4138-19-6

Usage

Uses

Used in Pharmaceutical Industry:
6-tert-Butyl-2-oxo-1,2-dihydropyridine-3-carbonitrile is used as a building block for the synthesis of various pharmaceuticals. Its chemical structure allows it to be a versatile intermediate in the development of bioactive molecules, making it an important compound in medicinal chemistry.
Used in Agrochemical Industry:
6-tert-Butyl-2-oxo-1,2-dihydropyridine-3-carbonitrile is also used as a building block in the synthesis of agrochemicals, contributing to the development of effective and targeted pest control solutions.
Used as a Calcium Channel Blocker:
6-tert-Butyl-2-oxo-1,2-dihydropyridine-3-carbonitrile has been studied for its potential therapeutic applications, including its role as a calcium channel blocker. This property makes it a candidate for the treatment of cardiovascular diseases.
Used as a Vasodilator:
Additionally, it has the ability to act as a vasodilator, which can help improve blood flow and reduce blood pressure, making it a potential candidate for the treatment of hypertension and other related conditions.

Upstream product

• 144456-85-9 2-<5-cyano-1,6-dihydro-2-(1,1-dimethylethyl)-6-oxo-3-pyridyl>-2-oxoacetic acid 
• 121017-83-2 2-tert-Butyl-5-cyano-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 4370-12-1 1-cyanoformamide 
• 109-94-4 formic acid ethyl ester 
• 116344-10-6 2-dimethylaminomethylene-4,4-dimethyl-3-oxo-pentanoic acid ethyl ester 
• 121017-77-4 ethyl 5-cyano-1,6-dihydro-2-tert-butyl-6-oxo-3-pyridine carboxylate 
• 107-91-5 cyanoacetic acid amide 
• 42731-37-3 sodium (1E)-4,4-dimethyl-3-oxopent-1-en-1-olate 
• 130187-99-4 3-[1-Dimethylamino-meth-(Z)-ylidene]-5,5-dimethyl-2,4-dioxo-hexanoic acid methyl ester 

Downstream Products

• 86776-92-3 6-tert-butyl-2-oxo-3-pyridinecarboxylic acid 
• 58498-57-0 6-tert-butyl-2-hydroxypyridine 
• 97691-23-1 2-(tert-butyl)-6-chloropyridine 

Relevant academic research and scientific papers

MODULATORS OF CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR

This disclosure provides modulators of Cystic Fibrosis Transmembrane Conductance Regulator (CFTR), pharmaceutical compositions containing at least one such modulator, methods of treatment of cystic fibrosis using such modulators and pharmaceutical compositions, and processes for making such modulators.

Novel Hepatitis C virus replicon inhibitors: Synthesis and structure-activity relationships of fused pyrimidine derivatives

The synthesis of several pyrido[2,3-d]pyrimidine and pyrimido[4,5-d] pyrimidine analogs is described with one such analog possessing subnanomolar potency in both genotype 1a and 1b cell culture HCV replicon assays.

Synthesis and solid-state structures of alkyl-substituted 3-cyano-2-pyridones

A series of 3-cyano-pyridones carrying a variety of alkyl substituents at C-5 and C-6 has been synthesized and their solid-state structures have been studied. Hydrogen bonding interactions between individual pyridone molecules lead either to the formation of symmetric dimers of the R2 2(8) type or to helical chains of the C(4) type. Based on known and calculated structures for the 2-pyridone parent system, the solid-state structures can be divided in two groups representing cases with little external influence on the hydrogen bonding array (group A) and those with a larger external influence (group B).

