1262888-28-7

Basic information

• Product Name: 6-fluoro-N-(4-fluorobenzyl)quinazolin-4-aMine
• Synonyms: 6-fluoro-N-(4-fluorobenzyl)quinazolin-4-aMine;6-Fluoro-N-[(4-fluorophenyl)methyl]-4-quinazolinamine;C43;Spautin-1;6-Fluoro-N-(4-fluorobenzyl)-4-quinazolinamine;4-((4-Fluorobenzyl)amino)-6-fluoroquinazoline;6-Fluoro-N-[(4-fluorophenyl)methyl]quinazolin-4-amine
• CAS NO: 1262888-28-7
• Molecular Formula: C₁₅H₁₁F₂N₃
• Molecular Weight: 271.2647464
• Product Categories: Inhibitors
• Mol File: 1262888-28-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 211 °C
• Boiling Point: 419.6±40.0 °C(Predicted)
• Appearance: white to beige/
• Density: 1.366±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble15mg/mL (clear solution)
• PKA: 5.75±0.50(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
• CAS DataBase Reference: 6-fluoro-N-(4-fluorobenzyl)quinazolin-4-aMine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-fluoro-N-(4-fluorobenzyl)quinazolin-4-aMine(1262888-28-7)
• EPA Substance Registry System: 6-fluoro-N-(4-fluorobenzyl)quinazolin-4-aMine(1262888-28-7)

Safety Data

• Hazard Codes: Xi
• Statements: 22-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 1262888-28-7(Hazardous Substances Data)

Usage

Description

6-fluoro-N-(4-fluorobenzyl)quinazolin-4-amine is a chemical compound belonging to the quinazoline class, characterized by the presence of a fluorine atom at the 6th position and a 4-fluorobenzyl group attached to the nitrogen atom. 6-fluoro-N-(4-fluorobenzyl)quinazolin-4-amine exhibits unique structural features and potential biological activities, making it a valuable candidate for pharmaceutical and chemical research.

Uses

Used in Pharmaceutical Research:
6-fluoro-N-(4-fluorobenzyl)quinazolin-4-amine is used as a chemical intermediate for the synthesis of various quinazoline-based drugs, which possess a wide range of pharmacological properties, including anticancer, antiviral, and anti-inflammatory activities.
Used in Chemical Synthesis:
6-fluoro-N-(4-fluorobenzyl)quinazolin-4-amine is used as a key building block in the synthesis of complex organic molecules and functional materials, such as fluorescent probes, sensors, and pharmaceutical agents.
Used in Medicinal Chemistry:
6-fluoro-N-(4-fluorobenzyl)quinazolin-4-amine is used as a lead compound in the discovery and optimization of novel therapeutic agents targeting various diseases, including cancer, neurological disorders, and infectious diseases.
Used in Drug Design:
6-fluoro-N-(4-fluorobenzyl)quinazolin-4-amine is used as a template for the rational design of new drugs with improved potency, selectivity, and pharmacokinetic properties, based on its unique chemical structure and biological activities.
Used in Biochemical Studies:
6-fluoro-N-(4-fluorobenzyl)quinazolin-4-amine is used as a research tool to investigate the molecular mechanisms of various biological processes, such as enzyme inhibition, receptor binding, and signal transduction pathways.
Used in Drug Discovery:
6-fluoro-N-(4-fluorobenzyl)quinazolin-4-amine is used as a starting point for the development of new drugs with innovative mechanisms of action, by exploring its potential interactions with target proteins and its effects on cellular processes.

Biochem/physiol Actions

Spautin-1 inhibits the activity of two ubiquitin-specific peptidases, USP10 and USP13, causing an increase in proteasomal degradation of class III PI3 kinase complexes, which have been shown to regulate autophagy.

in vitro

spautin-1 promotes the degradation of vps34 pi3 kinase complexes via inhibiting two ubiquitinspecific peptidases, usp10 and usp13, that target the beclin1 subunit of vps34 complexes. spautin-1 had no effect on the growth and survival of bcap-37 cells under normal culture conditions but dramatically enhanced cell death in glucose-free media. under glucose-free conditions, western blotting for lc3 further confirmed that autophagy was induced, which was inhibited by spautin-1. similar results were obtained with mcf-7 and bt549 cells. therefore, spautin-1 can sensitize tumor cells to apoptosis under nutritional deprived conditions [1].

IC 50

0.6 and 0.7 μm for usp10 and usp13 activity, respectively

References

1) Liu et al. (2011), Beclin1 controls the levels of p53 by regulating the deubiquitination activity of USP10 and USP13; Cell, 147 223 2) Mateo et al. (2013), Inhibition of cellular autophagy deranges dengue virion maturation; J. Virol., 87 1312 3) Correa et al. (2014), Combination of AKT inhibition with autophagy blockade effectively reduces ascites-derived ovarian cancer cell viability; Carcinogenesis,?35 1951 4) Vakifahmetoglu-Norburg et al. (1987), Chaperone-mediated autophagy degrades mutant p53; Genes Dev., 27 1718

Upstream product

• 446-08-2 2-amino-5-fluorobenzoic acid 
• 63069-49-8 2-amino-5-fluorobenzamide 
• 16499-56-2 6-fluoro-3,4-dihydroquinazolin-4-one 

Relevant articles and documents

Synthesis, modelling, and anticonvulsant studies of new quinazolines showing three highly active compounds with low toxicity and high affinity to the GABA-A receptor

Some novel fluorinated quinazolines (5a-j) were designed and synthesized to be evaluated for their anticonvulsant activity and their neurotoxicity. Structures of all newly synthesized compounds were confirmed by their infrared (IR), mass spectrometry (MS) spectra, 1H nuclear magnetic resonance (NMR), 13C-NMR, and elemental analysis (CHN). The anticonvulsant activity was evaluated by a subcutaneous pentylenetetrazole (scPTZ) test and maximal electroshock (MES)-induced seizure test, while neurotoxicity was evaluated by a rotorod test. The molecular docking was performed for all newly-synthesized compounds to assess their binding affinities to the GABA-A receptor in order to rationalize their anticonvulsant activities in a qualitative way. The data obtained from the molecular modeling was correlated with that obtained from the biological screening. These data showed considerable anticonvulsant activity for all newly-synthesized compounds. Compounds 5b, 5c, and 5d showed the highest binding affinities toward the GABA-A receptor, along with the highest anticonvulsant activities in experimental mice. These compounds also showed low neurotoxicity and low toxicity in the median lethal dose test compared to the reference drugs. A GABA enzymatic assay was performed for these highly active compounds to confirm the obtained results and explain the possible mechanism for anticonvulsant action. The most active compounds might be used as leads for future modification and optimization.

POTENT SMALL MOLECULE INHIBITORS OF AUTOPHAGY, AND METHODS OF USE THEREOF

Certain aspects of the invention relates to small molecule autophagy inhibitors, and their use for treatment and prevention of cancers and acute pancreatitis. As disclosed herein, a small molecule inhibitor of autophagy was been identified from an image-based screen in a known bioactive library. It was found that this autophagy inhibitor functions by promoting the degradation of type III PI3 kinase complex which is required for initiating autophagy. Medicinal chemistry studies led to small molecular autophagy inhibitors with improved potency and selectivity.