947599-36-2

Basic information

• Product Name: 9,10-dimethoxy-13-octyl-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride
• Synonyms: 9,10-dimethoxy-13-octyl-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride
• CAS NO: 947599-36-2
• Molecular Weight: 484.035
• Mol File: 947599-36-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 9,10-dimethoxy-13-octyl-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-dimethoxy-13-octyl-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride(947599-36-2)
• EPA Substance Registry System: 9,10-dimethoxy-13-octyl-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride(947599-36-2)

Safety Data

• Hazardous Substances Data: 947599-36-2(Hazardous Substances Data)

Upstream product

• 124-13-0 Octanal 
• 483-15-8 7,8-dihydroberberine 

Downstream Products

• 1375475-69-6 2,3-methylenedioxy-9-benzyloxy-10-methoxy-13-n-octylprotoberberine chloride 
• 1375475-70-9 2,3-methylenedioxy-9-O-(4-methylbenzoyl)-10-methoxy-13-n-octylprotoberberine chloride 
• 1375475-71-0 2,3-methylenedioxy-9-O-(4-methoxylbenzoyl)-10-methoxy-13-n-octylprotoberberine chloride 
• 1375475-72-1 2,3-methylenedioxy-9-O-(4-trifluoromethylbenzenesulfonyl)-10-methoxy-13-n-octylprotoberberine chloride 
• 1375475-73-2 2,3-methylenedioxy-9-O-(4-cyanobenzenesulfonyl)-10-methoxy-13-n-octylprotoberberine chloride 
• 1375475-77-6 2-hydroxy-3-benzyloxy-9,10-dimethoxy-13-n-octylprotoberberine chloride 
• 1375475-81-2 2,3-dibenzyloxy-9,10-dimethoxy-13-n-octylprotoberberine chloride 
• 1375475-85-6 2-hydroxy-3,9-dibenzyloxy-10-methoxy-13-n-octylprotoberberine chloride 
• 1375475-87-8 2,3,9-tribenzyloxy-10-methoxy-13-n-octylprotoberberine chloride 

Relevant articles and documents

Synthesis and anticancer activity of novel 9,13-disubstituted berberine derivatives

Novel berberine derivatives with disubstituents on positions C9 and C13 were synthesized and evaluated for antiproliferative activities against human prostate cancer cell lines (PC3 and DU145), breast cancer cell line (MDA-MB-231) and human colon cancer cell lines (HT29 and HCT116). All compounds showed significantly enhanced antiproliferative activities compared with berberine. Notably, compound 18e exhibited the strongest cytotoxicity against PC3 cells with an IC50 value of 0.19 μM, and the highest selectivity index (SIPC3 > 20). Further studies showed that 18e could arrest the cell cycle at G1 phase, and significantly inhibit tumor cell colony forming and migration even at low concentrations. Interestingly, 18e could significantly induce cytoplasmic vacuolation, suggesting a different mode of action from berberine.

Synthesis, structure-activity relationship and in vitro anti-mycobacterial evaluation of 13-n-octylberberine derivatives

Twenty-eight new 13-n-octylberberine derivatives were synthesized and evaluated for their activities against drug-susceptible Mycobacterium tuberculosis (M. tuberculosis) strain H37Rv. Among these compounds, compound 16e was the most effective anti-tubercular agent with a MIC value of 0.125 μg/mL. Importantly, compound 16e exhibited more potent effect against rifampicin (RIF)- and isoniazid (INH)-resistant M. tuberculosis strains than both RIF and INH, suggesting a new mechanism of action. Therefore, it has been selected as a drug candidate for further investigation, or as a chemical probe for identifying protein target and studying tuberculosis biology. We consider 13-n-octylberberine analogs to be a promising novel class of antituberculars against multi-drug-resistant (MDR) strains of M. tuberculosis.