15029-45-5

Usage

InChI:InChI=1/C7H12N2O2/c1-11-6-2-5-9-7(10)3-4-8/h2-3,5-6H2,1H3,(H,9,10)

Upstream product

• 105-56-6 ethyl 2-cyanoacetate 
• 5332-73-0 3-methoxypropylamine 
• 107-91-5 cyanoacetic acid amide 

Downstream Products

• 1202194-12-4 C₁₆H₂₀N₂O₂S 
• 1374399-93-5 2-(benzylthio)-N-(3-methoxypropyl)-5-oxo-7-hydroxy-4,5-dihydrothieno[3,2-b]pyridine-3-carboxamide 
• 1374399-97-9 7-hydroxy-N-(3-methoxypropyl)-5-oxo-2-[(2-oxo-2-phenylethyl)sulfanyl]-4H,5H-thieno[3,2-b]pyridine-3-carboxamide 
• 1374400-42-6 2-({[(4-chloro-2-methoxy-5-methylphenyl)carbamoyl]methyl}sulfanyl)-7-hydroxy-N-(3-methoxypropyl)-5-oxo-4H,5H-thieno[3,2-b]pyridine-3-carboxamide 
• 1374400-19-7 ethyl 4-[2-({7-hydroxy-3-[(3-methoxypropyl)carbamoyl]-5-oxo-4H,5H-thieno[3,2-b]pyridin-2-yl}sulfanyl)acetamido]benzoate 
• 1448184-52-8 8-amino-2-(benzylthio)-7-cyano-N-(3-methoxypropyl)-5-oxo-6-phenyl-4,6-dihydro-5H-pyrano[2,3-d]thieno[3,2-b]pyridine-3-carboxamide 
• 1448182-40-8 ethyl 4-({[(8-amino-7-cyano-3-{[(3-methoxypropyl)amino]carbonyl}-5-oxo-6-phenyl-4,6-dihydro-5H-pyrano[2,3-d]thieno[3,2-b]pyridin-2-yl)thio]acetyl}amino)benzoate 
• 1589638-44-7 2-cyano-3-(2,4-dimethoxy-6-((E)-4-methoxystyryl)phenyl)-N-(3-methoxypropyl)acrylamide 
• 1419401-87-8 (2Z)-2-cyano-N-(3-methoxypropyl)-2-{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene } ethanamide 
• 1419401-69-6 (2Z)-2-cyano-N-(3-methoxypropyl)-2-{3-[ (3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanamide 

Relevant academic research and scientific papers

Synthesis of resveratrol acrylamides derivatives and biological evaluation of their anti-proliferative effect on cancer cell lines

A new series of resveratrol acrylamides amine derivatives was designed, synthesized, and evaluated for their anti-proliferative activity against three cancer cell lines including human chronic myelocytic leukemia cell K562, human hepatoma HuH-7 and human lung carcinoma A549. Most of the compounds showed superior activity against three cell lines when compared to parent resveratrol. C13 had the best anti-tumor activity against the HuH-7 cell line and its IC 50 was 4.5 μmol/L; C16 had the best anti-tumor activity against the K562 cell line and its IC50 was 2.9 μmol/L; C18 had the best anti-tumor activity against the A549 cell line and its IC50 was 3.8 μmol/L. It could be seen that the activity of the aromatic amine derivatives was better than the fatty amine derivatives by analyzing the experimental data.

A simple and general approach for the synthesis of highly functionalized 6-oxo-1,6-dihydropyridines

A variety of 5-cyano-4-methylthio-6-oxo-1,6-dihydropyridine-3-carboxylates have been efficiently synthesized in a one-pot reaction from N-alkyl and N-aryl derivatives of 2-cyano-3,3-bis(methylthio)acrylamides and selected β-keto esters. The reaction proceeds via potassium hydrogen carbonate mediated conjugate addition of a β-keto ester to 2-cyano-3,3-bis(methylthio) acrylamide followed by loss of methyl mercaptan and subsequent intramolecular condensation of amide group with the acyl carbonyl group. The mechanism of the reaction has been established by isolation of the 2-acetyl-4-cyano-5-amino-3- (methylthio)-5-oxopent-3-enoate intermediate and its independent cyclization to the desired 6-oxo-1,6-dihydropyridine.