205264-33-1

Basic information

• Product Name: Tert-Butyl4-(Isoquinolin-1-Yl)Piperazine-1-Carboxylate
• Synonyms: Tert-Butyl4-(Isoquinolin-1-Yl)Piperazine-1-Carboxylate;1-Boc-4-Isoquinolin-1-yl-piperazine
• CAS NO: 205264-33-1
• Molecular Formula: C₁₈H₂₃N₃O₂
• Molecular Weight: 313.39412
• Mol File: 205264-33-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: Tert-Butyl4-(Isoquinolin-1-Yl)Piperazine-1-Carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Tert-Butyl4-(Isoquinolin-1-Yl)Piperazine-1-Carboxylate(205264-33-1)
• EPA Substance Registry System: Tert-Butyl4-(Isoquinolin-1-Yl)Piperazine-1-Carboxylate(205264-33-1)

Safety Data

• Hazardous Substances Data: 205264-33-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
Tert-Butyl4-(Isoquinolin-1-Yl)Piperazine-1-Carboxylate is used as a research compound for exploring its potential applications in the pharmaceutical industry. Its unique molecular structure and the presence of the isoquinoline unit suggest that it may possess valuable pharmacological properties, making it a promising candidate for further investigation and development.
Used in Drug Discovery:
Tert-Butyl4-(Isoquinolin-1-Yl)Piperazine-1-Carboxylate is used as a lead compound in drug discovery processes. Its complex structure and the presence of the piperazine ring system may contribute to the development of new therapeutic agents, particularly in the context of central nervous system disorders or other conditions where piperazine-based compounds have shown efficacy.
Used in Chemical Synthesis:
Tert-Butyl4-(Isoquinolin-1-Yl)Piperazine-1-Carboxylate is used as an intermediate in the synthesis of other complex organic compounds. Its reactivity and the presence of functional groups, such as the carboxylate, make it a versatile building block for the creation of novel molecules with potential applications in various fields, including materials science and medicinal chemistry.

Upstream product

• 1532-71-4 1-bromoisoquinoline 
• 57260-71-6 1-t-Butoxycarbonylpiperazine 
• 7742-73-6 1,3-dichloroisoquinoline 
• 19493-44-8 1-chloroisoquinoline 
• 634198-17-7 4-(3-chloro-1-isoquinolyl)-1-piperazinecarboxylic acid tert-butyl ester 
• 119-65-3 isoquinoline 
• 77278-40-1 tert-butyl 4-(benzoyloxy)piperazine-1-carboxylate 

Downstream Products

• 126653-00-7 1-(1-piperazinyl)-isoquinoline 

Relevant articles and documents

Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope, Mechanism, and Applications

C-N cross-coupling is one of the most valuable and widespread transformations in organic synthesis. Largely dominated by Pd- and Cu-based catalytic systems, it has proven to be a staple transformation for those in both academia and industry. The current study presents the development and mechanistic understanding of an electrochemically driven, Ni-catalyzed method for achieving this reaction of high strategic importance. Through a series of electrochemical, computational, kinetic, and empirical experiments, the key mechanistic features of this reaction have been unraveled, leading to a second generation set of conditions that is applicable to a broad range of aryl halides and amine nucleophiles including complex examples on oligopeptides, medicinally relevant heterocycles, natural products, and sugars. Full disclosure of the current limitations and procedures for both batch and flow scale-ups (100 g) are also described.

Virtual Screening Approach and Investigation of Structure-Activity Relationships to Discover Novel Bacterial Topoisomerase Inhibitors Targeting Gram-Positive and Gram-Negative Pathogens

Bacterial resistance is increasing rapidly, requiring urgent identification of new antibacterial drugs that are effective against multidrug-resistant pathogens. Novel bacterial topoisomerase inhibitors (NBTIs) provide a new strategy for investigating the well-validated DNA gyrase and topoisomerase IV targets while preventing cross-resistance issues. On this basis, starting from a virtual screening campaign and subsequent structure-based hit optimization guided by X-ray studies, a novel class of piperazine-like NBTIs with outstanding enzymatic activity against Staphylococcus aureus and Escherichia coli DNA gyrase and topoisomerase IV was identified. Notably, compounds (±)-33, (±)-35, and (±)-36 with potent and balanced multitarget enzymatic profiles exhibited excellent efficacy against selected Gram-positive and Gram-negative pathogens, as well as clinically relevant resistant strains. Overall, the new NBTI chemotype described herein, owing to the broad-spectrum antibacterial activity and favorable in vitro safety profile, might serve as a basis for the development of novel treatments against serious infections.

