28342-33-8

Basic information

• Product Name: 6-Oxochelerythrine
• Synonyms: 6-Oxochelerythrine;OXYCHELERYTHRINE;1,2-Dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridin-13(12H)-one;Dihydrooxochelerythrine
• CAS NO: 28342-33-8
• Molecular Formula: C₂₁H₁₇NO₅
• Molecular Weight: 363.36338
• Mol File: 28342-33-8.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 615.5°Cat760mmHg
• Flash Point: 326.1°C
• Appearance: /
• Density: 1.361g/cm³
• Vapor Pressure: 4.39E-15mmHg at 25°C
• Refractive Index: 1.668
• CAS DataBase Reference: 6-Oxochelerythrine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Oxochelerythrine(28342-33-8)
• EPA Substance Registry System: 6-Oxochelerythrine(28342-33-8)

Safety Data

• Hazardous Substances Data: 28342-33-8(Hazardous Substances Data)

Usage

General Description

6-Oxochelerythrine is a natural alkaloid compound found in certain plant species, particularly in the genus Zanthoxylum. It is known for its potential pharmacological properties, such as anti-inflammatory, anti-bacterial, and anti-fungal activities. Research has also shown that 6-Oxochelerythrine has cytotoxic effects on cancer cells, making it a promising candidate for the development of anticancer drugs. Additionally, this compound has demonstrated inhibitory effects on enzymes involved in the production of prostaglandins, which are important mediators of inflammation. Overall, 6-Oxochelerythrine shows promise as a compound with potential therapeutic applications in various medical conditions.

InChI:InChI=1/C21H17NO5/c1-22-19-13(5-4-11-8-16-17(9-14(11)19)27-10-26-16)12-6-7-15(24-2)20(25-3)18(12)21(22)23/h4-9H,10H2,1-3H3

Upstream product

• 3895-92-9 chelerythrine chloride 
• 67-56-1 methanol 
• 125031-99-4 12-iodo-oxychelerythrine 
• 93412-98-7 3-<2-(2-hydroxyethyl)-4,5-methylenedioxyphenyl>-7,8-dimethoxy-2-methylisoquinolin-1(2H)-one 
• 34316-15-9 chelerythrinium 
• 1620902-98-8 6,7-methylenedioxy-1-(2,2,2-trichloromethylcarbonylamino)naphthalene 
• 1620902-92-2 6,7-methylenedioxy-1-(2,2,2-trichloromethylcarbonylamino)-1,4-dihydronaphthalene 
• 1620902-84-2 (2E)-3-(2-allyl-4,5-methylenedioxyphenyl)prop-2-en-1-ol 
• 1620902-77-3 ethyl (2E)-3-(2-allyl-4,5-methylenedioxyphenyl)prop-2-enoate 
• 86838-09-7 ethyl (2E)-3-(2-bromo-4,5-methylenedioxyphenyl)prop-2-enoate 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 1356496-45-1 2-(3-(benzo[d][1,3]dioxol-5-yl)-7,8-dimethoxy-2-methyl-1-oxo-1,2-dihydroisoquin-4-yl)acetaldehyde 
• 56221-26-2 methyl 2,3-dimethoxy-6-iodobenzoate 
• 892150-32-2 C₉H₉IO₃ 

Downstream Products

• 3895-92-9 chelerythrine chloride 
• 21080-31-9 6-methoxy-5,6-dihydrochelerythrine 
• 4070-42-2 6-hydroxy-5,6-dihydrochelerythrine 

Relevant articles and documents

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In vitro antifungal activity of sanguinarine and chelerythrine derivatives against phytopathogenic fungi

In order to understand the antifungal activity of some derivatives of sanguinarine (S) and chelerythrine (C) and their structure-activity relationships, sixteen derivatives of S and C were prepared and evaluated for in vitro antifungal activity against seven phytopathogenic fungi by the mycelial growth rate method. The results showed that S, C and their 6-alkoxy dihydro derivatives S1-S4, C1-C4 and 6-cyanodihydro derivatives S5, C5 showed significant antifungal activity at 100 μg/mL against all the tested fungi. For most tested fungi, the median effective concentrations of S, S1, C and C1 were in a range of 14-50 μg/mL. The structure-activity relationship showed that the C=N+ moiety was the determinant for the antifungal activity of S and C. S1-S5 and C 1-C5 could be considered as the precursors of S and C, respectively. Thus, the present results strongly suggested that S and C or their derivatives S1-S5 and C1-C5 should be considered as good lead compounds or model molecules to develop new anti-phytopathogenic fungal agents.

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.