162046-66-4

Basic information

• Product Name: 4-[4-(tert-Butoxycarbonyl)piperazino]benzoic acid
• Synonyms: 1-BOC-4-(4-CARBOXY-PHENYL)-PIPERAZINE;1-(4-BOC-PIPERAZIN-1-YL)-BENZOIC ACID;1-(4-CARBOXY-PHENYL)-PIPERAZINE-4-CARBOXYLIC ACID TERT-BUTYL ESTER;4-[4-(TERT-BUTOXYCARBONYL)PIPERAZINO]BENZOIC ACID;4-(4-(TERT-BUTOXYCARBONYL)PIPERAZIN-1-YL)BENZOIC ACID;4-(4-TERT-BUTOXYCARBONYLPIPERAZINE)BENZOIC ACID;4-(4-CARBOXY-PHENYL)-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;BUTTPARK 98\06-97
• CAS NO: 162046-66-4
• Molecular Formula: C₁₆H₂₂N₂O₄
• Molecular Weight: 306.36
• Product Categories: API intermediates;piperazines;Building Blocks;C16 to C29;Chemical Synthesis;Heterocyclic Building Blocks;New Products for Chemical Synthesis
• Mol File: 162046-66-4.mol
• Article Data: 16

Chemical Properties

• Melting Point: 50 °C
• Boiling Point: 476.9 °C at 760 mmHg
• Flash Point: 242.2 °C
• Appearance: /
• Density: 1.213 g/cm³
• Vapor Pressure: 6.65E-10mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 5.12±0.10(Predicted)
• CAS DataBase Reference: 4-[4-(tert-Butoxycarbonyl)piperazino]benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[4-(tert-Butoxycarbonyl)piperazino]benzoic acid(162046-66-4)
• EPA Substance Registry System: 4-[4-(tert-Butoxycarbonyl)piperazino]benzoic acid(162046-66-4)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-26-36/37/39
• Hazardous Substances Data: 162046-66-4(Hazardous Substances Data)

Usage

General Description

4-[4-(tert-Butoxycarbonyl)piperazino]benzoic acid is a chemical compound with a molecular formula C18H24N204 and a molar mass of 324.39 g/mol. It is a derivative of benzoic acid that features a piperazine ring and a tert-butoxycarbonyl group. 4-[4-(tert-Butoxycarbonyl)piperazino]benzoic acid is commonly used in the field of medicinal chemistry as a building block for the synthesis of various pharmaceuticals and bioactive molecules. The tert-butoxycarbonyl (t-Boc) protecting group is often used to temporarily block the reactive amine group in organic synthesis, allowing for selective functionalization of other parts of the molecule. Additionally, the piperazine ring in the structure of this compound makes it a potential candidate for drug design and development, particularly in the field of central nervous system disorders and psychiatric medications.

InChI:InChI=1/C16H22N2O4/c1-16(2,3)22-15(21)18-10-8-17(9-11-18)13-6-4-12(5-7-13)14(19)20/h4-7H,8-11H2,1-3H3,(H,19,20)/p-1

Upstream product

• 163210-97-7 methyl 4-(piperazin-1-yl)benzoate 
• 619-45-4 4-methoxycarbonyl aniline 
• 451-46-7 4-fluorobenzoic acid ethyl ester 
• 57260-71-6 1-t-Butoxycarbonylpiperazine 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 403-33-8 methyl 4-flurobenzoate 
• 158985-36-5 4-(4-methoxycarbonyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester 
• 80518-57-6 ethyl 4-(piperazin-1-yl)benzoate 
• 234082-33-8 4-(4-ethoxycarbonylphenyl)piperazine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 406231-38-7 4-{4-[3-nitro-4-(2-phenylsulfanyl-ethylamino)-benzenesulfonylaminocarbonyl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester 
• 926933-96-2 (R)-tert-butyl 4-(4-(4-(4-(dimethylamino)-1-(phenylthio)butan-2-ylamino)-3-nitrophenylsulfonylcarbamoyl)phenyl)piperazine-1-carboxylate 
• 158985-37-6 1-hydroxymethyl-4-(4-(1,1-dimethylethoxycarbonyl)piperazinyl)benzene 
• 1224872-07-4 4-[4-(indan-5-ylcarbamoyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester 
• 868065-73-0 tert-butyl 4-{4-[(dimethylamino)carbonyl]phenyl}piperazine-1-carboxylate 
• 1374882-70-8 4-[4-(4'-{2-[(S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-1H-imidazol-4-yl}-biphenyl-4-ylcarbamoyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester 
• 1374882-66-2 {(S)-1-[(S)-2-(4-{4'-[4-(4-cyclopropanecarbonyl-piperazin-1-yl)-benzoylamino]-biphenyl-4-yl}-1H-imidazol-2-yl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester 
• 1018631-34-9 4-(4-cyclopropanecarbonyl-piperazin-1-yl)-benzoic acid 
• 1374891-49-2 N-(4-bromo-phenyl)-4-(4-cyclopropanecarbonyl-piperazin-1-yl)-benzamide 
• 1374891-52-7 (S)-2-(4-{4'-[4-(4-Cyclopropanecarbonyl-piperazin-1-yl)-benzoylamino]-biphenyl-4-yl}-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 85474-75-5 4-(piperazin-1-yl)benzoic acid 
• 1447331-89-6 {6-[4-(4-boc-piperazin-1-yl)benzoylamino]-1-oxo-1,3-dihydroisoindol-2-yl}acetic acid 
• 1447330-19-9 [1-oxo-6-(4-piperazinium-1-yl-benzoylamino)-1,3-dihydroisoindol-2-yl]acetic acid trifluoroacetate 
• 1447331-32-9 {6-[4-(4-boc-piperazin-1-yl)benzoylamino]-1-oxo-1,3-dihydroisoindol-2-yl}acetic acid methyl ester 

