1563175-22-3

Basic information

• Product Name: 1-([1,1′-biphenyl]-4-yl)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)piperazine
• Synonyms: 1-([1,1′-biphenyl]-4-yl)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)piperazine
• CAS NO: 1563175-22-3
• Molecular Weight: 396.648
• Mol File: 1563175-22-3.mol

Chemical Properties

• CAS DataBase Reference: 1-([1,1′-biphenyl]-4-yl)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)piperazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-([1,1′-biphenyl]-4-yl)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)piperazine(1563175-22-3)
• EPA Substance Registry System: 1-([1,1′-biphenyl]-4-yl)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)piperazine(1563175-22-3)

Safety Data

• Hazardous Substances Data: 1563175-22-3(Hazardous Substances Data)

Upstream product

• 92-66-0 4-bromo-1,1'-biphenyl 
• 86864-60-0 2-(tert-butyldimethylsilyloxy)ethyl bromide 
• 180698-19-5 1-(1,1′-biphenyl-4-yl)piperazine 
• 681482-18-8 t-butyl 4-([1,1′-biphenyl]-4-yl)piperazine-1-carboxylate 
• 92-54-6 4-phenyl-1-piperazine 
• 96530-59-5 1-(piperazin-1-yl)-4-iodobenzene 
• 151978-66-4 tert-butyl 4-(4-iodophenyl)tetrahydro-1(2H)-pyrazinecarboxylate 

Downstream Products

• 944678-48-2 2-(4-([1,1′-biphenyl]-4-yl)piperazin-1-yl)ethanol 
• 1563175-32-5 2-(4-([1,1′-biphenyl]-4-yl)piperazin-1-yl)acetaldehyde 
• 1563175-08-5 N-(2-(4-([1,1′-biphenyl]-4-yl)piperazin-1-yl)ethyl)-N-propyl-1,4-dioxaspiro[4.5]decan-8-amine 
• 1563175-15-4 4-((2-(4-([1,1′-biphenyl]-4-yl)piperazin-1-yl)ethyl)(propyl)amino)cyclohexanone 
• 1563175-17-6 N6-(2-(4-([1,1′-biphenyl]-4-yl)piperazin-1-yl)ethyl)-N6-propyl-5,6,7,8-tetrahydroquinazoline-2,6-diamine 
• 1026084-40-1 D-264 

Relevant articles and documents

Synthesis and characterization of brain penetrant prodrug of neuroprotective D-264: Potential therapeutic application in the treatment of Parkinson's disease

Parkinson's disease (PD) is one of the major debilitating neurodegenerative disorders affecting millions of people worldwide. Progressive loss of dopamine neurons resulting in development of motor dysfunction and other related non-motor symptoms is the hallmark of PD. Previously, we have reported on the neuroprotective property of a potent D3 preferring agonist D-264. In our goal to increase the bioavailability of D-264 in the brain, we have synthesized a modified cysteine based prodrug of D-264 and evaluated its potential in crossing the blood-brain barrier. Herein, we report the synthesis of a novel modified cysteine conjugated prodrug of potent neuroprotective D3 preferring agonist D-264 and systematic evaluation of the hydrolysis pattern of the prodrug to yield D-264 at different time intervals in rat plasma and brain homogenates using HPLC analysis. Furthermore, we have also performed in vivo experiments with the prodrug to evaluate its enhanced brain penetration ability.

Structural modifications of neuroprotective anti-parkinsonian (-)-N6-(2-(4-(biphenyl-4-yl)piperazin-1-yl)-ethyl)-N6-propyl-4,5,6, 7-tetrahydrobenzo[d]thiazole-2,6-diamine (D-264): An effort toward the improvement of in vivo efficacy of the parent molecule

In our overall goal to develop multifunctional dopamine D 2/D3 agonist drugs for the treatment of Parkinson's disease (PD), we previously synthesized potent D3 preferring agonist D-264 (1a), which exhibited neuroprotective properties in two animal models of PD. To enhance the in vivo efficacy of 1a, a structure-activity relationship study was carried out. Competitive binding and [35S]GTPγS functional assays identified compound (-)-9b as one of the lead molecules with preferential D3 agonist activity (EC50(GTPγS); D3 = 0.10 nM; D2/D3 (EC50): 159). Compounds (-)-9b and (-)-8b exhibited high in vivo activity in two PD animal models, reserpinized and 6-hydroxydopamine (OHDA)-induced unilateral lesioned rats. On the other hand, 1a failed to show any in vivo activity in these models unless the compound was dissolved in 5-10% beta-hydroxy propyl cyclodextrin solution. Lead compounds exhibited appreciable radical scavenging activity. In vitro experiments with dopaminergic MN9D cells indicated neuroprotection by both 1a and (-)-9b from toxicity of MPP+.