260254-74-8

Basic information

• Product Name: (2R,5S)-1-Benzyl-5-Isopropyl-2-Methyl-Piperazine
• Synonyms: (2R,5S)-1-Benzyl-5-Isopropyl-2-Methyl-Piperazine
• CAS NO: 260254-74-8
• Molecular Formula: C₁₅H₂₄N₂
• Molecular Weight: 232.36446
• Mol File: 260254-74-8.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2R,5S)-1-Benzyl-5-Isopropyl-2-Methyl-Piperazine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5S)-1-Benzyl-5-Isopropyl-2-Methyl-Piperazine(260254-74-8)
• EPA Substance Registry System: (2R,5S)-1-Benzyl-5-Isopropyl-2-Methyl-Piperazine(260254-74-8)

Safety Data

• Hazardous Substances Data: 260254-74-8(Hazardous Substances Data)

Usage

General Description

(2R,5S)-1-Benzyl-5-Isopropyl-2-Methyl-Piperazine is a chemical compound with the molecular formula C16H26N2. It is a piperazine derivative, with a benzyl group attached to the nitrogen atom at position 1, an isopropyl group at position 5, and a methyl group at position 2 of the piperazine ring. (2R,5S)-1-Benzyl-5-Isopropyl-2-Methyl-Piperazine is often used in pharmaceutical research and drug development due to its potential biological activities. It may have applications in the treatment of various medical conditions, although further research is needed to fully understand its pharmacological properties.

Upstream product

• 260254-72-6 (3S,6R)-1-Benzyl-3-isopropyl-6-methyl-piperazine-2,5-dione 
• 68858-20-8 Fmoc-Val-OH 
• 103321-53-5 (S)-(9H-fluoren-9-yl)methyl 1-chloro-3-methyl-1-oxobutan-2-ylcarbamate 
• 260254-70-4 N-α-(9-fluorenylmethoxycarbonyl)-L-valinyl-N-β-benzyl-L-alanine methyl ester 

Relevant articles and documents

Secondary amides of (R)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid as inhibitors of pyruvate dehydrogenase kinase

N'-Methyl-N-(4-tert-butyl-1,2,5,6-tetrahydropyridine)thiourea, SDZ048- 619 (1), is a modest inhibitor (IC50 = 180 μM) of pyruvate dehydrogenase kinase (PDHK). In an optimization of the N-methylcarbothioamide moiety of 1, it was discovered that amides with a small acyl group, in particular appropriately substituted amides of (R)-3,3,3-trifluoro-2-hydroxy-2- methylpropionic acid, are inhibitors of PDHK. Utilizing this acyl moiety, herein is reported the rationale leading to the optimization of a series of acylated piperazine derivatives. Methyl substitution of the piperazine at the 2- and 5-positions (with S and R absolute stereochemistry) markedly increased the potency of the lead compound (> 1000-fold). Oral bioavailability of the compounds in this series is good and is optimal (as measured by AUC) when the 4-position of the piperazine is substituted with an electron-poor benzoyl moiety. (+)-1-N-[2,5-(S,R)-Dimethyl-4-N-(4-cyanobenzoyl)piperazine]-(R)- 3,3,3-trifluoro-2-hydroxy-2-methylpropanamide (14e) inhibits PDHK in the primary enzymatic assay with an IC50 of 16 ± 2 nM, enhances the oxidation of [14C]lactate into 14CO2 in human fibroblasts with an EC50 of 57 ± 13 nM, diminishes lactate significantly 2.5 h post-oral-dose at doses as low as 1 μmol/kg, and increases the ex vivo activity of PDH in muscle, liver, and fat tissues in normal Sprague-Dawley rats. These PDHK inhibitors, however, do not lower glucose in diabetic animal models.