Relevant articles and documents

Protein degradation targeting chimera for degrading androgen receptor

The invention relates to a novel difunctional molecule compound based on VHL ligand induction and application of the difunctional molecule compound in synthesis of the compounds and pharmaceutical compositions thereof. The compound is shown as a formula I. The compound can selectively induce AR protein degradation and can be used for treating cancers such as prostatic cancer and breast cancer.

Design and characterization of cereblon-mediated androgen receptor proteolysis-targeting chimeras

Proteolysis-targeting chimera (PROTAC)-mediated protein degradation is a rapidly emerging therapeutic intervention that induces the degradation of targeted proteins. Herein, we report the design and biological evaluation of a series of androgen receptor (AR) PROTAC degraders for the treatment of metastatic castration-resistant prostate cancer. Predominantly, instead of thalidomide, we utilized the TD-106 scaffold, a novel cereblon (CRBN) binder that was identified in our previous study. Our results suggest that the linker position in the TD-106 CRBN binder is critical for the efficiency of AR degradation. The compounds attached to the 6-position of TD-106 promoted better degradation of AR than those at the 5- and 7-positions. Among the synthesized AR PROTACs, the representative degrader 33c (TD-802) effectively induced AR protein degradation, with a degradation concentration 50% of 12.5 nM and a maximum degradation of 93% in LNCaP prostate cancer cells. Additionally, most AR PROTAC degraders, including TD-802, displayed good liver microsomal stability and in vivo pharmacokinetic properties. Finally, we showed that TD-802 effectively inhibited tumor growth in an in vivo xenograft study.

Mechanisms of action of novel influenza A/M2 viroporin inhibitors derived from hexamethylene amiloride

The increasing prevalence of influenza viruses with resistance to approved antivirals highlights the need for new anti-influenza therapeutics. Here we describe the functional properties of hexamethylene amiloride (HMA)'derived compounds that inhibit the wildtype and adamantane-resistant forms of the influenza A M2 ion channel. For example, 6-(azepan-1-yl)-N-carbamimidoylnicotinamide (9) inhibits amantadine-sensitive M2 currents with 3- to 6-fold greater potency than amantadine or HMA (IC50 5 0.2 vs. 0.6 and 1.3 μM, respectively). Compound 9 competes with amantadine for M2 inhibition, and molecular docking simulations suggest that 9 binds at site(s) that overlap with amantadine binding. In addition, tert-butyl 4′-(carbamimidoylcarbamoyl)-2′,3-dinitro- [1,1′-biphenyl]-4-carboxylate (27) acts both on adamantanesensitive and a resistantM2variant encoding a serine to asparagine 31 mutation (S31N) with improved efficacy over amantadine and HMA (IC5050.6 μMand4.4mM, respectively).Whereas 9 inhibited in vitro replication of influenza virus encoding wild-type M2 (EC505 2.3 μM), both 27 and tert-butyl 4′-(carbamimidoylcarbamoyl)-2′,3- dinitro-[1,1′-biphenyl]-4-carboxylate (26) preferentially inhibited viruses encoding M2(S31N) (respective EC50 5 18.0 and 1.5 μM). This finding indicates thatHMAderivatives can be designed to inhibit viruses with resistance to amantadine. Our study highlights the potential of HMA derivatives as inhibitors of drug-resistant influenza M2 ion channels.