56304-64-4

Upstream product

• 103-79-7 1-phenyl-acetone 
• 107-91-5 cyanoacetic acid amide 
• 109-94-4 formic acid ethyl ester 
• 121017-79-6 2-benzyl-5-cyano-1,6-dihydro-6-oxo-3-methoxycarbonyl pyridine 
• 116344-11-7 methyl 2-((dimethylamino)methylene)-3-oxo-4-phenylbutanoate 
• 121017-85-4 2-Benzyl-5-cyano-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid 

Downstream Products

• 147283-33-8 {6-Benzyl-2-oxo-1-[(3,3,3-trifluoro-2-hydroxy-1-isopropyl-propylcarbamoyl)-methyl]-1,2-dihydro-pyridin-3-yl}-carbamic acid benzyl ester 
• 1025884-79-0 (6-Benzyl-3-benzyloxycarbonylamino-2-oxo-2H-pyridin-1-yl)-acetic acid 
• 56304-31-5 6-benzyl-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid 

Relevant academic research and scientific papers

Nonpeptidic inhibitors of human leukocyte elastase. 2. Design, synthesis, and in vitro activity of a series of 3-amino-6-arylopyridin-2-one trifluoromethyl ketones

A series of potent nonpeptidic inhibitors of the enzyme human leukocyte elastase (HLE) is reported. These inhibitors contain a 3-amino-2-pyridone ring as a central template in which the pyridone carbonyl and 3-position NH group are thought to form important hydrogen bonding interactions with the Val-216 residue of HLE. Substitution of the 6-position of the pyridone ring by various alkyl and aryl groups was found to afford increases in the in vitro potency of these inhibitors. A 6-position phenyl group, compound 10f, was found to result in a large increase in binding affinity, which was not obtained when the phenyl group was placed in either the 4- or 5-position of the molecule. Compound 10f was found to have good selectivity for HLE over other proteolytic enzymes, with the exception of bovine pancreatic chymotrypsin (BPC). Substitution of the 6-phenyl group in these molecules was found to decrease binding affinity for BPC without adversely affecting affinity for HLE.

Synthesis and cardiotonic activity of esters of 2-substituted 5-cyano-1,6-dihydro-6-oxo-3-pyridinecarboxylic acids. Crystal structure of 2-methyl, 2-t-butyl and 2-phenyl esters

The synthesis of ethyl and methyl esters of 2-substituted 5-cyano-1,6-dihydro-6-oxo-3-pyridinecarboxylic acids by reaction of ethyl or methyl 2-dimethylaminomethylene-3-oxoalkanoates with sodium cyanoacetamide is described. These esters gave by alkaline hydrolysis the corresponding carboxylic acids, which were decarboxylated to 6-substituted 1,2-dihydro-2-oxo-3-pyridinecarbonitriles. As milrinone analogues, nearly all the above compounds were tested on contractile activity and frequency rate of spontaneously beating atria and electrically driven left atria from guinea pigs. Among the esters, ethyl 5-cyano-1,6-dihydro-2-methyl-6-oxo-3-pyridinecarboxylate induced positive inotropic and chronotropic effects superior to those caused by milrinone. By increasing or branching the 2-substituent, the activity decreased until faded or even reversed. Carboxylic acids and nitriles were less active than milrinone. Some aspects of the structure-activity relationship of these compounds are discussed on the basis of X-ray structural analyses of 2-methyl, 2-t-butyl and 2-phenyl esters.

Substituted N-(1,2-dihydro-2-oxonicotinyl)-cephalexins and -cephaloglycins

Novel organic amide compounds which are substituted N-(1,2-dihydro-2-oxonicotinyl)-ampicillins, -cephalexins and -cephaloglycins having broad spectrum antibacterial utility are provided by (a) reacting the free amino acid ampicillin, cephalexin or cephaloglycin or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding 1,2-dihydro-2-oxonicotinic acid or (b) reacting the free amino acid 6-aminopenicillanic acid, 7-aminocephalosporanic acid or 7-amino-3-methylceph-3-em-4-carboxylic acid or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding N-(1,2-dihydro-2-oxonicotinyl)-2-phenylglycine.