 1997, Patent No. 5646176

[7]

HOLTON RA, 1990, Patent No. 5175315

[8]

HOLTON RA, 1986, Patent No. 5229526

[9]

KELLY RC, 1996, Patent No. 9600724

[10] IODONIUM PROMOTED REACTIONS OF DISARMED THIOGLYCOSIDES [J].

KONRADSSON, P ;

UDODONG, UE ;

FRASERREID, B .

TETRAHEDRON LETTERS, 1990, 31 (30) :4313-4316

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