Synthesis and tubulin-binding properties of new allocolchicinoids

被引：27

作者：

Boyer, Francois-Didier ^{[1
]}

Dubois, Joelle ^{[1
]}

Thoret, Sylviane ^{[1
]}

Dau, Marie-Elise Tran Huu ^{[1
]}

Hanna, Issam ^{[2
]}

机构：

[1] INRA, Ctr Rech Gif, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

[2] Ecole Polytech, Synth Organ Lab, CNRS, UMR 7652, F-91128 Palaiseau, France

来源：

BIOORGANIC CHEMISTRY | 2010年 / 38卷 / 4-6期

关键词：

Allocolchicinoids; Tubulin inhibitors; Enyne; Metathesis; Diets-Alder reaction; RING-CLOSING METATHESIS; ENYNE METATHESIS; ASYMMETRIC-SYNTHESIS; CARBENE COMPLEXES; N-ACETYLCOLCHINOL; B-RINGS; COLCHICINE; ANALOGS; INHIBITION; CHEMISTRY;

D O I：

10.1016/j.bioorg.2010.03.003

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：

Allocolchicinoids with B- and C-ring variations were synthesized using sequential enyne-metathesis/Diets-Alder reactions (A -> AB -> ABC approach) and evaluated for their inhibitory effect on tubulin assembly in vitro. (-)-Allocolchicine 11 with methyl ester at C10 and (+/-)-cyclopropyl allocolchicinoid 32 exhibit similar activity than (-)-colchicine (1), probably derived from a similar flexibility in the biphenyl system. The presence of methyl ester at C10 led to a little loss in potency in comparison with the series with methyl ester at C9. A complete loss of activity was observed for allocolchicine 9 with methyl ester at C11. (C) 2010 Elsevier Inc. All rights reserved.

引用

页码：149 / 158

页数：10

共 55 条

[1] SYNTHESIS AND TUBULIN-BINDING PROPERTIES OF SOME AC-RING AND ABC-RING ANALOGS OF ALLOCOLCHICINE [J].

BANWELL, MG ;

CAMERON, JM ;

CORBETT, M ;

DUPUCHE, JR ;

HAMEL, E ;

LAMBERT, JN ;

LIN, CM ;

MACKAY, MF .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1992, 45 (12) :1967-1982

[2] Stereochemical variations on the colchicine motif .2. Unexpected tetracyclic isoxazole derivatives [J].

Berg, U ;

Bladh, H ;

Hoff, M ;

Svensson, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (09) :1697-1704

[3] Novel B-ring modified allocolchicinoids of the NCME series:: Design, synthesis, antimicrotubule activity and cytotoxicity [J].

Bergemann, S ;

Brecht, R ;

Büttner, F ;

Guénard, D ;

Gust, R ;

Seitz, G ;

Stubbs, MT ;

Thoret, S .

BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (07) :1269-1281

[4] A synthesis of (aR,7S)-(-)-N-acetylcolchinol and its conjugate with a cyclic RGD peptide [J].

Besong, Gilbert ;

Billen, Denis ;

Dager, Indu ;

Kocienski, Philip ;

Sliwinski, Eric ;

Tai, Lik Ren ;

Boyle, F. Thomas .

TETRAHEDRON, 2008, 64 (21) :4700-4710

[5] Synthesis of (S)-(-)-N-acetylcolchinol using intramolecular biaryl oxidative coupling [J].

Besong, Gilbert ;

Jarowicki, Krzysztof ;

Kocienski, Philip J. ;

Sliwinski, Eric ;

Boyle, F. Thomas .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (11) :2193-2207

[6] Anti-mitotic activity of colchicine and the structural basis for its interaction with tubulin [J].

Bhattacharyya, Bhabatarak ;

Panda, Dulal ;

Gupta, Suvroma ;

Banerjee, Mithu .

MEDICINAL RESEARCH REVIEWS, 2008, 28 (01) :155-183

[7] Fluorine in medicinal chemistry [J].

Böhm, HJ ;

Banner, D ;

Bendels, S ;

Kansy, M ;

Kuhn, B ;

Müller, K ;

Obst-Sander, U ;

Stahl, M .

CHEMBIOCHEM, 2004, 5 (05) :637-643

[8]

Bourgeois D, 2000, SYNTHESIS-STUTTGART, P869

[9]

Boye O., 1992, ALKALOIDS, V41, P125

[10] Formal synthesis of (±)-guanacastepene A:: A tandem ring-closing metathesis approach [J].

Boyer, FD ;

Hanna, I ;

Ricard, L .

ORGANIC LETTERS, 2004, 6 (11) :1817-1820

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