1124227-92-4

Basic information

• Product Name: N-(4-(2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl)phenyl)-3-methoxy-5-nitrobenzamide
• Synonyms: N-(4-(2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl)phenyl)-3-methoxy-5-nitrobenzamide
• CAS NO: 1124227-92-4
• Molecular Weight: 491.544
• Mol File: 1124227-92-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-(4-(2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl)phenyl)-3-methoxy-5-nitrobenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-(2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl)phenyl)-3-methoxy-5-nitrobenzamide(1124227-92-4)
• EPA Substance Registry System: N-(4-(2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl)phenyl)-3-methoxy-5-nitrobenzamide(1124227-92-4)

Safety Data

• Hazardous Substances Data: 1124227-92-4(Hazardous Substances Data)

Upstream product

• 78238-12-7 3-methoxy-5-nitrobenzoic acid 
• 82925-02-8 4-<2-(1,2,3,4-tetrahydro-6,7-dimethoxy-2-isoquinolyl)ethyl>benzenamine 

Downstream Products

• 1124227-97-9 3-amino-N-(4-(2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl)phenyl)-5-methoxybenzamide 

Relevant articles and documents

Potent and selective inhibitors of breast cancer resistance protein (ABCG2) derived from the p-glycoprotein (ABCB1) modulator tariquidar

The efflux pumps ABCB1 (p-gp, MDR1) and ABCG2 (BCRP) are expressed to a high extent by endothelial cells at the blood-brain barrier (BBB) and other barrier tissues and are involved in drug resistance of tumor (stem) cells. Whereas numerous ABCB1 inhibitors are known, only a few ABCG2 modulators with submicromolar activity have been published. Starting from tariquidar (4) analogues as ABCB1 modulators, minimal structural modifications resulted in a drastic shift in favor of ABCG2 inhibition. Highest potency was found when the 3,4-dimethoxy-2-(quinoline-3-carbonylamino)benzoyl moiety in 4 was replaced with a 4-methoxycarbonylbenzoyl moiety bearing a hetarylcarboxamido group in 3-position, e.g., quinoline-3-carboxamido (5,IC50: 119 nM) or quinoline-2-carboxamido (6,IC50: 60 nM, flow cytometric mitoxantrone efflux assay, topotecan-resistant MCF-7 breast cancer cells); the selectivity for ABCG2 over ABCB1 was about 100-500 fold and the compounds were inactive at ABCC2 (MRP2). Chemosensitivity assays against MCF-7/Topo cells revealed that the nontoxic inhibitor 6 completely reverted ABCG2-mediated topotecan resistance at concentrations > 100 nM, whereas 5 showed ABCG2 independent cytotoxicity. ABCG2 inhibitors might be useful for cancer treatment with respect to reversal of multidrug resistance, overcoming the BBB and targeting of tumor stem cells.