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420831-40-9

420831-40-9 Structure

420831-40-9 Structure
IdentificationBack Directory
[Name]

3-(azepan-1-ylsulfonyl)-N-(3-broMophenyl)benzaMide
[CAS]

420831-40-9
[Synonyms]

AK-7
CS-922
AK 7, >=98%
AK-7;AK7;AK 7
SIRT2 Inhibitor II
SIRT2 Inhibitor,AK-7
SIRT2 Inhibitor II, AK-7
SIRT2 INHIBITOR II;AK7;AK 7
3-(azepan-1-ylsulfonyl)-N-(3-broMophenyl)benzaMide
N-(3-Bromophenyl)-3-[(hexahydro-1H-azepin-1-yl)sulfonyl]-benzamide
Benzamide, N-(3-bromophenyl)-3-[(hexahydro-1H-azepin-1-yl)sulfonyl]-
N-(3-Bromophenyl)-3-[(hexahydro-1H-azepin-1-yl)sulfonyl]-benzamide SIRT2 Inhibitor,AK-7
[Molecular Formula]

C19H21BrN2O3S
[MDL Number]

MFCD03140195
[MOL File]

420831-40-9.mol
[Molecular Weight]

437.35
Chemical PropertiesBack Directory
[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
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36
[Safety Statements ]

26
[WGK Germany ]

3
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Eye Irrit. 2
Hazard InformationBack Directory
[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) Tylor et al. (2011), A brain-permeable small molecule that reduces neuronal cholesterol by inhibiting activity of sirtuin 2 deacetylase; ACS Chem. Biol., 6 540 2) Chopra et al. (2012), The sirtuin 2 inhibitor AK-7 is neuroprotective in Huntington’s disease mouse models; Cell Rep., 2 1492
Spectrum DetailBack Directory
[Spectrum Detail]

3-(azepan-1-ylsulfonyl)-N-(3-broMophenyl)benzaMide(420831-40-9)1HNMR
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