72758-75-9

Upstream product

• 98-86-2 acetophenone 
• 105-07-7 4-cyanobenzaldehyde 
• 98-85-1 1-Phenylethanol 
• 874-89-5 4-Cyanobenzyl alcohol 
• 623-00-7 4-bromobenzenecarbonitrile 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 100-52-7 benzaldehyde 
• 583-06-2 3-benzoylacrylic acid 
• 536-74-3 phenylacetylene 
• 3058-39-7 4-iodobenzonitrile 
• 936-59-4 3-chloropropiophenone 
• 350015-18-8 4-(3-oxo-3-phenylprop-1-yn-1-yl)benzonitrile 
• 3032-92-6 4-cyanophenylacetylene 
• 98-88-4 benzoyl chloride 

Downstream Products

• 98258-72-1 (E)-methyl 4-(3-oxo-3-phenylprop-1-en-1-yl)benzoate 
• 86864-14-4 3-(p-cyanophenyl)-4,4-bis(phenylthio)-1,4-diphenyl-1-butanone 
• 59824-24-7 1-phenyl-3-(p-cyanophenyl)-1-propanone 
• 193205-46-8 3-(4-cyano)phenyl-3-morpholino-1-phenylpropan-1-one 
• 1186044-33-6 diisopropyl 2-(1-(4-cyanophenyl)-3-oxo-3-phenylpropyl)malonate 
• 1221402-57-8 4-{(S)-3-oxo-1-[(R)-2-oxocyclopentyl]-3-phenylpropyl}benzonitrile 
• 1266096-08-5 (R)-tert-butyl 2-oxo-5-((S)-1-(4-cyanophenyl)-3-oxo-3-phenylpropyl)-2,5-dihydro-1H-pyrrole-1-carboxylate 
• 1292816-43-3 C₂₁H₁₃NOS 
• 1292816-40-0 4-(2-(3-chlorophenyl)-5-phenylfuran-3-yl)benzonitrile 
• 1292816-41-1 4-(2-(2-chlorophenyl)-5-phenylfuran-3-yl)benzonitrile 

Relevant academic research and scientific papers

Borane-Catalyzed, Chemoselective Reduction and Hydrofunctionalization of Enones Enabled by B-O Transborylation

The use of stoichiometric organoborane reductants in organic synthesis is well established. Here these reagents have been rendered catalytic through an isodesmic B-O/B-H transborylation applied in the borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The reaction was found to proceed by a 1,4-hydroboration of the enone and B-O/B-H transborylation with HBpin, enabling catalyst turnover. Single-turnover and isotopic labeling experiments supported the proposed mechanism of catalysis with 1,4-hydroboration and B-O/B-H transborylation as key steps.

Heteroleptic copper(I) complexes as energy transfer photocatalysts for the intermolecular [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides

The [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides can be effectively catalyzed by heteroleptic copper(I) complexes. The reactions were carried out under mild reaction conditions and the products were obtained in 20–72% yield under visible light irradiation. The copper-based photocatalyst comprised of the rigid phenanthroline ligand with substituents at the 2,9-positions and the 4,7-positions showed high activity in the photodimerization via an energy transfer pathway.

Microwave-assisted synthesis of novel pyrazole derivatives and their biological evaluation as anti-bacterial agents

Aims and Objectives: Microwave-assisted condensation of acetophenone 1 and aromatic aldehydes 2 gave chalcone analogs 3, which were cyclized to pyrazole derivatives 6a-f via the reaction with hydrazine hydrate and oxalic acid in the presence of the catalytic amount of acetic acid in ethanol. Materials and Methods: The structural features of the synthesized compounds were characterized by melting point, FT-IR,1H,13C NMR and elemental analysis. Results: The antibacterial activities of the synthesized pyrazoles were evaluated against three gram-positive bacteria, such as Enterococcus durans, Staphylococcus aureus, Bacillus subtilis and two gram-negative bacteria such as Escherichia coli and Salmonella typhimurium. Conclusion: All the synthesized pyrazoles showed relatively high antibacterial activity against S. aureus strain, and none of them demonstrated antibacterial activity against E. coli.

Potassium Base-Catalyzed Michael Additions of Allylic Alcohols to α,β-Unsaturated Amides: Scope and Mechanistic Insights

We report herein the first KHMDS-catalyzed Michael additions of allylic alcohols to α,β-unsaturated amides through allylic isomerization. The reaction proceeds smoothly in the presence of only 5 mol% of KHMDS to afford a variety of 1,5-ketoamides in high yields. Mechanistic investigations, including experimental and computational studies, reveal that the KHMDS-catalyzed in-situ generation of the enolate from the allylic alcohol through a tunneling-assisted 1,2-hydride shift is the key to the success of this transformation. (Figure presented.).

Gold-catalyzed partial hydrogenation of activated alkynes mediated by triphenylphosphine

Gold(I) can exhibit a cooperative effect with triphenylphosphine, accelerating the triphenylphosphine-mediated partial hydrogenation of activated alkynes. In this protocol, 3-arylpropiolates are selectively reduced to the Z -isomer when the aryl ring bears an electron-donor substituent, whereas 3-arylpropynones are reduced to the E-isomers.

