68547-97-7

Usage

Chemical Properties

Off-White Solid

Upstream product

• 1570-45-2 isonicotinic acid ethylester 
• 1293370-62-3 di-tert-butyl 5,6-dihydropyridine-1,4(2H)-dicarboxylate 
• 503545-00-4 1-benzyl-2,6-dioxo-1,2,3,6-tetrahydropyridine-4-carboxylic acid ethyl ester 
• 158984-76-0 1,2,3,6-tetrahydro-1-(phenylmethyl)-4-pyridinemethanol 
• 503544-95-4 1-benzyl-1,2,3,6-tetrahydropyridine-4-carbaldehyde 
• 79858-48-3 1-benzyl-1,2,3,6-tetrahydro-pyridine-4-carboxylic acid 
• 76309-83-6 1,2,3,6-Tetrahydro-pyridine-4-carboxylic acid acetoxymethyl ester; compound with (E)-but-2-enedioic acid 

Downstream Products

• 70684-82-1 methyl 1,2,3,6-tetrahydropyridine-4-carboxylate hydrochloride 

Relevant academic research and scientific papers

Alternative Synthesis of Isoguvacine and Its N-(2-Aryl-2-hydroxyethyl) Derivatives

Isonicotinic acid ethyl ester reacted with substituted phenacyl bromides to give the corresponding quaternary salts which were reduced with sodium tetrahydridoborate to ethyl 1-(2-aryl-2-hydroxyethyl)-1,2,3,6- tetrahydropyridine-4-carboxylates. The presence of an electron-donating substituent in the benzene ring of the latter is a necessary condition for their acid hydrolysis with cleavage of the C–N bond and formation of isoguvacine. Analogous derivatives with electron-withdrawing substituents are not converted to isoguvacine under similar conditions.

Palladium catalyzed alkoxy- and aminocarbonylation of vinyl tosylates

Chemical equations presented. The palladium catalyzed alkoxycarbonylation and aminocarbonylation of vinyl tosylates are described. A variety of ketone and aldehyde derived vinyl tosylates may be carbonylated in the presence of primary, secondary, and tert

An efficient synthesis of N-alkyl-4-substituted 3H-pyridine-2,6-dione. Synthesis of isoguvacine and MDL-11,939

An efficient route towards the synthesis of N-alkyl-4-substituted 3H-pyridine-2,6-dione using various N-alkyl-α-sulfonylacetamides and two α,β-unsaturated esters as starting materials is described. Isoguvacine and MDL-11,939 with have potential biological activities were synthesized via this strategy.

Esters of Isoguvacine as Potential Prodrugs

The syntheses of the methyl ester, butyl ester, (ethoxycarbonyl)methyl ester, and 11 (acyloxy)methyl esters of the potent γ-aminobutyric acid agonist isoguvacine (1,2,3,6-tetrahydropyridine-4-carboxylic acid) are described.The chemical stability of the esters and their in vitro rates of hydrolysis under approximately physiological conditions by nonspecific esterases from human serum were examined.A selected number of the esters were tested for antagonism of convulsions induced by bicuculline, isoniazide, and by electroshock.While the compounds showed only weak activities in the bicuculline and isoniazide tests, a good correlation between in vitro rates of enzymatic hydrolysis and the time of onset of the antagonism of the electroshock-induced convulsions could be found.