Synthesis of combretastatins A-1 and B-1

被引：24

作者：

Odlo, K ^{[1
]}

Klaveness, J ^{[1
]}

Rongved, P ^{[1
]}

Hansen, TV ^{[1
]}

机构：

[1] Univ Oslo, Sch Pharm, Dept Pharmaceut Chem, N-0316 Oslo, Norway

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 07期

关键词：

combretastatins; tubulin inhibitors; Sonogashira reaction;

D O I：

10.1016/j.tetlet.2005.12.037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Combretastatins A-1 and B-1 have been synthesized by coupling MOM-protected p-iodomethoxycatechol with 3,4,5-trimethoxyphenylacetylene in a Sonogashira reaction. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1101 / 1103

页数：3

共 23 条

[1] New small-molecule tubulin inhibitors [J].

Bacher, G ;

Beckers, T ;

Emig, P ;

Klenner, T ;

Kutscher, B ;

Nickel, B .

PURE AND APPLIED CHEMISTRY, 2001, 73 (09) :1459-1464

[2] Comparative molecular field analysis of colchicine inhibition and tubulin polymerization for combretastatins binding to the colchicine binding site on β-tubulin [J].

Brown, ML ;

Rieger, JM ;

Macdonald, TL .

BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (06) :1433-1441

[3] Direct biooxidation of arenes to corresponding catechols with E-coli JM109 (pDTG602).: Application to synthesis of combretastatins A-1 and B-1 [J].

Bui, VP ;

Hudlicky, T ;

Hansen, TV ;

Stenstrom, Y .

TETRAHEDRON LETTERS, 2002, 43 (15) :2839-2841

[4] ONE-STEP CONVERSION OF CARBONYL-COMPOUNDS INTO ACETYLENES [J].

COLVIN, EW ;

HAMILL, BJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (05) :151-152

[5]

Dzierzbicka K, 2004, POL J CHEM, V78, P323

[6] Structural requirements for the interaction of combretastatins with tubulin: how important is the trimethoxy unit? [J].

Gaukroger, K ;

Hadfield, JA ;

Lawrence, NJ ;

Nolan, S ;

McGown, AT .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (17) :3033-3037

[7] Preparation and evaluation of diarylalkynes as antitumour agents [J].

Hadfield, JA ;

McGown, AT .

SYNTHETIC COMMUNICATIONS, 1998, 28 (08) :1421-1431

[8] ORTHO-FORMYLATION OF PHENOLS; PREPARATION OF 3-BROMOSALICYLALDEHYDE (3-Bromo-2-hydroxybenzaldehyde) \ [J].

Hansen, Trond Vidar ;

Skattebol, Lars .

ORGANIC SYNTHESES, 2005, 82 :64-68

[9] One-pot synthesis of substituted catechols from the corresponding phenols [J].

Hansen, TV ;

Skattebol, L .

TETRAHEDRON LETTERS, 2005, 46 (19) :3357-3358

[10] Convenient method for the ortho-formylation of phenols [J].

Hofslokken, NU ;

Skattebol, L .

ACTA CHEMICA SCANDINAVICA, 1999, 53 (04) :258-262

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