3-(azepan-1-ylsulfonyl)-N-(3-bromophenyl)benzamide

Base Information

• Chemical Name: 3-(azepan-1-ylsulfonyl)-N-(3-bromophenyl)benzamide
• CAS No.: 420831-40-9
• Molecular Formula: C19H21BrN2O3S
• Molecular Weight: 437.357
• Hs Code.: 2933990090
• European Community (EC) Number: 695-492-2
• UNII: 308B6B695N
• DSSTox Substance ID: DTXSID30194926
• Wikidata: Q27255930
• ChEMBL ID: CHEMBL3222141
• Mol file: 420831-40-9.mol

Synonyms:3-(1-azepanylsulfonyl)-N-(3-bromphenyl)benzamide;AK7 compound

Chemical Property of 3-(azepan-1-ylsulfonyl)-N-(3-bromophenyl)benzamide

Chemical Property:

• PKA: 12.28±0.70(Predicted)
• PSA: 74.86000
• Density: 1.469±0.06 g/cm3(Predicted)
• LogP: 5.35780
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥15mg/mL
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 436.04563
• Heavy Atom Count: 26
• Complexity: 570

Purity/Quality:

98%Min ^*data from raw suppliers

AK 7 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCCN(CC1)S(=O)(=O)C2=CC=CC(=C2)C(=O)NC3=CC(=CC=C3)Br
• 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.

Technology Process of 3-(azepan-1-ylsulfonyl)-N-(3-bromophenyl)benzamide

There total 3 articles about 3-(azepan-1-ylsulfonyl)-N-(3-bromophenyl)benzamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

hexamethylene imine (111-49-9) + C13H9BrClNO3S → 3-(1-azepanylsulfonyl)-N-(3-bromphenyl)benzamide (420831-40-9)

Guidance literature:

With triethylamine; In acetonitrile; at 40 ℃; Flow reactor;

DOI:10.3762/bjoc.13.33

Reference yield:

m-sulfobenzoic acid, monosodium salt (17625-03-5) → 3-(1-azepanylsulfonyl)-N-(3-bromphenyl)benzamide (420831-40-9)

Guidance literature:

Multi-step reaction with 3 steps

1: thionyl chloride / N,N-dimethyl-formamide / 6 h / 50 °C

2: triethylamine / acetonitrile / 20 °C / Flow reactor

3: triethylamine / acetonitrile / 40 °C / Flow reactor

With thionyl chloride; triethylamine; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.3762/bjoc.13.33

Reference yield:

3-chlorosulfonylbenzoyl dichloride (4052-92-0) → 3-(1-azepanylsulfonyl)-N-(3-bromphenyl)benzamide (420831-40-9)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / acetonitrile / 20 °C / Flow reactor

2: triethylamine / acetonitrile / 40 °C / Flow reactor

With triethylamine; In acetonitrile;

DOI:10.3762/bjoc.13.33

upstream raw materials:

m-sulfobenzoic acid, monosodium salt

3-chlorosulfonylbenzoyl dichloride

hexamethylene imine

Refernces