4-(Dimethylamino)-n-[7-(hydroxyamino)-7-oxoheptyl]benzamide

Base Information

• Chemical Name: 4-(Dimethylamino)-n-[7-(hydroxyamino)-7-oxoheptyl]benzamide
• CAS No.: 251456-60-7
• Molecular Formula: C16H25N3O3
• Molecular Weight: 307.393
• NSC Number: 718169
• UNII: J8W4VF5ZEJ
• DSSTox Substance ID: DTXSID90274415
• Nikkaji Number: J1.216.507B
• Wikidata: Q27216175
• Pharos Ligand ID: CXFN2FX9QYNN
• Metabolomics Workbench ID: 147142
• ChEMBL ID: CHEMBL140000
• Mol file: 251456-60-7.mol

Synonyms:4-(dimethylamino)-N-(7-(hydroxyamino)-7-oxoheptyl)benzamide;4-(dimethylamino)-NHAOBzNH2

Chemical Property of 4-(Dimethylamino)-n-[7-(hydroxyamino)-7-oxoheptyl]benzamide

Chemical Property:

• Melting Point: 161℃
• Refractive Index: 1.558
• PSA: 81.67000
• Density: 1.137 g/cm³
• LogP: 2.72010
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: DMSO: soluble10mg/mL, clear
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 307.18959167
• Heavy Atom Count: 22
• Complexity: 340

Purity/Quality:

98%,99%, ^*data from raw suppliers

M344 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=CC=C(C=C1)C(=O)NCCCCCCC(=O)NO
• Uses: Histone deacetylase inhibitor III. A cell-permeable amide analog of Trichostatin A that potently inhibits HDACs. M 344 is an inhibitor of histone deacetylases (HDACs), inhibiting maize HDAC (IC50 = 100 nM) as well as human HDAC1 (IC50 = 46 nM). It shows a three-fold selectivity for inhibition of HDAC6 over HDAC1. M 344 enhances the sensitivity of human squamous carcinoma cells to radiation and promotes cell cycle arrest and apoptosis in human endometrial cancer and ovarian cancer cells (ED50 = 2.3 μM).

Technology Process of 4-(Dimethylamino)-n-[7-(hydroxyamino)-7-oxoheptyl]benzamide

There total 7 articles about 4-(Dimethylamino)-n-[7-(hydroxyamino)-7-oxoheptyl]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: 78.0%

N-benzyloxy-7-(4-dimethylaminobenzoyl)aminoheptanamide (251456-84-5) → 4-dimethylamino-N-(6-hydroxycarbamoylhexyl)benzamide (251456-60-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 6h; under 760 Torr;

DOI:10.1021/jm991091h

Reference yield:

methyl 7-aminoheptanoate hydrochloride (17994-94-4) → 4-dimethylamino-N-(6-hydroxycarbamoylhexyl)benzamide (251456-60-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 56 percent / TEA; BOP-Cl / CH₂Cl₂

2: 1M aq. LiOH / tetrahydrofuran / 4 h / 20 °C

3: TEA; BOP-Cl / CH₂Cl₂

4: 78 percent / H₂ / 10 percent Pd/C / methanol / 6 h / 760 Torr

With lithium hydroxide; TEA; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; 1: Condensation / 2: Hydrolysis / 3: Condensation / 4: Hydrogenolysis;

DOI:10.1021/jm991091h

Reference yield:

p-N,N-dimethylaminobenzoic acid (619-84-1) → 4-dimethylamino-N-(6-hydroxycarbamoylhexyl)benzamide (251456-60-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 56 percent / TEA; BOP-Cl / CH₂Cl₂

2: 1M aq. LiOH / tetrahydrofuran / 4 h / 20 °C

3: TEA; BOP-Cl / CH₂Cl₂

4: 78 percent / H₂ / 10 percent Pd/C / methanol / 6 h / 760 Torr

With lithium hydroxide; TEA; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; 1: Condensation / 2: Hydrolysis / 3: Condensation / 4: Hydrogenolysis;

DOI:10.1021/jm991091h

upstream raw materials:

N-benzyloxy-7-(4-dimethylaminobenzoyl)aminoheptanamide

p-N,N-dimethylaminobenzoic acid

methyl 7-aminoheptanoate hydrochloride

methyl 7-(4-dimethylaminobenzoyl)aminoheptanoate

Refernces

• 1、 -. "OCULAR HYPOTENSIVE AGENT COMPRISING COMPOUND CAPABLE OF INHIBITING HISTONE DEACETYLASE AS ACTIVE INGREDIENT". . . Retrieved 2009/12/28.