20324-10-1

Basic information

• Product Name: 1,3-Dihydroxyacridin-9(10H)-one
• Synonyms: 1,3-Dihydroxyacridin-9(10H)-one
• CAS NO: 20324-10-1
• Molecular Formula: C₁₃H₉NO₃
• Molecular Weight: 227.22
• Mol File: 20324-10-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-Dihydroxyacridin-9(10H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dihydroxyacridin-9(10H)-one(20324-10-1)
• EPA Substance Registry System: 1,3-Dihydroxyacridin-9(10H)-one(20324-10-1)

Safety Data

• Hazardous Substances Data: 20324-10-1(Hazardous Substances Data)

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 134-20-3 2-carbomethoxyaniline 
• 118-92-3 anthranilic acid 

Downstream Products

• 260-94-6 acridine 
• 13161-83-6 1-hydroxy-3-methoxy-10-methyl-9-acridone 
• 1257333-35-9 10-benzyl-3-benzyloxy-1-hydroxy-10H-acridin-9-one 
• 13396-93-5 6-Hydroxy-3,3-dimethyl-3,12-dihydro-7H-pyrano<2,3-c>acridin-7-one 
• 1239586-23-2 1-hydroxy-3-phenethoxy-10H-acridin-9-one 
• 1239586-22-1 3-(benzyloxy)-1-hydroxy-10H-acridin-9-one 
• 17014-70-9 1,2-dihydronoracronycine 
• 7008-42-6 acronine 
• 13161-79-0 noracronycine 
• 6232-35-5 isoacronycine 

Relevant articles and documents

MHY440, a novel topoisomerase I inhibitor, induces cell cycle arrest and apoptosis via a ROS-dependent DNA damage signaling pathway in AGS human gastric cancer cells

We investigated the antitumor activity and action mechanism of MHY440 in AGS human gastric cancer cells. MHY440 inhibited topoisomerase (Topo) I activity and was associated with a DNA damage response signaling pathway. It exhibited a stronger anti-proliferative effect on AGS cells relative to Hs27 human foreskin fibroblast cells, and this effect was both time- and concentration-dependent. MHY440 also increased cell arrest in the G2/M phase by decreasing cyclin B1, Cdc2, and Cdc25c, and upregulating p53 and p73. MHY440 induced AGS cell apoptosis through the upregulation of Fas-L, Fas, and Bax as well as the proteolysis of BH3 interacting-domain death agonist and poly(ADP-ribose) polymerase. It also contributed to the loss of mitochondrial membrane potential. The apoptotic cell death induced by MHY440 was inhibited by pretreatment with Z-VAD-FMK, a pan-caspase inhibitor, indicating that apoptosis was caspase-dependent. Moreover, the apoptotic effect of MHY440 was reactive oxygen species (ROS)-dependent, as evidenced by the inhibition of MHY440-induced PARP cleavage and ROS generation via N-acetylcysteine-induced ROS scavenging. Taken together, MHY440 showed anticancer effects by inhibiting Topo I, regulating the cell cycle, inducing apoptosis through caspase activation, and generating ROS, suggesting that MHY440 has considerable potential as a therapeutic agent for human gastric cancer.

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

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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

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

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