4571-25-9

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Bromo-1-(2,5-dichlorophenyl)ethanone is employed as a key building block in the synthesis of pharmaceuticals. Its unique structure allows for the creation of various medicinal compounds, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Production:
In the agrochemical industry, 2-Bromo-1-(2,5-dichlorophenyl)ethanone serves as an essential intermediate in the production of various agrochemicals. Its reactivity and selectivity facilitate the synthesis of compounds used in crop protection and pest management.
Used in Organic Compounds Synthesis:
2-Bromo-1-(2,5-dichlorophenyl)ethanone is utilized as a versatile starting material in the synthesis of a wide range of organic compounds. Its haloketone nature makes it a valuable precursor for the preparation of complex organic molecules used in various applications, including materials science and specialty chemicals.

InChI:InChI=1/C8H5BrCl2O/c9-4-8(12)6-3-5(10)1-2-7(6)11/h1-3H,4H2

Upstream product

• 2476-37-1 2,5-dichloroacetophenone 

Downstream Products

• 7250-05-7 3-bromo-1-(2,5-dichloro-phenacyl)-pyridinium; bromide 
• 68301-45-1 4-(2,5-dichlorophenyl)-1,3-thiazol-2-amine 
• 19084-47-0 6-(2,5-dichloro-phenyl)-4-methoxy-6,7-dihydro-5H-pyrimido[4,5-b][1,4]thiazin-6-ol 
• 19084-53-8 6-(2,5-dichloro-phenyl)-4-methyl-7H-pyrimido[4,5-b][1,4]thiazin-2-ylamine 
• 19084-41-4 4-chloro-6-(2,5-dichloro-phenyl)-6,7-dihydro-5H-pyrimido[4,5-b][1,4]thiazin-6-ol 
• 143696-75-7 2-(2,5-Dichloro-phenyl)-imidazo[1,2-a]pyrimidine 
• 156897-24-4 6-(2,5-Dichloro-phenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine 
• 892405-56-0 1-(2,5-dichloro-phenyl)-2-{[3-(3-hydroxy-propoxy)-benzyl]-methyl-amino}-ethanone 
• 56719-08-5 2,5-Dichlorobenzoylacetonitrile 
• 2476-37-1 2,5-dichloroacetophenone 

Relevant academic research and scientific papers

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.

Microwave-assisted synthesis and luminescent activity of imidazo[1,2-a]pyridine derivatives

In this work, a series of phenacyl bromide derivatives was synthesized and employed as key intermediate for the synthesis of substituted imidazo[1,2-a]pyridines. First, phenacyl bromide molecules were obtained from the bromination reaction of acetophenones assisted by microwave irradiation, obtaining the products 4a-v in a 15 minutes reaction with yields in the range of 50% to 99%. Subsequently, the conjugation of these molecules with 2-aminopyridine conduced to the production of imidazo[1,2-a]pyridine derivatives (7a-v) in a 60-second reaction with yields of 24% to 99%. Improved yields were determined with respect to those obtained with more tedious methodologies like thermally and mechanically assisted routes. Intense luminescence emissions in the purple and blue regions of the electromagnetic spectra were observed under UV excitation according to the nature of the substituents. This environmentally friendly methodology is expected to constitute an important class of organic compounds for the development of biomarkers, photochemical sensors, and medicinal applications.

Structure-based design of potent human dihydroorotate dehydrogenase inhibitors as anticancer agents

It has been proven that inhibiting human dihydroorotate dehydrogenase (hDHODH) restricts the growth of rapidly proliferating cells, thus hDHODH can be developed as a promising target for the treatment of immunological disease and cancer. Here, a succession of substituted hydrazino-thiazole derivatives were designed, synthesized, and biologically evaluated through structure-based optimization, of which compound 22 was the most potent inhibitor of hDHODH with an IC50 value of 1.8 nM. Furthermore, 22 exhibited much better antiproliferative activity than brequinar, both in HCT-116 and BxPC-3 cancer cell lines. Flow cytometry analysis revealed that 22 induced S phase cell cycle arrest and promoted induction of apoptosis. All results established a proof that blocking the pyrimidine de novo synthesis pathway by inhibiting the rate-limiting enzyme hDHODH is an attractive therapy for cancer.

