1385840-65-2

Basic information

• Product Name: C₂₄H₂₅BrN₆O
• CAS NO: 1385840-65-2
• Molecular Weight: 493.406
• Mol File: 1385840-65-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₂₄H₂₅BrN₆O(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₄H₂₅BrN₆O(1385840-65-2)
• EPA Substance Registry System: C₂₄H₂₅BrN₆O(1385840-65-2)

Safety Data

• Hazardous Substances Data: 1385840-65-2(Hazardous Substances Data)

Upstream product

• 1385841-79-1 C₂₅H₁₉BrN₄O₄S 
• 2615-25-0 trans-1,4-cyclohexyldiamine 
• 1422435-04-8 C₁₈H₁₃BrN₄O₂ 
• 81881-74-5 5-aminomethylindole 
• 410544-37-5 5-bromo-8-hydroxy-[1,6]naphthyridine-7-carboxylic acid methyl ester 

Relevant articles and documents

Investigation on the 1,6-naphthyridine motif: Discovery and SAR study of 1H-imidazo[4,5-h][1,6]naphthyridin-2(3H)-one-based c-Met kinase inhibitors

The 1,6-naphthyridine motif is a multivalent scaffold in medicinal chemistry presenting various bioactivities when properly substituted. By incorporating a cyclic urea pharmacophore into the 1,6-naphthyridine framework through conformationally constraining the 7,8-positions, the resulting 1H-imidazo[4,5-h][1,6]naphthyridin-2(3H)-one was identified as a new class of c-Met kinase inhibitor. A comprehensive SAR study indicated that an N-1 alkyl substituent bearing a terminal free amino group, a hydrophobic substituted benzyl group at the N-3 position and the tricyclic core were essential for retaining effective Met inhibition of the 1H-imidazo[4,5-h][1,6]naphthyridin- 2(3H)-one chemotype. Further introduction of a 4′-carboxamide phenoxy group at the C-5 position significantly improved the potency. The best c-Met kinase inhibitory activity was exemplified by 2t with an IC50 = 2.6 μM, which also displayed effective inhibition against TPR-Met phosphorylation and the proliferation of the BaF3-TPR-Met cells at low micromolar concentrations.