4225-92-7

Usage

Uses

Used in Pharmaceutical Industry:
AKOS BBS-00003969 is used as an active pharmaceutical ingredient for its therapeutic properties in treating various medical conditions, such as inflammation, pain, and skin disorders.
Used in Personal Care Industry:
AKOS BBS-00003969 is used as an active ingredient in sunscreen and anti-aging skincare products for its antioxidant properties, which help protect the skin from environmental damage and promote a youthful appearance.
Used in Cancer Therapy Research:
AKOS BBS-00003969 is used in scientific research for its potential role in cancer therapy, as it may have cytotoxic effects on certain cancer cells, offering a promising avenue for the development of novel cancer treatments.

InChI:InChI=1/C11H13BrO/c1-7-4-8(2)11(9(3)5-7)10(13)6-12/h4-5H,6H2,1-3H3

Upstream product

• 598-21-0 2-Bromoacetyl bromide 
• 108-67-8 1,3,5-trimethyl-benzene 
• 1667-01-2 2,4,6-Trimethylacetophenone 
• 22118-09-8 2-bromoacetyl chloride 

Downstream Products

• 1667-01-2 2,4,6-Trimethylacetophenone 
• 65080-42-4 2,4,6-trimethylphenacyl benzoate 
• 23722-23-8 mesityl-glyoxal-2-hydrazone 
• 127677-28-5 Propionic acid (S)-2-dimethylamino-1-(2,4,6-trimethyl-phenyl)-ethyl ester 
• 127677-17-2 Dimethyl-[(S)-2-(2,4,6-trimethyl-phenyl)-2-((E)-1-trimethylsilanyloxy-propenyloxy)-ethyl]-amine 
• 127677-25-2 (S)-2-Dimethylamino-1-(2,4,6-trimethyl-phenyl)-ethanol 
• 127677-25-2 (R)-2-Dimethylamino-1-(2,4,6-trimethyl-phenyl)-ethanol 
• 13661-19-3 2-diazo-1-mesityl-ethanone 
• 1334921-00-4 N-(4-mesitylthiazol-2-yl)-2-(pyridin-4-yl)acetamide 
• 313252-23-2 4-cyano-N-(4-mesitylthiazol-2-yl)benzamide 
• 1334920-60-3 4-[(4-mesitylthiazol-2-yl)carbamoyl]pyridine 1-oxide 
• 313366-31-3 4-[(4-mesitylthiazol-2-yl)carbamoyl]pyridine 1-oxide 
• 60904-57-6 1-mesityl-2-phenoxy-ethanone 
• 102004-60-4 1-mesityl-2-morpholino-ethanone; hydrochloride 

Relevant academic research and scientific papers

Anomalous Rate of Bromination of a Ketone: First-order Dependence on Bromine Concentration

The rate of acid-catalysed bromination of 2,4,6-trimethylacetophenone in 50percent aqueous acetic acid is first-order in bromine, in contrast with acetophenone and other reported ketones at comparable concentrations.

One-Pot Preparation of Aromatic Amides, 4-Arylthiazoles, and 4-Arylimidazoles from Arenes

Simple treatment of arenes with α-bromoacetyl chloride and AlCl3, followed by the reaction with molecular iodine and aq. NH3, thioamides, or amidines gave the corresponding primary aromatic amides, 4-arylthiazoles, or 4-arylimidazoles in good yields, respectively. Aryl α-bromomethyl ketones are the key intermediates in those reactions. Primary aromatic amides were formed from arenes through the reaction of aryl α-bromomethyl ketones with molecular iodine and aq. NH3, and 4-arylthiazoles and 4-arylimidazoles were formed from arenes through the reactions of aryl α-bromomethyl ketones with thioamides and amidines, respectively, in one pot under transition-metal-free conditions.

Indolizine–Squaraines: NIR Fluorescent Materials with Molecularly Engineered Stokes Shifts

The development of deep red and near infrared emissive materials with high quantum yields is an important challenge. Several classes of squaraine dyes have demonstrated high quantum yields, but require significantly red-shifted absorptions to access the N

Identification of novel 2-aminothiazole conjugated nitrofuran as antitubercular and antibacterial agents

The emergence of antibiotic resistant pathogens is an ongoing main problem in the therapy of bacterial infections. In order to develop promising antitubercular and antibacterial lead compounds, we designed and synthesized a new series of derivatives of 2-aminothiazole conjugated nitrofuran with activities against both Mycobacterium tuberculosis and Staphylococcus aureus. Eight compounds 12e, 12k, 12l, 12m, 18a, 18d, 18e, and 18j emerged as promising antitubercular agents. Structure–activity relationships (SARs) were discussed and showed that the derivatives substituted at the position-3 of benzene of 5-nitro-N-(4-phenylthiazol-2-yl)furan-2-carboxamide exhibited superior potency. The most potent compound 18e, substituted with benzamide at this position, displayed minimum inhibitory concentrations (MICs) of 0.27 μg/mL against Mtb H37Ra and 1.36 μg/mL against S. aureus. Furthermore, compound 18e had no obvious cytotoxicity to normal Vero cells (IC50= 50.2 μM). The results suggest that the novel scaffolds of aminothiazole conjugated nitrofuran would be a promising class of potent antitubercular and antimicrobial agents.

