25700-04-3

Usage

Ketone derivative

Yes
The compound has a carbonyl group (C=O) attached to an alkyl or aryl group, classifying it as a ketone derivative.

Contains a triazole ring

Yes
The compound features a 1,2,4-triazole ring, which is a five-membered ring with three nitrogen atoms and two carbon atoms.

Common use

Pharmaceutical and chemical research
It is widely utilized in the development and study of various biologically active compounds, including potential drug candidates.

Building block

Synthesis of biologically active compounds
The compound serves as a versatile building block in the creation of different molecules with potential applications in the pharmaceutical industry.

Structure and reactivity

Versatile molecule in organic chemistry
Its unique structure and reactivity make it a valuable component in organic chemistry, allowing for various chemical reactions and modifications.

Potential applications

Drug discovery and development
The compound has been studied for its potential use in discovering and developing new drugs due to its unique properties and reactivity.

Biological activities

Research has shown potential
Studies have indicated that 1-[4-(1H-1,2,4-triazol-1-yl)phenyl]ethanone possesses potential biological activities, making it an interesting candidate for further investigation in the field of drug development.

InChI:InChI=1/C10H9N3O/c1-8(14)9-2-4-10(5-3-9)13-7-11-6-12-13/h2-7H,1H3

Upstream product

• 288-88-0 1,2,4-Triazole 
• 13329-40-3 4-Iodoacetophenone 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 99-91-2 para-chloroacetophenone 

Downstream Products

• 1050196-89-8 C₂₀H₁₉N₃O₄ 
• 1334929-03-1 (E)-1-(4-(1H-1,2,4-triazol-1-yl)phenyl)-3-(4-(2,5-dichlorobenzyloxy)phenyl)prop-2-en-1-one 
• 1334929-08-6 (E)-1-(4-(1H-1,2,4-triazol-1-yl)phenyl)-3-(4-(2,5-difluorobenzyloxy)phenyl)prop-2-en-1-one 
• 1334929-02-0 (E)-1-(4-(1H-1,2,4-triazol-1-yl)phenyl)-3-(4-(2,4-dichlorobenzyloxy)phenyl)prop-2-en-1-one 
• 1334929-01-9 (E)-1-(4-(1H-1,2,4-triazol-1-yl)phenyl)-3-(4-(3-chlorobenzyloxy)phenyl)prop-2-en-1-one 
• 1334929-35-9 (E)-1,3-bis(4-(1H-1,2,4-triazol-1-yl)phenyl)prop-2-en-1-one 
• 1334929-05-3 (E)-1-(4-(1H-1,2,4-triazol-1-yl)phenyl)-3-(4-(2,4-difluorobenzyloxy)phenyl)prop-2-en-1-one 
• 1212274-17-3 (S)-1-(4-(1H-1,2,4-triazol-1-yl)phenyl)ethanol 
• 1212397-44-8 (R)-1-(4-(1H-1,2,4-triazol-1-yl)phenyl)ethanol 
• 1393645-58-3 C₁₉H₁₇N₃O₃ 
• 1393645-71-0 C₁₉H₁₇N₃O₃ 
• 1095275-17-4 1-(4-(1H-1,2,4-triazol-1-yl)phenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutan-1-one 
• 1184924-20-6 1-(4-(1H-1,2,4-triazol-1-yl)-phenyl)-3-(4-chlorophenyl)prop-2-en-1-one 
• 1001055-33-9 C₂₈H₃₃N₇O₄ 

Relevant academic research and scientific papers

Unique CuI-pyridine based ligands catalytic systems for N-arylation of indoles and other heterocycles

Two pyridine-based ligands (N-((pyridin-2-yl) methyl) pyridin-2-amine) L1 and (N-((pyridin-2-yl) methylene) pyridin-2-amine) L2 are explored in present work which are inexpensive, effective and environmentally benign in their properties. These have been utilized for C-N cross coupling reaction resulting in N-arylation. The N-arylation of indole, imidazole and triazole have been successfully carried out with different aryl and heteroaryl halides using these ligands.

