Acetylcolchinyl methyl ether

The availability of ketone 68 made possible for the first time the introduction of an amide group at C-5 instead of C-7, as found in natural colchicine (1) and N-acetylcolchinyl methyl ether (58), and to study the effects of this modification on biological activity. The synthesis of the... 

Although the allocolchicinoids allocolchicine (12) and /V-acetylcolchinyl methyl ether (58) were found to be highly potent in vitro, their in vivo activity in the P388 lymphocytic leukemia mouse screen, with TIC values of 114 for 12, and 108 for 58, at the highest doses, was much less than expected (115). It may well be that the isomerization of these compounds to inactive isomers which occurs much easier in the alio series is the reason for the relatively weak in vivo activity of the alio compounds so far tested. 

F. R. Quinn, National Cancer Institute, National Institutes of Health, personal communication. Allocolchicine was tested under the code number NSC 406042, and N-acetylcolchinyl methyl ether was tested under the code number NSC 51046. 

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