502482-25-9

Usage

Properties

1. Chemical compound belonging to the piperazinedione class
2. Chiral molecule
3. White, crystalline solid at room temperature
4. Commonly used as a building block in organic chemistry
5. (3S)-enantiomer with specific three-dimensional arrangement of atoms

Specific content

1. Chemical compound: 2,5-Piperazinedione, 3-(2-methylpropyl)-1-(phenylmethyl)-, (3S)-
2. Class of compounds: Piperazinedione
3. Chirality: Chiral molecule with (3S)-enantiomer
4. Physical state: White, crystalline solid at room temperature
5. Usage: Building block in organic chemistry, particularly in pharmaceutical synthesis
6. Enantiomer: (3S)-enantiomer with specific biological or pharmacological effects

Upstream product

• 2666-93-5 (S)-Leu-OMe 
• 100-46-9 benzylamine 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 102115-71-9 2-chloro-N-[(S)[1-methoxycarbonyl-3-methyl] butyl] ethanamide 
• 1373396-49-6 C₂₀H₂₈N₂O₄ 

Downstream Products

• 444892-03-9 (3S)-1-benzyl-3-isobutylpiperazine 

Relevant academic research and scientific papers

Structure-Activity Relationship Studies on Oxazolo[3,4- a]pyrazine Derivatives Leading to the Discovery of a Novel Neuropeptide S Receptor Antagonist with Potent in Vivo Activity

Neuropeptide S modulates important neurobiological functions including locomotion, anxiety, and drug abuse through interaction with its G protein-coupled receptor known as neuropeptide S receptor (NPSR). NPSR antagonists are potentially useful for the treatment of substance abuse disorders against which there is an urgent need for new effective therapeutic approaches. Potent NPSR antagonists in vitro have been discovered which, however, require further optimization of their in vivo pharmacological profile. This work describes a new series of NPSR antagonists of the oxazolo[3,4-a]pyrazine class. The guanidine derivative 16 exhibited nanomolar activity in vitro and 5-fold improved potency in vivo compared to SHA-68, a reference pharmacological tool in this field. Compound 16 can be considered a new tool for research studies on the translational potential of the NPSergic system. An in-depth molecular modeling investigation was also performed to gain new insights into the observed structure-activity relationships and provide an updated model of ligand/NPSR interactions.

Efficient one-pot synthesis of enantiomerically pure: N -protected-α-substituted piperazines from readily available α-amino acids

A new pathway towards enantiomerically pure 3-substituted piperazines, bearing a benzyl protecting group, has been developed in good overall yields (83-92%), starting from commercially available N-protected amino acids. The methodology represents an efficient and simple one-pot procedure, employing a synthetic sequence consisting of an Ugi-4 component reaction, a Boc-deprotection, an intramolecular cyclisation reaction and a final reduction (UDCR). From the benzyl protected precursors, the 2-substituted piperazines bearing a Boc-protecting group could consequently also be obtained via a simple protection and deprotection step of the corresponding piperazines. The practical utility of this methodology was demonstrated for chiral drug synthesis.

Synthesis and structure of 1,4-dipiperazino benzenes: Chiral terphenyl-type peptide helix mimetics

(Chemical Equation Presented) The terphenyl structure has been proven to be an ideal scaffold mimicking side-chain functionalities of peptidic α-helices. The synthesis of 1,4-dipiperazino benzenes, using stepwise transition metal-catalyzed N-arylation of chiral piperazines to a central benzene core is reported. The structure determination by X-ray crystallography reveals a geometrical arrangement of the hydrophobic side chains resembling the orientation of key i, i + 3, and i + 7 positions in a peptidic α-helix or in terphenyl helix mimetics.

17-Beta hydroxysteroid dehydrogenase type 3 inhibitors for the treatment of androgen dependent diseases

There are disclosed compounds of the formula (I): prodrugs thereof, or pharmaceutically acceptable salts of the compounds or of said prodrugs which are useful as inhibitors of Type 3 17β-Hydroxysteroid Dehydrogenase. Also disclosed are pharmaceutical compositions containing said compounds and their use for the treatment or prevention of androgen dependent diseases.