220663-44-5

Usage

Chemical structure

Piperazine derivative with a benzyl group and an isopropyl group attached to the piperazine ring

Usage

Research and development of pharmaceuticals, synthesis of potential drug candidates and bioactive molecules

Unique structural properties

Valuable building block in medicinal chemistry

Potential

Precursor in the production of various biologically active compounds

Application

Study of structure-activity relationships in drug design and as a reference standard in analytical chemistry.

InChI:InChI=1/C14H22N2/c1-12(2)14-10-15-8-9-16(14)11-13-6-4-3-5-7-13/h3-7,12,14-15H,8-11H2,1-2H3/t14-/m1/s1

Upstream product

• 1492-06-4 methyl (S)-2-(2-chloroacetylamino)-2,3-dimethylbutanoate 
• 100-46-9 benzylamine 
• 4070-48-8 L-Valine methyl ester 
• 6306-52-1 L-valine methylester hydrochloride 
• 100-39-0 benzyl bromide 
• 16944-60-8 (2S)-isopropylpiperazine-3,6-dione 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 6436-90-4 ethyl 2-(benzylamino)acetate 
• 13734-41-3 t-Boc-L-valine 

Downstream Products

• 220663-46-7 (S)-2-Benzyl-4-isopropyl-1,2-dihydro-2,4a,9-triaza-anthracene-3,10-dione 
• 479681-24-8 (S)-1-benzyl-3-isopropyl-4-(4-methoxybenzyl)piperazine-2,5-dione 
• 479681-31-7 C₂₂H₂₆N₂O₃C₂₂H₂₆N₂O₃C₈H₆ 
• 324748-62-1 (S)-1-benzyl-3-isopropylpiperazine 

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.

Highly efficient enantioselective synthesis of 1,3-disubstituted 2,5-diketopiperazine derivatives via microwave irradiation

Chiral 2,5-diketopiperazine (2,5-DKP) derivatives have a broad range of biological activities in the medicinal field. The synthetic protocols of 1,3-disubstituted 2,5-DKPs via base-catalyzed cyclization of chloroacetamide have been reported. However, there are several drawbacks, such as an overly long reaction time, low to moderate yield, and racemization of the products. The sequence modified herein of 1,3-disubstituted 2,5-DKPs involves microwave-assisted cyclization. It increases yields and reduces reaction time. Furthermore, employing N-PMB protection prevents racemization, which frequently occurs in the base-catalyzed cyclization reaction. Consequently, the rapid synthetic method of enantiomerically pure 1,3-disubstituted 2,5-DKPs via microwave reaction was established successfully.

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.

PHENOXYACETIC ACID DERIVATIVES USEFUL FOR TREATING RESPIRATORY DISEASES

The invention relates to substituted phenoxyacetic acids as useful pharmaceutical compounds for treating respiratory disorders, pharmaceutical compositions containing them, and processes for their preparation.Formula (I)

Homochiral supramolecular polymerization of an "S"-shaped chiral monomer: Translation of optical purity into molecular weight distribution

An "S"-shaped chiral motif of a p-xylylene-bridged bis(cyclic dipeptide) (1), having four hydrogen-bonding amide functionalities, formed a homochiral supramolecular polymer in solution. X-ray crystallography of a slightly modified version of 1 for an enha

BENZOFURYLPIPERAZINES AND BENZOFURYLHOMOPIPERAZINES: SEROTONIN AGONISTS

The present invention provides serotonergic benzofurylpiperazines of Formula I: where: A is a piperazine of formula: and R, R1, R2, R3, R4, R5, R5', R6, R6', R7, R7', R8, and R8' are as described in the specification.

Asymmetrically induced alkylation of 2-benzyl-4-isopropyl-2,4-dihydro- 1H-pyrazino [2,1-b] quinazoline-3,6-dione

The substitution of the 4-methyl group by a 4-isopropyl group in the 2- benzyl-2,4-dihydro-1H-pyrazino[2,1b]quinazoline-3,6-dione system allows a notable improvement in the stereoselective alkylation at C-1. The configuration of the newly introduced stereogenic centre has been assigned on the basis of 1H NMR data and NOE measurements.