31949-21-0

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-2'-methoxyacetophenone is utilized as a pharmaceutical intermediate for the synthesis of various medicinal compounds. Its specific structural features make it a valuable building block in the development of drugs with targeted therapeutic effects.
As a pharmaceutical intermediate, 2-Bromo-2'-methoxyacetophenone is used for the synthesis of compounds with potential applications in treating a range of medical conditions. Its unique chemical structure allows for the creation of new molecules with specific biological activities, contributing to the advancement of pharmaceutical research and drug development.

Preparation

Also obtained according to the procedure of Buckman (80%).

Upstream product

• 579-74-8 2-Methoxyacetophenone 
• 118-93-4 o-hydroxyacetophenone 
• 4079-52-1 methoxymethyl phenyl ketone 
• 1121543-12-1 α,α-dibromo-2'-methoxyacetophenone 
• 123-54-6 acetylacetone 

Downstream Products

• 101604-86-8 (2-methoxy-phenacyl)-methyl-malonic acid diethyl ester 
• 108664-59-1 1-[2-(2-Methoxy-phenyl)-2-oxo-ethyl]-1H-pyridin-2-one 
• 143696-71-3 2-(2-methoxyphenyl)imidazo[1,2-a]pyrimidine 
• 79889-77-3 2-(o-methoxyphenyl)imidazo[2,1-b]-benzothiazole 
• 82158-43-8 2-(2-methoxybenzoyl)benzofuran 
• 92754-31-9 2-(2-Imino-thiazolidin-3-yl)-1-(2-methoxy-phenyl)-ethanone; hydrobromide 
• 92754-23-9 2-(2-Imino-5-methyl-thiazol-3-yl)-1-(2-methoxy-phenyl)-ethanone; hydrobromide 
• 84508-56-5 2-bromo-1,1-dimethoxy-1-(2-methoxyphenyl)ethane 
• 38922-83-7 2-(2'-methoxyphenyl)imidazo[1,2-a]pyridine 
• 152801-75-7 2-Bromo-1-(2-methoxy-phenyl)-ethanone O-methyl-oxime 
• 216854-25-0 2-phthalimido-1-(2-methoxy-phenyl)-ethanone 

Relevant academic research and scientific papers

Synthesis and bioactivity evaluation of novel 2-salicyloylbenzofurans as antibacterial agents

In order to discover new antibacterial agents, series of 2-salicyloylbenzofuran derivatives were designed, synthesized and evaluated for their antibacterial activities against three Gram-(+) strains (methicillin-sensitive Staphylococcus aureus (MSSA) ATCC 29213, methicillin-resistant Staphylococcus aureus (MRSA) ATCC 43300, and Streptococcus faecalis (S. faecalis) ATCC 29212) and one Gram-(-) strain (Escherichia coli (E. coli) ATCC 25922). The 2-salicyloylbenzofuran heterocycles were generated by Rap-Stoermer condensation of salicylaldehydes with phenacyl bromides and then converted to diverse O-ether derivatives by Williamson synthesis. The targeted products were screened for in vitro qualitative (zone of inhibition) and quantitative (MIC) antibacterial activities by agar well diffusion assay and agar dilution method. Amongst the compounds, those bearing carboxylic acid functional group were found to exhibit reasonable activity against Gram-(+) bacterial strains including S. faecalis, MSSA and MRSA with the most potent antibacterial agent 8h (MICs = 0.06-0.12 mM). Besides, the 2-salicyloylbenzofurans partly displayed inhibitory activity against MRSA with the best MICs = 0.14 mM (8f) and 0.12 mM (8h). Finally, the antibacterial results preliminarily suggested that the substituent bearing carboxylic acid group at salicyloyl-C2 and the bromine atoms on the benzofuran moiety seem to be the functionality necessary for antibacterial activities.

Efficient Synthesis and In Vitro Biological Evaluation of 2,5-Diaryloxazoles as Potential Nitric Oxide Production Inhibitors

An efficient first synthesis of 2,5-diaryloxazoles 1–5 was accomplished from commercially inexpensive precursors and in overall yields of 38–48%. The synthesis proceeds via α-aminoketones and cyclodehydration (Robinson–Gabriel reaction) as key step. Next, these oxazoles were examined for their inhibitory effect against nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW 264.7 cells and were found to display concentration-dependent inhibition of NO production without cytotoxicity. Of note, compound 3 (70.7%; IC50 = 2.33 μM) was identified as a potent inhibitor in view of its comparable inhibitory effect with the positive control, NG-monomethyl-L-arginine acetate (L-NMMA) (79.3%; IC50 = 4.51 μM) followed by compounds 5 (68.3%; IC50 = 2.30 μM) and 2 (53.9%; IC50 = 6.31 μM). As a whole, compound 3 may hold great promise for further development of NO production targeted anti-inflammatory agent.

