Antitumour benzothiazoles.: Part 20:: 3′-cyano and 3′-alkynyl-substituted 2-(4′-aminophenyl)benzothiazoles as new potent and selective analogues

被引：132

作者：

Hutchinson, I ^{[1
]}

Bradshaw, TD ^{[1
]}

Matthews, CS ^{[1
]}

Stevens, MFG ^{[1
]}

Westwell, AD ^{[1
]}

机构：

[1] Univ Nottingham, Sch Pharmaceut Sci, Canc Res Labs, Nottingham NG7 2RD, England

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2003年 / 13卷 / 03期

关键词：

D O I：

10.1016/S0960-894X(02)00930-7

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The synthesis of a new series of antitumour 2-(4-aminophenyl)benzothiazole analogues, substituted in the 3'-position by cyano or alkynyl groups, is described. Several of the analogues, notably the 5-fluorinated compounds 7c and 9c, were found to possess potent in vitro activity against MCF-7 and MDA 468 human cancer cell lines. More comprehensive in vitro analysis (NCI 60-cell line) established compound 7c as a particularly potent and selective 2-(4-aminophenyl)benzothiazole analogue. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：471 / 474

页数：4

共 10 条

[1] In vitro evaluation of amino acid prodrugs of novel antitumour 2-(4-amino-3-methylphenyl)benzothiazoles [J].

Bradshaw, TD ;

Chua, MS ;

Browne, HL ;

Trapani, V ;

Sausville, EA ;

Stevens, MFG .

BRITISH JOURNAL OF CANCER, 2002, 86 (08) :1348-1354

[2] The discovery of the potent and selective antitumour agent 2-(4-amino-3-methylphenyl)benzothiazole (DF 203) and related compounds [J].

Bradshaw, TD ;

Stevens, MFG ;

Westwell, AD .

CURRENT MEDICINAL CHEMISTRY, 2001, 8 (02) :203-210

[3] 2-(4-aminophenyl)benzothiazoles: novel agents with selective profiles of in vitro anti-tumour activity [J].

Bradshaw, TD ;

Wrigley, S ;

Shi, DF ;

Schultz, RJ ;

Paull, KD ;

Stevens, MFG .

BRITISH JOURNAL OF CANCER, 1998, 77 (05) :745-752

[4] Influence of 2-(4-aminophenyl)benzothiazoles on growth of human ovarian carcinoma cells in vitro and in vivo [J].

Bradshaw, TD ;

Schultz, RJ ;

Paull, KD ;

Kelland, L ;

Wilson, A ;

Garner, C ;

Fiebig, HH ;

Wrigley, S ;

Stevens, MFG .

BRITISH JOURNAL OF CANCER, 1998, 78 (04) :421-429

[5]

Chua MS, 2000, CANCER RES, V60, P5196

[6] Antitumor benzothiazoles. 16. Synthesis and pharmaceutical properties of antitumor 2-(4-aminophenyl)benzothiazole amino acid prodrugs [J].

Hutchinson, I ;

Jennings, SA ;

Vishnuvajjala, BR ;

Westwell, AD ;

Stevens, MFG .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (03) :744-747

[7] Antitumor benzothiazoles. 14. Synthesis and in vitro biological properties of fluorinated 2-(4-aminophenyl)benzothiazoles [J].

Hutchinson, I ;

Chua, MS ;

Browne, HL ;

Trapani, V ;

Bradshaw, TD ;

Westwell, AD ;

Stevens, MFG .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (09) :1446-1455

[8] The regiospecific synthesis of 5-and 7-monosubstituted and 5,6-disubstituted 2-arylbenzothiazoles [J].

Hutchinson, I ;

Stevens, MFG ;

Westwell, AD .

TETRAHEDRON LETTERS, 2000, 41 (03) :425-428

[9] Antitumor benzothiazoles.: 8.: Synthesis, metabolic formation, and biological properties of the C- and N-oxidation products of antitumor 2-(4-aminophenyl)benzothiazoles [J].

Kashiyama, E ;

Hutchinson, I ;

Chua, MS ;

Stinson, SF ;

Phillips, LR ;

Kaur, G ;

Sausville, EA ;

Bradshaw, TD ;

Westwell, AD ;

Stevens, MFG .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (20) :4172-4184

[10] Antitumor benzothiazoles .3. Synthesis of 2-(4-aminophenyl)benzothiazoles and evaluation of their activities against breast cancer cell lines in vitro and in vivo [J].

Shi, DF ;

Bradshaw, TD ;

Wrigley, S ;

McCall, CJ ;

Lelieveld, P ;

Fichtner, I ;

Stevens, MFG .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (17) :3375-3384

← 1 →