15462-10-9

Usage

Chemical compound

2,3,8,9-tetramethoxybenzo[c]phenanthridine

Class

Benzo[c]phenanthridine alkaloids

Source

Naturally occurring compound isolated from plants such as Corydalis ambigua and Corydalis incisa

Pharmacological properties

Studied for potential anti-cancer, anti-inflammatory, and anti-microbial activities

Chemical structure

Unique structure that makes it a subject of interest for further research and potential therapeutic applications

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 13575-75-2 6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydronaphthalene 
• 98799-43-0 trans-4-(3,4-dimethoxyphenyl)but-3-enoic acid 
• 89525-51-9 (2-bromo-4,5-dimethoxyphenyl)methanamine 
• 168643-48-9 6,7-dimethoxynaphthalen-1-yl trifluoromethanesulfonate 
• 37895-73-1 1,2-dibromo-4,5-dimethoxybenzene 
• 19061-37-1 1,4-dihydro-6,7-dimethoxy-1,4-epoxynaphthalene 
• 198204-67-0 2-bromo-4,5-dimethoxybenzaldehyde oxime 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 135678-71-6 6,7-dimethoxy-α-naphthol 
• 131769-61-4 2,3,8,9-Tetramethoxybenzophenanthridin-12-ol sulphate 
• 352545-29-0 N-acetyl-4,5-dimethoxy-2-iodobenzylamine 
• 98799-33-8 2-iodo-4,5-dimethoxybenzylamine 
• 5763-61-1 3,4-dimethoxybenzylamine 

Downstream Products

• 140169-38-6 5H-2,3,8,9-tetramethoxybenzophenanthridinium tosylate 
• 140169-39-7 5-methyl-2,3,8,9-tetramethoxybenzophenanthridinium tosylate 
• 51116-33-7 2,3,8,9-tetramethoxy-5-methyl-benzo[c]phenanthridinium; methyl sulfate 

Relevant academic research and scientific papers

Rapid and convergent assembly of natural benzo[c]phenanthridines by palladium/norbornene catalysis

A straightforward total synthesis of a small panel of natural benzo[c]phenanthridines is described. The selective coupling of an aryl triflate with a bromobenzylamine by means of palladium/norbornene joint catalysis and a sequential transfer hydrogenation

A Short Total Synthesis of Benzophenanthridine Alkaloids via a Rhodium(III)-Catalyzed C-H Ring-Opening Reaction

The biologically important naturally available benzophenanthridines were prepared efficiently in three steps with overall good yields. A new synthetic methodology involving a rhodium(III) catalyzed redox-neutral ring-opening of 7-azabenzonorbornadienes with aromatic aldoximes is developed to synthesize the target molecules. The developed C-H ring-opening reaction is highly diastereoselective and compatible with various sensitive functional group substituted aromatic aldoximes as well as substituted 7-azabenzonorbornadienes. The ring-opening products were transformed into highly sensitive 13,14-dehydrobenzo phenanthridine derivatives by HCl hydrolysis. Subsequently, 13,14-dehydrobenzophenanthridines were converted into biologically important benzophenanthridine alkaloids in the presence of DDQ. A possible reaction mechanism was proposed for the C-H ring-opening reaction and supported by the deuterium labeling studies.

(Z)-Ethyl 2-phenyl-1-(2-vinylphenyl)vinylcarbamates. Part 1: Synthesis and preliminary studies on their divergent transformation into benzo[c] phenanthridines and 2-phenyl-1,4-naphthoquinones

Treatment of N-carbethoxy-1-benzylideneisoquinolines with LDA gives N-ethoxycarbonyl-1-amino-1-(2-vinylphenyl)-2-phenylethylenes, which can easily be transformed into N-carbethoxy-1-amino-2-phenylnaphthalenes. Bischler-Napieralski reaction of these latter

BENZOPHENANTHRIDES. XV. SYNTHESIS OF O-METHYLFAGARONINE IODIDE AND CHLORIDE FROM 13α-HYDROXYXYLOPININE

Hydroborination of 3-(2-vinyl-4,5-dimethoxyphenyl)-6,7-dimethoxy-2-methyl-1,2-dihydro-1-isoquinolone gave 3--6,7-dimethoxy-2-methylisoquinolin-1-one, which was converted by the action of various oxidizing agents into a benzophenanthridone derivative. 5-Methyl-5,6-dihydro-2,3,8,9-tetramethoxybenzophenanthridine, obtained from the above benzophenanthridone by reduction with LiAlH4 in tetrahydrofuran at 0 deg C, was converted into O-methylfagaronine iodide by boiling in an ethanolic solution of I2 in the presence of Na acetate.On exchanging I- by Cl-, O-methylfagaronine chloride was obtained in a quantitative yield in boiling methanol with an excess of AgCl.

A Very Short Route to Fully Aromatic 2,3,8,9- and 2,3,8,9,12-Oxygenated Benzophenanthridines

Cyclisation of suitably substituted 2-benzylamino-2-phenylacetonitriles proceeds by rearrangement in sulphuric acid or anhydrous hydrogen fluoride, to give 3-aryl-1,2-dihydroisoquinolinones possessing all but two carbons of the benzophenanthridine ring system.These two carbon atoms are introduced in high yield by means of a modified Reformatski reaction and the resulting ester is cyclised in sulphuric acid, with concomitant dehydration and oxidation, to give the fully aromatic four-ring system in only four steps.

Direct Synthesis of Benzophenanthridines and Benzophenanthridones via SRN1 Reactions

A straightforward and high-yield route to the 11,12-dihydrobenzophenanthridine (3) and 11,12-dihydrobenzophenanthridone (14) ring systems is based upon an SRN1 reaction between 2-halobenzylamines 1 or 2-halobenzoic acids 11 and enolates derived from tetralones 2.The efficient dehydrogenation of 3 or 14 gives the benzophenthridines 4 or benzophenanthridones 15.Use of properly substituted reactants leads to nitidine, avicine, and fagaronine and to analogues of those natural products.

Synthesis and biological activity of some antitumor benzophenanthridinium salts

A facile synthesis of benzophenanthridinium salts was developed and used for preparing a number of these compounds. The antitumor activities in mouse leukemia L1210 (LE) and P388 (PS) were determined as well as some selected antimicrobial activities. Alth