221178-83-2

Upstream product

• 7357-70-2 Cyanothioacetamide 
• 3785-90-8 2-(4-hydroxyphenylmethylene)malononitrile 
• 133149-51-6 2-cyano-2-(4-hydroxybenzylidene)thioacetamide 
• 109-77-3 malononitrile 
• 123-08-0 4-hydroxy-benzaldehyde 
• 735273-33-3 2-amino-4-(4-hydrohyphenyl)-6-(phenylsulfanyl)-3,5-pyridinedicarbonitrile 
• 221178-81-0 2,6-diamino-4-(4-hydroxyphenyl)-4H-thiopyran-3,5-dicarbonitrile 

Downstream Products

• 221178-97-8 LDN-0028618 
• 221179-07-3 2-amino-6-(2-biphenyl-4-yl-2-oxo-ethylsulfanyl)-4-(4-hydroxy-phenyl)-pyridine-3,5-dicarbonitrile 
• 221179-00-6 6-amino-4-(4-hydroxyphenyl)-2-(carboxymethylthio)pyridine-3,5-dicarbonitrile 
• 221179-08-4 2-amino-4-(4-hydroxy-phenyl)-6-(2-oxo-2-p-tolyl-ethylsulfanyl)-pyridine-3,5-dicarbonitrile 
• 221179-05-1 2-amino-6-[2-(4-chloro-phenyl)-2-oxo-ethylsulfanyl]-4-(4-hydroxy-phenyl)-pyridine-3,5-dicarbonitrile 
• 221179-06-2 2-amino-6-[2-(3-bromo-phenyl)-2-oxo-ethylsulfanyl]-4-(4-hydroxy-phenyl)-pyridine-3,5-dicarbonitrile 
• 333959-07-2 6-amino-2-(aminocarbonylmethylthio)-3,5-dicyano-4-(4-hydroxyphenyl)pyridine 
• 333962-91-7 LUF₅₈₃₄ 

Relevant academic research and scientific papers

Pyridine-2(1H)-thiones: Versatile Precursors for Novel Pyrazolo[3,4-b]pyridine, Thieno[2,3-b]pyridines, and Their Fused Azines

Pyridine-2(1H)-thiones were prepared and reacted with several active halogenated reagents to afford novel thieno[2,3-b]pyridines in excellent yields. Thieno[2,3-b]pyridine-2-carbohydrazide derivative was prepared by the reaction of either ethyl 2-((3-cyanopyridin-2-yl)thio)acetate derivative or thieno[2,3-b]pyridine-2-carboxylate derivative with hydrazine hydrate. On the other hand, the reaction of either pyridine-2(1H)-thione or ethyl 2-((pyridin-2-yl)thio)acetate derivative with hydrazine hydrate afforded the corresponding 1H-pyrazolo[3,4-b]pyridine derivative. Thieno[2,3-b]pyridine derivatives reacted with several reagents to afford the corresponding pyrimidine-4(3H)-ones and [1,2,3]triazin-4-(3H)-one. Moreover, 2-carbohydrazide derivative reacted with β-dicarbonyl reagents to give 2-((3-methyl-1H-pyrazol-1-yl)carbonyl)thienopyridines. The structure of the target molecules is elucidated using elemental analyses and spectral data.

Structure-kinetics relationships of Capadenoson derivatives as adenosine A1 receptor agonists

Abstract We report the synthesis and biological evaluation of new derivatives of Capadenoson, a former drug candidate that was previously advanced to phase IIa clinical trials. 19 of the 20 ligands show an affinity below 100 nM at the human adenosine A1 receptor (hA1AR) and display a wide range of residence times at this target (from approx. 5 min (compound 10) up to 132 min (compound 5)). Structure-affinity and structure-kinetics relationships were established, and computational studies of a homology model of the hA1AR revealed crucial interactions for both the affinity and dissociation kinetics of this family of ligands. These results were also combined with global metrics (Ligand Efficiency, cLogP), showing the importance of binding kinetics as an additional way to better select a drug candidate amongst seemingly similar leads.

Structure-activity relationship study of prion inhibition by 2-aminopyridine-3,5-dicarbonitrile-based compounds: Parallel synthesis, bioactivity, and in vitro pharmacokinetics

2-Aminopyridine-3,5-dicarbonitrile compounds were previously identified as mimetics of dominant-negative prion protein mutants and inhibit prion replication in cultured cells. Here, we report findings from a comprehensive structure-activity relationship study of the 6-aminopyridine-3,5-dicarbonitrile scaffold. We identify compounds with significantly improved bioactivity (approximately 40-fold) against replication of the infectious prion isoform (PrPSc) and suitable pharmacokinetic profiles to warrant evaluation in animal models of prion disease.

New, non-adenosine, high-potency agonists for the human adenosine A 2B receptor with an improved selectivity profile compared to the reference agonist N-ethylcarboxamidoadenosine

The adenosine A2B receptor is the least well characterized of the four known adenosine receptor subtypes because of the absence of potent, selective agonists. Here, we present five non-adenosine agonists. Among them, 2-amino-4-(4-hydroxyphenyl)

Versatile starting materials for novel 1,ω-bis(pyridin-4-ylphenoxy)alkanes, and their corresponding bis(thieno[2,3-b]pyridin-4-ylphenoxy) derivatives

A synthesis is described, starting from p-hydroxybenzaldehyde, of some new bis(activated styrene) derivatives, and their conversion into novel bis(pyridin-4-yl) ethers and bis(thieno[2,3-b]pyridine) derivatives.

Synthesis and Recyclization of 4-Aryl-2,6-diamino-3,5-dicyano-4H-thiopyrans

Reaction of arylmethylenemalononitriles with cyanothioacetamide or of arylmethylenecyanothioacetamides with malononitrile affords 4-aryl-2,6-diamino-3,5-dicyano-4H-thiopyrans which were further recyclized into 6-amino-4-aryl-3,5-dicyanopyridine-2(1H)-thiones. On the basis of the latter compounds were synthesized substituted 2-alkylthiopyridines and thieno[2,3-b]pyridines. 4-Hydroxybenzalcyanothioacetamide reacts with α-bromoketones by Hantzsch with the formation of thiazolylsubstituted acrylonitriles acylated with acetic anhydride at the OH group.