856014-52-3

Basic information

• Product Name: 2-amino-4-(3-bromophenyl)-6-(2-dimethylamino-5-pyridyl)nicotinonitrile
• CAS NO: 856014-52-3
• Molecular Weight: 394.274
• Mol File: 856014-52-3.mol

Chemical Properties

• CAS DataBase Reference: 2-amino-4-(3-bromophenyl)-6-(2-dimethylamino-5-pyridyl)nicotinonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-4-(3-bromophenyl)-6-(2-dimethylamino-5-pyridyl)nicotinonitrile(856014-52-3)
• EPA Substance Registry System: 2-amino-4-(3-bromophenyl)-6-(2-dimethylamino-5-pyridyl)nicotinonitrile(856014-52-3)

Safety Data

• Hazardous Substances Data: 856014-52-3(Hazardous Substances Data)

Upstream product

• 923034-23-5 dimethyl 2-(6-chloronicotinoyl)malonate 
• 55676-22-7 3-acetyl-6-chloropyridine 
• 58757-38-3 6-Chloronicotinoyl chloride 
• 2972-74-9 2-(3-bromobenzylidene)malononitrile 
• 265107-41-3 1-[6-(dimethylamino)-3-pyridinyl]ethanone 
• 3132-99-8 m-bromobenzoic aldehyde 
• 109-77-3 malononitrile 

Relevant articles and documents

5-(3-Bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d] pyrimidin-4-ylamine: Structure-activity relationships of 7-substituted heteroaryl analogs as non-nucleoside adenosine kinase inhibitors

4-Amino-5,7-disubstituted pyridopyrimidines are potent, non-nucleoside inhibitors of adenosine kinase (AK). We recently identified a potent, orally efficacious analog, 4 containing a 7-pyridylmorpholine substituted ring system as the key structural element of this template. In this report, we disclose the pharmacologic effects of five- and six-membered heterocyclic ring replacements for the pyridine ring in 4. These replacements were found to have interesting effects on in vivo efficacy and genotoxicity as well as in vitro potency. We discovered that the nitrogen in the heterocyclic ring at C(7) is important for the modulation of mutagenic side effects (Ames assay).

Discovery of 4-amino-5-(3-bromophenyl)-7-(6-morpholino-pyridin-3-yl)pyrido [2,3-d]pyrimidine, an orally active, non-nucleoside adenosine kinase inhibitor

Adenosine (ADO) is an endogenous homeostatic inhibitory neuromodulator that reduces cellular excitability at sites of tissue injury and inflammation. Inhibition of adenosine kinase (AK), the primary metabolic enzyme for ADO, selectively increases ADO concentrations at sites of tissue trauma and enhances the analgesic and antiinflammatory actions of ADO. Optimization of the high-throughput screening lead, 4-amino-7-aryl-substituted pteridine (5) (AK IC50 = 440 nM), led to the identification of compound 21 (4-amino-5-(3-bromophenyl)-7-(6-morpholino-pyridin-3-yl)pyrido [2,3-d]pyrimidine, ABT-702), a novel, potent (AK IC50 = 1.7 nM) nonnucleoside AK inhibitor with oral activity in animal models of pain and inflammation.