22563-58-2Relevant academic research and scientific papers
Synthesis, Protein Tyrosine Phosphatase 1B Inhibitory, and Anti-hyperglycemic Activities of Some “(E)-3-aryl-1-(2-pyrrolyl)-2-propenone” Derivatives
Jain, Ankit,Jain, Dinesh K.
, p. 517 - 525 (2022/01/26)
This study aims at design, as protein tyrosine phosphatase 1B (PTP1B) synthesis and biological evaluation of some heterocyclic derivatives of chalcone inhibitors. These derivatives were designed on the basis of prerequisite structural features required fo
Studies of NMR Chemical Shifts of Chalcone Derivatives of Five-membered Monoheterocycles and Determination of Aromaticity Indices
Jeong, Eun Jeong,Lee, In-Sook Han
, p. 668 - 673 (2019/07/12)
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.
Novel (E)-1-(pyrrole-2-yl)-3-(aryl)-2-(propen-1-one) derivatives as efficient singlet oxygen quenchers: Kinetics and quantum chemical calculations
Diaz-Uribe, Carlos E.,Vallejo, William,Castellar, Wilmar,Trilleras, Jorge,Ortiz, Stephanie,Rodriguez-Serrano, Angela,Zarate, Ximena,Quiroga, Jairo
, p. 71565 - 71572 (2015/09/08)
Chalcones constitute an important group of natural and synthetic products that have been screened due to their wide range of pharmacological applications. Herein, we studied the antioxidant activity of five newly synthetized (E)-1-(pyrrole-2-yl)-3-(aryl)-2-(propen-1-one) (PAPs) derivatives against singlet oxygen (1O2). The differences among the compounds are related to aryl substitution in the p-position where: 3a = C6H5, 3b = 4-H3COC6H4, 3c = 4-FC6H4, 3d = 4-ClC6H4, 3e = 4-BrC6H4. The PAPs were synthesized using a Claisen-Schmidt condensation reaction between 2-acetylpyrrole and aromatic aldehydes under ultrasonic irradiation (yields between 79-86%) and were characterized by IR, mass spectrometry, NMR and quantum chemical calculations. The total singlet oxygen quenching rate constants (kQ) of the PAPs were measured spectrophotometrically in ethanol at 25°C and determined by using the Stern-Volmer model. As the character of the EWGs is increased from 3a to 3e, the kQ diminishes smoothly. The best quencher is found to be the 3a compound (where the aryl group is unsubstituted) with a kQ = 5.71 (±0.21) × 107 M-1 s-1, which is similar to those for other antioxidants e.g. flavonoids. These results suggest these compounds are efficient quenchers of singlet oxygen and their potential applicability in biological systems.
Synthesis and selective inhibitory activity against human COX-1 of novel 1-(4-substituted-thiazol-2-yl)-3,5-di(hetero)aryl-pyrazoline derivatives
Carradori, Simone,Secci, Daniela,Bolasco, Adriana,De Monte, Celeste,Yá?ez, Matilde
, p. 973 - 979 (2013/02/23)
Novel 1-(4-ethyl carboxylate-thiazol-2-yl)-3,5-di(hetero)aryl-2-pyrazoline derivatives were obtained by reacting 3,5-di(hetero)aryl-1-thiocarbamoyl-2- pyrazolines with the ethyl ester of α-bromo-pyruvic acid. The synthesized compounds were confirmed by spectroscopic data and assayed to evaluate their in vitro ability to inhibit both isoforms of human cyclooxygenase (hCOX). Some derivatives (compounds 5, 6, 13, 16, and 17) displayed promising selectivity against hCOX-1 in the micromolar range and were shown to have a selectivity index similar or better than the reference drugs (indometacin, diclofenac). The introduction of a phenyl or a 4-F-phenyl ring on the C5 associated with a 4-substituted phenyl or a heteroaryl group on the C3 of (4-substituted-thiazol- 2-yl)pyrazoline derivatives improved the activity against hCOX-1. Thanks to these preliminary results it could be possible to extend our knowledge of the pharmacophoric requirements for the discovery of new pyrazoline-based hCOX-1 inhibitors. Novel 1-(4-ethyl carboxylate-thiazol-2-yl)-3,5-di(hetero)aryl-2- pyrazoline derivatives were obtained by reacting 3,5-di(hetero)aryl-1- thiocarbamoyl-2-pyrazolines with the ethyl ester of α-bromo-pyruvic acid. Some derivatives displayed promising selectivity against human cyclooxygenase 1 (hCOX-1) in the micromolar range, with a selectivity index similar or better than the reference drugs, indometacin and diclofenac. Copyright
Anti-bacterial and anti-leishmanial studies of 4, 6-diarylpyrimidin-2- amines
Bukhari, Mujahid Hussain,Siddiqui, Hamid Latif,Ashraf, Chaudhary Muhammad,Hussain, Tanvir
scheme or table, p. 720 - 725 (2012/06/18)
Seven new chalcones along with nine already reported ones were synthesized from aryl aldehydes and substituted acetophenones by Claisen-Schmidt condensation. Each chalcone was treated with guanidine hydrochloride followed by oxidation with H2O
Synthesis, pharmacological and biological screening of new isoxazolines
Ishwar Bhat,Anil Kumar,Kumar, Abhishek
, p. 163 - 166 (2013/09/24)
A new series of 3-(substituted phenyl)-5-(1 H-pyrrol-2-yl)-2,3- dihydroisoxazoles (Al1-Al10) have been synthesized by reacting various substituted chalcones with hydroxyl amine in presence of 2% NaOH. The intermediate chalcones were
Synthesis of some pyridine, thiopyrimidine, and isoxazoline derivatives based on the pyrrole moiety
Radwan, Mohamed A. A.,Abbas, Eman M. H.
experimental part, p. 229 - 233 (2010/03/26)
Condensation of 2-acetylpyrrole with 5-methylfuran-2-carboxyaldehyde and 4-chlorobenzaldehyde in 20% NaOH give the corresponding 2-chalconylpyrroles. Some new 2-alkoxy-3-cyano-4,6-diarylpyridines were synthesized by condensation of chalcones with malononi
