Glycinamides

Another CNS active agent in this structural class is the tranquilizer-antidepressant caroxazone (52). Its published synthesis begins by reductive aminatiwi of salicylaldehyde and glycinamide to give The synthesis is completed by reaction with phosgene and sodium bicarbonate. ... 

In a similar vein, acylation of ami noketone 67 with chloroacetyl chloride affords the corresponding chloroamide 68. Reaction of that intermediate with ammonia serves to form the diazepine ring, possibly via the glycinamide. The product bentazepam (69) is described as a tranquilizer. ... 

Benzylmercaptopropionyl-L-tyrosyl-L-phenyalanyl-L-glutaminyl-L-asparaginyl-S-benzyl-L-cysteinyl-L-prolyl-N-tosyl-D-arginyl glycinamide Sodium Ammonia Acetic acid... 

The mixture is allowed to stand for 2 days at 20°C, after which twice its volume of ethyl-acetate is added and the resultant precipitate then washed with warm methanol. There are obtained 45 parts by weight of N-carbobenzoxy-S-benzyl-L-cysteinyl-L-phenylalanyl-L-phenylalanyl-L-glutaminyl-L-asparaginyl-S-benzyl-L-cysteinyl-L-prolyl-e-N-p-toluenesulfonyl-L-lysyl-glycinamide MP 222 C. 

CN [2S-(2a,5a,6P)]-iV-methyl-D-asparaginyl-A-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-l-azabicyclo[3.2.0]hept-6-yl)-D-2-(4-hydroxyphenyl)glycinamide... 

The ammonioacetonitrile complex (206) reacts with NH3 to produce the amidine-bonded aminoacetamidine (207) complex, whereas in aqueous base it hydrolyzes to the amid o-A -bo ruled glycinamide complex (208).908 Acid-catalyzed linkage isomerization to first the O-bound form (209) precedes formation ultimately of the amino-bonded isomer (210) as the stable product upon deprotonation of the free amine above pH 6. 

Reaction Enthalpies for ML = M + L, where M = Na and K and L = Acetamide, N,N-ethylacetamide, N,N-Dimethylacetamide, Glycine, Glycinamide, Glycylglycine and Succinamide... 

Jiao, D., M. Barfield, and V. J. Hruby. 1993. Ab Initio IGLO Study of the ip- and < i-Angle Dependence of the I3C Chemical Shifts in the Model Peptide N-Acetyl-N -methyl-glycinamide. J. Am. Chem. Soc. 115, 10883-10887. 

Subsequently, in a patent application, isoquinoline glycinamides such as 2 were claimed as collagen PHD inhibitors [40], and an additional patent application claimed isoquinoline glycinamides as HIF PHD inhibitors [41]. 

Equation 1 is catalyzed by glycinamide ribotide (GAR) trans-formylase and Equation 2 is catalyzed by aminoimidazole-carboxamide ribotide (AICAR) transformylase. 

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