One-Pot Catalytic Enantioselective Synthesis of 2-Pyrazolines

A scalable, one-pot, enantioselective catalytic synthesis of 2-pyrazolines from beta-substituted enones and hydrazines is described. Pivoting on a two-stage catalytic Michael addition/condensation strategy, the use of an aldehyde to generate a suitable hydrazone derivative of the hydrazine was found to be key for curtailing background reactivity and tuning the catalyst-controlled enantioselectivity. The new synthetic method is easy to perform, uses a new and readily prepared cinchona-derived bifunctional catalyst, is broad in scope, and tolerates a range of functionalities with high enantioselectivity (up to >99:1 e.r.). The significant scalability of this methodology was demonstrated with the synthesis of more than 80 grams of a pyrazoline product with 89 % catalyst recovery.

Evaluation of novel chalcone-thiosemicarbazones derivatives as potential Anti-leishmania amazonensis agents and its HSA binding studies

A series of seven chalcone-thiosemicarbazones (5a–5g) were synthesized and evaluated as potential new drugs (anti-leishmanial effect). Although four of the chalcone-thiosemicarbazones are already known, none of them or any compound in this class has been previously investigated for their effects on parasites of the Leishmania genus. The compounds were prepared in satisfactory yields (40–75%) and these compounds were evaluated against promastigotes, axenic amastigotes and intracellular amastigotes of L. amazonensis after 48 h of culture. The half maximal inhibitory concentration (IC50) values of the intracellular amastigotes were determined to be in the range of 3.40 to 5.95 μM for all compounds assayed. The selectivity index showed value of 15.05 for 5a, whereas pentamidine (reference drug) was more toxic in our model (SI = 2.32). Furthermore, to understand the preliminary relationship between the anti-leishmanial activity of the chalcone-thiosemicarbazones, their electronic (σ), steric (MR) and lipophilicity (π) properties were correlated, and the results indicated that moieties with electronic withdrawing effects increase the anti-leishmanial activity. The preliminary pharmacokinetic evaluation of one of the most active compound (5e) was studied via interaction to human serum albumin (HSA) using multiple spectroscopic techniques combined with molecular docking. The results of antiparasitic effects against L. amazonensis revealed the chalcone-thiosemicarbazone class to be novel prototypes for drug development against leishmaniasis.

Reaction condition controlled nickel(ii)-catalyzed C-C cross-coupling of alcohols

The challenge in the C-C cross-coupling of secondary and primary alcohols using acceptorless dehydrogenation coupling (ADC) is the difficulty in accurately controlling product selectivities. Herein, we report a controlled approach to a diverse range of β-alkylated secondary alcohols, α-alkylated ketones and α,β-unsaturated ketones using the ADC methodology employing a Ni(ii) 4,6-dimethylpyrimidine-2-thiolate cluster catalyst under different reaction conditions. This catalyst could tolerate a wide range of substrates and exhibited a high activity for the annulation reaction of secondary alcohols with 2-aminobenzyl alcohols to yield quinolines. This work is an example of precise chemoselectivity control by careful choice of reaction conditions.

Chalcone derivatives enhance ATP-binding cassette transporters A1 in human THP-1 macrophages

Atherosclerosis is a process of imbalanced lipid metabolism in the vascular walls. The underlying pathology mainly involves the deposition of oxidized lipids in the endothelium and the accumulation of cholesterol in macrophages. Macrophages export excessive cholesterol (cholesterol efflux) through ATP-binding cassette transporter A1 (ABCA1) to counter the progression of atherosclerosis. We synthesized novel chalcone derivatives and assessed their effects and the underlying mechanisms on ABCA1 expression in macrophages. Human THP-1 macrophages were treated with synthetic chalcone derivatives for 24 h. In Western blot and flow cytometry analyses, a chalcone derivative, (E)-1-(3,4-diisopropoxyphenyl)-3-(4-isopropoxy-3-methoxyphenyl)prop- 2-en-1-one (1m), was observed to significantly enhance ABCA1 protein expression in THP-1 cells (10 μM, 24 h). Levels of mRNA of ABCA1 and liver X receptor alpha (LXRα) were quantified using a real-time quantitative polymerase chain reaction technique and were found to be significantly increased after treatment with the novel chalcone derivative 1m. Several microRNAs, including miR155, miR758, miR10b, miR145, miR33, and miR106b, which functionally inhibit ABCA1 expression were suppressed after treatment with 1m. Collectively, 1m increases ABCA1 expression in human THP-1 macrophages. The mechanisms involve the activation of the LXRα-ABCA1 pathway and suppression of certain microRNAs that regulate ABCA1 expression.

Design and synthesis of novel natural clinoptilolite-MnFe2O4 nanocomposites and their catalytic application in the facile and efficient synthesis of chalcone derivatives through Claisen-Schmidt reaction

A series of three novel nanocomposites were prepared by modifying the surface of natural clinoptilolite using various amounts of manganese ferrite (MnFe2O4) nanoparticles. These manganese ferrite-modified nanocomposites (MFO–NC) were fully characterized by XRD, FT-IR, EDX, VSM and TEM analyses. One of these novel nanocomposites with 40?wt% of manganese ferrite in clinoptilolite (MFO–NC-3) showed a strong catalytic behavior in the aldol-type Claisen–Schmidt reaction for the synthesis of chalcones. A strong catalytic synergy was observed between nano-MnFe2O4 particles and natural clinoptilolite in the structure of these nanocomposites. The products with a broad range of substituents on the reactants were efficiently obtained under room-temperature conditions within relatively short reaction times with good to excellent yields in the presence of one of the prepared MFO–NC nanocomposites. This nanocomposite also showed a strong stability and substantial reusability in the synthesis of chalcones.