Basic information Safety Supplier Related

3-(azepan-1-ylsulfonyl)-N-(3-broMophenyl)benzaMide

Basic information Safety Supplier Related

3-(azepan-1-ylsulfonyl)-N-(3-broMophenyl)benzaMide Basic information

Product Name:
3-(azepan-1-ylsulfonyl)-N-(3-broMophenyl)benzaMide
Synonyms:
  • N-(3-Bromophenyl)-3-[(hexahydro-1H-azepin-1-yl)sulfonyl]-benzamide
  • SIRT2 Inhibitor,AK-7
  • N-(3-Bromophenyl)-3-[(hexahydro-1H-azepin-1-yl)sulfonyl]-benzamide SIRT2 Inhibitor,AK-7
  • SIRT2 Inhibitor II
  • SIRT2 INHIBITOR II;AK7;AK 7
  • AK 7, >=98%
  • 3-(azepan-1-ylsulfonyl)-N-(3-broMophenyl)benzaMide
  • AK-7
CAS:
420831-40-9
MF:
C19H21BrN2O3S
MW:
437.35
Mol File:
420831-40-9.mol
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3-(azepan-1-ylsulfonyl)-N-(3-broMophenyl)benzaMide Chemical Properties

Density 
1.469±0.06 g/cm3(Predicted)
storage temp. 
Sealed in dry,2-8°C
solubility 
DMSO: ≥15mg/mL
form 
powder
pka
12.28±0.70(Predicted)
color 
white to tan
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
InChI
InChI=1S/C19H21BrN2O3S/c20-16-8-6-9-17(14-16)21-19(23)15-7-5-10-18(13-15)26(24,25)22-11-3-1-2-4-12-22/h5-10,13-14H,1-4,11-12H2,(H,21,23)
InChIKey
IYAYHZZWYNXHEQ-UHFFFAOYSA-N
SMILES
C(NC1=CC=CC(Br)=C1)(=O)C1=CC=CC(S(N2CCCCCC2)(=O)=O)=C1
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36
Safety Statements 
26
WGK Germany 
3
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3-(azepan-1-ylsulfonyl)-N-(3-broMophenyl)benzaMide Usage And Synthesis

Description

The sirtuin SIRT2 is a deacetylase which targets α-tubulin, histone 4, forkhead transcription factors, and several other substrates. It has roles in metabolic diseases, cancer, age-related disorders, and neurodegenerative diseases, potentially including Alzheimer’s, Huntington’s, and Parkinson’s diseases. AK-7 is a cell- and brain-permeable inhibitor of SIRT2 (IC50 = 15.5 μM). In culture, it diminishes neuronal cell death induced by mutant huntingtin fragment. In addition, AK-7 down-regulates cholesterol biosynthetic gene expression and reduces total cholesterol levels in neurons in vivo.

Uses

AK-7 is a deacetylase which targets α-tubulin, histone 4, forkhead transcription factors, and several other substrates it is also a selective SIRT2 inhibitor.

in vivo

AK-7 (15 mg/kg/dose, i.p.) is brain-permeable in wild-type and HD mice[1]. AK-7 (10, 20 mg/kg, i.p.) improves the behavior and neuropathological phenotype and extends survival of R6/2 HD mice. AK-7 (20 mg/kg) ameliorates HD neuropathology in R6/2 mice. AK-7 also reduces the polyglutamine aggregation in R6/2 brain. In addition, AK-7 treated 140CAG mice show motor performance changes that parallel untreated wild-type mice, with the 20 mg/kg dose being most effective and significantly different from untreated 140CAG mice[2].

IC 50

SIRT2: 15.5 μM (IC50)

storage

+4°C

References

[1] DAVID M. TAYLOR. A Brain-Permeable Small Molecule Reduces Neuronal Cholesterol by Inhibiting Activity of Sirtuin 2 Deacetylase[J]. ACS Chemical Biology, 2011, 6 6: 540-546. DOI:10.1021/cb100376q
[2] VANITA CHOPRA. The sirtuin 2 inhibitor AK-7 is neuroprotective in Huntington’s disease mouse models.[J]. Cell reports, 2012, 2 6: 1492-1497. DOI:10.1016/j.celrep.2012.11.001

3-(azepan-1-ylsulfonyl)-N-(3-broMophenyl)benzaMideSupplier

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