ChemicalBook > CAS DataBase List > 3-(1-METHYL-4-PHENYLACETYL-1H-2-PYRROLYL)-N-HYDROXY-2-PROPENAMIDE

3-(1-METHYL-4-PHENYLACETYL-1H-2-PYRROLYL)-N-HYDROXY-2-PROPENAMIDE

Product Name
3-(1-METHYL-4-PHENYLACETYL-1H-2-PYRROLYL)-N-HYDROXY-2-PROPENAMIDE
CAS No.
676599-90-9
Chemical Name
3-(1-METHYL-4-PHENYLACETYL-1H-2-PYRROLYL)-N-HYDROXY-2-PROPENAMIDE
Synonyms
APHA-8;MC1353;MC-1353;MC 1353;APHA COMPOUND 8;Aroyl pyrrole hydroxy amide #8;3-(1-METHYL-4-PHENYLACETYL-1H-2-PYRROLYL)-N-HYDROXY-2-PROPENAMIDE;(E)-N-hydroxy-3-(1-Methyl-4-(2-phenylacetyl)-1H-pyrrol-2-yl)acrylaMide;2-Propenamide, N-hydroxy-3-[1-methyl-4-(2-phenylacetyl)-1H-pyrrol-2-yl]-
CBNumber
CB4360159
Molecular Formula
C16H16N2O3
Formula Weight
284.31
MOL File
676599-90-9.mol
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3-(1-METHYL-4-PHENYLACETYL-1H-2-PYRROLYL)-N-HYDROXY-2-PROPENAMIDE Property

storage temp. 
2-8°C
solubility 
DMSO: 10 mg/mL, soluble
form 
solid
InChI
1S/C16H16N2O3/c1-18-11-13(10-14(18)7-8-16(20)17-21)15(19)9-12-5-3-2-4-6-12/h2-8,10-11,21H,9H2,1H3,(H,17,20)/b8-7+
InChIKey
UFQOXIMRSMFQRI-BQYQJAHWSA-N
SMILES
Cn1cc(cc1\C=C\C(=O)NO)C(=O)Cc2ccccc2
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Safety

Hazard Codes 
Xn
Risk Statements 
22-41-43
Safety Statements 
26-36/37/39
WGK Germany 
2
Storage Class
11 - Combustible Solids
Hazard Classifications
Acute Tox. 4 Oral
Eye Dam. 1
Skin Sens. 1
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H317May cause an allergic skin reaction

H318Causes serious eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
A2478
Product name
APHA Compound 8
Purity
≥98% (HPLC), solid
Packaging
1mg
Price
$161
Updated
2025/07/31
Cayman Chemical
Product number
21228
Product name
APHA Compound 8
Packaging
500μg
Price
$62
Updated
2024/03/01
Cayman Chemical
Product number
21228
Product name
APHA Compound 8
Packaging
1mg
Price
$92
Updated
2024/03/01
AK Scientific
Product number
3575DN
Product name
3-(1-Methyl-4-phenylacetyl-1H-2-pyrrolyl)-N-hydroxy-2-propenamide
Packaging
1mg
Price
$199
Updated
2021/12/16
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3-(1-METHYL-4-PHENYLACETYL-1H-2-PYRROLYL)-N-HYDROXY-2-PROPENAMIDE Chemical Properties,Usage,Production

Description

APHA compound 8 is an inhibitor of class I histone deacetylases (HDACs; IC50s = 3.7, 7.4, 0.42, and 2.8 μM for HDAC1, -2, -3, and -8, respectively) as well as class II HDACs (IC50s = 3.1, 0.1, 3.1, and 4.2 μM for HDAC4, -6, -7, and -10, respectively). It is selective for class I and II HDACs over class III HDACs (IC50s = >30 μM for SIRT1, SIRT2, and SIRT3) and the histone acetyltransferase PCAF (IC50 = >30 μM). At 48 hours post-infection, APHA compound 8 increases replication of oncolytic herpes simplex virus (oHSV) in MDA-MB-231 and 4T1 breast cancer cells when used prior to viral infection at concentrations of 10 and 50 μM.

Uses

HDAC-IN-69 (Compound 2) is a derivative of an HDAC inhibitor with inhibitory activity targeting maize histone deacetylase HD2[1].

IC 50

HD2

References

[1] Ragno R, et al. 3-(4-Aroyl-1-methyl-1H-pyrrol-2-yl)-N-hydroxy-2-propenamides as a new class of synthetic histone deacetylase inhibitors. 3. Discovery of novel lead compounds through structure-based drug design and docking studies. J Med Chem. 2004 Mar 11;47(6):1351-9. DOI:10.1021/jm031036f

3-(1-METHYL-4-PHENYLACETYL-1H-2-PYRROLYL)-N-HYDROXY-2-PROPENAMIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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3-(1-METHYL-4-PHENYLACETYL-1H-2-PYRROLYL)-N-HYDROXY-2-PROPENAMIDE Suppliers

China 21 Switzerland 1 United States 8 USA 1 Global 31
VDM Biochemicals
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676599-90-9, 3-(1-METHYL-4-PHENYLACETYL-1H-2-PYRROLYL)-N-HYDROXY-2-PROPENAMIDERelated Search:


  • 3-(1-METHYL-4-PHENYLACETYL-1H-2-PYRROLYL)-N-HYDROXY-2-PROPENAMIDE
  • APHA COMPOUND 8
  • (E)-N-hydroxy-3-(1-Methyl-4-(2-phenylacetyl)-1H-pyrrol-2-yl)acrylaMide
  • 2-Propenamide, N-hydroxy-3-[1-methyl-4-(2-phenylacetyl)-1H-pyrrol-2-yl]-
  • APHA-8
  • Aroyl pyrrole hydroxy amide #8
  • MC 1353
  • MC1353
  • MC-1353
  • 676599-90-9
  • Biochemicals and Reagents
  • BioChemical
  • Histone deacetylase
  • D to K
  • Enzyme Inhibitors
  • Enzyme Inhibitors by Enzyme
  • Enzymes, Inhibitors, and Substrates
  • Histone Deacetylase (HDAC) inhibitor.