18815-75-3

Usage

InChI:InChI=1/C9H8BrNO3/c10-7-3-1-6(2-4-7)9(14)11-5-8(12)13/h1-4H,5H2,(H,11,14)(H,12,13)

Upstream product

• 56-40-6 glycine 
• 586-75-4 4-chlorobenzoyl chloride 
• 6000-43-7 2-aminoethanoic acid hydrochloride 
• 138119-50-3 N-(4-bromobenzyl-1-carbonyl)-glycine methyl ester 
• 586-76-5 4-Bromobenzoic acid 
• 861568-36-7 N-(4-bromo-benzoyl)-glycyl azide 
• 7732-18-5 water 
• 99208-44-3 4-bromo-N-(cyanomethyl)benzamide 

Downstream Products

• 95719-83-8 2-(4-Bromphenyl)-4,5-dihydro-1,3-oxazol-5-on 
• 22739-28-2 2-(4-bromo-phenyl)-4-isopropylidene-4H-oxazol-5-one 
• 699012-66-3 2-(4-bromophenyl)-4-<(Z)-1-ethoxyethylidene>-5-oxazolone 
• 849770-61-2 (Z)-4-benzylidene-2-(4-bromophenyl)oxazol-5(4H)-one 
• 800394-49-4 (Z)-2-(4-bromophenyl)-4-(1-naphthylmethylene)-5(4H)-oxazolone 
• 75446-59-2 N-([1,1'-biphenyl]-4-ylcarbonyl)glycine 
• 356570-58-6 N-(4-bromobenzyl-1-carbonyl)-glycyl-tyrosine methyl ester 
• 356570-60-0 N-(4-bromobenzyl-1-carbonyl)-glycyl-glycine methyl ester 
• 800393-88-8 (Z)-2-(4-bromobenzoylamino)-N-methyl-3-(1-naphthyl)-2-propenamide 
• 1123761-51-2 4-bromo-N-(formamidomethyl)benzamide 
• 1206976-15-9 2-(2-(4-bromophenyl)oxazol-5-yl)acetonitrile 
• 1447964-09-1 (Z)-2-(4-bromophenyl)-4-(2-(piperidin-1-yl)benzylidene)-oxazol-5(4H)-one 

Relevant academic research and scientific papers

Synthesis, characterization, antioxidant power and acute toxicity of some new azo-benzamide and azo-imidazolone derivatives with in vivo and in vitro antimicrobial evaluation

In this research paper, a stepwise chemical reaction was conducted to synthesize and develop of a new potent azo-oxazolone, which was used as prototypical molecule for production of two series of azo-benzimide (5a–j) and azo-imidazolone (6a–j). FT-IR, su

Synthesis and evaluation of new phenyl acrylamide derivatives as potent non-nucleoside anti-HBV agents

As a continuation of our previous work, a series of new phenyl acrylamide derivatives (4Aa-g, 4Ba-t, 5 and 6a-c) were designed and synthesized as non-nucleoside anti-HBV agents. Among them, compound 4Bs could potently inhibit HBV DNA replication in wild-type and lamivudine (3TC)/entecavir resistant HBV mutant strains with IC50 values of 0.19 and 0.18 μM, respectively. Notably, the selective index value of 4Bs was above 526, indicating the favorable safety profile. Interestingly, unlike nucleoside analogue 3TC, 4Bs could significantly inhibit 3.5 kb pgRNA expression. Molecular docking study revealed that 4Bs could fit well into the dimer-dimer interface of HBV core protein by hydrophobic, π–π and H-bond interactions. Considering the potent anti-HBV activity, low toxicity and diverse anti-HBV mechanism from that of nucleoside anti-HBV agent 3TC, compound 4Bs might be a promising lead to develop novel non-nucleoside anti-HBV therapeutic agents, and warranted further investigation.

