13161-83-6

Usage

InChI:InChI=1/C15H13NO3/c1-16-12-6-4-3-5-10(12)15(18)11-7-9(19-2)8-13(17)14(11)16/h3-8,17H,1-2H3

Upstream product

• 13146-23-1 copper(I) phenylacetylenide 
• 88901-72-8 1-Hydroxy-2-iodo-3-methoxy-10-methyl-9-acridone 
• 28333-02-0 N-methyl-1,3-dihydroxyacridone 
• 74-88-4 methyl iodide 
• 20324-10-1 1,3-dihydroxyacridin-9(10H)-one 
• 77-78-1 dimethyl sulfate 
• 108-73-6 3,5-dihydroxyphenol 
• 88901-73-9 1,3-Dihydroxy-2-iodo-10-methyl-9-acridone 
• 82354-37-8 3-O-methylglycocitrine-II 
• 56964-06-8 (3-methyl-3-buten-1-yn-1-yl)copper 
• 115-18-4 2-methyl-3-buten-2-ol 

Downstream Products

• 13082-10-5 1,3-dimethoxy-N-methylacridone 
• 1027644-70-7 N-[2-(3-methoxy-10-methyl-9-oxo-9,10-dihydro-acridin-1-yl)-phenyl]-2,2-dimethyl-propionamide 
• 171919-96-3 tert-butyl 4-methoxy-2-(3-methoxy-10-methyl-1-oxo-1,10-dihydroacridin-9-yl)phenylcarbamate 
• 171919-98-5 N-<2-(3-methoxy-10-methyl-1-oxo-1,10-dihydroacridin-9-yl)phenyl>-2,2-dimethylpropionamide 

Relevant academic research and scientific papers

Easy access to pyranoacridines, pyranoxanthenes, and arylchromenes through a domino reaction

A series of pyrano[2,3,4-kl]acridines has been synthesized through an unprecedented domino reaction involving1-hydroxy-3-methoxy-10-methylacridone and Grignard reagents. This method has been successfully applied to xanthone, anthracenone, and benzophenone

N8, n13 -disubstituted quino[4,3,2-kl]acridinium salts as therapeutic agents

The present invention pertains to certain N8,N13-disubstituted quino[4,3,2-kl]acridinium salts of formula (Q?) which inhibit telomerase wherein: p is an integer from 0 to 4; q is an integer from 0 to 3; r is an integer from 0 to 4; each RA is —H or a ring substituent; each RB is —H or a ring substituent; each RC is —H or a ring substituent; RN8 is a nitrogen substituent; RN13 is a nitrogen substituent; and, Q is an anion. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit telomerase, to regulate cell proliferation, and in the treatment of proliferative conditions, such as cancer.

Antitumour polycyclic acridines. Palladium(0) mediated syntheses of quino[4,3,2-kl]acridines bearing peripheral substituents as potential telomere maintenance inhibitors

Pd(0) mediated couplings between substituted 2-(pivaloylamino)benzeneboronic acids and 3,6-disubstituted-10-methylacridones 13 bearing a bromo or trifluoromethylsulfonyloxy substituent in the 1-position yield intermediate 1-arylacridones 16 which can be c

Reaction of Noracronycine and 1-Hydroxy-3-methoxy-10-methylacridone with Alkyl- and Aryl-lithiums: Formation of Quinone Methides

Alkyl- and aryl-lithiums reacted with noracronycine and 1-hydroxy-3-methoxy-10-methylacridone in a one-step addition-dehydration transformation to provide the corresponding 7- and 9-substituted derivatives having a quinone methide function and, therefore,

Natural Product Chemistry, 143 Convenient Synthesis of Isoacronycine and Some Other New Acridone Derivatives

The iodination of 1,3-dihydroxy-9-acridone (1), 1-hydroxy-3-methoxy-10-methyl-9-acridone (2) and 1,3-dihydroxy-10-methyl-9-acridone (3) yields 1,3-dihydroxy-2,4-diiodo-9-acridone (4), 1-hydroxy-2-iodo-3-methoxy-10-methyl-9-acridone (5) and 1,3-dihydroxy-2-iodo-10-methyl-9-acridone (6), respectively.The methylation of 4 and 5 gives 2,4-diiodo-1,3-dimethoxy-10-methyl-9-acridone (7) and 2-iodo-1,3-dimethoxy-10-methyl-9-acridone (9), respectively.The direct C-C coupling of 2-methyl-3-buten-2-ol to the compounds 5, 7 and 9 by palladium catalysed Heck condensation method gives three new acridone derivatives 1-hydroxy-2-(3-hydroxy-3-methyl-1-butenyl)-3-methoxy-10-methyl-9-acridone (10), 2,4-bis(3-hydroxy-3-methyl-1-butenyl)-1,3-dimethoxy-10-methyl-9-acridone (12) and 2-(3-hydroxy-3-methyl-1-butenyl)-1,3-dimethoxy-10-methyl-9-acridone (13) while compound 6 is converted into isonoracronycine (11).The methylation of 11 yields isoacronycine (14). Key words: Acridone alkaloids / Heck condensation / Isonoracronycine / Isoacronycine

A Two-step Synthesis of 1-Hydroxy-3-methoxy-10-methylacridone: An Acridone Alkaloid

A two-step synthesis of 1-hydroxy-3-methoxy-10 methylacridone 1, an acridone alkaloid is reported.The synthesis involved the preparation of 1,3-dihydroxyacridone 2 followed by direct methylation to give 1.

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).

New alkaloids from Glycosmis mauritiana

Chemical investigation of the roots of G. mauritiana resulted in the isolation of two new alkaloids; 1-hydroxy-3-methoxy-2-(3-methylbut-2-enyl)-N-methylacridan-9-one (1) and 4,8-dimethoxy-3-(3-methylbut-2-enyl)-N-methyl-2-quinolone (6). The structures of these new bases have been established by chemical and spectroscopic methods and confirmed in the case of 6 by its synthesis. Interestingly, the formic acid-catalysed cyclisation of 1 gave the dealkylated product 3 along with the pyrano-[2, 3-a]-acridine (4).

Alkaloids, limonoids and furocoumarins from three Mexican Esenbeckia species

The chemical constituents of three Mexican Esenbeckia species have been determined. Rutaevin was the main limonoid present in the seeds of all three species, E. litoralis, E. flava and E. berlandieri. The husks, leaves, wood and bark contained a wide array of known furocoumarins and furoquinoline alkaloids. In addition, 1-hydroxy-3-methoxy-N-methylacridone was obtained from E. litoralis bark and a new natural 2-quinolone alkaloid, formulated as 3,3-diisopropyl-N-methyl-2,4-quinoldione, was obtained from E. flava wood. The structure was assigned from spectroscopic considerations and conversion to N-methylhaplofoline.