Efficient and recyclable copper-based MOF-catalyzed N-arylation of N-containing heterocycles with aryliodides

Copper-based MOF-199 was used as an efficient heterogeneous catalyst to catalyze cross-coupling reactions between N-containing heterocycles and aryliodides with high yields. The catalyst can be easily separated from the reaction mixture, and can be reused at least 5 times without significantly decreasing the activity. The XRD results showed that the crystallinity and structure of MOF-199 can be maintained well during the coupling reaction.

Antimalarial Activity of Newly Synthesized Chalcone Derivatives In Vitro

Twenty-seven novel chalcone derivatives were synthesized using Claisen-Schmidt condensation and their antimalarial activity against asexual blood stages of Plasmodium falciparum was determined. Antiplasmodial IC50 (half-maximal inhibitory concentration) activity of a compound against malaria parasites in vitro provides a good first screen for identifying the antimalarial potential of the compound. The most active compound was 1-(4-benzimidazol-1-yl-phenyl)-3-(2, 4-dimethoxy-phenyl)-propen-1-one with IC50 of 1.1μg/mL, while that of the natural phytochemical, licochalcone A is 1.43μg/mL. The presence of methoxy groups at position 2 and 4 in chalcone derivatives appeared to be favorable for antimalarial activity as compared to other methoxy-substituted chalcones. Furthermore, 3, 4, 5-trimethoxy groups on chalcone derivative probably cause steric hindrance in binding to the active site of cysteine protease enzyme, explaining the relative lower inhibitory activity.

Novel aryloxy azolyl chalcones with potent activity against Mycobacterium tuberculosis H37Rv

A series of twenty seven novel aryloxy azolyl chalcones were synthesized and evaluated in vitro for the growth inhibition of Mycobacterium tuberculosis H37Rv. Ten compounds from this series exhibited good activity with MIC in the range of 3.12-0.78 μg/mL

Trinuclear copper(I) complexes with triscarbene ligands: Catalysis of C-N and C-C coupling reactions

Novel synthetic routes for the preparation of trinuclear copper(I) complexes with triscarbene ligands are presented, which yield higher purity products than the one previously described. The first crystal structure of one of these complexes is reported an

Synthesis of novel substituted 1,3-diaryl propenone derivatives and their antimalarial activity in vitro

The synthesis of novel 1,3-diaryl propenone derivatives and their antimalarial activity in vitro against asexual blood stages of human malaria parasite, Plasmodium falciparum, are described. Chalcone derivatives were prepared via Claisen-Schmidt condensation of substituted aldehydes with substituted methyl ketones. Antiplasmodial IC50 (half maximal inhibitory concentration) activity of these compounds ranged between 1.5 and 12.3 μg/ml. The chloro-series, 1,2,4-triazole substituted chalcone was found to be the most effective in inhibiting the growth of P. falciparum in vitro while pyrrole and benzotriazole substituted chalcones showed relatively less inhibitory activity. This is the first report on antiplasmodial activity of chalcones with azoles on acetophenone ring.

Efficient catalysis of Ullmann-type arylation reactions by a novel trinuclear copper(I) complex with a chelating tricarbene ligand

A novel trinuclear copper(I) complex with a chelating tricarbene ligand is shown to be an efficient catalyst for the arylation of different classes of compounds containing N-H or O-H functions. Different kinds of azole rings (pyrazole, imidazole, 1,2,4-triazole) can be arylated with comparable efficiencies at relatively mild temperatures (100 °C). The catalyst activates aryl iodides, bromides and even chlorides for the reaction. An unusually strong influence of the nature of the aryl substituent on the reaction yield is observed. The synthetic protocol can be extended to other substrate classes, such as phenols and amides, although the catalytic efficiency with amides is significantly reduced.

Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles

This paper details the copper-catalyzed N-arylation of π-excessive nitrogen heterocycles. The coupling of either aryl iodides or aryl bromides with common nitrogen heterocycles (pyrroles, pyrazoles, indazoles, imidazoles, and triazoles) was successfully performed in good yield with catalysts derived from diamine ligands and CuI. General conditions were found that tolerate functional groups such as aldehydes, ketones, alcohols, primary amines, and nitriles on the aryl halide or heterocycle. Hindered aryl halides or heterocycles were also found to be suitable substrates using the conditions reported herein.