Synthesis and bioactivity of 2,4-diacyl analogues of paclitaxel

被引：16

作者：

Chordia, MD

Yuan, HQ

Jagtap, PG

Kadow, JF

Long, BH

Fairchild, CR

Johnston, KA

Kingston, DGI ^{[1
]}

机构：

[1] Virginia Polytech Inst & State Univ, Dept Chem, Blacksburg, VA 24061 USA

[2] Bristol Myers Squibb Co, Pharmaceut Res Inst, Wallingford, CT 06492 USA

[3] Bristol Myers Squibb Co, Pharmaceut Res Inst, Princeton, NJ USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2001年 / 9卷 / 01期

关键词：

D O I：

10.1016/S0968-0896(00)00233-9

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The 2,4-diacyl paclitaxel analogues 8a-8r were prepared from paclitaxel by acylation of 4-deacetyl-2-debenzoylpaclitaxel 1,2-carbonate (3) followed either by hydrolysis of the carbonate and acylation or by direct treatment of the carbonate with an aryllithium. Some of the resulting derivatives showed significantly improved tubulin assembly activity and cytotoxicity as compared with paclitaxel; in some cases this improvement was especially significant for paclitaxel-resistant cell lines. (C) 2000 Elsevier Science Ltd. All rights reserved.

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页码：171 / 178

页数：8

相关论文

共 34 条

[1] 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

[2] NOVEL C-4 PACLITAXEL (TAXOL(R)) ANALOGS - POTENT ANTITUMOR AGENTS [J].

CHEN, SH ;

WEI, JM ;

LONG, BH ;

FAIRCHILD, CA ;

CARBONI, J ;

MAMBER, SW ;

ROSE, WC ;

JOHNSTON, K ;

CASAZZA, AM ;

KADOW, JF ;

FARINA, V ;

VYAS, DM ;

DOYLE, TW .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (22) :2741-2746

[3] FIRST SYNTHESES OF NOVEL PACLITAXEL(TAXOL) ANALOGS MODIFIED AT THE C4-POSITION [J].

CHEN, SH ;

KADOW, JF ;

FARINA, V ;

FAIRCHILD, CR ;

JOHNSTON, KA .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6156-6158

[4] Synthesis of a paclitaxel isomer: C-2-acetoxy-C-4-Benzoate paclitaxel [J].

Chen, SH ;

Farina, V ;

Vyas, DM ;

Doyle, TW .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (16) :2227-2230

[5]

CHEN SH, 1994, ACS SYM SER, V583, P247

[6] SYNTHESIS AND BIOLOGICAL EVALUATION OF 4-DEACETOXYPACLITAXEL [J].

CHORDIA, MD ;

CHAUDHARY, AG ;

KINGSTON, DGI ;

JIANG, YQ ;

HAMEL, E .

TETRAHEDRON LETTERS, 1994, 35 (37) :6843-6846

[7] Synthesis and biological activity of beta-glucuronyl carbamate-based prodrugs of paclitaxel as potential candidates for ADEPT [J].

deBont, DBA ;

Leenders, RGG ;

Haisma, HJ ;

vanderMeulenMuileman, I ;

Scheeren, HW .

BIOORGANIC & MEDICINAL CHEMISTRY, 1997, 5 (02) :405-414

[8] SYNTHESIS OF CONGENERS AND PRODRUGS .3. WATER-SOLUBLE PRODRUGS OF TAXOL WITH POTENT ANTITUMOR-ACTIVITY [J].

DEUTSCH, HM ;

GLINSKI, JA ;

HERNANDEZ, M ;

HAUGWITZ, RD ;

NARAYANAN, VL ;

SUFFNESS, M ;

ZALKOW, LH .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (04) :788-792

[9] SELECTIVE C-2 AND C-4 DEACYLATION AND ACYLATION OF TAXOL - THE FIRST SYNTHESIS OF A C-4 SUBSTITUTED TAXOL ANALOG [J].

GEORG, GI ;

ALI, SM ;

BOGE, TC ;

DATTA, A ;

FALBORG, L ;

HIMES, RH .

TETRAHEDRON LETTERS, 1994, 35 (48) :8931-8934

[10]

GEORG GI, 1995, TAXOL SCI APPL, P317

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