22563-48-0

Upstream product

• 1072-83-9 2-Acetylpyrrole 
• 100-52-7 benzaldehyde 
• 108-24-7 acetic anhydride 
• 86726-90-1 2-hydroxyl-2-phenylethyl 2<1H>-pyrrolyl ketone 
• 73654-18-9 3-phenyl-1-(pyrrol-2-yl)-2-propen-1-one 

Downstream Products

• 136927-34-9 3-phenyl-1-(1H-pyrrol-2-yl)propan-1-one 
• 1354541-52-8 (3,4-diphenylcyclobutane-1,2-diyl)bis((1H-pyrrol-2-yl)methanone) 
• 73654-18-9 3-phenyl-1-(pyrrol-2-yl)-2-propen-1-one 

Relevant academic research and scientific papers

Preliminary insight of pyrrolylated-chalcones as new anti-methicillin-resistant staphylococcus aureus (Anti-mrsa) agents

Bacterial infections are regarded as one of the leading causes of fatal morbidity and death in patients infected with diseases. The ability of microorganisms, particularly methicillin-resistant Staphylococcus aureus (MRSA), to develop resistance to current drugs has evoked the need for a continuous search for new drugs with better efficacies. Hence, a series of non-PAINS associated pyrrolylated-chalcones (1–15) were synthesized and evaluated for their potency against MRSA. The hydroxyl-containing compounds (8, 9, and 10) showed the most significant anti-MRSA efficiency, with the MIC and MBC values ranging from 0.08 to 0.70 mg/mL and 0.16 to 1.88 mg/mL, respectively. The time-kill curve and SEM analyses exhibited bacterial cell death within four hours after exposure to 9, suggesting its bactericidal properties. Furthermore, the docking simulation between 9 and penicillin-binding protein 2a (PBP2a, PDB ID: 6Q9N) suggests a relatively similar bonding interaction to the standard drug with a binding affinity score of ?7.0 kcal/mol. Moreover, the zebrafish model showed no toxic effects in the normal embryonic development, blood vessel formation, and apoptosis when exposed to up to 40 μM of compound 9. The overall results suggest that the pyrrolylated-chalcones may be considered as a potential inhibitor in the design of new anti-MRSA agents.

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.

Inhibition of nitric oxide and prostaglandin E2 production by pyrrolylated-chalcones: Synthesis, biological activity, crystal structure analysis, and molecular docking studies

In search of potent anti-inflammatory agents, twenty-four chalcone derivatives including seven new compounds (13 – 17, 21 and 23) containing pyrrole moiety were designed, synthesized, and assessed for their nitric oxide (NO) and prostaglandin E2 (PGE2) suppression ability on IFN-γ/LPS-induced RAW 264.7 macrophage cells. Results showed that none of the synthesized compounds were PAINS-associated molecules, with 3-(2,5-dimethoxyphenyl)-1-(1H-pyrrol-2-yl)-prop-2-en-1-one (compound 16) exhibiting remarkable inhibition activity towards PGE2 and NO production with IC50 values of 0.5 ± 1.5 μM and 12.1 ± 1.5 μM, respectively. Physicochemical and ADMET studies showed that majority of the compounds obey to Lipinski's rule of five (RO5) having high blood brain barrier (BBB) penetration, human intestinal absorption (HIA), P- glycoprotein (PgP) inhibition and plasma binding protein (PPB) inhibition. The obtained atomic coordinates for the single-crystal XRD of 16 were then applied in a molecular docking simulation, and compound 16 was found to participate in a number of important binding interactions in the binding sites of ERK and mPGES-1. Based on these results, we have observed the potential of compound 16 as a new hit anti-inflammatory agent, and these findings could serve as a basis for further studies on its mechanism of action.

Novel (E)-1-(pyrrole-2-yl)-3-(aryl)-2-(propen-1-one) derivatives as efficient singlet oxygen quenchers: Kinetics and quantum chemical calculations

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.