Site-Selective Copper-Catalyzed Amination and Azidation of Arenes and Heteroarenes via Deprotonative Zincation

Arene amination is achieved by site-selective C-H zincation followed by copper-catalyzed coupling with O-benzoylhydroxylamines under mild conditions. Key to this success is ortho-zincation mediated by lithium amidodiethylzincate base that is effective for a wide range of arenes, including nonactivated arenes bearing simple functionalities such as fluoride, chloride, ester, amide, ether, nitrile, and trifluoromethyl groups as well as heteroarenes including indole, thiophene, pyridine, and isoquinoline. An analogous C-H azidation is also accomplished using azidoiodinane for direct introduction of a useful azide group onto a broad scope of arenes and heteroarenes. These new transformations offer rapid access to valuable and diverse chemical space of aminoarenes. Their broad applications in organic synthesis and drug discovery are demonstrated in the synthesis of novel analogues of natural product (-)-nicotine and antidepressant sertraline by late-stage amination and azidation reactions.

COMPOUNDS USEFUL AS CHEMOKINE RECEPTOR ANTAGONISTS

The present invention relates to compounds useful as Chemokine Receptor antagonists. Compounds of general formula I are provided: or pharmaceutically acceptable salts thereof. The invention also provides pharmaceutically acceptable compositions comprising said compounds and methods of using the compounds and compositions for the inhibition of Chemokine Receptors and also for the treatment of various diseases, conditions, or disorders, including acute or chronic inflammatory disease, cancer or osteolytic bone disorders.

ARYLPIPERAZINYL-CYCLOHEXYL INDOLE DERIVATIVES FOR THE TREATMENT OF DEPRESSION

Compounds are provided which are useful for the treatment of serotonin-affected neurological disorders which comprise (I) wherein: Ra, R1, R2 and R3 are each, independently, hydrogen, or a substituent selected from halogen, CF3, alkyl, alkoxy, MeSO2, amino or aminocarbonyl (each optionally substituted by one or two groups selected from alkyl and benzyl) carboxy, or alkoxycarbonyl; or two adjacent of Ra and R1-4 together can form a 5-7 membered carbocyclic or heterocyclic ring which is optionally substituted by a substituent defined above; R4 is hydrogen, halogen, or alkyl; R5 is hydrogen, alkyl, arylalkyl, or aryl; R6 is hydrogen, halogen, CF3, CN, carbamide, alkoxy or benzyloxy; X1, X2 and X3 are each carbon or one of X1, X2 or X3 may be nitrogen; Y is CH or nitrogen; and Z is carbon or nitrogen; or pharmaceutically acceptable salts thereof.

Potent and Selective Inhibitors of Platelet-Derived Growth Factor Receptor Phosphorylation. 3. Replacement of Quinazoline Moiety and Improvement of Metabolic Polymorphism of 4-[4-(N-Substituted (thio)carbamoyl)-1-piperazinyl]-6,7-dimethoxyquinazoline Derivatives

We have previously reported that a series of 4-[4-(N-substituted (thio)carbamoyl)-1-piperazinyl]-6,7-dimethoxyquinazoline derivatives were potent and selective inhibitors of platelet-derived growth factor receptor (PDGFR) phosphorylation and demonstrated several biological effects such as suppression of neointima formation following balloon injury in rat carotid artery by oral administration. Here, we investigated structure-activity relationships of the 6,7-dimethoxyquinazolinyl moiety. In regard to 6,7-dimethoxy groups, ethoxy analogues showed potent activity (IC50 of 16b is 0.04 μM; IC50 of 17a is 0.01 μM) and further extension of the alkyl group reduced activity. Interestingly, methoxyethoxy (IC50 of 16j is 0.02μM; IC50 of 17h is 0.01 μM) and ethoxyethoxy (IC50 of 17j is 0.02 μM) analogues showed the most potent activity, suggesting that the inserted oxygen atom significantly interacts with β-PDGFR. Among tricyclic quinazoline derivatives, the 2-oxoimidazo[4,5-e]quinazoline derivative 21a showed potent activity (IC 50 = 0.10 μM). Regarding replacements of quinazoline by other heterocyclic rings, pyrazolo[3,4-d]pyrimidine (39a, IC50 = 0.17 μM) and quinoline (IC50 of 40a is 0.18 μM; IC50 of 40b is 0.09 μM) derivatives showed potent activity. Isoquinoline and some pyridopyrimidine derivatives were completely inactive; therefore, 1-aza has an important role. Also 7-aza and 8-aza substitution on the parent quinazoline ring has a detrimental effect on the interaction with β-PDGFR. We also demonstrated that the substituents on the quinazoline ring possess major consequences for metabolic polymorphism. Although there existed extensive metabolizers and poor metabolizers in Sprague-Dawley rats administrated 6,7-dimethoxyquinazoline derivatives (1b and 1c), 6-(2-methoxy)ethoxy-7-methoxyquinazoline analogue 16k showed no metabolic polymorphism.