Conformational Analysis of Colchicine and Isocolchicine by Molecular Mechanics

Document Type

Article

Language

eng

Publication Date

1988

Publisher

Elsevier

Source Publication

Tetrahedron

Source ISSN

0040-4020

Abstract

The structures of isocolchicine (3) and colchicine (1) have been calculated using the MMX routine. The low energy conformations for isocolchicine and colchicine fit well with x-ray crystallographic data. The B ring atropisomer of isocolchicine, which can be spectroscopically observed, is calculated to be <1 kcalmole higher in energy than 3. The boat-boat inversion conformer of colchicine, which has been predicted to be important in the binding of 1 to tubulin, is also calculated. The B ring geometry of this isomer does not differ to the extent previously predicted.

Comments

Tetrahedron, Vol. 44, No. 24 (1988): 7409-7412. DOI.

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