943-88-4

Usage

Occurrence

Has apparently not been reported to occur in nature.

Preparation

From anisaldehyde and acetone by condensation using a suitable catalyst.

Metabolism

When the side chain of a mixed ketone contains a double bond, both the keto group and the double bond are potentially reducible in vivo. In a related material, methyl styryl ketone ( C6 H5 CH:CHCOCH3 ) , the keto group appears to be more readily reduced than the double bond,with reduction via C6 H5 CH:CH.CH(OH)CH3to the completely reduced carbinol compoundC6 H5[CH2]2CH(OH) CH3, which is found as the main product (Fischer & Bielig, 1940). The ether link is relatively stable in substituted anisoles, such as anethole (p-CH3OC 6H4CH:CH CH4), containinga potential carboxyl group attached to the aromatic ring (Williams, 1959).

InChI:InChI=1/C11H12O2/c1-9(12)3-4-10-5-7-11(13-2)8-6-10/h3-8H,1-2H3/b4-3-

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 67-64-1 acetone 
• 696-62-8 para-iodoanisole 
• 78-94-4 methyl vinyl ketone 
• 104-46-1 anethole 
• 550358-35-5 1-(4-methoxyphenyl)-2-butyn-1-ol 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 2033-24-1 cycl-isopropylidene malonate 
• 15795-54-7 5-(4-methoxybenzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 1261958-96-6 1-(3-benzyloxybut-1-enyl)-4-methoxylbenzene 
• 67-63-0 isopropyl alcohol 
• 105-13-5 4-Methoxybenzyl alcohol 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 53440-94-1 4-(4-methoxy-phenyl)-6-methyl-2-oxo-4H-[1,3]oxazine-3-sulfonyl chloride 
• 39025-19-9 6-(4-methoxy-phenyl)-4-methyl-2-phenyl-6H-[1,3]thiazine; perchlorate 
• 85191-54-4 2-[(E)-2-(4-Methoxy-phenyl)-vinyl]-[1,8]naphthyridine 
• 130028-18-1 (E)-4-(4-Methoxy-phenyl)-but-3-enoic acid methyl ester 
• 95646-58-5 1,11-Bis-(4-methoxy-phenyl)-3-methyl-2,10-dihydro-1H-indolo[3,2-b]quinoline 
• 97481-58-8 6-Amino-5-[(E)-3-(4-methoxy-phenyl)-1-methyl-prop-2-en-(Z)-ylideneamino]-1,3-dimethyl-1H-pyrimidine-2,4-dione 
• 90904-36-2 1,4-dioxo-1-phenyl-2-(4-methoxyphenyl)pentane 
• 50548-82-8 4-(4-methoxyphenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile 
• 1774-12-5 5-(4-methoxyphenyl)-1,3-cyclohexanedione 
• 104-20-1 4-(4-methoxyphenyl)-2-butanone 
• 335162-61-3 C₃₀H₃₀N₆O₂ 
• 86069-36-5 4-(p-methoxyphenyl)-3-buten-2-one oxime 
• 107203-08-7 3-(4-methoxyphenyl)cyclohexanone 
• 92251-85-9 3-methoxy-5-(4-methoxyphenyl)-2-cyclohexan-1-one 

Relevant academic research and scientific papers

8-Hydroxyquinolin-2(1H)-one analogues as potential β2-agonists: Design, synthesis and activity study

β2-Agonists that bind to plasmalemmal β2-adrenoceptors causing cAMP accumulation are widely used as bronchodilators in chronic respiratory diseases. Here, we designed and synthesized a group of 8-hydroxyquinolin-2(1H)-one analogues and studied their β2-agonistic activities with a cellular cAMP assay. Compounds B05 and C08 were identified as potent (EC50 2-agonists among the compounds tested. They behaved as partial β2-agonists in non-overexpressed HEK293 cells, and possessed rapid smooth muscle relaxant actions and long duration of action in isolated guinea pig tracheal strip preparations. In summary, B05 and C08 are β2-agonists with potential applicability in chronic respiratory diseases.

Decarboxylation-triggered homo-Nazarov cyclization of cyclic enol carbonates catalyzed by rhenium complex

Decarboxylative homo-Nazarov cyclization catalyzed by a Lewis acid was achieved using a cyclic enol carbonate bearing a cyclopropane moiety as a substrate. Various substrates were converted into the corresponding multi-substituted cyclohexenones in good yieldsviadecarboxylation, followed by 6-membered ring formation involving cyclopropane-ring-opening.