Synthesis and biological evaluation of N-(4-phenylthiazol-2-yl)cinnamamide derivatives as novel potential anti-tumor agents

In this study, a series of novel N-(4-phenylthiazol-2-yl)cinnamamide derivatives (7a-8n) were synthesized and evaluated for their anti-proliferative activities in vitro by MTT assay and a possible antitumor mechanism was also explored. SAR analysis showed that steric effects played an important role on the anti-tumor activity. The most potent analogue 8f showed excellent inhibitions on the K562, Bel7402, A549 and Jurkat cells ranging from sub-micromolar to nanomolar concentration. Compound 8f inhibited Jurkat cells with an IC50 value of 0.035 μM with no apparent toxicity in different non-cancerous cells. Furthermore, it was suggested that the possible mechanism of 8f might be associated with inducing cancer cell apoptosis following flow cytometer analysis and Hoechst 33358 staining assays.

Discovery of 4-aryl-N-arylcarbonyl-2-aminothiazoles as Hec1/Nek2 inhibitors. Part I: Optimization of in vitro potencies and pharmacokinetic properties

A series of 4-aryl-N-arylcarbonyl-2-aminothiazoles of scaffold 4 was designed and synthesized as Hec1/Nek2 inhibitors. Structural optimization of 4 led to compound 32 bearing C-4′ 4-methoxyphenoxy and 4-(o-fluoropyridyl) carbonyl groups that showed low nanomolar in vitro antiproliferative activity (IC50: 16.3-42.7 nM), high intravenous AUC (64.9 μM·h, 2.0 mg/kg) in SD rats, and significant in vivo antitumor activity (T/C = 32%, 20 mg/kg, IV) in mice bearing human MDA-MB-231 xenografts. Cell responses resulting from Hec1/Nek2 inhibition were observed in cells treated with 32, including a reduced level of Hec1 coimmunoprecipitated with Nek2, degradation of Nek2, mitotic abnormalities, and apoptosis. Compound 32 showed selectivity toward cancer cells over normal phenotype cells and was inactive in a [ 3H]astemizole competitive binding assay for hERG liability screening. Therefore, 32 is as a good lead toward the discovery of a preclinical candidate targeting Hec1/Nek2 interaction.

IMPROVED MODULATORS OF HEC1 ACTIVITY AND METHODS THEREFOR

Compounds, compositions, and methods for modulation of Hec1/Nek2 interaction are provided. Such compounds disrupt Nek2/Hec1 binding and may be useful as chemotherapeutic agents for neoplastic diseases

Temperature dependent product distribution in photolysis of o-alkylphenacyl benzoates

Temperature effect on photochemical reactions of ortho-alkylphenacyl benzoates, one of the recently developed photoremovable protecting groups (PPG), giving indanones (IN) and benzocyclobutenols (CB) was examined. As temperature was lowered, CB was formed preferentially over IN and the amount of IN increased as temperature was elevated. Arrhenius plot of ln(IN/CB) versus 1/T gave a straight line from which EaIN-EaCB and A IN/ACB were obtained. The least sterically hindered 2-methylphenacyl benzoate (1) gave the highest EaIN-EaCB and AIN/ACB among the ortho-alkylphenacyl benzoates tested in this research including 2,4,6-trimethylphenacyl benzoate (2) and 2,4,6-triisopropylphenacyl benzoate (3).

Modulators Of HEC1 Activity And Methods Therefor

Compounds, compositions, and methods for modulation of Hec1/Nek2 interaction are provided. Especially preferred compounds disrupt Nek2/Hec1 binding and are therefore useful as chemotherapeutic agent for neoplastic diseases.

α-Telluration of 2,4,6-trimethylacetophenone under mild conditions: Role of steric factor in the solid state structures of Te(II and IV) compounds

Elemental tellurium inserts into the Csp3-Br bond of α-bromomesitylmethyl ketone and due to its strong carbophilic character affords the crystalline C-tellurated derivative of 2,4,6-trimethylacetophenone, (MesCOCH2)2TeBr2, 1b in over 80% yield. Electrophilic substitution of the parent ketone with aryltellurium trichlorides, at room temperature, gives nearly quantitative yields of unsymmetrical alkylaryltellurium dichlorides (MesCOCH2)ArTeCl2 (Ar = mesityl, Mes, 2a; 1-naphthyl, Np, 3a; anisyl, Ans, 4a). Fairly stable mesitoylmethyltellurium(II) derivatives, (MesCOCH2)2Te, 1 and (MesCOCH2)ArTe (Ar = Mes, 2; Np, 3 and Ans, 4) obtained as the reduction products of their dihalotellurium(IV) analogues, readily undergo oxidative addition of dihalogens to afford the corresponding (MesCOCH 2)2TeX2 (X = Cl, 1a; Br 1b; I, 1c) and (MesCOCH2)ArTeX2 (X = Cl, Br, I, Ar = Mes, 2a, 2b, 2c; Np, 3a, 3b, 3c and Ans, 4a, 4b, 4c). Crystallographic structural characterization of 1, 1b, 2, 2a, 2b, 2c, 3, 3a and 4c illustrates that the steric demand of mesityl group appreciably influences primary geometry around the 5-coordinate Te(IV) atom when it is bound directly to it. It also makes the Te atom inaccessible for the ubiquitous Te?X intermolecular secondary bonding interactions that result in supramolecular structures. In the crystal lattice of symmetrical telluroether 1, an interesting supramolecular synthon based upon reciprocatory weak C-H?O H-bonding interaction gives rise to chains via self-assembly. α-Bromo-2,4,6-trimethylacetophenone adds oxidatively to Te0/TeII to give the dialkyl- or alkylarylTeIV species which on reduction afford carbonyl-functionalized telluroethers.