218608-96-9

Usage

Uses

Used in Pharmaceutical Research and Development:
BOC-(R)-3-AMINO-4-(4-CHLORO-PHENYL)-BUTYRIC ACID is used as a key intermediate in the synthesis of pharmaceuticals for its potential to target the central nervous system. Its role in the development of new drugs is significant, as it can contribute to the creation of compounds with specific therapeutic effects.
Used in the Synthesis of Bioactive Compounds:
In the field of medicinal chemistry, BOC-(R)-3-AMINO-4-(4-CHLORO-PHENYL)-BUTYRIC ACID is utilized as a building block for the synthesis of bioactive compounds. Its structural features allow for the design of molecules with potential biological activity, making it a versatile component in drug discovery processes.
Used in the Study of GABA Analogs:
BOC-(R)-3-AMINO-4-(4-CHLORO-PHENYL)-BUTYRIC ACID is employed as a research tool for studying the structure-activity relationships of GABA analogs. This helps researchers understand how modifications to the GABA molecule can influence its interaction with receptors and its overall pharmacological profile.
Used in the Development of CNS-targeting Drugs:
Given its relation to GABA, a neurotransmitter that plays a crucial role in reducing neuronal excitability, BOC-(R)-3-AMINO-4-(4-CHLORO-PHENYL)-BUTYRIC ACID is used in the development of drugs targeting the central nervous system. Its potential applications in this area include the treatment of neurological disorders and conditions related to neuronal hyperactivity.

InChI:InChI=1/C15H20ClNO4/c1-15(2,3)21-14(20)17-12(9-13(18)19)8-10-4-6-11(16)7-5-10/h4-7,12H,8-9H2,1-3H3,(H,17,20)(H,18,19)/t12-/m1/s1

Upstream product

• 57292-44-1 N-Boc-D-(4-Cl)Phe-OH 

Downstream Products

• 1365884-15-6 (3R)-1-(3-(1H-Benzo[d]imidazol-2-yl)piperidin-1-yl)-3-amino-4-(4-chlorophenyl)butan-1-one trifluoroacetate 
• 1365884-16-7 tert-butyl (2R)-1-(4-chlorophenyl)-4-(3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-4-oxobutan-2-ylcarbamate 
• 1365884-14-5 tert-butyl (2R)-4-(3-(1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-1-(4-chlorophenyl)-4-oxobutan-2-ylcarbamate 

Relevant academic research and scientific papers

Synthesis method of chiral N-Boc-3-amino-4-aryl-butyric acid

The invention relates to a synthesis method of chiral N-Boc-3-amino-4-aryl-butyric acid. The method is as below: 1, conducting a cross metathesis reaction, an asymmetric conjugate addition reaction and an oxidation reaction on starting materials including an allyl aromatic compound and crotonaldehyde by a continuous reaction one-pot method to synthesize an N-Boc-3-aryl methyl-5-oxo isoxazole intermediate; or conducting an asymmetric conjugate addition reaction and an oxidation reaction on a starting material (E)-4-aryl-2-crotonaldehyde by a continuous reaction one-pot method to synthesize an N-Boc-3-aryl methyl-5-oxo isoxazole intermediate; and 2, subjecting (3R)-N-Boc-3-aryl methyl-5-oxo isoxazole intermediate by high-pressure hydrogenation to directly prepare the chiral N-Boc-3-amino-4-aryl-butyric acid. The synthesis method provided by the invention has the advantages of simple operation, mild reaction conditions, target product yield reaching 60-69%, and ee value of the target product reaching as high as 96%. The synthetic route has industrialization prospect.

Discovery of potent and selective β-homophenylalanine based dipeptidyl peptidase IV inhibitors

Modification of in-house screening lead β-aminoacyl proline 8 gave an equipotent thiazolidide 9. Extensive SAR studies on the phenyl ring of 9 led to the discovery of a novel series of potent and selective DP-IV inhibitors. Introduction of a fluorine at the 2-position proved to be crucial for the potency of this series. The 2,5-difluoro (22q) and 2,4,5-trifluoro (22t) analogues were potent inhibitors of DP-IV (IC50 = 270, 119 nM, respectively).