151978-66-4

Basic information

• Product Name: TERT-BUTYL 4-(4-IODOPHENYL)TETRAHYDRO-1(2H)-PYRAZINECARBOXYLATE
• Synonyms: 4-(4-IODO-PHENYL)-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;1-TERT-BUTOXYCARBONYL-4(4-IODOPHENYL)PIPERAZINE;TERT-BUTYL 4-(4-IODOPHENYL)PIPERAZINE-1-CARBOXYLATE;TERT-BUTYL 4-(4-IODOPHENYL)TETRAHYDRO-1(2H)-PYRAZINECARBOXYLATE;1-tert-Butoxycarbonyl-4-(4-iodophenyl)piperazine 97%;1-(tert-Butoxycarbonyl)-4-(4-iodophenyl)piperazine, tert-butyl 4-(4-iodophenyl)piperazine-1-carboxylate;4-(4-Iodophenyl)piperazine, N1-BOC protected;1-BOC-4-(4-Iodophenyl)piperazine
• CAS NO: 151978-66-4
• Molecular Formula: C₁₅H₂₁IN₂O₂
• Molecular Weight: 388.24
• Product Categories: Aryl;Organohalides
• Mol File: 151978-66-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 150 °C
• Boiling Point: 439.5 °C at 760 mmHg
• Flash Point: 219.6 °C
• Appearance: /
• Density: 1.481 g/cm³
• Vapor Pressure: 6.36E-08mmHg at 25°C
• Refractive Index: 1.584
• PKA: 2.93±0.10(Predicted)
• CAS DataBase Reference: TERT-BUTYL 4-(4-IODOPHENYL)TETRAHYDRO-1(2H)-PYRAZINECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL 4-(4-IODOPHENYL)TETRAHYDRO-1(2H)-PYRAZINECARBOXYLATE(151978-66-4)
• EPA Substance Registry System: TERT-BUTYL 4-(4-IODOPHENYL)TETRAHYDRO-1(2H)-PYRAZINECARBOXYLATE(151978-66-4)

Safety Data

• Hazard Codes: Irritant:
• Hazardous Substances Data: 151978-66-4(Hazardous Substances Data)

Usage

General Description

TERT-BUTYL 4-(4-IODOPHENYL)TETRAHYDRO-1(2H)-PYRAZINECARBOXYLATE is a chemical compound with the molecular formula C17H23IN2O2. It is a derivative of tetrahydro-1(2H)-pyrazinecarboxylic acid, with a tert-butyl group and an iodophenyl group attached to the tetrahydro pyrazine ring. TERT-BUTYL 4-(4-IODOPHENYL)TETRAHYDRO-1(2H)-PYRAZINECARBOXYLATE is often used in organic synthesis and pharmaceutical research. Its unique structure and properties make it a potentially valuable building block for the development of new drugs and biologically active compounds. The iodine atom contributes to its reactivity and potential applications in medicinal chemistry. However, as with any chemical compound, proper handling and safety precautions should be taken when working with TERT-BUTYL 4-(4-IODOPHENYL)TETRAHYDRO-1(2H)-PYRAZINECARBOXYLATE.

InChI:InChI=1/C15H21IN2O2/c1-15(2,3)20-14(19)18-10-8-17(9-11-18)13-6-4-12(16)5-7-13/h4-7H,8-11H2,1-3H3

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 96530-59-5 1-(piperazin-1-yl)-4-iodobenzene 
• 352437-09-3 tert-butyl 4-(4-bromophenyl)piperazine-1-carboxylate 
• 92-54-6 4-phenyl-1-piperazine 
• 77278-63-8 4-phenyl-piperazine-1-carboxylic acid tert-butyl ester 
• 624726-35-8 1-(4-iodophenyl)piperazine hydrochloride 

Downstream Products

• 202806-52-8 4-[4-(3-Oxo-prop-1-ynyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester 
• 235793-04-1 4-{4-[(E)-4-(3-Hydroxy-4-nitro-phenyl)-but-3-en-1-ynyl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester 
• 235793-02-9 5-(4-{4-[(E)-4-(3-Hydroxy-4-nitro-phenyl)-but-3-en-1-ynyl]-phenyl}-piperazin-1-yl)-5-oxo-pentanoic acid methyl ester 
• 202806-51-7 tert-butyl 4-(4-(3-hydroxyprop-1-ynyl)phenyl)piperazine-1-carboxylate 
• 374930-84-4 tert-butyl 4-(4-(pyridin-3-yl)phenyl)piperazine-1-carboxylate 
• 1202880-76-9 tert-butyl 4-(4-(pyridin-4-yl)phenyl)piperazine-1-carboxylate 

Relevant articles and documents

Design of highly potent urea-based, exosite-binding inhibitors selective for glutamate carboxypeptidase II

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Multifunctional D2/D3 agonist D-520 with high in vivo efficacy: Modulator of toxicity of alpha-synuclein aggregates

We have developed a series of dihydroxy compounds and related analogues based on our hybrid D2/D3 agonist molecular template to develop multifunctional drugs for symptomatic and neuroprotective treatment for Parkinson"s disease (PD). The lead compound (-)-24b (D-520) exhibited high agonist potency at D2/D3 receptors and produced efficacious activity in the animal models for PD. The data from thioflavin T (ThT) assay and from transmission electron microscopy (TEM) analysis demonstrate that D-520 is able to modulate aggregation of alpha-synuclein (αSN). Additionally, coincubation of D-520 with αSN is able to reduce toxicity of preformed aggregates of αSN compared to control αSN alone. Finally, in a neuroprotection study with dopaminergic MN9D cells, D-520 clearly demonstrated the effect of neuroprotection from toxicity of 6-hydroxydopamine. Thus, compound D-520 possesses properties characteristic of multifunctionality conducive to symptomatic and neuroprotective treatment of PD.

Further delineation of hydrophobic binding sites in dopamine D 2/D3 receptors for N-4 substituents on the piperazine ring of the hybrid template 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]-propyl-amino}-5, 6,7,8-tetrahydro-naphthalen-2-ol

Here we report a structure-activity relationship (SAR) study of analogues of 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]-propyl-amino}-5,6,7,8-tetrahydro- naphthalen-2-ol. Our SAR is focused on introduction of various substitutions in the piperazine ring of the hybrid template. The goal behind this study is to delineate the nature of the binding pocket for N-aryl substitution in the piperazine ring by observing the effect of various hydrophobic and other heteroaromatic substitutions on binding affinity (Ki), as measured with tritiated spiperone and HEK-293 cells expressing either D2 or D3 receptors. Functional activity of selected compounds was assessed with the GTPγS binding assay. Compound 8d was the most selective for the D3 receptor in the spiperone binding assay. An interesting similarity in binding affinity was observed between isoquinoline derivative D-301 and the 2-substituted pyridine derivative 8d, suggesting the importance of relative spatial relationships between the N-atom of the ligand and the molecular determinants of the binding pocket in D2/D3 receptors. Functional activity assays demonstrated high potency and selectivity of (+)-8a and (-)-28b (D2/D3 (ratio of EC50): 105 and 202, respectively) for the D3 receptor and both compounds were more selective compared to the reference drug ropinirole (D2/D3 (ratio of EC50): 29.5).