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3-Amino-6-[4-(methylsulfonyl)phenyl]-N-phenyl-2-pyrazinecarboxamide

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3-Amino-6-[4-(methylsulfonyl)phenyl]-N-phenyl-2-pyrazinecarboxamide Basic information

Product Name:
3-Amino-6-[4-(methylsulfonyl)phenyl]-N-phenyl-2-pyrazinecarboxamide
Synonyms:
  • VE-821;VE821;VE 821
  • 3-Amino-6-[4-(methylsulfonyl)phenyl]-N-phenyl-2-pyrazinecarboxamide
  • 2-Pyrazinecarboxamide, 3-amino-6-[4-(methylsulfonyl)phenyl]-N-phenyl-
  • 3-Amino-6-[4-(methylsulfonyl)phenyl]-N-phenyl-2-pyrazinecarboxamide VE-821
  • VE-821 3-Amino-6-[4-(methylsulfonyl)phenyl]-N-phenyl-2-pyrazinecarboxamide
  • VE821;VE 821
  • CS-634
  • 3-Amino-6-[4-(methlsulfonyl)phenyl)-N-phenyl-2-pyrazinecarboxamide
CAS:
1232410-49-9
MF:
C18H16N4O3S
MW:
368.41
Product Categories:
  • Inhibitors
  • API
Mol File:
1232410-49-9.mol
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3-Amino-6-[4-(methylsulfonyl)phenyl]-N-phenyl-2-pyrazinecarboxamide Chemical Properties

Melting point:
247-249°C
Boiling point:
568.4±50.0 °C(Predicted)
Density 
1.394
storage temp. 
-20°C
solubility 
Soluble in DMSO (40 mg/ml)
pka
9.97±0.70(Predicted)
form 
powder
color 
white to beige
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
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3-Amino-6-[4-(methylsulfonyl)phenyl]-N-phenyl-2-pyrazinecarboxamide Usage And Synthesis

Description

Ataxia-telangiectasia and Rad3-related protein (ATR) is a serine/threonine kinase that activates DNA processes related to the DNA damage response. VE-821 is an ATP-competitive inhibitor of ATR (IC50 = 26 nM). It augments DNA damage and cell death of cancer cells in response to radiation under normal and hypoxic conditions. VE-821 also sensitizes cancer cells to chemotherapy.

Chemical Properties

Bright Yellow Solid

Uses

VE 821 is a potent and selective inhibitor of DNA damage response kinase, ATR. VE 821 functions to disrupt DNA damage repair system of tumor cells, limiting their abilities for further growth.

Uses

VE-821 has been used as an inhibitor of ATM- and Rad3-related (ATR) protein in human cancer cells.

Biochem/physiol Actions

VE-821 is a potent ATP-competitive inhibitor of the DNA damage response (DDR) kinase Ataxia telangiectasia-mutated (ATM) and ATM- and Rad3-related (ATR) with a Ki of 13 nM. VE-821 has minimal cross-reactivity against the related PIKKs ATM, DNA-dependent protein kinase (DNA-PK), mTOR and PI3-kinase-γ (Ki of 16 μM, 2.2 μM, >1 μM and 3.9 μM, respectively) and against a large panel of unrelated protein kinases. VE-821 used alone caused death in a large fraction of cancer cell populations and also showed strong synergy with genotoxic agents. VE-821 increased sensitivity of cells to radiation and also sensitized cancer cells to a variety of chemotherapeutic agents.

References

Reaper et al. (2011), Selective killing of ATM- or p53-deficient cancer cells through inhibition of ATR; Nat. Chem. Biol., 7 428 Prevo et al. (2012), The novel ATR inhibitor VE-821 increases sensitivity of pancreatic cancer cells to radiation and chemotherapy; Cancer Biol. Ther., 13 1072 Huntoon et al. (2013), ATR inhibition broadly sensitizes ovarian cancer cells to chemotherapy independent of BRCA status; Cancer Res., 73 3683 King et al. (2021), Increased Replication Stress Determines ATR Inhibitor Sensitivity in Neuroblastoma Cells; Cancers (Basel), 13 6215 Moolmuang and Ruchirawat (2021), The antiproliferative effects of ataxia-telangiectasia mutated and ATM- and Rad3-related inhibitions and their enhancements with the cytotoxicity of DNA damaging agents in cholangiocarcinoma cells; J. Pharm. Pharmacol., 73 40

3-Amino-6-[4-(methylsulfonyl)phenyl]-N-phenyl-2-pyrazinecarboxamideSupplier

Shanghai Boyle Chemical Co., Ltd.
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J & K SCIENTIFIC LTD.
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010-82848833 400-666-7788
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Chembest Research Laboratories Limited
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Chemsky(shanghai)International Co.,Ltd.
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