50892-83-6

Basic information

• Product Name: 1-Acetyl-carboline
• Synonyms: 1-Acetyl-beta-carboline;1-(9H-pyrido[3,4-b]indol-1-yl)ethanone;1-(9H-Pyrido[3,4-b]indol-1-yl)ethan-1-one
• CAS NO: 50892-83-6
• Molecular Formula: C13H10N2O
• Molecular Weight: 210.2313
• Mol File: 50892-83-6.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 438.2 °C at 760 mmHg
• Flash Point: 219.3 °C
• Appearance: /
• Density: 1.307 g/cm³
• CAS DataBase Reference: 1-Acetyl-carboline(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Acetyl-carboline(50892-83-6)
• EPA Substance Registry System: 1-Acetyl-carboline(50892-83-6)

Safety Data

• Hazardous Substances Data: 50892-83-6(Hazardous Substances Data)

Usage

General Description

1-Acetyl-carboline, also known as norharmane, is a chemical compound found in various plants and foods, as well as in tobacco smoke. It is a naturally occurring alkaloid and is considered to be a potential carcinogen. 1-Acetyl-carboline has been studied for its potential role in various biological processes, including its interaction with neurotransmitter receptors in the brain. It is also being investigated for its potential as an anti-inflammatory and antioxidant agent. Additionally, 1-Acetyl-carboline has been identified as a precursor to the formation of harmful substances in tobacco smoke, making it a target for research in the development of cancer prevention strategies. Overall, 1-Acetyl-carboline is a compound of interest for its potential health effects and toxicological properties.

Upstream product

• 148683-93-6 1-(1-hydroxyethyl)9H-pyrido<3,4-b>indole 
• 20127-61-1 1-ethyl-9H-β-carboline 
• 20602-39-5 oxaloacetaldehyde 
• 73-22-3 L-Tryptophan 
• 54-12-6 Trp 
• 934463-33-9 1-acetyl-3,4-dihydro-β-carboline 
• 78-98-8 2-oxopropanal 
• 75-16-1 methylmagnesium bromide 
• 79960-43-3 9H-pyrido[3,4-b]indole-1-carbonitrile 
• 244-63-3 betacarboline 
• 75-07-0 acetaldehyde 
• 709029-79-8 1-(1-ethoxyvinyl)-9H-pyrido[3,4-b]indole 
• 75304-03-9 methyl 1-ethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 
• 97674-02-7 tributyl(1-ethoxyvinyl)stannane 

Downstream Products

• 38940-60-2 9H-pyrido[3,4-b]indole-1-carboxamide 

Relevant articles and documents

Synthesis and investigations into the anticancer and antibacterial activity studies of β-carboline chalcones and their bromide salts

A series of sixteen β-carbolines, bearing chalcone moiety at C-1 position, were prepared from easily accessible 1-acetyl-β-carboline and various aldehydes under basic conditions followed by N2-alkylation using different alkyl bromides. The prepared compounds were evaluated for in vitro cytotoxicity against a panel of human tumor cell lines. N2-Alkylated-β-carboline chalcones 13a-i represented the interesting anticancer activities compared to N2-unsubstituted β-carboline chalcones 12a-g. Off the prepared β-carbolines, 13g exhibited broad spectrum of activity with IC50 values lower than 22.5 μM against all the tested cancer cell lines. Further, the N2-alkylated-β-carboline chalcone 13g markedly induced cell death in MDA-MB-231 cells by AO/EB staining assay. The most cytotoxic compound 13g possessed a relatively high drug score of 0.48. Additionally, the prepared β-carboline chalcones displayed moderate antibacterial activities against tested bacterial strains.

Discovery of McbB, an enzyme catalyzing the β-carboline skeleton construction in the marinacarboline biosynthetic pathway

Three genes, mcbABC, that drive the biosynthesis of marinacarbolines, have been elucidated through genome mining, gene inactivation, heterologous expression, feeding, and site-directed mutagenesis experiments. McbB is highlighted as a novel enzyme for the β-carboline core construction, which involves a Pictet-Spengler cyclization process and requiring E97 for biochemical activity.

Preparation method of 1-carbonyl-beta-carboline compound

The invention discloses a preparation method of a 1-carbonyl-beta-carboline compound. The preparation method comprises the following step: in an air or oxygen atmosphere, in the presence of an additive and under the condition of illumination, performing oxidation reaction on tetrahydrocarboline compound as shown in a formula II to obtain the 1-carbonyl-beta-carboline compound as shown in a formula I, wherein the additive is tetrabutyl quaternary ammonium salt selected from any one of tetrabutylammonium bromide, tetrabutylammonium iodide, tetrabutylammonium chloride, tetrabutylammonium acetate and tetrabutylammonium fluoride; and the molar ratio of the tetrahydrocarboline compound as shown in the formula II to the additive is 1:(0.2-2). The preparation method provided by the invention is high in yield, wherein most of the yield is between 60% and 90%. When R3 is an aromatic group, the variety and the position of a substituent group on an aromatic ring do not have substantial influence on the yield of the reaction. In addition, the R3 group has wider applicability and also comprises an alkyl R3 group besides the aromatic R3 group, and in this aspect, the preparation method provided by the invention is substantially improved compared with the existing synthesis.