Some derivatives of 4(or 5)-methyl-glyoxaline / by Arthur James Ewins.

  • Ewins, Arthur James.
Date:
[between 1910 and 1919?]
Catalogue details

Licence: In copyright

Credit: Some derivatives of 4(or 5)-methyl-glyoxaline / by Arthur James Ewins. Source: Wellcome Collection.

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    fl, % ! ? COXXXII.—Some Derivatives of 4(or b)-Methyl- glyoxaline. By Arthur James Ewins. The recent discovery of the high degree of physiological activity attaching to the base 4(or5)-j8-aminoethylglyoxaline (Dale and Laidlaw, J. Physiol., 1910, 41, 318) and its possible therapeutical importance, has served to stimulate research in the direction of glyoxaline derivatives generally. The most interesting result so far has been the synthesis and resolution of the biochemically important amino-acid histidine (a-amino-/3-glyoxaline-4(or 5)-propionic acid) by Pyman (this vol., p. 1386), who has also devised a new synthetic method of preparing the base 4(or 5)-/3-aminoethylglyoxaline (this vol., p. 668) in place of the tedious and expensive method employed by Windaus and Vogt (Per., 1907, 40, 3691). Of the numerous derivatives obtained in the course of this work, however, none was found to be possessed of physiological activity in any marked degree. Quite recently Windaus and Opitz (Per., 1911, 44, 1721) have obtained the alcohol 4(or 5)-/3-hydroxyethylglyoxaline corresponding with the active base already mentioned, and, moreover, have syn¬ thesised 4(or 5)-/3-aminomethylglyoxaline, the lower homologue of this base. From experiments carried out in these laboratories, this new base has been found, however, to- be almost devoid of physiological action. The present communication deals in the main with the synthesis of a methyl homologue of 4(or 5)-/3-aminoethylglyoxaline, namely, ^ 4 (or 5 )-m ethyl-5 (or 4)-/3-aminoethylglyoxaline, which it was expected might prove physiologically interesting. The structural relationship of the two bases is best seen from the following formulae: CH-NH 11 C--N >CH ch2-ch2*nh2 4(or 5)-j3-Amino- ethylglyoxaline. SMe-NH>CH. c N5 ch2-ch2-nh2 4(or 5)-Methyl-5(or 4)-/3-amino- ethylglyoxaline. these bases in each case being tautomeric (compare Byman, Trans.* 1910, 97, 1814). The synthesis of this methyl homologue of 4 (or 5)-/3 aminoethyl- glyoxaline was suggested by an observation made by Windaus (Per., 1909, 42, 758). It had been recorded by O. Gerngross (Per., 1909) 42, 398) that 4(or 5)-methylglyoxaline on treatment with chloral formed an additive product, which he considered to be