72454-54-7

Upstream product

• 67-64-1 acetone 
• 6630-33-7 ortho-bromobenzaldehyde 
• 18982-54-2 o-bromobenzyl alcohol 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 

Downstream Products

• 1056017-60-7 diethyl 2-((S)-1-(2-bromophenyl)-3-oxobutyl)malonate 
• 1170965-23-7 (S)-4-(1H-benzotriazol-1-yl)-4-(2-bromophenyl)butan-2-one 
• 1236557-08-6 (S)-9-(1-(2-bromophenyl)-3-oxobutyl)anthracen-10(9H)-one 
• 1258422-83-1 (1S,6S)-1'-benzyl-6-(2-bromophenyl)-2-methylspiro[cyclohex[2]ene-1,3'-indoline]-2',4-dione 
• 1238945-94-2 C₁₀H₉BrN₂ 
• 1377071-28-7 (R)-dibenzyl 2-(1-(2-bromophenyl)-3-oxobutyl)malonate 
• 1421315-17-4 C₁₆H₂₀O 
• 1421315-18-5 C₁₈H₁₆O 
• 1421315-19-6 C₁₅H₁₆O 
• 3506-68-1 4-(2-bromophenyl)-2-butanone 
• 1421315-03-8 (Z)-1-benzylidene-2-(prop-1-en-2-yl)-2,3-dihydro-1H-indene 
• 1421314-93-3 1-(3,3-dimethylbut-1-yn-1-yl)-2-(3-methylbut-3-en-1-yl)benzene 
• 1421314-94-4 1-(3-methylbut-3-en-1-yl)-2-(phenylethynyl)benzene 
• 1421314-95-5 1-(cyclopropylethynyl)-2-(3-methylbut-3-en-1-yl)benzene 

Relevant academic research and scientific papers

Polysubstituted Indole Synthesis via Palladium/Norbornene Cooperative Catalysis of Oxime Esters

Polysubstituted indoles are prevalent in pharmaceuticals, agrochemicals, and organic materials. Presented herein is the fact that polyfunctionalized indoles can be efficiently constructed from easily accessible oxime esters and aryl iodides, involving a palladium/norbornene synergistic synthesis. The reaction is enabled by a unique class of electrophiles in palladium/norbornene cooperative catalysis, which are oxime esters derived from simple ketone. The broad substrate scope and high functional group tolerance could make this method attractive for the synthesis of polysubstituted indoles.

Inhibition of Autophagy by a Small Molecule through Covalent Modification of the LC3 Protein

The autophagic ubiquitin-like protein LC3 functions through interactions with LC3-interaction regions (LIRs) of other autophagy proteins, including autophagy receptors, which stands out as a promising protein–protein interaction (PPI) target for the intervention of autophagy. Post-translational modifications like acetylation of Lys49 on the LIR-interacting surface could disrupt the interaction, offering an opportunity to design covalent small molecules interfering with the interface. Through screening covalent compounds, we discovered a small molecule modulator of LC3A/B that covalently modifies LC3A/B protein at Lys49. Activity-based protein profiling (ABPP) based evaluations reveal that a derivative molecule DC-LC3in-D5 exhibits a potent covalent reactivity and selectivity to LC3A/B in HeLa cells. DC-LC3in-D5 compromises LC3B lipidation in vitro and in HeLa cells, leading to deficiency in the formation of autophagic structures and autophagic substrate degradation. DC-LC3in-D5 could serve as a powerful tool for autophagy research as well as for therapeutic interventions.

Synthesis of Polysubstituted Pyridines via a One-Pot Metal-Free Strategy

An efficient strategy for the one-pot synthesis of polysubstituted pyridines via a cascade reaction from aldehydes, phosphorus ylides, and propargyl azide is reported. The reaction sequence involves a Wittig reaction, a Staudinger reaction, an aza-Wittig reaction, a 6π-3-azatriene electrocyclization, and a 1,3-H shift. This protocol provides quick access to the polysubstituted pyridines from readily available substrates in good to excellent yields.

