57728-67-3

Usage

Uses

Used in Organic Synthesis:
4-BROMO-N-(2-HYDROXYETHYL)BENZENECARBOXAMIDE is used as a building block for the synthesis of various organic compounds due to its versatile reactivity and functional groups.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-BROMO-N-(2-HYDROXYETHYL)BENZENECARBOXAMIDE is used as a scaffold for drug design, allowing researchers to explore its potential in developing new therapeutic agents.
Used in Material Science:
4-BROMO-N-(2-HYDROXYETHYL)BENZENECARBOXAMIDE may have potential applications in the development of new materials and chemical processes, contributing to advancements in various fields.
Safety Considerations:
4-Bromo-N-(2-hydroxyethyl)benzenecarboxamide is considered to be a hazardous substance and should be handled with caution due to its potential health and environmental risks. Proper safety measures and disposal methods should be followed to minimize any adverse effects.

InChI:InChI=1/C9H10BrNO2/c10-8-3-1-7(2-4-8)9(13)11-5-6-12/h1-4,12H,5-6H2,(H,11,13)

Upstream product

• 5798-75-4 Ethyl 4-bromobenzoate 
• 141-43-5 ethanolamine 
• 586-76-5 4-Bromobenzoic acid 
• 951885-58-8 2-(4-bromobenzamido)ethyl 4-bromobenzoate 
• 586-75-4 4-chlorobenzoyl chloride 
• 623-00-7 4-bromobenzenecarbonitrile 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 18292-63-2 1-(p-bromobenzoyl)aziridine 

Downstream Products

• 914076-87-2 C₁₈H₁₅NO 
• 914076-81-6 C₆(C₆H₄CH₃)3(C₆H₄C₃H₄NO)3 
• 189120-01-2 2-(4-bromo-phenyl)-4,5-dihydro-oxazole 
• 1073353-51-1 N-(2-hydroxyethyl)benzamide-4-boronic acid pinacol ester 
• 120047-91-8 n-butyl 4-bromobenzoate 

Relevant academic research and scientific papers

Illuminating a Dark Kinase: Structure-Guided Design, Synthesis, and Evaluation of a Potent Nek1 Inhibitor and Its Effects on the Embryonic Zebrafish Pronephros

NIMA-related kinase 1 (Nek1) has lately garnered attention for its widespread function in ciliogenesis, apoptosis, and the DNA-damage response. Despite its involvement in various diseases and its potential as a cancer drug target, no directed medicinal chemistry efforts toward inhibitors against this dark kinase are published. Here, we report the structure-guided design of a potent small-molecule Nek1 inhibitor, starting from a scaffold identified by kinase cross-screening analysis. Seven lead compounds were identified in silico and evaluated for their inhibitory activity. The top compound, 10f, was further profiled for efficacy, toxicity, and bioavailability in a zebrafish polycystic kidney disease model. Administration of 10f caused the expansion of fluorescence-labeled proximal convoluted tubules, supporting our hypothesis that Nek1-inhibition causes cystic kidneys in zebrafish embryos. Compound 10f displayed insignificant inhibition in 48 of 50 kinases in a selectivity test panel. The findings provide a powerful tool to further elucidate the function and pharmacology of this neglected kinase.

Discovery of 1,1′-Biphenyl-4-sulfonamides as a New Class of Potent and Selective Carbonic Anhydrase XIV Inhibitors

New 1,1′-biphenylsulfonamides were synthesized and evaluated as inhibitors of the ubiquitous human carbonic anhydrase isoforms I, II, IX, XII, and XIV using acetazolamide (AAZ) as reference compound. The sulfonamides 1-21 inhibited all the isoforms, with Ki values in the nanomolar range of concentration, and were superior to AAZ against all of them. X-ray crystallography and molecular modeling studies on the adducts that compound 20, the most potent hCA XIV inhibitor of the series (Ki = 0.26 nM), formed with the five hCAs, provided insight into the molecular determinants responsible for the high affinity of this molecule toward the target enzymes. The results pave the way to the development of 1.1′-biphenylsulfonamides as a new class of highy potent hCA XIV inhibitors.

A Mild and Regioselective Route to Functionalized Quinazolines

A Rh-catalyzed ortho-amidation cyclocondensation sequence gave a range of 4-aminoquinazolines in high yield. The method features a remarkably mild C(sp2)-H activation step and can be exploited to rapidly access compounds with established biological activity.

Synthesis of 2-aryl/heteroaryloxazolines from nitriles under metaland catalyst-free conditions and evaluation of their antioxidant activities

The synthesis of structurally diverse 2-aryl/heteroaryloxazolines from nitriles and aminoalcohols has been achieved under metal- and catalyst-free conditions in good to excellent yields. An array of functional groups are well-tolerated, thus, allowing the introduction of many important biologically active motifs such as azoles, ring-fused azoles, saturated heterocyclics, and amines in 2-aryloxazoline scaffolds. An evaluation of the antioxidant properties using the DPPH (diphenyl picryl hydrazyl) assay method shows the pyrrole-functionalized 2-aryloxazoline to be the best antioxidant among all the synthesized 2-aryl/heteroaryloxazolines.