Design and synthesis of 7-O-1,2,3-triazole hesperetin derivatives to relieve inflammation of acute liver injury in mice

Based on the previous research results of our research group, to further improve the anti-inflammatory activity of hesperetin, we substituted triazole at the 7-OH branch of hesperetin. We also evaluated the anti-inflammatory activity of 39 new hesperetin derivatives. All compounds showed inhibitory effects on nitric oxide (NO) and inflammatory factors in lipopolysaccharide-induced RAW264.7 cells. Compound d5 showed a strong inhibitory effect on NO (half maximal inhibitory concentration = 2.34 ± 0.7 μM) and tumor necrosis factor-α, interleukin (IL)-1β, and (IL-6). Structure–activity relationships indicate that 7-O-triazole is buried in a medium-sized hydrophobic cavity that binds to the receptor. Compound d5 can also reduce the reactive oxygen species production and significantly inhibit the expression of inducible NO synthase and cyclooxygenase-2 through the nuclear factor-κB signaling pathway. In vivo results indicate that d5 can reduce liver inflammation in mice with acute liver injury (ALI) induced by CCI4. In conclusion, d5 may be a candidate drug for treating inflammation associated with ALI.

Synthesis and anti-methicillin-resistant Staphylococcus aureus activity of 5,7-dibromo-2-benzoylbenzofurans alone and in combination with antibiotics

A series of 5,7-dibromo-2-benzoylbenzofurans were synthesized by the Rap–Stoermer condensation of 5,7-dibromosalicylaldehyde with diverse phenacyl bromides and evaluated for in-vitro antibacterial activities against methicillin-sensitive Staphylococcus aureus (MSSA) ATCC 29213, methicillin-resistant Staphylococcus aureus (MRSA) ATCC 43300, and MRSA ATCC 33591 by agar dilution method. The synergistic effects were determined by using the agar dilution checkerboard assay. The derivatives bearing carboxylic acid functional groups exhibited reasonable activity against MRSA strains with the best MIC = 32 μg/mL (9b, 9d). Moreover, the additive or synergistic interactions against MRSA strains was observed in six combinations (1b + cefuroxime/gentamicin, 1c + ciprofloxacin/gentamicin, 9b + gentamicin, and 9c + ciprofloxacin) with the fractional inhibitory concentration index (FICI) values in the range of 0.375–1.0. Significantly, the MICs of these antibiotics were reduced 2–4-fold. The results of the MTT assay illustrated the low mammalian cell cytotoxicity of these potent compounds.

Ru-Tethered (R,R)-TsDPEN with DMAB as an efficient catalytic system for high enantioselective one-pot synthesis of chiral β-aminolviaasymmetric transfer hydrogenation

This work reflects Ru-tethered-TsDPEN as an active chiral catalyst for one pot selective synthesis of optically active α-substituted alcohols and its derivatives from α-bromo ketones in the presence of dimethylamine borane (DMAB) as the hydrogen source. Various Ru-chiral catalysts have been screened and the methodology proceededviaa (R,R) Ru-tethered TsDPEN catalyst through asymmetric transfer hydrogenation (ATH) of the in-situ formed ketones to the corresponding chiral β-aminol product. Thus, the Ru-tethered TsDPEN-DMAB catalytic system works efficiently with higher yield and high enantiomeric excess over others for the ATH process. Based on a study ofortho,metaandparasubstituted α-bromo acetophenone derivatives, effective enantioselectivity has been observed fororthosubstituted β-aminol. The mechanism has been optimized depending on product analysis with the help of its kinetic AT-IR study. This work also focusses on the synthesis of various β-amino alcohol derivatives where the effect of an EWG and EDG on enantio-selectivity has been studied.

An umpolung oxa-[2,3] sigmatropic rearrangement employing arynes for the synthesis of functionalized enol ethers

An oxa-[2,3] sigmatropic rearrangement involving arynes is reported featuring the umpolung of ketones, where the C=O bond polarity is reversed. The in situ-generated sulfur ylides from β-keto thioethers and arynes undergo efficient rearrangement allowing the facile and robust synthesis of functionalized enol ethers in high yields and excellent functional group compatibility. Preliminary mechanistic studies rule out the possibility of Pummerer-type rearrangement operating in this case.