Aerobic ligand-free domino Suzuki coupling - Michael addition reaction catalyzed by in situ generated palladium nanoparticles in water: A general method for the synthesis of benzo[c]chromene derivatives

A general method has been developed for the synthesis of benzo[c]chromene derivatives via aerobic ligand-free domino Suzuki coupling and Michael addition reaction catalyzed by in situ generated palladium nanoparticles in water leading to C-C and C-O bond

Synthesis of phenanthridine and its analogues via aerobic ligand-free domino Suzuki coupling-Michael addition reaction catalyzed by in situ generated palladium-nanoparticles in water

A convenient methodology has been developed towards the synthesis of substituted phenanthridines and analogous benzo[k] and benzo[i] derivatives via aerobic ligand-free domino Suzuki coupling-Michael addition reaction in the presence of Pd(OAc)2 and K3PO4 as a catalytic system in H2O at 90 C in good yields. Reaction was believed to be catalyzed by in situ generated palladium nanoparticles in water with the elimination of acetone.

Co2(CO)8-mediated cycloisomerization of arylene 1,7-enynes

Co2(CO)8 was found to be effective for cycloisomerization reaction of arylene 1,7-enynes to form 2,3-dihydroindene derivatives, and a catalytic version assisted by different Lewis base ligands was also studied.

Enantioselective [4 + 2] cycloaddition of cyclic N-sulfimines and acyclic enones or ynones: A concise route to sulfamidate-fused 2,6-disubstituted piperidin-4-ones

A concise route to valuable sulfamate-fused 2,6-disubstituted piperidin-4-ones or 2,3-dihydropyridin-4(1H)-ones in good yield with high diastereo- and enantioselectivity is presented. The combination of chiral primary amine and o-fluorobenzoic acid efficiently promoted an asymmetric [4 + 2] cycloaddition reaction of N-sulfonylimines and enones or ynones. The cycloaddition reaction between cyclic N-sulfonylimines and ynones is first reported.

Cyclohexane 1,3-diones and their inhibition of mutant SOD1-dependent protein aggregation and toxicity in PC12 cells

Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease characterized by the progressive loss of motor neurons. Currently, there is only one FDA-approved treatment for ALS (riluzole), and that drug only extends life, on average, by 2-3 months. Mutations in Cu/Zn superoxide dismutase (SOD1) are found in familial forms of the disease and have played an important role in the study of ALS pathophysiology. On the basis of their activity in a PC12-G93A-YFP high-throughput screening assay, several bioactive compounds have been identified and classified as cyclohexane-1,3-dione (CHD) derivatives. A concise and efficient synthetic route has been developed to provide diverse CHD analogs. The structural modification of the CHD scaffold led to the discovery of a more potent analog (26) with an EC50 of 700 nM having good pharmacokinetic properties, such as high solubility, low human and mouse metabolic potential, and relatively good plasma stability. It was also found to efficiently penetrate the blood-brain barrier. However, compound 26 did not exhibit any significant life span extension in the ALS mouse model. It was found that, although 26 was active in PC12 cells, it had poor activity in other cell types, including primary cortical neurons, indicating that it can penetrate into the brain, but is not active in neuronal cells, potentially due to poor selective cell penetration. Further structural modification of the CHD scaffold was aimed at improving global cell activity as well as maintaining potency. Two new analogs (71 and 73) were synthesized, which had significantly enhanced cortical neuronal cell permeability, as well as similar potency to that of 26 in the PC12-G93A assay. These CHD analogs are being investigated further as novel therapeutic candidates for ALS.

A simple route to 9-fluorenylidenes by domino Suzuki/Heck coupling reactions

A palladium catalyzed domino intermolecular Suzuki followed by intramolecular Heck coupling is described. This strategy afforded a novel and convenient synthesis of various 9-fluorenylidene derivatives in one-pot under relatively mild reaction condition.

A simple and efficient synthesis of pyrazoles in water

A simple, highly efficient, and environmentally friendly method for the synthesis of substituted 1H-pyrazoles by one-pot condensation reaction of α,β-unsaturated carbonyl compounds with tosyl hydrazide in water was developed. The reaction system exhibited tolerance with various functional groups, Aromatic moiety with both electron-rich and electron-deficient substituents could give desired products in good to excellent yields.