52126-76-8

Basic information

• Product Name: 5-Pyrimidinecarbonitrile, 4-amino-2-phenyl-
• CAS NO: 52126-76-8
• Molecular Formula: C11H8N4
• Molecular Weight: 196.211
• Mol File: 52126-76-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 5-Pyrimidinecarbonitrile, 4-amino-2-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Pyrimidinecarbonitrile, 4-amino-2-phenyl-(52126-76-8)
• EPA Substance Registry System: 5-Pyrimidinecarbonitrile, 4-amino-2-phenyl-(52126-76-8)

Safety Data

• Hazardous Substances Data: 52126-76-8(Hazardous Substances Data)

Upstream product

• 38111-44-3 phenylzinc(II) bromide 
• 94741-70-5 4-Amino-2-bromo-5-pyrimidinecarbonitrile 
• 94741-69-2 4-amino-2-chloropyrimidine-5-carbonitrile 
• 98-80-6 phenylboronic acid 
• 1670-14-0 benzamidine monohydrochloride 
• 123-06-8 Ethoxymethylenemalononitrile 

Downstream Products

• 41307-30-6 4,4'-(7-phenylpyrimido[4,5-d]pyrimidin-2,4-diyl)dimorpholine 
• 41307-29-3 2,4-dichloro-7-phenylpyrimido[4,5-d]pyrimidine 
• 82302-13-4 4-amino-2-phenyl-5-pyrimidinecarboxamidoxime 

Relevant articles and documents

Negishi cross-coupling enabled synthesis of novel NAD+-dependent DNA ligase inhibitors and SAR development

Two novel compounds, pyridopyrimidines (1) and naphthyridines (2) were identified as potent inhibitors of bacterial NAD+-dependent DNA ligase (Lig) A in a fragment screening. SAR was guided by molecular modeling and X-ray crystallography. It was observed that the diaminonitrile pharmacophore made a key interaction with the ligase enzyme, specifically residues Glu114, Lys291, and Leu117. Synthetic challenges limited opportunities for diversification of the naphthyridine core, therefore most of the SAR was focused on a pyridopyrimidine scaffold. The initial diversification at R1 improved both enzyme and cell potency. Further SAR developed at the R2 position using the Negishi cross-coupling reaction provided several compounds, among these compounds 22g showed good enzyme potency and cellular potency.

ALPHA-HELIX MIMETIC USING A 2,5-OLIGOPYRIMIDINE SCAFFOLD

Alpha-helix mimetics and associated methods of making are provided. These compounds are constructed using a 2,5-oligopyrimidine scaffold. The semi-rigid scaffold holds individual side chain-like residues in orientations that mimic the orientations of side chain residues of an ?-helical protein domain. The new scaffold is easier to make than previous scaffolds and has much more favorable physical properties than previous alpha-helix mimics. The amphiphilic alpha-helix mimetics have application for making libraries and for treating diseases or conditions effected by the inhibition or disruption of interactions with the alpha helix of a protein.