32979-83-2

Usage

Uses

Used in Pharmaceutical Industry:
(3E)-4-biphenyl-4-ylbut-3-en-2-one is used as a potential candidate for the development of new drugs or pharmaceuticals due to its pharmacological properties, such as antioxidant, anti-inflammatory, and anticancer activities.
Used in Organic Synthesis:
(3E)-4-biphenyl-4-ylbut-3-en-2-one is used as a key intermediate in the synthesis of various organic compounds for different industrial applications, leveraging its unique structure and reactivity.

Upstream product

• 1458-98-6 2-methyl-3-bromo-1-propene 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 98-80-6 phenylboronic acid 
• 3218-36-8 4-Phenylbenzaldehyde 
• 67-64-1 acetone 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 4202-14-6 dimethyl (2-oxopropyl)phosphonate 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 78-94-4 methyl vinyl ketone 

Downstream Products

• 56578-34-8 4-([1,1’-biphenyl]-4-yl)butan-2-one 
• 69172-04-9 5H-r,5-(p-biphenylyl)-cis-4-bromo-cis-3-hydroxy-trans-3-methylpentan-5-olide 
• 69172-05-0 5H-r,5-(p-biphenylyl)-cis-3-hydroxy-trans-3-methylpentan-5-olide 
• 102705-07-7 4t-biphenyl-4-yl-but-3-en-2-one-(2,4-dinitro-phenylhydrazone) 

Relevant academic research and scientific papers

Investigation on the ZBG-functionality of phenyl-4-yl-acrylohydroxamic acid derivatives as histone deacetylase inhibitors

A series of alternative Zn-binding groups were explored in the design of phenyl-4-yl-acrylohydroxamic acid derivatives as histone deacetylase (HDAC) inhibitors. Most of the synthesized compounds were less effective than the parent hydroxamic acid. However

Selective Cross-Dehydrogenative C(sp3)-H Arylation with Arenes

Selective C(sp3)-C(sp2) bond construction is of central interest in chemical synthesis. Despite the success of classic cross-coupling reactions, the cross-dehydrogenative coupling between inert C(sp3)-H and C(sp2)-H bonds represents an attractive alternative toward new C(sp3)-C(sp2) bonds. Herein, we establish a selective inter-and intramolecular C(sp3)-H arylation of alcohols with nondirected arenes that thereby provides a general pathway to access a wide range of β-arylated alcohols, including tetrahydronaphthalen-2-ols and benzopyran-3-ols, with high to excellent chemo-and regioselectivity.

TRIAZOLE-PHENYL-THIAZOLE HETEROCYCLES AS INNOVATIVE INHIBITORS OF TRYPANOTHIONE REDUCTASE AND THEIR USE AS LEISHMANICIDES

The present invention refers to new compounds useful in the treatment of leishmaniasis and, more particularly, to a series of 5-6-5 triazole-phenyl-thiazole heterocycles capable of inhibiting both activity and dimerization of L. infantum TryR in enzymatic assays at low micromolar concentrations and endowed with potent in vitro activity against promastigote and amastigote forms of Leishmania which indicates a good permeability across the plasma membrane of the parasites.

Pyrrolopyrimidine vs Imidazole-Phenyl-Thiazole Scaffolds in Nonpeptidic Dimerization Inhibitors of Leishmania infantum Trypanothione Reductase

Disruption of protein-protein interactions of essential oligomeric enzymes by small molecules represents a significant challenge. We recently reported some linear and cyclic peptides derived from an α-helical region present in the homodimeric interface of Leishmania infantum trypanothione reductase (Li-TryR) that showed potent effects on both dimerization and redox activity of this essential enzyme. Here, we describe our first steps toward the design of nonpeptidic small-molecule Li-TryR dimerization disruptors using a proteomimetic approach. The pyrrolopyrimidine and the 5-6-5 imidazole-phenyl-thiazole α-helix-mimetic scaffolds were suitably decorated with substituents that could mimic three key residues (K, Q, and I) of the linear peptide prototype (PKIIQSVGIS-Nle-K-Nle). Extensive optimization of previously described synthetic methodologies was required. A library of 15 compounds bearing different hydrophobic alkyl and aromatic substituents was synthesized. The imidazole-phenyl-thiazole-based analogues outperformed the pyrrolopyrimidine-based derivatives in both inhibiting the enzyme and killing extracellular and intracellular parasites in cell culture. The most active imidazole-phenyl-thiazole compounds 3e and 3f inhibit Li-TryR and prevent growth of the parasites at low micromolar concentrations similar to those required by the peptide prototype. The intrinsic fluorescence of these compounds inside the parasites visually demonstrates their good permeability in comparison with previous peptide-based Li-TryR dimerization disruptors.

