15575-49-2

Basic information

• Product Name: 6-acetonyldihydrochelerythrine
• CAS NO: 15575-49-2
• Molecular Weight: 405.45
• Mol File: 15575-49-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 6-acetonyldihydrochelerythrine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-acetonyldihydrochelerythrine(15575-49-2)
• EPA Substance Registry System: 6-acetonyldihydrochelerythrine(15575-49-2)

Safety Data

• Hazardous Substances Data: 15575-49-2(Hazardous Substances Data)

Upstream product

• 67-64-1 acetone 
• 74866-17-4 3,4-dimethoxy-2-methyl-1-bromobenzene 
• 180411-17-0 2-bromo-6,7-methylenedioxy-1-naphthylamine 
• 213698-51-2 N-(6-bromonaphtho[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-2-methylpropionamide 
• 180411-13-6 2-(6-bromo-naphtho[2,3-d][1,3]dioxol-5-yloxy)-2-methylpropionamide 
• 180411-09-0 6,6-dibromo-7,8-dihydro-6H-naphtho[2,3-d][1,3]dioxol-5-one 
• 41303-45-1 6,7-methylenedioxy-1-tetralone 
• 4463-33-6 1,2-dimethoxy-3-methylbenzene 
• 175844-54-9 6-bromo-2,3-dimethoxybenzyl bromide 
• 91-16-7 1,2-dimethoxybenzene 
• 6880-91-7 12,13-dihydrochelerythrine 
• 180411-11-4 6-bromonaphtho[2,3-d][1,3]dioxol-5-ol 
• 34316-15-9 chelerythrinium 

Relevant articles and documents

Dihydrochelerythrine and its derivatives: Synthesis and their application as potential G-quadruplex DNA stabilizing agents

A convenient route was envisaged toward the synthesis of dihydrochelerythrine (DHCHL), 4 by intramolecular Suzuki coupling of 2-bromo-N-(2-bromobenzyl)-naphthalen-1-amine derivative 5 via in situ generated arylborane. This compound was converted to (±)-6-acetonyldihydrochelerythrine (ADC), 3 which was then resolved by chiral prep-HPLC. Efficiency of DHCHL for the stabilization of promoter quadruplex DNA structures and a comparison study with the parent natural alkaloid chelerythrine (CHL), 1 was performed. A thorough investigation was carried out to assess the quadruplex binding affinity by using various biophysical and biochemical studies and the binding mode was explained by using molecular modeling and dynamics studies. Results clearly indicate that DHCHL is a strong G-quadruplex stabilizer with affinity similar to that of the parent alkaloid CHL. Compounds ADC and DHCHL were also screened against different human cancer cell lines. Among the cancer cells, (±)-ADC and its enantiomers showed varied (15-48%) inhibition against human colorectal cell line HCT116 and breast cancer cell line MDA-MB-231 albeit low enantio-specificity in the inhibitory effect; whereas DHCHL showed 30% inhibition against A431 cell line only, suggesting the compounds are indeed cancer tissue specific.

Structural modification of sanguinarine and chelerythrine and their antibacterial activity

In this study, five derivatives of sanguinarine (1) and chelerythrine (2) were prepared, with 1 and 2 as starting materials, by reduction, oxidation and nucleophilic addition to the iminium bond C=N+. The structures of all compounds were elucidated on account of their MS, 1H-NMR and 13C-NMR data. The antibacterial activities of all compounds were screened, using Staphylococcus aureus, Escherichia coli, Aeromonas hydrophila and Pasteurella multocida as test bacteria. The minimum bacteriostatic concentration and minimum bactericidal concentration of the active compounds were determined by the turbidity method. The structure-activity relationships of 1 and 2 were discussed. The results showed that 1, 2 and their pseudoalcoholates were found to be potent inhibitors to S. aureus, E. coli and A. hydrophila, while the other derivatives were found to be inactive. The pseudoalcoholates might be the prodrugs of 1 and 2. The iminium bond in the molecules of 1 or 2 was the determinant for antibacterial activity, and the substituents at the 7 and 8 positions influenced the antibacterial activities of 1 and 2 against different bacteria.