Nucleophilic aromatic substitution of methacrylamide anion and its application to the synthesis of the anticancer drug bicalutamide

被引：29

作者：

Chen, BC ^{[1
]}

Zhao, RL ^{[1
]}

Gove, S ^{[1
]}

Wang, B ^{[1
]}

Sundeen, JE ^{[1
]}

Salvati, ME ^{[1
]}

Barrish, JC ^{[1
]}

机构：

[1] Bristol Myers Squibb Co, Pharmaceut Res Inst, Discovery Chem, Princeton, NJ 08543 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 26期

关键词：

D O I：

10.1021/jo035377c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The anticancer drug (R,S)-biscaltamide was prepared in three steps in >90% overall yield. A key step in the new synthesis involved a new nucleophilic aromatic substitution reaction of methacrylamide anion.

引用

页码：10181 / 10182

页数：2

共 14 条

[1] Discovery of nonsteroidal androgens [J].

Dalton, JT ;

Mukherjee, A ;

Zhu, ZX ;

Kirkovsky, L ;

Miller, DD .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1998, 244 (01) :1-4

[2]

FLEMING L, 1986, J CHEM SOC P1, P349

[3]

Furr BJA, 1996, EUR UROL, V29, P83

[4] The preclinical development of bicalutamide: Pharmacodynamics and mechanism of action [J].

Furr, BJA ;

Tucker, H .

UROLOGY, 1996, 47 (1A) :13-25

[5] Bicalutamide in advanced prostate cancer - A review [J].

Goa, KL ;

Spencer, CM .

DRUGS & AGING, 1998, 12 (05) :401-422

[6]

James KD, 2002, SYNTHESIS-STUTTGART, P850

[7] A general and efficient copper catalyst for the amidation of aryl halides [J].

Klapars, A ;

Huang, XH ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (25) :7421-7428

[8] ANTIPROLIFERATIVE ACTIVITY OF CASODEX (ICI-176.334) IN HORMONE-DEPENDENT TUMORS [J].

MAUCHER, A ;

VONANGERER, E .

JOURNAL OF CANCER RESEARCH AND CLINICAL ONCOLOGY, 1993, 119 (11) :669-674

[9] Synthesis of imidazo[1,5-a]quinoxalin-4(5H)-one template via a novel intramolecular cyclization process [J].

Norris, D ;

Chen, P ;

Barrish, JC ;

Das, J ;

Moquin, R ;

Chen, BC ;

Guo, P .

TETRAHEDRON LETTERS, 2001, 42 (26) :4297-4299

[10]

Schellhammer P, 1999, Expert Opin Investig Drugs, V8, P849, DOI 10.1517/13543784.8.6.849

← 1 2 →