152706-83-7

Usage

Type of compound

Derivative of 1,3-butanedione

Usage

Organic synthesis and research

Applications

Building block for the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals

Physical state

Pale yellow liquid

Odor

Distinctive

Hazards

Skin and eye irritant

Safety precautions

Handle and use with caution, following strict safety guidelines and protocols

Upstream product

• 141-78-6 ethyl acetate 
• 2142-63-4 1-(3-Bromophenyl)ethanone 
• 24398-88-7 ethyl 3-bromobenzoate 
• 67-64-1 acetone 

Downstream Products

• 10272-70-5 Diethyl N-(1-methyl-3-m-bromophenyl-3-oxo-propylidene)-aminomalonate 
• 95346-60-4 C₁₆H₁₁BrN₃O₈^(1-) 
• 134259-96-4 4-Bromo-1-(3-bromo-phenyl)-butane-1,3-dione 
• 38177-84-3 1-(m-Brom-phenyl)-butadiin-(1,3) 
• 500903-44-6 (3-bromo-phenyl)-(7-chloro-3-methyl-4H-benzo[1,4]thiazin-2-yl)-methanone 
• 526220-87-1 (3-bromo-phenyl)-(7-ethoxy-3-methyl-4H-benzo[1,4]thiazin-2-yl)-methanone 
• 500169-93-7 6-(3-bromophenyl)-2-mercapto-4H-thiopyran-4-one 

Relevant academic research and scientific papers

A General Proline-Catalyzed Synthesis of 4,5-Disubstituted N-Sulfonyl-1,2,3-Triazoles from 1,3-Dicarbonyl Compounds and Sulfonyl Azide

An efficient proline-catalyzed synthesis of 4,5-disubstituted-N-sulfonyl-1,2,3-triazoles has been accomplished from 1,3-dicarbonyl compounds and sulfonyl azides. The developed reaction is suitable for various symmetrical and unsymmetrical 1,3-dicarbonyl compounds, tolerates various functional groups and affords 4,5-disubstituted-N-sulfonyl-1,2,3-triazoles in good yield with excellent regioselectivity. Rhodium-catalyzed denitrogenative functionalization of 4,5-disubstituted-N-sulfonyl-1,2,3-triazoles further demonstrates their utility in organic synthesis.

Biphenyl Pyridazinone Derivatives as Inhaled PDE4 Inhibitors: Structural Biology and Structure-Activity Relationships

Cyclic nucleotide cAMP is a ubiquitous secondary messenger involved in a plethora of cellular responses to biological agents involving activation of adenylyl cyclase. Its intracellular levels are tightly controlled by a family of cyclic nucleotide degrading enzymes, the PDEs. In recent years, cyclic nucleotide phosphodiesterase type 4 (PDE4) has aroused scientific attention as a suitable target for anti-inflammatory therapy in respiratory diseases, particularly in the management of asthma and COPD. Here we describe our efforts to discover novel, highly potent inhaled inhibitors of PDE4. Through structure based design, with the inclusion of a variety of functional groups and physicochemical profiles in order to occupy the solvent-filled pocket of the PDE4 enzyme, we modified the structure of our oral PDE4 inhibitors to reach compounds down to picomolar enzymatic potencies while at the same time tackling successfully an uncovered selectivity issue with the adenosine receptors. In vitro potencies were demonstrated in a rat lung neutrophilia model by administration of a suspension with a Penn-Century MicroSprayer Aerosolizer.

3-(5-Amino-6-oxo-1,6-dihydropyridazin-3-yl)-biphenyl derivatives as PDE4 inhibitors

New pyridazin-3(2H)-one derivatives having the chemical structure of formula (I) are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of the phosphodiesterase IV (PDE4).

(3-oxo)pyridazin-4-ylurea derivatives as PDE4 inhibitors

New (3-oxo)pyridazin-4-ylurea derivatives having the chemcial structure of formula (I) are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of the phosphodiesterase IV (PDE4).

Synthesis of 5-acyl-3,4-dihydropyrimidine-2-thiones via solvent-free, solution-phase and solid-phase Biginelli procedures

Compounds belonging to the 5-acyl-3,4-dihydropyrimidine-2-thione family were obtained using a solvent-free Biginelli condensation with or without the use of a catalyst. An unprecedented solid-phase procedure involving a polymer-supported aldehyde allowed

Pyranone, thiopyranone, and pyridone inhibitors of phosphatidylinositol 3-kinase related kinases. Structure-activity relationships for DNA-dependent protein kinase inhibition, and identification of the first potent and selective inhibitor of the ataxia telangiectasia mutated kinase

Structure-activity relationships have been investigated for inhibition of DNA-dependent protein kinase (DNA-PK) and ATM kinase by a series of pyran-2-ones, pyran-4-ones, thiopyran-4-ones, and pyridin-4-ones. A wide range of IC50 values were observed for pyranones and thiopyranones substituted at the 6-position, with the 3- and 5-positions proving intolerant to substitution. Related pyran-2-ones, pyran-4-ones, and thiopyran-4-ones showed similar IC50 values against DNA-PK, whereas the pyridin-4-one system proved, in general, ineffective at inhibiting DNA-PK. Extended libraries exploring the 6-position of 2-morpholinopyran-4-ones and 2-morpholino- thiopyrano-4-ones identified the first highly potent and selective ATM inhibitor 2-morpholin-4-yl-6-thianthren-1-yl-pyran-4-one (151C; ATM; IC50 = 13 nM) and revealed constrained SARs for ATM inhibition compared with DNA-PK. One of the most potent DNA-PK inhibitors identified, 2-(4-methoxyphenyl)-6- (morpholin-4-yl)pyran-4-one (16; DNA-PK; IC50 = 220 nM) effectively sensitized HeLa cells to the topoisomerase II inhibitor etoposide in vitro.

A convenient synthesis of 5/7-chloro-4H-1, 4-benzothiazines

5/7-Chloro-4H-1,4-benzothiazines have been synthesized by the condensation of sustituted 2-amino-3/5-chlorobenzenethiol with compounds containing active methylene group in dimethylsulfoxide which causes oxidative cyclization via enaminoketone intermediate. The IR, NMR and Mass spectra have been also included.