Imidazole pyrimidine amides as potent, orally bioavailable cyclin-dependent kinase inhibitors

The development of a novel series of imidazole pyrimidine amides as cyclin-dependent kinase (CDK) inhibitors is described. The series was found to have much improved CDK2 inhibition and potent in vitro anti-proliferative effects against cancer cell lines. Control of overall lipophilicity was important to achieve good in vitro potency along with acceptable physiochemical properties and margins against inhibition of both CYP isoforms and the hERG potassium ion channel. A compound with an attractive overall balance of properties was profiled in vivo and possessed suitable physiochemical and pharmacokinetic profiles for oral dosing.

PYRIDINYLQUINAZ0LINAMINE DERIVATIVES AND THEIR USE AS B-RAF INHIBITORS

The invention relates to chemical compounds of the formula (I) or pharmaceutically acceptable salts thereof, which possess B-Raf inhibitory activity and are accordingly useful for their anti cancer activity and thus in methods of treatment of the human or animal body. The invention also relates to processes for the manufacture of said chemical compounds, to pharmaceutical compositions containing them and to their use in the manufacture of medicaments of use in the production of an anti-cancer effect in a warm blooded animal such as man.

4- (4- (IMIDAZOL-4-YL) PYRIMIDIN-2-YLAMINO) BENZAMIDES AS CDK INHIBITORS

Compounds of the formula: (I): wherein variable groups are as defined within and a pharmaceutically acceptable salts and in vivo hydrolysable esters are described. Also described are processes for their preparation and their use as medicaments, particularly medicaments for producing a cell cycle inhibitory (anti-cell-proliferation) effect in a warm-blooded animal, such as man.

Electrostatically controlled hierarchical arrangement of monocationic silver(I) and dicationic mercury(II) ions between disk-shaped template ligands

This paper describes hierarchical arrangement of three Ag+ and three Hg2+ ions using two disk-shaped hexa-monodentate template ligands in which three oxazolyl rings are arranged each on the two concentric circles. The hierarchical manner of ligand arrangement allows the selective binding of monocationic Ag+ and dicationic Hg2+ ions to the inner first and the outer second generation coordination sites, respectively. This hierarchically well-balanced metal assembly should arise primarily from a minimized electrostatic repulsion between positively charged six metal ions arranged within the heteronuclear complex. Copyright

Study of synthesis and cardiovascular activity of some furoxan derivatives as potential NO-donors

A series of hybrid molecules incorporating the furoxan and nicorandil moieties were designed as potential NO donors with cardiovascular and cerebrovascular activities. Thirty-six target molecules were successfully synthesized by conventional methods and characterized by infrared spectroscopy, 1H-NMR spectroscopy and high resolution mass spectra. The compounds were tested for their effects on KCl-induced contraction of rabbit thoracic aorta whose endothelium was denuded. Eight compounds were found to reduce KCl-induced contraction by more than 30% at 10 μM. All except one of these compounds are characterized by the presence of electron withdrawing groups in the phenyl ring attached via an amide or ester linkage to the furoxan moiety. The nature of the terminal carbonyl linkage (ester or amide) and the length or type of the alkyl chain bridging the two carbonyl functions have little effect on the activity. One of the active compounds, N-(4- methoxy-benzoyl)-N'-[3-methylfuroxanyl-4-carbonyl)piperazine (17i) was tested for hypotensive effects on anaesthetized rats at 1.5 mg/kg, and found to demonstrate a gradual and sustained hypotensive effect. The results suggest that the furoxannicorandil derivatives are a useful lead in the design of NO- donor compounds for hypertension.

A novel electrochemical method for benzoylation of aminoalcohols with methyl benzoates at room temperature

A novel electrochemical method of benzoylating aminoalcohols 2 by use of methyl benzoates 1 at room temperature was developed. 2-Aminoethanols 2 (n=0, R3=H) and 3-aminopropanols 2 (n=1, R3=H) gave the corresponding benzamides 4, as a result of electrochemical transesterification followed by O,N-acyl migration.In contrast, o- and m-aminobenzylalcohols (7a and 7b) and trans-4-(aminomethyl)cyclohexanemethanol (8a) afforded the corresponding benzoic esters, since their acyl migration is hindered.A local anesthetic, procaine, was prepared by using this electrochemical reaction.A mechanism for electrochemical transesterification, which involves a formation of alcoholate anion by a one-electron reduction of alcohol, is presented.