ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Some 27 N-acyl derivatives of isonicotinic acid hydrazide and 2-methylisonicotinic acid hydrazide with amino acids and acylamino acids have been synthesized. The synthesis of the acylamino acyl compounds was carried out according to three different methods:(1) condensation of an acylated amino acid hydrazide with isonicotinic acid chloride hydrochloride or 2-methylisonicotinic acid chloride hydrochloride, resp.,(2) condensation of an acylated amino acid chloride with isonicotinic acid hydrazide or 2-methylisonicotinic acid hydrazide, resp., and(3) condensation of an acylated amino acid thiol ester with isonicotinic acid hydrazide.The synthesis of the amino acid compounds with a free amino group was carried out in all cases by condensation of a carbobenzoxy amino acid with isonicotinic acid hydrazide according to the peptide synthesis of Boissonnas-Wieland with subsequent hydrogenolysis of the carbobenzoxy group. These substances have been isolated either as free bases or as the respective chlorohydrates.Biological tests revealed that, as a rule, derivatives of α-amino acids possess an activity comparable to that of unsubstituted isonicotinic acid hydrazide or 2-methylisonicotinic acid hydrazide, resp., derivatives of β- and γ-amino acids being almost inactive. All the derivatives exhibit lower acute toxicity than isoniazide. Some of them are practically non-toxic. The optical configuration of the amino acids frequently has a pronounced influence on the activity of the condensation products.
Additional Material:
9 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19560390127
Permalink
