5574-24-3

Usage

Uses

Used in Pharmaceutical Industry:
Oxoglaucine is used as a cytotoxic agent for its potential anticancer properties. oxoglaucine's ability to exhibit cytotoxic effects against 9-KB experimental tumors suggests that it may have applications in the development of cancer treatments, particularly for targeting and eliminating cancer cells.
Used in Drug Discovery and Development:
Oxoglaucine's cytotoxic nature also makes it a valuable compound for drug discovery and development. Researchers can investigate its potential as a lead compound in the creation of new pharmaceuticals targeting various diseases, including cancer. Further studies on its mechanism of action, bioavailability, and safety profile would be necessary to advance its use in this field.

References

Sonnet, Jacobson,J. Pharm. Sci., 60, 1254 (1971)

InChI:InChI=1/C20H17NO5/c1-23-13-8-11-12(9-14(13)24-2)19(22)18-16-10(5-6-21-18)7-15(25-3)20(26-4)17(11)16/h5-9H,1-4H3

Upstream product

• 22212-26-6 dehydroglaucine 
• 39945-40-9 (+/-)-norglaucine 
• 103769-57-9 3,4,6,7-Tetramethoxy-1-(2-methylamino-ethyl)-phenanthrene-9,10-dione 
• 41823-67-0 1-(2'-bromo-4',5'-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline 
• 38726-64-6 tetradehydroglaucine 
• 83511-44-8 1-(2'-amino-4',5'-dimethoxy-α-oxobenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 55974-08-8 oxoglaucine methiodide 
• 80041-85-6 6,7,9,10-Tetramethoxy-3,4-dihydro-1H-2a-aza-benzo[fg]aceanthrylen-2-one 
• 78178-94-6 isatine 
• 38764-84-0 1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-4-ol 
• 5630-11-5 (+/-)-glaucine 
• 39945-38-5 4H-1,2,9,10-tetramethoxy-5,6-dihydrodibenzo[de,g]quinoline 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 16251-41-5 1-(2'-nitro-4',5'-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline 

Downstream Products

• 1357565-67-3 [oxoglaucineH][AuCl₄]*DMSO 
• 75652-86-7 Threo-N-methyl-7-hydroxy-1,2,9,10-teramethoxyaporphine 
• 75652-86-7 erythro-N-methyl7-hydroxy-1,2,9,10-tetramethoxyaporphine 
• 103769-59-1 corrunine 
• 77520-88-8 cis-7-hydroxy-1,2,9,10-tetramethoxyaporphine 
• 55974-08-8 oxoglaucine methiodide 

Relevant academic research and scientific papers

Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs

Novel total syntheses of oxoaporphine alkaloids such as liriodenine, dicentrinone, cassameridine, lysicamine, oxoglaucine and O-methylmoschatoline were developed. The key step of these total syntheses is Cu-catalyzed conversion of 1-benzyl-3,4-dihydro-isoquinolines (1-Bn-DHIQs) to 1-benzoyl-isoquinolines (1-Bz-IQs) via tandem oxidation/aromatization. This novel Cu-catalyzed conversion has been studied in detail, and was successfully used for constructing the 1-Bz-IQ core.

A divergent approach to benzylisoquinoline-type and oxoaporphine alkaloids via regioselective direct ring metalation of alkoxy isoquinolines

Methoxy- and benzyloxy-substituted isoquinolines are regioselectively metalated at C-1 with the Knochel-Hauser base, subsequent trapping with aromatic aldehydes gives aryl(isoquinolin-1-yl)carbinols as building blocks for divergent syntheses of different types of benzylisoquinoline alkaloids. Photochemical cyclization of ortho-bromo analogues under reductive conditions gives oxoaporphine alkaloids. Nine benzylisoquinoline alkaloids and two oxoaporphine alkaloids were obtained in two or three steps from appropriate isoquinolines.

TCM active ingredient oxoglaucine metal complexes: Crystal structure, cytotoxicity, and interaction with DNA