Novel Aryl-Substituted Pyrimidones as Inhibitors of 3-Mercaptopyruvate Sulfurtransferase with Antiproliferative Efficacy in Colon Cancer

The enzyme 3-mercaptopyruvate sulfurtransferase (3-MST) is one of the more recently identified mammalian sources of H2S. A recent study identified several novel 3-MST inhibitors with micromolar potency. Among those, (2-[(4-hydroxy-6-methylpyrimidin-2-yl)sulfanyl]-1-(naphthalen-1-yl)ethan-1-one) or HMPSNE was found to be the most potent and selective. We now took the central core of this compound and modified the pyrimidone and the arylketone sides independently. A 63-compound library was synthesized; compounds were tested for H2S generation from recombinant 3-MST in vitro. Active compounds were subsequently tested to elucidate their potency and selectivity. Computer modeling studies have delineated some of the key structural features necessary for binding to the 3-MST's active site. Six novel 3-MST inhibitors were tested in cell-based assays: they exerted inhibitory effects in murine MC38 and CT26 colon cancer cell proliferation; the antiproliferative effect of the compound with the highest potency and best cell-based activity (1b) was also confirmed on the growth of MC38 tumors in mice.

Chiral Bidentate Phosphoramidite-Pd Catalyzed Asymmetric Decarboxylative Dipolar Cycloaddition for Multistereogenic Tetrahydrofurans with Cyclic N-Sulfonyl Ketimine Moieties

An asymmetric [3 + 2] cycloaddition of vinyl ethylenecarbonates (VECs) and (E)-3-arylvinyl substituted benzo[d] isothiazole 1,1-dioxides has been developed using the Pd complex of a bidentate phosphoramidite (Me-BIPAM) as the catalyst, providing a wide variety of chiral multistereogenic vinyltetrahydrofurans in good yields with excellent diastereo- and enantioselectivities (up to >20:1 dr, 99% ee).

Nucleus-independent chemical shift (NICS) as a criterion for the design of new antifungal benzofuranones

The assertion made by Wu et al. that aromaticity may have considerable implications for molecular design motivated us to use nucleus-independent chemical shifts (NICS) as an aromaticity criterion to evaluate the antifungal activity of two series of indol-4-ones. A linear regression analysis of NICS and antifungal activity showed that both tested variables were significantly related (p –1 for Candida glabrata, Candida krusei and Candida guilliermondii with compounds 15-32, 15-15 and 15-1. The MIC for filamentous fungi was 1.95 μg·mL–1 for Aspergillus niger for compounds 15-1, 15-33 and 15-34. The results obtained support the use of NICS in the molecular design of compounds with antifungal activity.

Benzo[d]thiazole-2-thiol bearing 2-oxo-2-substituted-phenylethan-1-yl as potent selectivelasBquorum sensing inhibitors of Gram-negative bacteria

Quorum sensing is a well-known term for describing bacterial cell-cell communication. Bacteria use quorum sensing pathways to respond to external factors such as nutrient availability, defense mechanisms, and coordinate host toxic behaviors such as biofilm formation, virulence production, and other pathogenesis. Discovery of novel compounds which inhibit quorum sensing without being antibiotic are currently emerging fields. Herein, the library of fifteen benzo[d]thiazole/quinoline-2-thiol bearing 2-oxo-2-substituted-phenylethan-1-yl compounds was designed, synthesized and evaluated to find novel quorum sensing inhibitors. Firstly, compounds were evaluated for their growth inhibitory activities at high concentrations up to 1000 μg mL?1towardPseudomonas aeruginosa. Under our conditions, twelve compounds showed moderate growth inhibitory activities in the concentration tested. To our delight, three compounds3,6and7do not affect the growth of the bacteria which were chosen for the evaluation of quorum sensing inhibitor activities. In theLasBsystem, our compounds3,6,7showed promising quorum-sensing inhibitors with IC50of 115.2 μg mL?1, 182.2 μg mL?1and 45.5 μg mL?1, respectively. In thePqsRsystem, no activity observed suggesting that the selectivity of the compound toward theLasBsystem. In addition,7showed the moderate anti-biofilm formation ofPseudomonas aeruginosa. Docking studies revealed that3,6and7binding to the active site ofPseudomonas aeruginosaquorum sensingLasRsystem with better affinity compared to reference compounds4-NPO. Finally, computation calculations suggest that compounds are a good template for further drug development.