479-43-6

Basic information

• Product Name: Canthin-6-one
• Synonyms: Canthin-6-one
• CAS NO: 479-43-6
• Molecular Formula: C₁₄H₈N₂O
• Molecular Weight: 220.22612
• EINECS: 200-258-5
• Mol File: 479-43-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 161-161.5 °C
• Boiling Point: 346.5 °C at 760 mmHg
• Flash Point: 163.4 °C
• Appearance: /
• Density: 1.4 g/cm³
• Vapor Pressure: 5.74E-05mmHg at 25°C
• Refractive Index: 1.763
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.40±0.20(Predicted)
• CAS DataBase Reference: Canthin-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: Canthin-6-one(479-43-6)
• EPA Substance Registry System: Canthin-6-one(479-43-6)

Safety Data

• Hazardous Substances Data: 479-43-6(Hazardous Substances Data)

Usage

Uses

Canthin-6-one is used as an anticancer agent compromising cancer cells showing multi-drug resistance. Also used in the synthesis of β-carbolinium compounds as antimalarial agents.

Definition

ChEBI: An indole alkaloid that is 6H-indolo[3,2,1-de][1,5]naphthyridine substituted by an oxo group at position 6.

InChI:InChI=1/C14H8N2O/c17-13-6-5-11-14-10(7-8-15-11)9-3-1-2-4-12(9)16(13)14/h1-8H

Upstream product

• 65284-99-3 N_b-benzyl-1,2,3,3a,4,5-hexahydrocanthin-6-one 
• 55854-62-1 6-oxo-6H-indolo[3,2,1-de][1,5]naphthyridine-5-carboxylic acid 
• 525-41-7 1-methyl-4,9-dihydro-3H-β-carboline 
• 55854-61-0 6-oxo-6H-indolo[3,2,1-de][1,5]naphthyridine-5-carboxylic acid methyl ester 
• 18122-85-5 4,5-dihydro-canthin-6-one 
• 557789-34-1 3-(9H-β-carbolin-1-yl)-acrylic acid 
• 879551-86-7 3t-(9H-β-carbolin-1-yl)-acrylic acid 
• 92870-51-4 N'-<3-(methoxycarbonyl)propanoyl>tryptamine 
• 91147-07-8 3-(9H-Pyrido<3,4-b>indol-1-yl)propansaeure-methylester 
• 16979-93-4 N-benzylidene-2-(1H-indol-3-yl)ethylamine 
• 26400-25-9 1,2,3,3a,4,5-hexahydrocanthin-6-one 
• 141-78-6 ethyl acetate 
• 20127-63-3 kumujian C 
• 143217-69-0 canthine 

Downstream Products

• 90686-24-1 ethyl-β-carboline-1-propionate 
• 91147-07-8 3-(9H-Pyrido<3,4-b>indol-1-yl)propansaeure-methylester 
• 89915-39-9 β-carboline-1-propionic acid 
• 60755-87-5 canthin-6-one-3-N-oxide 

Relevant articles and documents

Selective Oxidation of Canthines to Canthin-6-ones with Triethylbenzylammonium Permanganate

Oxidation of canthines, prepared from intramolecular inverse electron demand Diels-Alder reactions of indole with tethered triazines, produced the corresponding canthin-6-ones regiospecifically, with no detected canthin-4-ones.

Solution phase and nanoparticular biosynthetically inspired interconnections in the canthin-6-one β-carboline series and study of phenotypic properties on C. elegans

Based on the biosynthetic line of canthin-6-one alkaloids from their simple precursors such as tryptamine, the present work is focused on the study of alternative protocol of the Bischler-Napieralski reaction and has led to a full coverage of the different biosynthetic intermediates. Nanoparticles were also prepared as mimics of biosynthetic assembly lines and some interesting biological results in term of chemical ecology are also reported. Canthin-6-one, a particular representative β-carboline alkaloid, was targeted for synthesis keeping in mind its biosynthetic origin. In fact, several biosynthetic intermediates were synthesized and nanoparticular mimicry of key steps was also achieved permitting further evaluation of biological properties for this class of alkaloids. Copyright

Synthesis, in vitro antibacterial activities of a series of 3-N-substituted canthin-6-ones

An improved synthetic route of canthin-6-one was accomplished. To further enhance the antibacterial potency and improve water solubility, a series of 3-N-alkylated and 3-N-benzylated canthin-6-ones were designed and synthesized, and their in vitro antibacterial activities were evaluated. A clear structure-activity relationship with peak minimal inhibitory concentration (MIC) values of 0.98 (μg·mL-1) was investigated. Particularly, compounds 6i-r and 6t were found to be the most potent compounds with minimal inhibitory concentration (MIC) values lower than 1.95 (μg·mL-1) against Staphylococcus aureus.

Two-step total syntheses of Canthin-6-one alkaloids: New one-pot sequential Pd-catalyzed Suzuki-Miyaura coupling and Cu-catalyzed amidation reaction

Chemical Equation Presented Canthin-6-one (1) and nine analogues including the naturally occurring 9-methoxycanthin-6-one (2) and amaroridine (3) are prepared rapidly and in high yields via a convergent non-classical strategy that focuses on construction of the central ring B. The strategy relies on concomitant Pd-catalyzed Suzuki-Miyaura C-C coupling followed by a Cu-catalyzed C-N coupling that can be achieved either stepwise or in a new one-pot protocol starting from the appropriate 8-bromo-1,5-naphthyrldine.