The alkaloid oxoglaucine (OG), which is a bioactive component from traditional Chinese medicine (TCM), was synthesized by a two-step reaction and used as the ligand to react with transition metal salts to give four complexes: [OGH][AuCl4]·DMSO (1), [Zn(OG)2(H 2O)2]- (NO3)2 (2), [Co(OG) 2(H2O)2](ClO4)2 (3), and [Mn- (OG)2(H2O)2](ClO4)2 (4). The crystal structures of the metal complexes were confirmed by single crystal X-ray diffraction. Complex 1 is an ionic compound consisting of a charged ligand [OGH]+ and a gold complex [AuCl4] -. Complexes 2-4 all have similar structures (inner-spheres), that is, octahedral geometry with two OG coordinating to one metal center and two aqua ligands occupying the two apical positions of the octahedron, and two NO3- or ClO4 - as counteranions in the outer-sphere. The complexation of OG to metal ion was confirmed by ESI-MS, capillary electrophoresis and fluorescence polarization. The in vitro cytotoxicity of these complexes toward a various tumor cell lines was assayed by the MTT method. The results showed that most of these metal-oxoglaucine complexes exhibited enhanced cytotoxicity compared with oxoglaucine and the corresponding metal salts, with IC5 values ranging from 1.4 to 32.7 μM for sensitive cancer cells, which clearly implied a positive synergistic effect. Moreover, these complexes appeared to be selectively active against certain cell lines. The interactions of oxoglaucine and its metal complexes with DNA and topoisomerase I were investigated by UV-vis, fluorescence, CD spectroscopy, viscosity, and agarose gel electrophoresis, and the results indicated that these OG-metal complexes interact with DNA mainly via intercalation. Complexes 2-4 are metallointercalators, but complex 1 is not. These metal complexes could effectively inhibit topoisomerase I even at low concentration. Cell cycle analysis revealed that 1-3 caused S-phase cell arrest.

Manganese(III) acetate mediated oxidation of aporphines: a convenient and useful synthesis of oxoaporphines

Manganese(III) acetate mediated oxidation of aporphines to oxoaporphines is described. The developed methodology was conveniently applied for the synthesis of naturally occurring oxoaporphine alkaloids, oxoglaucine, and atheroline, starting from commercially available boldine.

Glaucine analogues as inhibitors of mouse splenocyte activity

The inhibitory effect of 15 semi-synthetic analogues of glaucine (1) on the lipopolysaccharide (LPS)-induced and the concanavalin A (Con A)-induced proliferation of mouse splenocytes was compared in vitro. Isoboldine (3), bracteoline (4) and dehydroglaucine (9) showed a significantly higher potency to suppress LPS-induced proliferation than 1, while 7-hydroxy-4-methylglaucine (8), 7-formyldehydroglaucine (11), 7-acetyldehydroglaucine (13), 7- benzoyldehydroglaucine (14), oxoglaucine (15) and glaucine-quinol (16) were less inhibitory. Compounds 3, 4, boldine (5), 15 and 16 surpassed significantly the inhibition expressed by 1 on Con A-induced proliferative response. The effect was equal to the inhibition determined for mitomycin C (Mit C) with both mitogens. In contrast to all others analogues, thaliporphine (2) stimulated splenocyte proliferation in both assays. Antibody response against sheep red blood cells (SRBC) was lowered most strongly by cataline (6), 7- methyldehydroglaucine (10) and 16.

THE SYNTHESIS OF OXOAPORPHINES AND PHENANTHRENEDIONES FROM 7-HYDROXYDEHYDRONORAPORPHINES

Oxidation of 7-hydroxydehydronoraporphines with air over platinum or palladium yields oxoaporphines in high yield.When the nitrogen is acylated, oxidation with air in the presence of copper ions causes an oxidative ring fragmentation to form phenanthrenediones, also in high yield.

Intermolecular Benzyne Cycloaddition Approach to Aporphinoids. Total Syntheses of Norcepharadione B, Cepharadione B, Dehydroanonaine, Duguenaine, Dehydronornuciferine, Pontevedrine, O-Methylatheroline, Lysicamine, and Alkaloid PO-3

We describe a useful novel approach to the synthesis of aporphinoids, including dehydroaporphines, aristolactams, 4,5-dioxoaporphines, and 7-oxoaporphines, by means of intermolecular benzyne cycloaddition (IBC).Specifically, we report the total synthesis of the isoquinoline alkaloids norcepharadione B, cepharadione B, dehydroanonaine, deguenaine, dehydronornuciferine, pontevedrine, O-methylatheroline, lysicamine, and alkaloid PO-3.

A DIRECT CONVERSION OF PHENANTHRENES TO APORPHINOIDS

We desribe a single-step conversion of phenanthrene alkaloid derivatives into oxoaporphines based on the cyclization of 9,10-phenanthrenediones with ethanamine side-chains under basic conditions.

THE INTERMOLECULAR BENZYNE CYCLOADDITION APPROACH TO DEHYDRONORAPORPHINES AND OXOAPORPHINES. TOTAL SYNTHESIS OF PO-3

The synthesis of dehydronoraporphines and oxoaporphines has been achieved by means of the convergent and highly regioselective intermolecular benzyne cycloaddition approach.The first total synthesis of the quaternary oxoaporphine PO-3 is described.

STUDY ON THE COUPLING REACTIONS OF BENZYLISOQUINOLINES WITH LEAD TETRAACETATE

Lead tetraacetate (LTA) oxidation of different mono- or non-phenolic tetrahydrobenzylisoquinolines containing secondary amino group leads to dibenzopyrrocoline derivative or oxoaporphine, respectively.The substrate selectivity of LTA has been discussed.