1345014-85-8

Basic information

• Product Name: 4-[(1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)amino]-2-phenyl-7,8-dihydro-1,6-naphthyridin-5(6H)-one
• CAS NO: 1345014-85-8
• Molecular Weight: 370.414
• Mol File: 1345014-85-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 4-[(1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)amino]-2-phenyl-7,8-dihydro-1,6-naphthyridin-5(6H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)amino]-2-phenyl-7,8-dihydro-1,6-naphthyridin-5(6H)-one(1345014-85-8)
• EPA Substance Registry System: 4-[(1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)amino]-2-phenyl-7,8-dihydro-1,6-naphthyridin-5(6H)-one(1345014-85-8)

Safety Data

• Hazardous Substances Data: 1345014-85-8(Hazardous Substances Data)

Upstream product

• 1345013-95-7 tert-butyl 4-(methylthio)-5-oxo-2-phenyl-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate 
• 98-86-2 acetophenone 
• 1345013-92-4 tert-butyl 3-[bis(methylthio)methylene]-2,4-dioxopiperidine-1-carboxylate 
• 1345014-05-2 tert-butyl 4-(methylsulfonyl)-5-oxo-2-phenyl-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate 
• 72583-83-6 3-amino-1-methylpyrazolo<3,4-b>pyridine 

Relevant articles and documents

4-Amino-7,8-dihydro-1,6-naphthyridin-5(6 H)-ones as Inhaled Phosphodiesterase Type 4 (PDE4) Inhibitors: Structural Biology and Structure-Activity Relationships

Rational design of a novel template of naphthyridinones rapidly led to PDE4 inhibitors with subnanomolar enzymatic potencies. X-ray crystallography confirmed the binding mode of this novel template. We achieved compounds with double-digit picomolar enzymatic potencies through further structure-based design by targeting both the PDE4 enzyme metal-binding pocket and occupying the solvent-filled pocket. A strategy for lung retention and long duration of action based on low aqueous solubility was followed. In vivo efficacies were measured in a rat lung neutrophilia model by suspension microspray and dry powder administration. Suspension microspray of potent compounds showed in vivo efficacy with a clear dose-response. Despite sustained lung levels, dry powder administration performed much less well and without proper dose-response, highlighting clear differences between the two formulations. This indicates a deficiency in the low aqueous solubility strategy for long duration lung efficacy.