The chemistry of new nitrosyltungsten complexes with pyridyl- functionalized phosphane ligands

The coordination chemistry of pyridylphosphanes, such as 2(6-tert- butylpyridyl)diphenylphosphane (Ph2P-tert-Bupy) (6) and 2-(6-tert- butylpyridyl)dimethylphosphane (Me2P-tert-Bupy) (7) towards a number of nitrosyltungsten complexes is reported. Displacement of the loosely coordinated MeCN from [W(CH3CN)3(CO)2(NO)][BF4] led to the following cationic compounds incorporating mono- and bidentate coordinated phosphane ligands: cis,cis-[W(CO)2(NO)(Ph2PR)(η2-Ph2PR)][BF4], [R = 2-pyridyl (9a), 2-picolyl (11)], cis,cis-[W(CO)(NO)(η2-Ph2Ppy)2][BF4] (20), trans,trans-[W(CO)(NO)(η2-Ph2Ppy)2][BPh4] (21), fac-[W(CO)2(NO) (Me2P- py)3][BF4] (16), fac-[W(CO)2(NO)(Me2P-tert-Bupy)3][BF4] (18), cis,cis- [W(CO)2(NO)(Me2Ppy)(η2-Me2Ppy)][BF4] (22), and cis,cis- [W(CO)2(CH3CN)(NO)(Me2P-tert-Bupy)2][BF4] (23a). The cationic complex cis,mer-[W(CO)3(NO)(Ph2P-tert-Bupy)2][PF6] (14) has been prepared by nitrosylation of cis/trans-W(CO)4(Ph2P-tert-Bupy)2 (13). Reactions of 9a, 11, 14, 16, and 18 with hydride transfer reagents afforded trans,- trans- HW(CO)2(NO)(Ph2Ppy)2 (10), trans, trans-HW(CO)2(NO)(Ph2Ppic)2 (12), trans, trans-HW(CO)2(NO)(Ph2-tBupy)2 (15), cis/trans- HW(CO)2(NO)(Me2Ppy)2 (17), and cis/trans-HW(CO)2(NO)(Me2P-tert-Bupy)2 (19), respectively. Reactivity experiments with acetic acid, hydroiodic acid, carbon dioxide, and acetylenedicarboxylic acid were performed, and were found to afford trans-W(CO)(NO)(Ph2Ppy)2(η2-CH3CO2) (24), trans, trans- IW(CO)2(NO)(Ph2Ppy)2 (25), trans-W(HCO2)(CO)2(NO)(Ph2Ppy)2 (26), and trans-W{η2-(Z)C(CO2Me)=CH[C(O)OMe]}(CO)(NO)(Ph2Ppic)2 (27), respectively. The influence of the pyridyl substituent in 10 was probed by a comparative H/D exchange experiment in which 10 and the analogous complex HW(CO)2(NO)(PPh3)2 were treated with MeOD. The deuterated complex trans,trans-WD(CO)2(NO)(Ph2Ppy)2 (28) could be isolated. The structures of 9a, 11, 14, and 20 have been determined by single-crystal X-ray diffraction analysis.

Synthesis and cardiotonic activity of 2-substituted 5-cyano-1,6-dihydro-6-oxo-3-pyridinecarboxylic acids and their methyl or ethyl esters

The synthesis of ethyl or methyl esters of 5-cyano-1,6-dihydro-6-oxo-3-pyridinecarboxylic acids carrying as 2-substituent a polar group such as CO2C2H5, (CH2)2CO2CH3, (CH2)3CO2C2H5, CH2OCH3, or CF3 group is described. Also 2-[5-cyano-1,6-dihydro-2-(1,1-dimethylethyl)-6-oxo-3-pyridyl]-2-oxoace tic acid and 2,5,6,8-tetrahydro-2,5-dioxo-1H-thiopyrano[3,4-b]pyridine-3-carbonitri le were prepared. Nearly all the above esters gave routinely the corresponding carboxylic acids by alkaline hydrolysis followed by acidification. As milrinone analogues, the above compounds were tested on contractile activity and frequency rate of spontaneously beating atria from reserpine-treated guinea-pigs. 5-Cyano-2-trifuoromethyl-1,6-dihydro-6-oxo-3-pyridinecarboxylic acid and, in a lesser degree, the relative ethyl ester showed an appreciable positive inotropic activity, although inferior to that of milrinone.

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.