Aminoalkylglyoxalines / by Frank Lee Pyman.

  • Pyman, Frank Lee.
Date:
[between 1910 and 1919?]
Catalogue details

Licence: In copyright

Credit: Aminoalkylglyoxalines / by Frank Lee Pyman. Source: Wellcome Collection.

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    (G> CCXLV.—AminoaJ kylglyoxalines. By Frank Lee Pyman. In view of the great physiological activity of 4(or 5)-£-aminoethyl- glyoxaline (compare Dale and Laidlaw, J. Physiol., 1910, 41, 318), the preparation of several of its homologues has been carried out, and these have been physiologically tested by Dr. P. P. Laidlaw, of the Wellcome Physiological Research Laboratories, to whom the author is indebted for the results given in this paper. In this connexion the recent preparation of other homologues of this base by Ewins (this vol., p. 2052) may be noted. Barger and Dale (J. Physiol., 1910, 41, 19), in dealing with the relationship between the chemical constitution of the amines and tlieir physiological action, have shown that the activity varies greatly with the length of the side-chain; in the fatty series the maximum of activity is attained at hexylamine, whilst the most active phenylalkylamine is phenylethylamine, having a fatty side- chain of two carbon atoms. It appeared, therefore, of interest to determine the optimum length of side-chain for physiological effect in the aminoalkylglyoxalines. For comparison with 4(or 5)-£-amino- ethylglyoxaline, 4(or 5)-aminomethylglyoxaline and 4(or 5)-y-amino- propylglyoxaline were required, but since the latter was not readily accessible its methyl homologue, 4(or 5)-y-aminobutylglyoxaline, was prepared and tested in its place. Compared with 4(or 5)-/3-amino- ethylglyoxaline, the activity of these bases proved to be negligible. 4(or 5)-Aminomethylglyoxaline (I) has recently been described by Windaus and Opitz (Per., 1911, 44, 1721), who prepared it by Curtius method from glyoxaline-4(or 5)-acetic acid obtained from histidine. It may, however, readily be prepared synthetically by suitably oxidising 2-thiol-4(or 5)-aminomethylglyoxaline (II). It has previously been shown (this vol., p. 669) that the customary method of oxidising thiolglyoxalines to glyoxalines by means of nitric acid leads, m the case of this compound, to 4(or 5)-hydroxymethylgly- oxaline (III). If, however, an oxidising agent not producing nitrous acid were employed, the formation of 4(or 5)-aminomethylglyoxaline would be possible. Other oxidising agents were therefore tried, and * 2-CH2.< (I.) 2 v~ (II.) CH-NH ^ HOCH./C-1ST °H (IH.) HNOo --^
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