Nickel-Catalyzed Asymmetric Hydrogenation of 2-Amidoacrylates

Earth-abundant nickel, coordinated with a suitable chiral bisphosphine ligand, was found to be an efficient catalyst for the asymmetric hydrogenation of 2-amidoacrylates, affording the chiral α-amino acid esters in quantitative yields and excellent enantioselectivity (up to 96 % ee). The active catalyst component was studied by NMR and HRMS, which helped us to realize high catalytic efficiency on a gram scale with a low catalyst loading (S/C=2000). The hydrogenated products could be simply converted into chiral α-amino acids, β-amino alcohols, and their bioactive derivatives. Furthermore, the catalytic mechanism was investigated using deuterium-labeling experiments and computational calculations.

Lewis acid catalyzed formation of 3-amino-3-carboxy-tetrahydroquinoline derivatives via tandem 1,5-hydride transfer/cyclization process

A Sc(OTf)3-catalyzed intramolecular tandem 1,5-hydride transfer/cyclization process to construct 3-amino-3-carboxy-tetrahydroquinoline derivatives has been developed. The methodology gives access to a range of relatively complex tetrahydroquinolines (tetracyclic and pentacyclic heterocycles bearing spirocyclic skeleton and two stereogenic centers) in good to excellent yields with diastereoselectivities ranging from 57:43 to 73:27. The synthetic utility of the method was also demonstrated by an efficient ring opening derivatization reaction.

Synthesis and structural characterization of amino acid and peptide derivatives featuring N-(p-bromobenzoyl) substituents as promising connection unit for bio-inspired hybrid compounds

Using a sequence of activation, blocking and peptide coupling procedures, a series of ten amino acid and peptide derivatives 1-6 (a, b, respectively) featuring a p-bromobenzoyl substituent attached to the amino group of the parent compound has been synthe

A convenient method for synthesis of 5-chloro-2-aryloxazole-4-carbaldehyde with vilsmeier reagent

A convenient method for synthesis of 5-chloro-2-aryloxazole-4-carbaldehyde 3 in moderate to good yields had been developed via the Vilsmeier reaction of readily available N-arylglycine 2 at 100 °C, provided a novel route for the construction of nitrogen heterocycles. A series of these compounds were synthesized by this method and optimization of conditions was performed. The Japan Institute of Heterocyclic Chemistry.

Phenylpropenamide derivatives: Anti-hepatitis B virus activity of the Z isomer, SAR and the search for novel analogs

Phenylpropenamides have been reported to be a class of non-nucleoside inhibitors of the hepatitis B virus (HBV). This class of compounds was explored with the objective of developing potent anti-HBV agents, with a novel mechanism of action, that could be combined with nucleos(t)ide analogs currently used to treat HBV infection. To accomplish this objective a series of substituted arylpropenamide derivatives were prepared and the E and Z geometrical isomers were separated. The structural identity of each of the E and Z isomers was determined by single crystal X-ray crystallography. Contrary to previous reports, the activity of this class of molecules resides in the Z isomer. Further structure-activity relationship studies around the active Z isomer identified compounds that displayed potent antiviral activity against HBV with EC90 value of approximately 0.5 μM in vitro. Attempts to develop ring constrained analogs did not lead to active HBV inhibitors.

A facile synthesis of N-formylbenzamides by oxidative decarboxylation of N-aroylglycine induced by Ag+/S2O82-

A facile method is described for the synthesis of N-formylbenzamides by oxidative decarboxylation of N-aroylglycine using catalytic silver(I) and 2 equivalents of ammonium persulfate as an oxidant in a biphasic system (CHCl 3/water).

Potent and selective inhibitors of bacterial methionyl tRNA synthetase derived from an oxazolone-dipeptide scaffold

The preparation and structure-activity relationships (SARs) of potent and selective small molecule inhibitors of bacterial methionyl-tRNA synthetase (MetRS) derived from an oxazolone-dipeptide scaffold are described. Examples combine Staphylococcus aureus MetRS (SaMetRS) potency with selectivity over human MetRS. As a result of the SAR expansion compound 14a was identified, as a potent SaMetRS inhibitor (IC50=18 nM) having moderate inhibition of MetRS derived from Enterococci faecalis (IC50=3.51 μM).

Neutral peptide biradicals formed by dissociative electron transfer

(Matrix presented) A new method for the generation of transient neutral biradicals in liquid solution is reported. Photoinduced electron transfer in aqueous solution of the structures shown above leads to neutral biradicals with peptide spacers. Exchange