923565-98-4

Basic information

• Product Name: (S)-1-N-CBZ-2-METHYL-PIPERAZINE
• Synonyms: REF DUPL: (S)-1-N-Cbz-2-methyl-piperazine;1-Piperazinecarboxylic acid, 2-Methyl-, phenylMethyl ester, (2S)-;(S)-2-Methyl-1-piperazinecarboxylic acid benzyl ester;Benzyl (2S)-2-methyl-1-piperazinecarboxylate;(S)-1-Cbz-2-Methyl-piperazine HCl
• CAS NO: 923565-98-4
• Molecular Formula: C13H18N2O2
• Molecular Weight: 234.297
• Mol File: 923565-98-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 358°C at 760 mmHg
• Flash Point: 170.3°C
• Appearance: /
• Density: 1.105
• Vapor Pressure: 2.62E-05mmHg at 25°C
• Refractive Index: 1.53
• PKA: 8.48±0.40(Predicted)
• CAS DataBase Reference: (S)-1-N-CBZ-2-METHYL-PIPERAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-N-CBZ-2-METHYL-PIPERAZINE(923565-98-4)
• EPA Substance Registry System: (S)-1-N-CBZ-2-METHYL-PIPERAZINE(923565-98-4)

Safety Data

• Hazardous Substances Data: 923565-98-4(Hazardous Substances Data)

Usage

General Description

"(S)-1-N-CBZ-2-METHYL-PIPERAZINE" is a chemical compound typically used in organic chemistry research and pharmaceutical industries. It is a derivative of piperazine, which is a popular building block in the synthesis of various pharmaceutical drugs. Specifically, this compound is a chiral version with a (S)- configuration, signifying the spatial arrangement of its atoms. The 'N-CBZ' part indicates that the nitrogen atom is protected by a carboxybenzyl group, which is often used in chemistry to shield reactive sites in a molecule during a chemical reaction. The '2-Methyl' indicates a methyl group is attached to the second carbon in the piperazine ring. Its exact properties, such as melting point, boiling point, or toxicity, would depend on its specific preparation and purity. The compound is usually prepared in a laboratory setting, using standardized methods for piperazine derivatization.

InChI:InChI=1/C13H18N2O2/c1-11-9-14-7-8-15(11)13(16)17-10-12-5-3-2-4-6-12/h2-6,11,14H,7-10H2,1H3/t11-/m0/s1

Upstream product

• 1025927-13-2 (R)-2-Methyl-4-(2-nitro-benzenesulfonyl)-piperazine-1-carboxylic acid benzyl ester 
• 75336-86-6 (2R)-methylpiperazine 
• 501-53-1 benzyl chloroformate 
• 243982-41-4 (R)-3-methyl-1-((2-nitrophenyl)sulfonyl)piperazine 
• 1163793-25-6 1-benzyl 4-(tert-butyl) (R)-2-methylpiperazine-1,4-dicarboxylate 
• 1163793-31-4 1-benzyl 4-(tert-butyl) (S)-2-methylpiperazine-1,4-dicarboxylate 
• 109-07-9 (RS)-2-methylpiperazine 

Relevant articles and documents

Design, synthesis and SAR of antitubercular benzylpiperazine ureas

Abstract: N-furfuryl piperazine ureas disclosed by scientists at GSK Tres Cantos were chosen as antimycobacterial hits from a phenotypic whole-cell screen. Bioisosteric replacement of the furan ring in the GSK Tres Cantos molecules with a phenyl ring led to molecule (I) with an MIC of 1?μM against Mtb H37Rv, low cellular toxicity (HepG2 IC50 ~ 80?μM), good DMPK properties and specificity for Mtb. With the aim of delineating the SAR associated with (I), fifty-five analogs were synthesized and screened against Mtb. The SAR suggests that the piperazine ring, benzyl urea and piperonyl moieties are essential signatures of this series. Active compounds in this series are metabolically stable, have low cellular toxicity and are valuable leads for optimization. Molecular docking suggests these molecules occupy the Q0 site of QcrB like Q203. Graphic Abstract: Bioisosteric replacement of N-furfuryl piperazine-1-carboxamides yielded molecule (I) a novel lead with satisfactory PD, metabolism, and toxicity profiles.[Figure not available: see fulltext.]

CERTAIN CHEMICAL ENTITIES, COMPOSITIONS AND METHODS

Certain substituted urea derivatives selectively modulate the cardiac sarcomere, for example by potentiating cardiac myosin, and are useful in the treatment of systolic heart failure including congestive heart failure.

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.