13161-79-0

Usage

Uses

Used in Pharmaceutical Industry:
Noracronycine is used as a pharmaceutical compound for its potential therapeutic properties. Its weak basic nature and unique spectral characteristics make it a candidate for the development of new drugs and treatments.
Used in Chemical Research:
Noracronycine is utilized in chemical research to study the properties and reactions of acridinone alkaloids. Its methylation reaction with methyl sulfate and potassium carbonate provides insights into the synthesis of related compounds, such as acronycine.
Used in Analytical Chemistry:
The distinctive ultraviolet spectrum of noracronycine, with its absorption maxima and shoulders, can be employed in analytical chemistry for the identification and quantification of noracronycine in various samples.
Used in Material Science:
The bright yellow color and crystalline nature of noracronycine make it a potential candidate for applications in material science, such as the development of pigments or other colorants for various industries.

References

Govindachari, Pai, Subramaniam., Tetrahedron, 22, 3245 (1966)

InChI:InChI=1/C19H17NO3/c1-19(2)9-8-12-15(23-19)10-14(21)16-17(12)20(3)13-7-5-4-6-11(13)18(16)22/h4-10,21H,1-3H3

Upstream product

• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 88901-73-9 1,3-Dihydroxy-2-iodo-10-methyl-9-acridone 
• 28333-13-3 1,3-dihydroxy-10-methyl-4-(3-methylbut-2-enyl)-9(10H)-acridinone (glyocitrine-II) 
• 28333-02-0 N-methyl-1,3-dihydroxyacridone 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 16718-49-3 1-hydroxy-4-(3-hydroxy-3-methyl-butyl)-3-methoxy-10H-acridin-9-one 
• 2190-48-9 3-chloro-3-methyl-1-butene 
• 20324-10-1 1,3-dihydroxyacridin-9(10H)-one 
• 31525-67-4 dimethylacetal of 3-methyl-3-hydroxybutyraldehyde 
• 13396-93-5 6-Hydroxy-3,3-dimethyl-3,12-dihydro-7H-pyrano<2,3-c>acridin-7-one 
• 74-88-4 methyl iodide 
• 85-91-6 Methyl N-methylanthranilate 
• 16727-39-2 6-hydroxy-3,3-dimethyl-1,2,3,12-tetrahydro-pyrano[2,3-c]acridin-7-one 
• 70509-95-4 6-methoxy-3,3,12-trimethyl-3,12-dihydro-pyrano[2,3-c]acridin-7-one; hydrochloride 

Downstream Products

• 13255-09-9 3,3,12-trimethyl-6-[[(4-methylphenyl)sulfonyl]oxy]-3H,7H-pyrano[2,3-c]acridin-7-one 
• 17014-70-9 1,2-dihydronoracronycine 
• 7008-42-6 acronine 
• 36380-14-0 3,12-Dihydro-6-acetoxy-3,3,12-trimethyl-7H-pyrano<2,3-c>acridin-7-on 

Relevant academic research and scientific papers

Acetylene Chemistry, Part XXII: Synthesis of Noracronycine and Some of its Analogs via Mitsunobu-Reaction

The natural product noracronycine as well as some of its analogs were synthesized by Mitsunobu-etherisation, using propinol derivatives.Keywords.Acridone alkaloids; Analogs of noracronycine; Chromene synthesis; Noracronycine; Mitsunobu-etherisation.

Natural Product Chemistry, Part 132: Synthesis and Oxidative Cyclisation of 1,3-Dihydroxy-10-methyl-4-(3-methylbut-2-enyl)-9(10H)-acridinone (Glycocitrine-II)

Reaction of 1,3-dihydroxy-10-methyl-9(10H)-acridinone (1) and 1-bromo-3-methylbut-2-ene (mol. ratio 1 : 1) in tetrahydrofuran at 20 deg C in the presence of alumina gave prenylacridinones 2 (glycocitrine-II) and 8 and the diprenylacridinone 9; with an excess of 1-bromo-3-methylbut-2-ene, the prenyldihydroyranoacridinones 12 and 13 were formed.Oxidation of glycocitrine-II (2) with m-chloroperbenzoic acid furnished the furanoacridinone 5 and the pyranoacridinone 6; dehydration of the latter compound gave noracronycine (10).

Total synthesis of acronycine and noracronycine: An aryne amination approach

Acronycine and noracronycine are chromene-containing alkaloids with significant biological activity. We have accomplished a concise total synthesis of acronycine and noracronycine. The key step, regioselective nucleophilic addition of anthranilate to chromene-type arynes under mild and transition-metal-free conditions was achieved. In addition, further modifications of nucleophilic addition products, such as hydrogenation, O-functionalization and palladium-catalyzed coupling reactions have also been developed, providing a concise procedure for these alkaloids and their derivatives.

Anti-AIDS agents 83. Efficient microwave-assisted one-pot preparation of angular 2,2-dimethyl-2H-chromone containing compounds

A novel and efficient microwave-assisted one-pot reaction was developed to synthesize angular 2,2-dimethyl-2H-chromone-containing compounds, which is the first and key step in the synthesis of potent DCK and DCP anti-HIV agents. The newly developed microwave synthesis conditions dramatically shortened the reaction time from 2 days to 4 h with improved yields.

New acridone derivatives obtained by heating the HCl salt of acronycine

By heating the HCl salt of acronycine (1), the new acridone derivatives (6, 9, 13 and 15) were obtained together with noracronycine (2), dihydronoracronycine (3), 1,3-dihydroxy-10-methylacridone (4) and (5). Compound (5), one of the main products of this reaction, is a linear type dihydro derivative of 2, compound (9) is a furanoacridone derivative with a geminal methyl group and compound (15) is a derivative of 5 with an additional C5 unit.

Acridone Alkaloids. Part 9. Chemical Constituents of Glycosmis citrifolia (Willd.) Lindl. Structures of Novel Linear Pyranoacridones, Furoacridones, and Other New Acridone Alkaloids

Sixteen acridone alkaloids were isolated from Glycosmis citrifolia (Willd.) Lindl. (Rutaceae) collected in Taiwan.Seven of them are novel and are reported for the first time, and can be divided into four groups: the linear pyranoacridones glucofoline (1a) and pyranofoline (2a), the furanoacridone furofoline-II (3b), the hexa-oxygenated acridone (4a), and the prenylated acridones glycocitrine-I (5a), -II (5c), and 3-O-methylglycocitrine-II (5d).The structures were elucidated from spectral data and chemical transformations.N.O.e. experiments on the methoxymethyl derivatives of phenolic acridones were successfully applied to the determination of the position of the hydroxy group on the acridone nucleus.The location of the phenyl group of (5c) was established by correlation with compound (8), employing cyclization of (5c) with benzeneselenenyl chloride.Formic acid-catalysed cyclization of (5c) induced undesirable rearrangement of the prenyl group to form the products (9) and (10).