AZ32 - ≥99% , CAS No.2288709-96-4

CAS: 2288709-96-4 Cat. No.: A414140 Molecular Weight: 328.37

GRADE & PURITY ≥99%

Synonyms

N-methyl-4-(6-phenylimidazo[1,2-a]pyrazin-3-yl)benzamide

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

AZ32 is a specific inhibitor of theATM kinasethat possesses good BBB penetration in mouse with an IC50 value of <0.0062 μM for ATM enzyme. It shows adequate selectivity over ATR and also has high cell permeability.

Targets

ATM (Cell-free assay) <0.0062 μM

In vitro

AZ32 blocks the DNA damage response (DDR) and radiosensitized GBM cells in vitro. AZ32 shows moderate potency against ATM in cell (IC50 = 0.31 μM) and adequate selectivity over ATR, while also having high cell permeability.

In vivo

AZ32, with enhanced blood-brain barrier (BBB) penetration, was highly efficient in vivo as radiosensitizer in syngeneic and human, orthotopic mouse glioma model compared with AZ31. AZ32 is the first ATMi with oral bioavailability shown to radiosensitize glioma and improve survival in orthotopic mouse models. Following a single oral dose of AZ32 (200 mg/kg) in mice, the free brain concentrations of AZ32 was in excess of the cellular IC50 for approximately 22 hr. AZ32 has enhanced BBB penetration at 8.7-fold and improved brain coverage over AZ31 but with reduced ATM selectivity.

Cell Research(from reference)

Cell lines：U1242 cells 

Concentrations：3 μM 

Incubation Time：48 h 

Specifications

Synonyms

N-methyl-4-(6-phenylimidazo[1, 2-a]pyrazin-3-yl)benzamide

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

AZ32 is a specific inhibitor of the ATM kinase that possesses good BBB penetration in mouse with an IC50 value of <0.0062 μM for ATM enzyme. It shows adequate selectivity over ATR and also has high cell permeability.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 504773185
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504773185
• Canonical Smiles: CNC(=O)C1=CC=C(C=C1)C2=CN=C3N2C=C(N=C3)C4=CC=CC=C4
• IUPAC Name: N-methyl-4-(6-phenylimidazo[1,2-a]pyrazin-3-yl)benzamide
• InChIKey: LCRTUEXVVKVKBD-UHFFFAOYSA-N
• INCHI: 1S/C20H16N4O/c1-21-20(25)16-9-7-15(8-10-16)18-11-23-19-12-22-17(13-24(18)19)14-5-3-2-4-6-14/h2-13H,1H3,(H,21,25)
• Isomeric SMILES: CNC(=O)C1=CC=C(C=C1)C2=CN=C3N2C=C(N=C3)C4=CC=CC=C4
• Molecular Weight: 328.37
• Reaxy-Rn: 33284113
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=33284113&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzamides
• Alternative Parents: Imidazopyrazines Benzoyl derivatives Pyrazines N-acyl amines Heteroaromatic compounds Azoles Carboxylic acid amides Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Imidazopyrazine - Benzamide - Benzoyl - Pyrazine - N-acyl-amine - Heteroaromatic compound - Azole - Carboxamide group - Azacycle - Organoheterocyclic compound - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 66 mg/mL (200.99 mM); Ethanol: 7 mg/mL (21.31 mM); Water: Insoluble
• Molecular Weight: 328.400 g/mol
• XLogP3: 3.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 328.132 Da
• Monoisotopic Mass: 328.132 Da
• Topological Polar Surface Area: 59.300 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 457.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1