STUDIES OF PHENANTHRENE DERIVATIVES V. HOMOLOGOUS ACIDS AND ALDEHYDES AND SOME OF THEIR DERIVATIVES

¹ From the Laboratory of Pharmacology, University of Michigan Medical School, Ann Arbor, Michigan

The group of phenanthrene derivatives described in this paper permits comparison (a) of a number of homologs, (b) of carboxylic and propionic acids and their amides and methyl esters, (c) of ketones and alcohols, and (d) of some additional position isomers.

Effectiveness is slightly increased in the higher homologs, in the alcohols as compared with the ketones and especially in propionic as compared with carboxylic acid. It is definitely decreased by the formation of the amide and the methyl ester of either phenanthrene carboxylic or phenanthryl propionic acid. On the other hand, the dimethyl amide of phenanthrene-3-carboxylic acid has as great an effect as the free acid itself.

The conclusion previously drawn in regard to position isomers is confirmed. 3-derivatives are uniformly more effective than phenanthrene derivatives formed by the introduction of the same substituent in either the 2- or the 9-position.

The peculiar incoordination, characterized by veratrine-like delayed relaxation, first seen with phenanthrene-9-carboxylic acid is also obtained although in less degree with each of the other 9-derivatives described in this paper.