Design, synthesis, and molecular docking study of novel quinoline-based bis-chalcones as potential antitumor agents

A novel series of quinoline-based symmetrical and unsymmetrical bis-chalcones was synthesized via a Claisen–Schmidt condensation reaction between 3-formyl-quinoline/quinolone derivatives with acetone or arylidene acetones, respectively, by using KOH/MeOH/H2O as a reaction medium. Twelve of the obtained compounds were evaluated for their in vitro cytotoxic activity against 60 different human cancer cell lines according to the National Cancer Institute protocol. Among the screened compounds, the symmetrical N-butyl bis-quinolinyl-chalcone 14g and the unsymmetrical quinolinyl-bis-chalcone 17o bearing a 7-chloro-substitution on the N-benzylquinoline moiety and 4-hydroxy-3-methoxy substituent on the phenyl ring, respectively, exhibited the highest overall cytotoxicity against the evaluated cell lines with a GI50 range of 0.16–5.45 μM, with HCT-116 (GI50 = 0.16) and HT29 (GI50 = 0.42 μM) (colon cancer) representing best-case scenarios. Notably, several GI50 values for these compounds were lower than those of the reference drugs doxorubicin and 5-FU. Docking studies performed on selected derivatives yielded very good binding energies in the active site of proteins that participate in key carcinogenic pathways.

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.

NOVEL SMALL MOLECULES THAT BIND AND/OR MODULATE DIFFERENTFORMS OF TAU OLIGOMERS

The present invention relates to novel small molecules of Formulas I, II, III, Ilia, Illb, and IV and pharmaceutically acceptable salts thereof, as well as the preparation and the use thereof.

Iron(ii)-folded single-chain nanoparticles: a metalloenzyme mimicking sustainable catalyst for highly enantioselective sulfa-Michael addition in water

Metalloenzyme is a source of inspiration for chemists who attempt to create versatile synthetic catalysts for aqueous catalysis. Herein, we impart metalloenzyme-like characteristics to a chiral FeII-oxazoline complex by incorporating an Fe(ii) ion into a chiral oxazoline-containing discrete self-folded polymer, to realize highly enantioselective sulfa-Michael addition (SMA) in water. Intrachain FeII-oxazoline complexation together with hydrophobic interactions triggers the self-folding of the oxazoline-containing single polymeric chain in water. The formed FeII-folded single-chain polymeric nanoparticles (SCPNs) significantly accelerate the aqueous asymmetric SMA reaction via a self-folded hydrophobic compartment around the catalytic sites, reminiscent of metalloenzymatic catalysis. In addition, they can be facilely recovered for reuse by simple thermo-controlled separation due to their thermo-responsive properties. Such metallo-folded SCPNs combine the benefits of transition metal- and bio-catalyst, and avoid the tedious procedures of separation, which is a benefit for energy-saving and industrial applications.

β-Carbolines: synthesis of harmane, harmine alkaloids and their structural analogs by thermolysis of 4-aryl-3-azidopyridines and investigation of their optical properties

[Figure not available: see fulltext.] Interest in β-carbolines is caused by the biological activity of these compounds and the use of their fluorescent properties in the study of their interaction with DNA and other biological targets, as well as with drug delivery vehicles. A new general method for the synthesis of harmane, harmine, and their structural analogs by thermolysis of substituted 4-aryl-3-azidopyridines was developed, and their optical properties were studied.

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.

Design, synthesis and biological evaluation of novel diaryl pyrazole derivatives as anticancer agents

Cancer is one of the major causes of mortality all around the world. Globally, nearly 1 in 6 deaths is due to cancer. Researchers are trying to synthesize new anticancer agents. Previous studies demonstrated that some pyrazole derivatives could be considered as potential anticancer agents. Herein, ten novel derivatives of 1,5-diarylpyrazole were synthesized in four step reactions and cytotoxic activity was investigated by MTT cell viability assay. All of the compounds were characterized by1H NMR and13C NMR and their purity was confirmed by elemental analysis. The cytotoxicity was determined against three cancerous cell lines (HT-29, U87MG and MDA-MB 468) and AGO1522 as a normal cell line. Compound 5a showed the best cytotoxic activity on cancerous cell lines in comparison to paclitaxel. Annexin V/ PI staining assay also showed that compounds 5a and 5i would lead to significant apoptosis induction in MDA-MB 486 cell line.