Structure of condensation products between isonicotinylhydrazine and reducing sugars by ¹³C nmr spectroscopy

Abstract

. Can. J. Chem. 59,641 (1981). The structures of the condensation products of isonicotinylhydrazine (isoniazid) with galactose, glucose, lactose, maltose, glycolaldehyde and glyceraldehyde were investigated by examination of their I3C nmr spectra, determined in D,O and DMSO-d, solution. Spectroscopic data and their interpretation are presented. Spectroscopic and chromatographic (hplc) evidence are combined to show that the products formed with the four sugars exist in solution predominantly as I-(1P-pyranosy1)-2-isonicotinylhydrazines, and to a lesser extent as the analogous la-pyranosyl anomers. 'The products formed with glycolaldehyde and glyceraldehyde are normal hydrazones.KEITH BAILEY et ANDREW G. BUTTERFIELD. Can. J. Chem. 59,641 (1981). Nous avons etudik les structures chimiques des produits de condensation entre I'isonicotinyl-hydrazine (isoniazide) et le galactose, le glucose, le maltose, le glyceraldehyde et le glycolaldehyde g r k e B leur spectres I3C rmn en solutions dans D,O et d,-DMSO. Les donnees spectroscopiques ainsi que leurs interpretations seront presentees. Ces donntes spectroscopiques renforcees avec des donnees chromatographiques (hplc) demontrent que les produits glucidiques se trouvent surtout dans la forme de 1-(lp-pyranosy1)-2-isonicotinyl hydrazine contenant une quantite moindre d'anomkres la-pyranosyl, tandis que les produits des deux aldehydes sont des hydrazones ordinaires. Introductionand hplc. Shortly after the completion of our work, Impurities in isonicotinylhydrazine (isoniazid, Take& (7) reported 13C nmr and other data for the isonicotinic acid hydrazide) drug formulations, INH-glucose product and some related substances formed by condensation of the drug with either lac-which Prompts us to repo* the

Chemical Incompatibility Between Procainamide Hydrochloride and Glucose Following Intravenous Admixture

“…Carbons near the procainamide-glucose bond (C, -C5, C6, and Cl,) all showed the appearance of multiple signals in keeping with their being procainamide and the aand p-anomers of glucose and glucosylamine present ( Table 2). The CIt anomeric carbon displayed four distinct signals in keeping with the presence of aand p-glucose and aand P-glucosylamines, the chemical shifts being confirmed by their relationship to authentic values for a-and p-glucose and to the analogous phenylglucosylamines (Bailey & Butterfield 1981;Chavis et a1 1983).…”

Effect of the Nonionic Surfactant Poloxamer 338 on the Fate and Deposition of Polystyrene Microspheres Following Intravenous Administration

“…Clark and Chan (1) have reported the advantages of combining conventional reverse-phase chromatography and postcolumn ionization into a single system. In this study, their analytical approach has been successfully employed in the assay of butabarbital sodium elixir.…”

Synthesis of Biologically Active [4‐(4‐Bromophenyl)‐2‐thiazolyl]hydrazones and their D‐Galactose Derivatives

“…The presence of 13 in the pyranosyl form was deduced by comparing its 13 C NMR spectrum with those of α-and β-D-galactopyranose 15 and 16, [22][23][24] and 1-(1β-Dgalactopyranosyl)-2-isonicotinoylhydrazine (17). 25 Substitution of the hydroxyl group at C-1 of 16 with the hydrazine residue causes a shift for all carbon signals of 13, but with a small effect on the magnitude of chemical shifts of C-3 and C-5 because they have the same stereochemical relationship to the anomeric C-1, consequently C-3 and C-5 can be identified at δ c 72.81 and 77.00, respectively. The C-5 in 13 resonated at almost a similar chemical shift to that of 17, while C-6 appeared in the highest field at δ c 61.15.…”

“…The aromatic and thiazole carbons were resonated in the range of δ c 104.46-175.28. [22] 62.00 [23] 61.90 [24] 61.90 [22] 61.81 [23] 61.70 [24] 60.55 [25] 61.15…”