Synthesis and structure-activity relationships of new second-generation taxoids

被引：82

作者：

Ojima, I ^{[1
]}

Wang, T

Miller, ML

Lin, SN

Borella, CP

Geng, XD

Pera, P

Bernacki, RJ

机构：

[1] SUNY Stony Brook, Dept Chem, Stony Brook, NY 11794 USA

[2] Roswell Pk Canc Inst, Dept Expt Therapeut, Buffalo, NY 14263 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1999年 / 9卷 / 24期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0960-894X(99)00629-0

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of second-generation taxoids bearing a substituent on the C-2-benzoyl group and modifications at C-3'/C-10 positions was synthesized. These taxoids exhibited 2-3 orders of magnitude higher potency than that of paclitaxel against drug-resistant human breast cancer cell lines. It is also noteworthy that three taxoids showed almost no difference in activity against drug-resistant and drug-sensitive cell lines, which are categorized as "advanced second generation taxoids". (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：3423 / 3428

页数：6

相关论文

共 18 条

[1]

[Anonymous], 1999, ADV MED CH

[2] A NEW SERIES OF PHOTOACTIVATABLE AND IODINATABLE LINEAR VASOPRESSIN ANTAGONISTS [J].

CARNAZZI, E ;

AUMELAS, A ;

BARBERIS, C ;

GUILLON, G ;

SEYER, R .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (12) :1841-1849

[3] UNEXPECTEDLY FACILE HYDROLYSIS OF THE 2-BENZOATE GROUP OF TAXOL AND SYNTHESES OF ANALOGS WITH INCREASED ACTIVITIES [J].

CHAUDHARY, AG ;

GHARPURE, MM ;

RIMOLDI, JM ;

CHORDIA, MD ;

GUNATILAKA, AAL ;

KINGSTON, DGI ;

GROVER, S ;

LIN, CM ;

HAMEL, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (09) :4097-4098

[4] STRUCTURE-ACTIVITY-RELATIONSHIPS OF TAXOL(R) - SYNTHESIS AND BIOLOGICAL EVALUATION OF C2 TAXOL ANALOGS [J].

CHEN, SH ;

FARINA, V ;

WEI, JM ;

LONG, B ;

FAIRCHILD, C ;

MAMBER, SW ;

KADOW, JF ;

VYAS, D ;

DOYLE, TW .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (03) :479-482

[5] PACLITAXEL AND DOCETAXEL PHOTOAFFINITY LABELS [J].

GEORG, GI ;

BOGE, TC ;

PARK, H ;

HIMES, RH .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (06) :615-620

[6]

GEORG GI, 1995, TAXOL SCI APPL, P317

[7] TAXOL AND TAXOTERE - DISCOVERY, CHEMISTRY, AND STRUCTURE-ACTIVITY-RELATIONSHIPS [J].

GUENARD, D ;

GUERITTEVOEGELEIN, F ;

POTIER, P .

ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (04) :160-167

[8] Synthesis and biological evaluation of 2-acyl analogues of paclitaxel (Taxol) [J].

Kingston, DGI ;

Chaudhary, AG ;

Chordia, MD ;

Gharpure, M ;

Gunatilaka, AAL ;

Higgs, PI ;

Rimoldi, JM ;

Samala, L ;

Jagtap, PG ;

Giannakakou, P ;

Jiang, YQ ;

Lin, CM ;

Hamel, E ;

Long, BH ;

Fairchild, CR ;

Johnston, KA .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (19) :3715-3726

[9]

KINGSTON DGI, 1969, ACS SYM SER, V583, P203

[10] Synthesis and biological evaluation of D-ring-modified taxanes: 5(20)-azadocetaxel analogs [J].

MarderKarsenti, R ;

Dubois, J ;

Bricard, L ;

Guenard, D ;

GueritteVoegelein, F .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (19) :6631-6637