36937-90-3

Usage

Physical form

Yellow powder

Common uses

Organic synthesis, building block in pharmaceuticals and agrochemicals, precursor for synthesis of derivatives with biological activities

Toxicity

Can be toxic if ingested or inhaled

Hazards

Can cause skin and eye irritation upon contact

Importance

Versatile and valuable chemical compound with many industrial applications

InChI:InChI=1/C11H5F3N2/c12-11(13,14)10-3-1-2-8(5-10)4-9(6-15)7-16/h1-5H

Upstream product

• 454-89-7 3-Trifluoromethylbenzaldehyde 
• 109-77-3 malononitrile 

Downstream Products

• 791619-76-6 2-amino-4-(3-trifluoromethylphenyl)-6-phenylsulfanylpyridine-3,5-dicarbonitrile 
• 791619-85-7 6-amino-2-thioxo-4-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3,5-dicarbonitrile 
• 1467065-59-3 2-(2,2,2-trifluoro-1-(4-(trifluoromethyl)phenyl)ethyl)malononitrile 
• 791619-85-7 2-amino-4-(3-trifluoromethylphenyl)-6-mercaptopyridine-3,5-dicarbonitrile 

Relevant academic research and scientific papers

Preparation of O-Protected Cyanohydrins by Aerobic Oxidation of α-Substituted Malononitriles in the Presence of Diarylphosphine Oxides

A mild, reagent-cyanide-free, and efficient synthesis of O-phosphinoyl-protected cyanohydrins from readily available α-substituted malononitriles was realized using diarylphosphine oxides in the presence of O2. Mechanistic studies indicated that in addition to the initial aerobic oxidation of the malononitrile derivative notable features of this process include the formation of a tetrahedral intermediate and a subsequent intramolecular rearrangement. The phosphinoyl-protecting group can be removed by alcoholysis or by reduction with DIBAL-H.

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.

A series of ligands displaying a remarkable agonistic-antagonistic profile at the adenosine A1 receptor

Adenosine receptor agonists are usually variations of the natural ligand, adenosine. The ribose moiety in the ligand has previously been shown to be of great importance for the agonistic effects of the compound. In this paper, we present a series of nonadenosine ligands selective for the adenosine A 1 receptor with an extraordinary pharmacological profile. 2-Amino-4-benzo-[1,3]dioxol-5-yl-6-(2-hydroxyethylsulfanyl)pyridine-3, 5-dicarbonitrile (70, LUF 5853) shows full agonistic behavior comparable with the reference compound CPA, while also displaying comparable receptor binding affinity (Ki = 11 nM). In contrast, compound 58 (2-amino-4-(3- trifluoromethylphenyl)-6-(2-hydroxyethylsulfanyl)pyridine-3,5-dicarbonitrile, LUF 5948) has a binding affinity of 14 nM and acts as an inverse agonist. Also present within this same series are compounds that show neutral antagonism of the adenosine A1 receptor, for example compound 65 (2-amino-4-(4-difluoromethoxyphenyl)-6-(2-hydroxyethylsulfanyl)pyridine-3, 5-dicarbonitrile, LUF 5826).

Pyrano[3,2-h]quinolines for treating restenosis

Pharmaceutical compound of the formula STR1 R1 is phenyl or heteroaryl selected from thienyl, pyridyl, benzothienyl, quinolinyl, benzofuranyl or benzimidazolyl, said phenyl and heteroaryl groups being optionally substituted, or R1 is

Therapy for diabetic complications

This invention provides a method of treating diabetic complications in mammals which comprises the administration of a compound of the Formula I: STR1 in which n, R1, R2, R3, and R4 are variables.