Synthesis and antimicrobial activity evaluation of new dithiocarbamate derivatives bearing thiazole/benzothiazole rings

The synthesis of 2-(substituted phenyl)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (A1-A24) derivatives and 2-(4-substituted thiazol-2-ylamino)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (B1-B14) derivatives was undertaken starting from the potassium salt of 4-(2-pyrimidinyl)piperazine dithiocarbamate. The structures of the obtained compounds were elucidated by1H NMR,13C NMR, MS spectral data, and elemental analysis. The antimicrobial activity of the thirty eight newly synthesized compounds were tested against 12 microorganism strains using the microdilution technique. Compounds 2-(4-ethoxycarbonylthiazol-2-ylamino)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (B12), 2-(3-fluorophenyl)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (A18) and 2-(3,4-difluorophenyl)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (A21) were determined to possess high antimicrobial activity.

IMIDAZOPYRIDAZINE DERIVATIVES AS MODULATORS OF TNF ACTIVITY

A series of substituted imidazo[1,2-b]pyridazine derivatives of formula (I), being potent modulators of human TNFa activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory dis

Imidazopyrazine Derivatives as Modulators of TNF Activity

A series of imidazo[1,2-α]pyrazine derivatives, being potent modulators of human TNFα activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory disorders; neurological and neurodegenerative disorders; pain and nociceptive disorders; cardiovascular disorders; metabolic disorders; ocular disorder; and oncological disorders.

Synthesis and structure-activity relationship of aminoarylthiazole derivatives as correctors of the chloride transport defect in cystic fibrosis

Abstract The cystic fibrosis transmembrane conductance regulator (CFTR) is a chloride channel present in the membrane of epithelial cells. Mutations affecting the CFTR gene cause cystic fibrosis (CF), a multi-organ severe disease. The most common CF mutation, F508del, impairs the processing and activity (gating) of CFTR protein. Other mutations, like G551D, only cause a gating defect. Processing and gating defects can be targeted by small molecules called generically correctors and potentiators, respectively. Aminoarylthiazoles (AATs) represent an interesting class of compounds that includes molecules with dual activity, as correctors and potentiators. With the aim to improve the activity profile of AATs, we have now designed and synthesized a library of novel compounds in order to establish an initial SAR that may provide indications about the chemical groups that are beneficial or detrimental for rescue activity. The new compounds were tested as correctors and potentiators in CFBE41o-expressing F508del-CFTR using a functional assay. A dual active compound, AAT-4a, characterized by improved efficacy and marked synergy when combined with the corrector VX-809 has been identified. Moreover, by computational methods, a possible binding site for AATs in nucleotide binding domain NBD1 has been detected. These results will direct the synthesis of new analogues with possibly improved activity.

Design, Synthesis and Biological Evaluation of Imidazo[1,2-a]pyridine Derivatives as Novel DPP-4 Inhibitors

A new series of DPP-4 inhibitors with imidazo[1,2-a]pyridine scaffold were designed by exploiting scaffold hopping strategy and docking study. Based on docking binding model, structural modifications of 2-benzene ring and pyridine moieties of compound 5a led to the identification of compound 5d with 2, 4-dichlorophenyl group at the 2-position as a potent (IC50 = 0.13 μm), selective (DPP-8/DPP-4 = 215 and DPP-9/DPP-4 = 192) and in vivo efficacious DPP-4 inhibitor. Further, molecular docking revealed that compound 5d could retain key binding features of DPP-4 with the pyridine moiety of imidazo[1,2-a]pyridine ring providing an additional π-π interaction with Phe357 of DPP-4. Compound 5d might be a promising lead for further development of novel DPP-4 inhibitor treating T2DM.

IMIDAZOPYRIDINE DERIVATIVES AS MODULATORS OF TNF ACTIVITY

A series of imidazo[l,2-a]pyridine derivatives of formula (I), being potent modulators of human TNFa activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory disorders; neurological and neurodegenerative disorders; pain and nociceptive disorders; cardiovascular disorders; metabolic disorders; ocular disorders; and oncological disorders.

IMIDAZOPYRAZINE DERIVATIVES AS MODULATORS OF TNF ACTIVITY

A series of imidazo[1,2-α]pyrazine derivatives, being potent modulators of human TNFα activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory disorders; neurological and neurodegenerative disorders; pain and nociceptive disorders; cardiovascular disorders; metabolic disorders; ocular disorders; and oncological disorders.