Structure of Colchicine

  title={Structure of Colchicine},
  author={M. Dewar},
IN view of the remarkable physiological properties of colchicine its chemical nature is of some interest. Until recently, the structure (I) proposed by Windaus1 has been generally accepted, although the stability of colchicine did not suggest a 9-amino-9: 10-di-hydrophenanthrene system, and although the salicylaldehyde enol structure of ring C appeared fantastic. Cohen, Cook and Roe2 have now provided evidence that ring B must be 7-membered, but the exact location of the acetamido group remains… Expand
Structure of Colchicine
THE suggestion of Dewar1 that ring G of colchicine is 7-membered is interesting, and the arguments which he advances in favour of this merit consideration. I cannot, however, accept his statementExpand
Recent developments in colchicum alkaloids
Partial synthesis of a variety of minor Colchicum alkaloids, including demecolcine, cornigerine, colchifoline, and phenolic congeners has been accomplished, and Affinity labelled colchicine which binds well to tubulin has been prepared and is potentially useful for mapping the colchichine binding site on tubulin. Expand
Conformational analysis of colchicine and isocolchicine by molecular mechanics
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-rayExpand
Chapter X Colchicine
This chapter presents a study on colchicine, an intensely poisonous substance and its toxic symptoms, which are described in the chapter. Expand
Colchicine, A Phenylethylisoquinoline Alkaloid Derived from L-Tyrosine
It is interesting to know the genesis of the name of the genus Colchicium, which derives its name from “Colchis,” a region of east black sea, the abode of the notorious poisoner Medea (Greek mythology), which is now the commercial source of colchicine. Expand
Enantioselective total synthesis of (-)-colchicine, (+)-demecolcinone and metacolchicine: determination of the absolute configurations of the latter two alkaloids.
Here, we describe a concise, enantioselective, and scalable synthesis of (-)-colchicine (9.2% overall yield, >99% ee). Moreover, we have also achieved the first syntheses of (+)-demecolcinone andExpand
Chemical mechanisms involved during the biosynthesis of tropolones.
Tropolones are seven-membered aromatic rings which feature in the core of several important bioactive natural products including colchicine and stipitatic acid and the key steps all involve ring expansion of an alkylated 6- Membered ring. Expand
Natural Tropolones and Some Related Troponoids
Cycloheptatriene, a seven-membered ring polyene, was obtained by Ladenburg (118) in 1881, and by Merling (122) in 1891, by the systematic degradation of an alkaloid, tropine. Its structure wasExpand
Synthesis of allocolchicinoids: a 50 year journey
Published data on the stereo- and enantioselective synthesis of allocolchicinoids, which are of interest as antitumour agents, are summarized. The stereochemistry of these compounds is described. TwoExpand
The interactions of tropolone with magnesium ions and tubulin.
Fluorescence and difference absorption spectroscopy experiments performed at essentially constant Mg2 activity indicate that tubulin does bind tropolone, but the optical effects are too weak to use in quantitative studies. Expand


Structure of Stipitatic Acid
Birkinshaw, Chambers and Raistrick1 have described stipitatic acid, a metabolite of the mould Penicillium stipitatum, to which, after lengthy examination, they could ascribe no reasonable structure.Expand