Über Colchiceinamide

Abstract

Am Beispiel des Monomethylamids des Colchiceins wird gezeigt, dass sich die freien Tropolone, ähnlich wie Carbonsäuren, mit Aminen zu den entsprechenden Amiden umsetzen lassen. Dabei entstehen naturgemäss die beiden isomeren Formen nebeneinander.

Tropones and Tropolones

“…Numerous transformations have been carried out starting with colchicine and the above naturally occurring derivatives, both with the object of identifying the latter by partial synthesis and in order to prepare numerous analogs for biological testing. They include changes of substituents on the nitrogen (217, 381), numerous ethers in which the alkyl group (R = 0Alkyl in formula XXXVII) is changed (148, 360) as well as a large number of derivatives in which this group is replaced by amino (XXXVII: R = NH2) or various substituted amino (XXXVII: R = NHR" or NR") groups both in the colchicine series and in the isocolchicine series (partial formula XXXVIII) (28,129,148,360,362,381,439,440).…”

Reaction of colchicine with peptide amino groups

“…Absorption spectra, in water, pH 7-8, of'(1) colchicine, 4.55 X 10-5M;( 2 ) colchiceine N-methylamide, 4.0 X lO-'M;( 3 ) colchicineinyl-PDLL; ( 4 ) colchicineinyl-melittin; ( 5 ) colchiceinate anion, pH 8, 5 X 10-'MM. Spectra 3 and 4 are for diluted dialysate or column eluate, respectively, without isolation of products.…”