59215-41-7

Basic information

• Product Name: 4-piperazin-1-ylquinazoline
• Synonyms: 4-piperazin-1-ylquinazoline;4-piperazin-1-ylquinazoline(SALTDATA: 2HCl 1.7H2O);4-piperazin-1-ylquinazoline 2HCl 1.7H2O;4-(1-piperazinyl)quinazoline;4-piperazin-1-ylquinazoline hydrochloride;4-Piperazin-1-yl-quinazoline 2HCl
• CAS NO: 59215-41-7
• Molecular Formula: C₁₂H₁₄N₄
• Molecular Weight: 214.26636
• Mol File: 59215-41-7.mol

Chemical Properties

• Boiling Point: 411°C at 760 mmHg
• Flash Point: 202.4°C
• Appearance: /
• Density: 1.201g/cm³
• Vapor Pressure: 5.78E-07mmHg at 25°C
• Refractive Index: 1.634
• Storage Temp.: 2-8°C(protect from light)
• PKA: 8.60±0.10(Predicted)
• CAS DataBase Reference: 4-piperazin-1-ylquinazoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-piperazin-1-ylquinazoline(59215-41-7)
• EPA Substance Registry System: 4-piperazin-1-ylquinazoline(59215-41-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 59215-41-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-piperazin-1-ylquinazoline is used as a therapeutic agent for its potential to treat a range of conditions, including cancer, cardiovascular diseases, and central nervous system disorders. Its unique structure and biological activities make it a promising candidate for further research and development in medicinal chemistry.
4-piperazin-1-ylquinazoline's potential applications are attributed to its ability to modulate various biological pathways and interact with different targets in the body, offering a broad spectrum of therapeutic possibilities. As research progresses, 4-piperazin-1-ylquinazoline may lead to the development of new drugs and treatment strategies for a variety of health issues.

InChI:InChI=1/C12H14N4/c1-2-4-11-10(3-1)12(15-9-14-11)16-7-5-13-6-8-16/h1-4,9,13H,5-8H2

Upstream product

• 110-85-0 piperazine 
• 5190-68-1 4-chloroquinazoline 
• 57260-71-6 1-t-Butoxycarbonylpiperazine 
• 209733-20-0 4-piperazinylquinazoline hydrochloride 
• 491-36-1 4-quinazolinol 
• 827598-29-8 4-(quinazolin-4-yl)piperazine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 1186588-61-3 C₃₂H₄₂N₆O₅S₂ 
• 1059629-08-1 [4-benzyloxy-5-methoxy-2-nitro-phenyl](4-(4-quinazolinyl)piperazino)-methanone 
• 1065540-41-1 N₁-[4-chloro-2-(2-chlorobenzoyl)phenyl]-2-[4-(4-quinazolinyl)piperazino]acetamide 
• 853678-27-0 (2R)-2-amino-3-phenyl-1-(4-quinazolin-4-yl-piperazin-1-yl)-propan-1-one 

Relevant articles and documents

MODULATORS OF RAS GTPASE

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Piperazinone compound containing piperidine ring and preparation method and application thereof

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Molecular docking and synthesis of novel quinazoline analogues as inhibitors of transcription factors NF-κB activation and their anti-cancer activities

NF-kB is a transcription factor protein complex that can be found in almost all animal cell types and is a key player in some cancers and inflammatory responses. It can enhance the proliferation rate, reduce apoptosis, as well as creating more blood flow to ensure the survival of cancer, thus blocking the NF-kB pathway has potential therapeutic benefit. We designed a series of compounds based on a quinazoline scaffold pharmacophore model which may have high binding affinity with the p50 subunit of NF-kB. The compound series with phenyl substitution at the 2 position of the quinazoline proved to be more effective at inhibiting NF-kB function both theoretically and experimentally. These compounds also reduce the proliferation of numerous tumor cell lines and the mean GI50 for compound 2a is 2.88 μM against the NCI-60 cell line. At the same time, compound 2a can induce significant apoptosis in EKVX cell line at the concentration of 1 μM.

AKT PROTEIN KINASE INHIBITORS

The present invention provides compounds, including resolved enantiomers, diastereomers, solvates and pharmaceutically acceptable salts thereof, comprising the Formula: A-L-CR where CR is a cyclical core group, L is a linking group and A is as defined herein. Also provided are methods of using the compounds of this invention as AKT protein kinase inhibitors and for the treatment of hyperproliferative diseases such as cancer.

Potent and selective inhibitors of platelet-derived growth factor receptor phosphorylation. Part 4: Structure-activity relationships for substituents on the quinazoline moiety of 4-[4-(N-substituted(thio)carbamoyl)-1-piperazinyl]-6,7-dimethoxyquinazoline derivatives

Here, we investigated the structure-activity relationships of the 6,7-dimethoxyquinazoline moiety. With regard to exploration of positions and varieties of substituents on the quinazoline ring, 6,7-dialkoxy substitution was optimal. This study suggests the possibility of further modifications for this moiety.

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.

PROLINE DERIVATIVES AND USE THEREOF AS DRUGS

The present invention aims at providing compounds having therapeutic effects due to a DPP-IV inhibitory action, and satisfactory as pharmaceutical products. The present inventors have found that derivatives having a substituent introduced into the γ-position of proline represented by the formula (I) wherein each symbol is as defined in the specification, have a potent DPP-IV inhibitory activity, and completed the present invention by increasing the stability.