28342-33-8

Usage

Uses

Used in Pharmaceutical Industry:
6-Oxochelerythrine is used as a potential therapeutic agent for its anti-inflammatory properties, leveraging its ability to inhibit enzymes that produce prostaglandins, which are crucial in inflammatory responses.
Used in Anticancer Applications:
6-Oxochelerythrine is used as an anticancer agent due to its demonstrated cytotoxic effects on cancer cells. It shows promise in the development of drugs that could target various types of cancer, potentially leading to novel treatment options for patients.
Used in Antimicrobial Applications:
Given its anti-bacterial and anti-fungal activities, 6-Oxochelerythrine is used as an antimicrobial agent in the development of new antibiotics and antifungal medications, which could be beneficial in combating drug-resistant strains of pathogens.
Used in Drug Delivery Systems:
6-Oxochelerythrine's potential is also being explored in drug delivery systems to enhance its bioavailability and therapeutic efficacy. This could involve encapsulation in nanoparticles or other carriers to improve the compound's delivery to target sites within the body.

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

• 67257-99-2 7,8-dimethoxy-2-methyl-3-(4,5-methylenedioxy-2-vinylphenyl)isoquinolin-1(2H)-one 
• 5138-09-0 chelerythrine φ-cyanide 
• 181634-57-1 2,3-dimethoxy-6-iodo-N-methyl-N-(6,7-methylenedioxy-1-naphthyl)benzamide 
• 181634-60-6 6-bromo-2,3-dimethoxy-N-methyl-N-(6,7-methylenedioxynaphthalen-1-yl)benzamide 
• 53811-49-7 naphtho[2,3-d][1,3]dioxol-5-amine 
• 56517-24-9 6,7-bis(methylsulfonyloxy)-1-nitronaphthalene 
• 65341-21-1 N-(3,4-dihydro-6,7-methylenedioxy-1-naphthyl)-2,3,6-trimethoxy-N-methylbenzamide 
• 41303-45-1 6,7-methylenedioxy-1-tetralone 
• 58093-61-1 2,3,6-Trimethoxybenzoesaeurechlorid 
• 34316-15-9 chelerythrinium 
• 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 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 86838-09-7 ethyl (2E)-3-(2-bromo-4,5-methylenedioxyphenyl)prop-2-enoate 
• 1620902-77-3 ethyl (2E)-3-(2-allyl-4,5-methylenedioxyphenyl)prop-2-enoate 

Downstream Products

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

Relevant academic research and scientific papers

Preparation of amino-substituted indenes and 1,4-dihydronaphthalenes using a one-pot multireaction approach: Total synthesis of oxybenzo[c]phenanthridine alkaloids

Allylic trichloroacetimidates bearing a 2-vinyl or 2-allylaryl group have been designed as substrates for a one-pot, two-step multi-bond-forming process leading to the general preparation of aminoindenes and amino-substituted 1,4-dihydronaphthalenes. The synthetic utility of the privileged structures formed from this one-pot process was demonstrated with the total synthesis of four oxybenzo[c]phenanthridine alkaloids, oxychelerythrine, oxysanguinarine, oxynitidine, and oxyavicine. An intramolecular biaryl Heck coupling reaction, catalyzed using the Hermann-Beller palladacycle was used to effect the key step during the synthesis of the natural products.

One-pot synthesis of isoquinolinium salts by rhodium-catalyzed C-H bond activation: Application to the total synthesis of oxychelerythrine

It's worth its salt: The title reaction leads to the synthesis of highly substituted isoquinolinium salts (see scheme; Cp=Me5C 5). The reaction proceeds through a C-H activation and a subsequent annulation in the presence of a rhodium catalyst. The reaction mechanism is discussed as well as its application to the synthesis of the natural product oxychelerythrine.

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.

Palladium-catalyzed tandem reaction to construct benzo[c]phenanthridine: Application to the total synthesis of benzo[c]phenanthridine alkaloids

A concise and efficient synthesis of benzo[c]phenanthridines was accomplished by the palladium-catalyzed ring-opening coupling of azabicyclic alkene with o-iodobenzoates, followed by tandem cyclization. The strategy was successfully applied in the total synthesis of benzo[c]phenanthridine alkaloids such as sanguinarine, chelerythrine, nitidine and avicine.

Synthesis of oxychelerythrine using lithiated toluamide-benzonitrile cycloaddition

Oxychelerythrine, benzo[c]phenanthridine alkaloid, was synthesized from easily available starting toluamide 5 and benzonitrile 6 using toluamide-benzonitrile cycloaddition reaction in 6 steps.

Intramolecular Pd-catalyzed biaryl coupling reaction of N-aryl-2-triflyloxybenzamides using Pd(OAc)2, 1,3-bis[diphenylphosphino]propane, Bu3P, and DBU

Intramolecular Pd-catalyzed coupling reactions of N-aryl-2-triflyloxybenzamides were examined. The procedure using DBU as a base was effective for even in the reaction of oxygen-substituted benzamides.

Synthesis of benzo[c]phenanthridine alkaloids, using a novel palladium-phosphine combination system - Pd(OAc)2, DPPP, and Bu3P

Total synthesis of several benzo[c]phenanthridine alkaloids was accomplished via an aryl-aryl coupling reaction using a novel Pd reagent prepared from Pd(OAc)2 DPPP, and Bu3P. This is a versatile method for the coupling reactions of not only aryl triflates and arenes but also aryl halides and arenes.

Aryl-aryl coupling reaction catalyzed by a palladium reagent prepared from Pd(OAc)2 and n-Bu3P

A palladium reagent prepared from Pd (OAc)2 (0.2 eq) and n-Bu3P (0.6 eq) catalyzed an aryl-aryl coupling reaction. This procedure is effective for coupling reactions of aryl triflate possessing no oxygen groups with arene, and of aryl iodide with arene.

Total synthesis of benzo[c]phenanthridine alkaloids, chelerythrine and 12-methoxydihydrochelerythrine, by a palladium-assisted internal biaryl coupling reaction

A covenient and versatile synthesis of benzo[c]phenanthridine alkaloids, chelerythrine (1) and 12-methoxydihydrochelerythrine (5), was accomplished via an internal aryl-aryl coupling reaction of haloamides 8 and 9 by a palladium-assisted cyclization reaction.