53661-33-9

Upstream product

• 74745-12-3 3-Methoxy-5,6,7,8-tetrahydro-isoquinoline-4-carbonitrile 
• 4354-73-8 2-(cyclohexylidene)malononitrile 
• 68-12-2 N,N-dimethyl-formamide 
• 108-94-1 cyclohexanone 
• 53661-31-7 3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile 

Downstream Products

• 1644599-76-7 methyl 1-(4-phenyl-1H-1, 2, 3-triazol-1-yl)-6,7,8,9-tetrahydrothieno[2,3-c]isoquinoline-2-carboxylate 
• 155412-89-8 1-Amino-6,7,8,9-tetrahydro-thieno<2,3-c>isochinolin-2-carbonsaeuremethylester 
• 184648-03-1 4-Cyan-5,6,7,8-tetrahydro-isochinolin-3-ylsulfanylessigsaeuremethylester 
• 103589-68-0 3-(3-Isopropyl-2-phenyl-oxazolidin-5-ylmethoxy)-5,6,7,8-tetrahydro-isoquinoline-4-carbonitrile 

Relevant academic research and scientific papers

Synthesis of methyl 3-azidothieno[2,3-b]pyridine-2-carboxylates and application of the huisgen reaction

The preparation of new substituted methyl 3-azidothieno[2,3-b]pyridine carboxylates by azotization of methyl 3-aminothieno[2,3-b]pyridine and subsequent treatment with sodium azide is described. Via Huisgen's 1,3-dipolar cycloaddition between substituted alkynes and the prepared azides, methyl 1,2,3-triazolo-thieno[2,3-b]pyridine carboxylates have been obtained.

Synthesis and bioactivity of novel amino-pyrazolopyridines

Here we describe the synthesis and biological activity of novel amino-pyrazolopyridines with anti-NF-κB and pro-apoptotic potential. α-Methylene ketones were used as a starting point for synthesis of amino-pyrazolopyridine 3. The alkylidene malononitriles 1 were obtained by the Knoevenagel reaction of ketones with malononitriles. Vilsmeier-Haack reaction allowed direct access to 2-chloro-3-cyanopyridines 2. Those products, by refluxing with hydrazine hydrate, allowed cyclization to amino-pyrazolopyridines 3a-g, which were not previously described in the literature. Bioactivity results indicated that amino-pyrazolopyridines 3a, 3b and 3g induced apoptotic cell death in K562 cancer cells with an IC50 of 36.5 ± 3.9 μM, 27.6 ± 4.5 μM and 35.0 ± 2.3 μM, respectively, after 72 h. In addition, compounds 3a, 3b and 3g exerted NF-κB inhibition activity with an IC50 of 4.7 ± 1.6 μM, 6.9 ± 1.9 μM and 39.8 ± 3.9 μM, respectively, after 8 h in K562 cells activated with TNFα. Compounds 3b and 3g showed interesting differential toxicity as viability of peripheral blood mononuclear cells (PBMCs) from healthy donors remained largely unaffected by this treatment.

SYNTHESE DE NOUVEAUX DERIVES 3-AMINO THIENO ET SELENOLOPYRIDINIQUES

Cyclisation of alkylidenemalonitriles by the Vilsmeier-Haack reagent gives 2-chloro 3-cyano pyridines.These compounds are used as starting material for the synthesis of thieno and selenolopyridines.Key words: Alkylidenemalonitriles; Vilsmeier-Haack; 2-chloro 3-cyano pyridines; thienopyridines; selenolopyridines.

A one-pot synthesis of 2-chloronicotinonitriles and fused 2-chloro-3-cyanopyridines

2-Chloronicotinonitriles (2a-d) and fused bi- and tricyclo-2-chloro-3-cyanopyridines (2e-h) are obtained from alkylidenemalononitriles (1a-h) by Vilsmeier reaction.Generation in situ of an aldehyde equivalent species in the Vilsmeier reaction at the γ-carbon with respect to the nitrile carbon of the alkylidenemalononitriles, followed by cylization, both occurring in one-pot, are presumed to be involved in the pyridoannulation.