206879-94-9

Basic information

• Product Name: TERT-BUTYL 4-(3-NITROPHENYL)PIPERAZINE-1-CARBOXYLATE
• Synonyms: TERT-BUTYL 4-(3-NITROPHENYL)PIPERAZINE-1-CARBOXYLATE;2-methyl-2-propanyl 4-(3-nitrophenyl)-1-piperazinecarboxylate;4-(3-Nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester
• CAS NO: 206879-94-9
• Molecular Formula: C₁₅H₂₁N₃O₄
• Molecular Weight: 307.34
• Mol File: 206879-94-9.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: TERT-BUTYL 4-(3-NITROPHENYL)PIPERAZINE-1-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL 4-(3-NITROPHENYL)PIPERAZINE-1-CARBOXYLATE(206879-94-9)
• EPA Substance Registry System: TERT-BUTYL 4-(3-NITROPHENYL)PIPERAZINE-1-CARBOXYLATE(206879-94-9)

Safety Data

• Hazardous Substances Data: 206879-94-9(Hazardous Substances Data)

Upstream product

• 34619-03-9 tert-butyldicarbonate 
• 54054-85-2 1-(3-nitrophenyl)piperazine 
• 585-79-5 m-nitrobromobenzene 
• 57260-71-6 1-t-Butoxycarbonylpiperazine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 294210-79-0 1-(3-nitrophenyl)piperazine monohydrochloride 
• 294210-79-0 1-(3-nitro-phenyl)-piperazine hydrochloride 
• 402-67-5 3-fluoro-1-nitrobenzene 

Downstream Products

• 206879-72-3 4-(3-amino-phenyl)-piperazine-1-carboxylic acid tert-butyl ester 
• 1374213-82-7 4-(1-phenylcyclopropylamino)-6-(3-(piperazin-1-yl)phenylamino)nicotinamide 
• 1374213-83-8 6-(3-(4-acetylpiperazin-1-yl)phenylamino)-4-(1-phenylcyclopropylamino)nicotinamide 
• 1374215-26-5 C₃₀H₃₆N₆O₃ 
• 54054-85-2 1-(3-nitrophenyl)piperazine 

Relevant articles and documents

MONOACYLGLYCEROL LIPASE INHIBITORS

Provided are compounds of formula (I), or a pharmaceutically acceptable salt or solvate thereof: Also provided are compositions comprising compounds of formula (I). The compounds and compositions are also provided for use as medicaments, for example as medicaments useful in the treatment of a condition modulated by monoacylglycerol lipase (MAGL). Also provided are the use of compounds and compositions for the inhibition of monoacylglycerol lipase (MAGL).

Synthesis and structure-activity relationships of new 2-phenoxybenzamides with antiplasmodial activity

The 2-phenoxybenzamide 1 from the Medicines for Malaria Venture Malaria Box Project has shown promising multi-stage activity against different strains of P. falciparum. It was successfully synthesized via a retrosynthetic approach. Subsequently, twenty-one new derivatives were prepared and tested for their in vitro activity against blood stages of the NF54 strain of P. falciparum. Several insights into structure-activity relationships were revealed. The antiplasmodial activity and cytotoxicity of compounds strongly depended on the substitution pattern of the anilino partial structure as well as on the size of substituents. The diaryl ether partial structure had further impacts on the activity. Additionally, several physicochemical and pharmacokinetic parameters were calculated (log P, log D7.4 and ligand efficiency) or determined experimentally (passive permeability and CYP3A4 inhibition). The tert-butyl-4-{4-[2-(4-fluorophenoxy)-3-(trifluoromethyl)benzamido]phenyl}piperazine-1-carboxylate possesses high antiplasmodial activity against P. falciparum NF54 (PfNF54 IC50 = 0.2690 μM) and very low cytotoxicity (L-6 cells IC50 = 124.0 μM) resulting in an excellent selectivity index of 460. Compared to the lead structure 1 the antiplasmodial activity was improved as well as the physicochemical and some pharmacokinetic parameters.

Covalent inhibition of the histamine H3 receptor

Covalent binding of G protein-coupled receptors by small molecules is a useful approach for better understanding of the structure and function of these proteins. We designed, synthesized and characterized a series of 6 potential covalent ligands for the histamine H3 receptor (H3R). Starting from a 2-amino-pyrimidine scaffold, optimization of anchor moiety and warhead followed by fine-tuning of the required reactivity via scaffold hopping resulted in the isothiocyanate H3R ligand 44. It shows high reactivity toward glutathione combined with appropriate stability in water and reacts selectively with the cysteine sidechain in a model nonapeptide equipped with nucleophilic residues. The covalent interaction of 44 with H3R was validated with washout experiments and leads to inverse agonism on H3R. Irreversible binder 44 (VUF15662) may serve as a useful tool compound to stabilize the inactive H3R conformation and to study the consequences of prolonged inhibition of the H3R.