75381-46-3

Usage

InChI:InChI=1/C11H11ClO3/c12-9-4-1-3-8(7-9)10(13)5-2-6-11(14)15/h1,3-4,7H,2,5-6H2,(H,14,15)

Upstream product

• 1026608-91-2 2-(3-Chloro-benzoyl)-pentanedioic acid diethyl ester 
• 618-46-2 m-Chlorobenzoyl chloride 
• 893643-63-5 2-(3-chloro-benzoyl)-3-oxo-butyric acid ethyl ester 
• 108-55-4 glutaric anhydride, 
• 625-98-9 3-chlorofluorobenzene 
• 36229-42-2 (3-chlorophenyl)magnesium bromide 
• 108-37-2 1-bromo-3-chlorobenzene 

Relevant academic research and scientific papers

Iridium-Catalyzed Asymmetric Hydrogenation of ?- A nd ?-Ketoacids for Enantioselective Synthesis of ?- A nd ?-Lactones

A highly efficient asymmetric hydrogenation of ?- A nd ?-ketoacids was developed by using a chiral spiro iridium catalyst (S)-1a, affording the optically active ?- A nd ?-hydroxy acids/lactones in high yields with excellent enantioselectivities (up to >99% ee) and turnover numbers (TON up to 100000). This protocol provides an efficient and practical method for enantioselective synthesis of Ezetimibe.

Diaryl hydroxylamines as pan or dual inhibitors of indoleamine 2,3-dioxygenase-1, indoleamine 2,3-dioxygenase-2 and tryptophan dioxygenase

Tryptophan (Trp) catabolizing enzymes play an important and complex role in the development of cancer. Significant evidence implicates them in a range of inflammatory and immunosuppressive activities. Whereas inhibitors of indoleamine 2,3-dioxygenase-1 (IDO1) have been reported and analyzed in the clinic, fewer inhibitors have been described for tryptophan dioxygenase (TDO) and indoleamine 2,3-dioxygenase-2 (IDO2) which also have been implicated more recently in cancer, inflammation and immune control. Consequently the development of dual or pan inhibitors of these Trp catabolizing enzymes may represent a therapeutically important area of research. This is the first report to describe the development of dual and pan inhibitors of IDO1, TDO and IDO2.

Achiral counterion control of enantioselectivity in a Bronsted acid-catalyzed lactonization

Highly enantioselective halolactonizations have been developed that employ a chiral proton catalyst-N-iodosuccinimide (NIS) reagent system in which the Bronsted acid is used at catalyst loadings as low as 1 mol %. An approach that modulates the achiral counterion (equimolar to the neutral chiral ligand-proton complex present at low catalyst loadings) to optimize the enantioselection is documented for the first time in this transformation. In this way, unsaturated carboxylic acids are converted to γ-lactones in high yields (up to 98% ee) using commercially available NIS.

Synthesis and pharmacological evaluation of a new series of substituted benzoyl-γ-butyrolactone derivatives

A series of substituted benzoyl-γ-butyrolactones (1-3) has been synthesized and tested for their ability to affect central dopaminergic and GABAergic function in comparison to γ-butyrolactone (GBL).Similarly to GBL, α-, β- and γ-substituted GBLs 1-3 with one or more chlorine on the phenyl ring were found to induce central depressant effects in rats, though at different degrees.However, the test compounds modified dopamine (DA) metabolism in rat striatum differently from GBL.In fact, whereas GBL increased both DA and dihydroxyphenylacetic acid (DOPAC) content, GBL derivatives 1-3 increased DA levels, but reduced the DOPAC concentration.Moreover, some of them, unlike GBL, effectively antagonized pentylenetetrazole (PTZ)-induced seizures in mice.In particular, α-3,5-dichlorobenzoyl-GBL (1g) was effective at a dose as low a 36 mg/kg in decressing the number of animals having convulsions.However, in vitro addition and in vivo administration of the test compounds failed to modify -t-butylbicyclophosphorothionate (-TBPS) binding, which is a very sensitive tool for revealing changes in the GABAergic function. γ-butyrolactone / benzoyl-γ-butyrolactone / dopamine / anticonvulsant effect