4-acetamido-N-(2-amino-5-thiophen-2-ylphenyl)benzamide

Category	Human immunodeficiency Virus (HIV)
CAS	849234-64-6
Description	4-acetamido-N-(2-amino-5-thiophen-2-ylphenyl)benzamide is a selective HDAC1/2 inhibitor, exhibiting selectivity over class II HDACs 3-8. It shows high-affinity to HDAC1 and HDAC2 with Ki of 0.2 and 1.5 nM, respectively.

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Product Information

Synonyms	BRD-6929; Merck60; N-[2-Amino-5-(2-thienyl)phenyl]-4-(acetylamino)benzamide
IUPAC Name	4-acetamido-N-(2-amino-5-thiophen-2-ylphenyl)benzamide
Molecular Weight	351.42
Molecular Formula	C19H17N3O2S
Canonical SMILES	CC(=O)NC1=CC=C(C=C1)C(=O)NC2=C(C=CC(=C2)C3=CC=CS3)N
InChI	InChI=1S/C19H17N3O2S/c1-12(23)21-15-7-4-13(5-8-15)19(24)22-17-11-14(6-9-16(17)20)18-3-2-10-25-18/h2-11H,20H2,1H3,(H,21,23)(H,22,24)
InChIKey	ABZSPJVXTTUFAA-UHFFFAOYSA-N
Purity	97%
Solubility	In Vitro: DMSO : 5 mg/mL(14.23 mM;Need ultrasonic) In Vivo: 1.Add each solvent one by one:10% DMSO >> 90% (20%SBE-β-CDin saline) Solubility: ≥ 2.08 mg/mL (5.92 mM); Clear solution
Appearance	Off-white to gray (Solid)
Storage	Powder: -20°C 3 years In solvent: -80°C 6 months -20°C 1 months
Complexity	479
Exact Mass	351.10414797
In Vitro	In vitro IC50 for HDAC1-9 by BRD-6929 using recombinant human HDAC enzymes and HDAC class-specific substrates. BRD-6929 and substrate are incubated for 180 min (HDAC1-3) to control for HDAC1-3 inhibition, BRD-6929 is against HDAC1, HDAC2, HDAC3 and HDAC4-9 with IC50s of 0.001 µM, 0.008 µM, 0.458 µM and >30 µM, respectively. BRD-6929 (1 and 10 uM) does not cause an increase or decrease in overall cell number in brain region specific primary cultures. Additionally, BRD-6929 (10 uM) causes an increase in H4K12 acetylation in brain region specific primary cultures (striatum). BRD-6929 (1-10 uM; 6 hours) causes a significant increase in H2B acetylation in primary neuronal cell cultures. BRD-6929 (1-20 uM; 24 hours) induces a dose-dependent acetylation of H4K12ac with an EC50 of 7.2 µM in cultured neurons. BRD-6929 potentiates the efficacy of gnidimacrin (a PKC Agonist) against latent HIV-1.
In Vivo	BRD-6929 (intraperitoneal injection; 45 mg/kg; 10 days) acts as a deacetylase inhibitor in mouse brain. It significantly increases acetylation in each brain region by 1.5- to 2.0-fold compared to vehicle. The western blotting reveals that BRD-6929 significantly increases acetylation of histone H2B (tetra-acetylated), H3K9 and H4K12 in cortex, ventral striatum and hippocampus after the 10th daily treatment in adult male C57BL/6J mice.
PSA	112.46000
Target	HDAC1:1 nM (IC50) HDAC2:8 nM (IC50) HIV
XLogP3-AA	2.6