4912-12-3

Usage

Organic compound

Consists of a phenyl group and a pyrrole ring

Uses

Commonly used in the synthesis of pharmaceuticals and agrochemicals due to its reactivity and versatility

Biological activity

Potential biological activity, of interest in the field of medicinal chemistry

Importance in production

An important intermediate in the production of various compounds

Applications in research and development

Used in research and development in the pharmaceutical industry.

Upstream product

• 1003-29-8 2-pyrrole aldehyde 
• 98-86-2 acetophenone 
• 109-97-7 pyrrole 
• 3623-15-2 phenyl propargyl ketone 
• 1072-83-9 2-Acetylpyrrole 
• 100-52-7 benzaldehyde 

Downstream Products

• 82619-72-5 4-phenyl-6-(1H-pyrrol-2-yl)pyrimidin-2-amine 
• 89144-92-3 1-Methyl-3-phenyl-5-(1H-pyrrol-2-yl)-4,5-dihydro-1H-pyrazole 
• 133617-54-6 3-cyano-2-methyl-6-phenyl-4-(2-pyrrolyl)pyridine 
• 89144-78-5 3-Phenyl-5-(1H-pyrrol-2-yl)-4,5-dihydro-1H-pyrazole 
• 1356400-02-6 2,6-diphenyl-4-(1H-pyrrol-2-yl)pyridine 
• 1354541-52-8 (3,4-diphenylcyclobutane-1,2-diyl)bis((1H-pyrrol-2-yl)methanone) 

Relevant academic research and scientific papers

Synthesis, docking, machine learning and antiproliferative activity of the 6-ferrocene/heterocycle-2-aminopyrimidine and 5-ferrocene-1H-Pyrazole derivatives obtained by microwave-assisted Atwal reaction as potential anticancer agents

A simple and fast methodology under microwave irradiation for the synthesis of 2-aminopyrimidine and pyrazole derivatives using Atwal reaction is reported. After the optimization of the reaction conditions, eight 2-aminolpyrimidines containing ferrocene a

A Novel Pseudo-Three-Component Synthetic Strategy for the Synthesis of 1,6-Dihydroazaazulenes via Cyclization of Pyrrolyl-enones

A synthetic novel strategy involving a pseudo-three-component reaction to obtain 1,6-dihydroazaazulenes derivates via cyclization of pyrrolyl-enones was developed. This reaction is carried out under mild conditions from simple starting materials and catal

Studies of NMR Chemical Shifts of Chalcone Derivatives of Five-membered Monoheterocycles and Determination of Aromaticity Indices

A series of the chalcone derivatives of the five-membered monoheterocyclic compounds, (E)-1-aryl-3-heteroarylpropen-1-ones, were prepared by aldol condensation of the corresponding aldehydes of thiophene, pyrrole, and furan with m- and p-substituted acetophenones. Similar condensation of the acetyl compounds of the heterocycles with m- and p-substituted benzaldehydes gave another series of the chalcone derivatives, (E)-1-heteroaryl-3-arylpropen-1-ones. The 13C chemical shift values (δC) of the chalcone derivatives were determined in order to find if they correlated with the Hammett σ values. A good correlation, especially for the β-C for both series, was found for the 13C chemical shift values (δC) of the chalcone derivatives with the Hammett σ values. The chemical shift values of the β-C of the heterocyclic compounds were plotted against those of the benzene derivatives. The resulting slopes were found to be close to the values of the aromaticity indices.

Isothiourea-catalysed enantioselective pyrrolizine synthesis: Synthetic and computational studies

The catalytic enantioselective synthesis of a range of cis-pyrrolizine carboxylate derivatives with outstanding stereocontrol (14 examples, >95:5 dr, >98:2 er) through an isothiourea-catalyzed intramolecular Michael addition-lactonisation and ring-opening

Effects of structural and electronic characteristics of chalcones on the activation of peroxisome proliferator-activated receptor gamma

Chalcones share some structural similarities with GW-1929, a highly-selective and potent agonist for peroxisome proliferator-activated receptor-gamma (PPARγ). In this study, we tested 53 structurally diverse chalcones to identify characteristics essential for PPARγ activation in a GAL4-based transactivation assay. This screen identified several novel chalcone agonists of PPARγ. Our results indicate that chalcones with an electron rich group or sterically large groups such as naphthyl on the carbonyl side tend to activate PPARγ. The absence of any strict structural or electronic requirements suggests that the flexibility of the PPARγ ligand binding pocket may allow binding of diverse chalcones with some preference for a slightly larger electron-rich group on the carbonyl side. We predict that further structure-activity relationship studies on chalcones with naphthalene or electron-rich groups near the carbonyl moiety will lead to the development of more potent PPARγ agonists.

Stereoselective photodimerization and antimicrobial activities of heteroaryl chalcones and their photoproducts

Stereoselective photodimerization of heteroaryl chalcones 1-(furan-2-yl)-3-phenylprop-2-en-1-one (1), 3-phenyl-1-(thiophen-2-yl)prop-2-en- 1-one (2) and 3-phenyl-1-(1H-pyrrol-2-yl)prop-2-en-1-one (3) has been studied. The heteroaryl chalcones and their ph

DNA-targeting pyrroloquinoline-linked butenone and chalcones: Synthesis and biological evaluation

A series of conjugates of α,β-unsaturated ketone systems, phenyl-butenone and diaryl-propenones (chalcones), with the tricyclic planar pyrroloquinoline nucleus were synthesised and evaluated for their anticancer properties. The aim was to target DNA by bu

Synthesis and biological evaluation of aromatic enones related to curcumin

Curcumin, a natural product isolated from the spice turmeric, has been shown to exhibit a wide range of pharmacological activities including certain anti-cancer properties. It has been specifically shown to be an effective inhibitor of angiogenesis both in vitro and in vivo. Using curcumin as a lead compound for anti-angiogenic analog design, a series of structurally related compounds utilizing a substituted chalcone backbone have been synthesized and tested via an established SVR cell proliferation assay. The results have yielded a wide range of compounds that equal or exceed curcumin's ability to inhibit endothelial cell growth in vitro. Due to both their commercial availability and their fairly straightforward synthetic preparation, these low molecular weight compounds are attractive leads for developing future angiogenic inhibitors.

Novel formation of 6-acyl-5-(2-pyrrolyl)-3H-pyrrolizines by base-catalysed condensation of pyrrole-2-aldehyde with methyl ketones

Pyrrole-2-aldehyde undergoes condensation with methyl ketones in aqueous ethanolic alkali in a 2:1 mole ratio yielding 6-acyl-5-(2-pyrrolyl)-3H-pyrrolizines as novel products in moderate yield.

Pyrroles as C-nucleophiles in reactions with acylacetylenes

The reactions of substituted pyrroles with terminal acylacetylenes occur selectively to form 2-(Z/E-2-acylvinyl)pyrroles. When the reactions are performed on the surface of silica gel, C-vinylation is noticeably accelerated to form predominantly E-isomers