Spectral and computational studies in substituted pyrrolyl styryl ketones - Assessment of substituent effects

A series of newly synthesized potent bioactive 2-pyrrolyl styryl ketone derivatives were characterized by spectral techniques. The effect of substituent on the absorption maximum, IR stretching frequencies and NMR chemical shifts were investigated. DFT calculations were made to calculate HOMO-LUMO energies and natural bond orbital analysis [NBO]. The electric dipole moment (μ) and the hyperpolarisability (β) of the investigated molecules have also been studied and found that these synthesized molecules exhibits microscopic non-linear optical (NLO) behavior with non-zero tensor components.

Solvent-free synthesis, spectral correlations and antimicrobial activities of some aryl e 2-propen-1-ones

Totally 38 aryl E 2-propen-1-ones including nine substituted styryl 4-iodophenyl ketones have been synthesised using solvent-free SiO 2-H3PO4 catalyzed Aldol condensation between respective methyl ketones and substituted benzaldehydes under microwave irradiation. The yields of the ketones are more than 80%. The synthesised chalcones were characterized by their analytical, physical and spectroscopic data. The spectral frequencies of synthesised substituted styryl 4-iodophenyl ketones have been correlated with Hammett substituent constants, F and R parameters using single and multi-linear regression analysis. The antimicrobial activities of 4-iodophenyl chalcones have been studied using Bauer-Kirby method.

Photodimerization of heteroaryl chalcones: Comparative antimicrobial activities of chalcones and their photoproducts

The heterocyclic analogues of chalcones were synthesized by Claisen Schmidt reaction of (a) benzaldehyde with 2-acetylfurane, 2-acetylpyrrole and 2-acetylthiophene and (b) acetophenone with furfural, thiophene-2-carbaldehyde and pyrrole-2-carbaldehyde. The photolysis of class (a) and (b) chalcones under UV lamp gave different products. The stereoselective photodimerization of 1-(furane-2-yl)-3-phenylprop-2-en-1-one (1), 3-phenyl-1-(1H-pyrrole-2-yl)-prop- 2-en-1-one (2) gave b-truxinic type dimers, (3,4-diphenylcyclobutane-1,2-diyl) bis (furane-2-yl methanone) (7), (3,4-diphenylcyclobutane-1,2-diyl)bis ((1H-pyrrol-2-yl) methanone) (8) by syn head-to-head coupling whereas 3-phenyl-1-(thiophen-2-yl)-prop-2-en-1-one (3) gave d-truxinic type dimers, (3,4-diphenylcyclobutane-1,2-diyl)bis (thiophen-2-yl methanone) (9) by anti head-to-head coupling. The photolytic products of 3-(furane-2-yl)-1-phenylprop- 2-en-1-one (4), 1-phenyl-3-(thiophen-2-yl)-prop-2-en-1-one (5) and 1-phenyl-3-(1H-pyrrole-2-yl)- prop-2-en-1-one (6) were identified as corresponding 1,6-di(furane-2-yl)-3,4-diphenylhexa-1,5-diene-3,4-diol (10), 3,4-diphenyl-1,6-di(thiophen-2-yl)hexa-1,5-diene-3,4-diol (11) and 3,4-diphenyl-1,6-di (1H-pyrrol-2-yl)hexa-1,5-diene-3,4-diol (12) pinacol dimers. The antibacterial and antifungal activity of the precursor chalcones and the dimeric products showed antimicrobial activities of different extents with respect to individual compounds. In general, photolysis of heteroaryl chalcones causes the depletion of antimicrobial activity. Springer Science+Business Media, LLC 2011.

Efficient synthesis of chalcones by a solid base catalyst

A simple and efficient heterogeneous procedure has been developed for the synthesis of chalcones (α,β-unsaturated ketones) by the Claisen-Schmidt condensation between arylaldehydes and ketones using Mg-Al-OtBu hydrotalcite (HT-OtBu) as catalyst. Copyright Taylor & Francis, Inc.

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.

Design, synthesis, and evaluation of novel boronic-chalcone derivatives as antitumor agents

A series of boronic-chalcone derivatives were synthesized and tested for antitumor activity against human breast cancer cell lines. The results show the boronic-chalcones are more toxic to breast cancer cells compared to normal breast cells than other known chalcones.