Palladium-Catalyzed Cleavage of α-Allenylic Aryl Ether toward Pyrazolemethylene-Substituted Phosphinyl Allenes and Their Transformations via Alkenyl C-P(O) Cleavage

A palladium-catalyzed two-component coupling of allenylphosphine oxides with conjugated N-tosylhydrazones is revealed. For the first time, the cleavage of α-allenylic aryl ether toward pyrazolemethylene-substituted phosphinyl allenes enabled facile synthesis of combined motifs with pyrazole and allene. Moreover, the obtained adducts could be easily transformed to potential bioactive multifunctionalized phosphinates via a novel alkenyl C-P(O) cleavage.

Novel Benzo[a]quinolizidine Analogs Induce Cancer Cell Death through Paraptosis and Apoptosis

Paraptosis is nonapoptotic cell death characterized by massive endoplasmic reticulum (ER)- or mitochondria-derived vacuoles. Induction of paraptosis offers significant advantages for the treatment of chemotherapy-resistant tumors compared with anticancer drugs that rely on apoptosis. Because some natural alkaloids induce paraptotic cell death, a novel series of benzo[a]quinolizidine derivatives were synthesized, and their antiproliferative activity and ability to induce cytoplasmic vacuolation were analyzed. Structural optimization led to the identification of the potent compound 22b, which inhibited cancer cell proliferation in vitro and in vivo and profoundly facilitated paraptosis-like cell death and induced caspase-dependent apoptosis. Further investigation revealed that 22b-mediated vacuolation originated from persistent ER stress and upregulation of LC3B. Paraptosis induced by benzo[a]quinolizidine derivatives thus represents an alternative strategy for cancer chemotherapy.

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.

Organocatalyzed Asymmetric Conjugate Addition of Heteroaryl and Aryl Trifluoroborates: A Synthetic Strategy for Discoipyrrole D

Bis-heteroaryl or bis-aryl stereocenters were formed by an organocatalytic enantioselective conjugate addition using the respective trifluoroborate salts as nucleophiles. Control studies suggested that fluoride dissociation is necessary in the anhydrous conditions. This strategy is applicable to the synthesis of discoipyrrole D, an inhibitor of BR5 fibroblast migration.

Iridium(I)-catalyzed regioselective C-H activation and hydrogen-isotope exchange of non-aromatic unsaturated functionality

Isotopic labelling is a key technology of increasing importance for the investigation of new C-H activation and functionalization techniques, as well as in the construction of labelled molecules for use within both organic synthesis and drug discovery. Herein, we report for the first time selective iridium-catalyzed C-H activation and hydrogen-isotope exchange at the β-position of unsaturated organic compounds. The use of our highly active [Ir(cod)(IMes)(PPh3)][PF6] (cod = 1, 5-cyclooctadiene) catalyst, under mild reaction conditions, allows the regioselective β-activation and labelling of a range of α, β-unsaturated compounds with differing steric and electronic properties. This new process delivers high levels of isotope incorporation over short reaction times by using low levels of catalyst loading.

Asymmetric crossed-conjugate addition of nitroalkenes to enones by a chiral bifunctional diamine organocatalyst

The crossed-conjugate addition involving the electronwithdrawing group (EWG) of activated alkenes is considered one of the most important C-C bond-forming reactions in organic synthesis. Among them, the β,β-disubstituted nitroolefins as powerful synthons have attracted considerable attention recently because the functionalized products can undergo transformations into useful skeletons. Asymmetric intermolecular crossed-conjugate addition between β-alkyl nitroalkenes and a,b-unsaturated carbonyl compounds to provide allylic nitro compounds with multiple stereogenic centers is still rare. The key challenges are to avoid the homo-crossed addition and realize perfect stereochemical control. Shi and co-workers developed the first asymmetric crossed-conjugate addition of β-alkyl nitroalkenes and enals catalyzed by a chiral diphenylprolinol though a dual activation strategy using a stoichiometric amount of (MeO)3P as a Lewis base (LB) (Scheme 1, path A). Although the secondary amines proved to be effective catalysts in the crossed-Michael addition of nitro activated olefins to carbonyl compounds through the LB nucleophilic mechanism, the enantioselective process awaits further investigation.We envisioned that a chiral diamine catalyst would promote the enantioselective crossed-conjugate addition by a bifunctional activation approach (Scheme 1, path B). Herein, we report the chiral primary-secondary diamine Bronsted acid catalyzed asymmetric crossed-conjugate addition of β-methyl nitroalkenes with α, β-unsaturated acyclic and cyclic ketones with excellent enantioselectivities under mild conditions.