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Rigid Analogues of Antimitotic Indolobenzazepinones: New Insights into Tubulin Binding via Molecular Modeling.

Abstract：

:Two rigid analogues of 5-ethylindolobenzazepinone 4, a potent cytotoxic agent and inhibitor of tubulin polymerization, were prepared. The first was the indane derivative 5, in which the ethyl group is attached to the benzo moiety. The second was the pyrrolidine analogue 6, in which the ethyl chain was bound to the lactam nitrogen. While both compounds were considerably less active inhibitors of KB cell growth as compared to 4, inhibition of tubulin polymerization was only moderately reduced. Tubulin docking studies indicated that the aR and aS atropoisomers of 5 and 6 occupy different binding pockets at the colchicine binding site. Conversely, both aS-5 and aS-6 occupy the same binding pocket as aSS-4 but do not benefit from the favorable hydrophobic interactions provided by the C5 alkyl group of 4, thus possibly explaining their lower activities.

journal_name

ACS Med Chem Lett

journal_title

ACS medicinal chemistry letters

authors

Pons V,Beaumont S,Tran Huu Dau ME,Iorga BI,Dodd RH

doi

10.1021/ml200024y

subject

Has Abstract

pub_date

2011-06-05 00:00:00

pages

565-70

issue

8

issn

1948-5875

journal_volume

2

pub_type

杂志文章

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