935881-37-1

Basic information

• Product Name: AR-42
• Synonyms: AR-42;(S)-HDAC-42,AR-42;(S)-(+)-N-Hydroxy-4-(3-methyl-2-phenyl-butyrylamino)benzamide;(S)-HDAC 42;AR-42 (HDAC-42);HDAC-42;OSU-HDAC42;AR-42 (OSU-HDAC42)
• CAS NO: 935881-37-1
• Molecular Formula: C18H20N2O3
• Molecular Weight: 312.363
• EINECS: -0
• Product Categories: Inhibitor;Inhibitors
• Mol File: 935881-37-1.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Density: 1.223
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: insoluble in EtOH; insoluble in H2O; ≥15.62 mg/mL in DMSO
• CAS DataBase Reference: AR-42(CAS DataBase Reference)
• NIST Chemistry Reference: AR-42(935881-37-1)
• EPA Substance Registry System: AR-42(935881-37-1)

Safety Data

• Hazardous Substances Data: 935881-37-1(Hazardous Substances Data)

Usage

Description

AR-42 is a broad-spectrum deacetylase inhibitor that targets both histone and non-histone proteins. It has shown greater potency and activity in solid tumors and hematological malignancies, making it a promising candidate for cancer therapy.

Uses

Used in Oncology:
AR-42 is used as a novel, oral cancer therapy for its ability to inhibit the deacetylation of proteins involved in the regulation of gene expression, cell cycle progression, and apoptosis. This leads to the suppression of tumor growth and the induction of cell death in cancer cells.
Used in Clinical Development:
AR-42 is currently in early clinical development, where it is being evaluated for its safety, tolerability, and efficacy in treating various types of cancer. Its oral administration and broad-spectrum activity make it a potentially valuable addition to the arsenal of cancer treatments.

Biological Activity

ar-42 (also known as osu-hdac42), a derivative of hydroxamate-tethered phenylbutyrate, is a novel and potent inhibitor of histone deacetylase (hdac) that potently inhibits the activity of hdac with 50% inhibition concentration ic50 value of 16 nm and induces histone h3 acetylation, α-tubulin acetylation and p21 up-regulation, which have been considered as the hallmark indicators of hdac inhibition. ar-42 has been found to modulate several apoptosis inhibitors as well as cell survival regulator, including akt, bcl-xl, bax, ku70 and surviving, and exert potent antitumor activity against multiple tumor types, such as human prostate and hepatic cancers, at least partially through pi3k/akt pathway inhibition.matthew l. bush?, janet oblinger?, victoria brendel, griffin santarelli, jie huang, elena m. akhmametyeva, sarah s. burns, justin wheeler, jeremy davis, charles w. yates, abhik r. chaudhury, samuel kulp, ching-shih chen, long-sheng chang, d. bradley welling, and abraham jacob. ar42, a novel histone deacetylase inhibitor, as a potential therapy for vestibular schwannomas and meningiomas. neuro-oncology 13(9):983–999, 2011aaron m. sargeant, robert c. rengel, samuel k. kulp, et al. osu-hdac42, a histone deacetylase inhibitor, blocks prostate tumor progression in the transgenic adenocarcinoma of the mouse prostate model cancer res 2008;68:3999-4009.qiang lu, da-sheng wang, chang-shi chen, yuan-dong hu, and ching-shih chen. structure-based optimization of phenylbutyrate-derived histone deacetylaseinhibitors. j. med. chem. 2005, 48, 5530-5535

Upstream product

• 854780-19-1 N-benzyloxy-4-(3-methyl-2-phenyl-butyrylamino)benzamide 
• 101-41-7 benzeneacetic acid methyl ester 
• 72615-27-1 2-phenyl-3-methylbutyric acid methyl ester 
• 51631-26-6 α-isopropyl-α-phenylacetyl chloride 
• 3508-94-9 3-methyl-2-phenylbutyric acid 
• 854780-18-0 4-(3-methyl-2-phenyl-butyrylamino)benzoic acid 
• 854780-17-9 C₁₉H₂₁NO₃ 
• 854779-93-4 N-hydroxy-4-[(3-methyl-2-phenylbutanoyl)amino]benzamide 
• 150-13-0 4-amino-benzoic acid 
• 13491-13-9 (R)-2-isopropyl-2-phenylacetic acid 
• 66493-39-8 4-(N-tert-butoxycarbonyl)aminobenzoic acid 
• 863666-11-9 tert-butyl (4-((benzyloxy)carbamoyl)phenyl)carbamate 
• 863666-15-3 4-amino-N-(benzyloxy)benzamide 
• 934838-72-9 N-benzyloxy-4-(3-methyl-2-phenyl-butyrylamino)-benzamide 

Relevant articles and documents

Determination of AR-42 enantiomeric purity by HPLC on chiral stationary phase

A sensitive and accurate liquid chromatographic method for the determination of AR-42 enantiomeric purity has been developed and validated. Baseline separation with a resolution higher than 1.9 was accomplished within 10?min using a CHIRALPAK AD column (250?mm?×?4.6?mm; particle size 5?μm) and n-hexane/2-propanol/diethylamine (75:25:0.1 v/v/v) as mobile phase at a flow rate of 1?mL?min?1. Eluted analytes were monitored by UV absorption at 260?nm. The effects of mobile phase components, temperature and flow rate on enantiomeric selectivity and resolution of enantiomers were investigated. Calibration curves were plotted within the concentration range between 0.001 and 0.5?mg?mL?1 (n?=?10), and the recoveries between 98.23 and 101.87% were obtained, with relative standard deviation lower than 1.31%. Limit of detection and limit of quantitation for AR-42 were 0.39 and 1.28?μg?mL?1 and for its enantiomer were 0.36 and 1.19?μg?mL?1, respectively. It was demonstrated that the developed method was accurate, robust and sensitive for the determination of enantiomeric purity of AR-42, especially for the analysis of bulk samples.

ZN -CHELATING MOTIF-TETHERED SHORT -CHAIN FATTY ACIDS AS A NOVEL CLASS OF HISTONE DEACETYLASE INHIBITORS

Zn -chelating motif-tethered fatty acids as histone deacetylase (HDAC) inhibitors. Compounds performed well in in vitro and in vivo tests.