414864-00-9

Basic information

• Product Name: Belinostat (PXD101)
• Synonyms: PXD101, Beliomsta;PXD101;N-HYDROXY-3-[3-[(PHENYLAMINO)SULFONYL]PHENYL]-2-PROPENAMIDE;N-HYDROXY-3-(3-PHENYLSULFAMOYLPHENYL)ACRYLAMIDE;Belinostat;Belinostat(PXD101);2-PropenaMide, N-hydroxy-3-[3-[(phenylaMino)sulfonyl]phenyl]-;PX105684
• CAS NO: 414864-00-9
• Molecular Formula: C₁₅H₁₄N₂O₄S
• Molecular Weight: 318.35
• Product Categories: Inhibitors;Inhibitor;API
• Mol File: 414864-00-9.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Density: 1.428 g/cm³
• Refractive Index: 1.667
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 8.31±0.10(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: Belinostat (PXD101)(CAS DataBase Reference)
• NIST Chemistry Reference: Belinostat (PXD101)(414864-00-9)
• EPA Substance Registry System: Belinostat (PXD101)(414864-00-9)

Safety Data

• Hazardous Substances Data: 414864-00-9(Hazardous Substances Data)

Usage

Description

Belinostat (PXD101), also known as Beleodaq, is a hydroxamic acid-type histone deacetylase (HDAC) inhibitor developed by Spectrum Pharmaceuticals and marketed by Onxeo. It has received fast track designation by the United States Food and Drug Administration (US FDA) and is approved for the treatment of hematological malignancies and solid tumors associated with peripheral T-cell lymphoma (PTCL). Belinostat is the third HDAC inhibitor to receive accelerated approval for PTCL, after vorinostat (Zolinza) and pralatrexate (Folotyn). It exhibits a safety profile considered acceptable for HDAC inhibitors, with less than 25% of patients reporting adverse effects such as nausea, fatigue, pyrexia, anemia, and emesis.

Uses

Used in Oncology:
Belinostat (PXD101) is used as an antineoplastic agent for the treatment of hematological malignancies and solid tumors associated with peripheral T-cell lymphoma (PTCL). It functions as a histone deacetylase 3 selective inhibitor, protecting the β cells from cytokine-induced apoptosis and modulating oncological signaling pathways.
Used in Drug Development:
Belinostat (PXD101) is used as a research compound in the development of novel histone deacetylase inhibitors for various cancer treatments. Its success as an approved drug for PTCL has paved the way for further research into HDAC inhibitors and their potential applications in oncology.
Used in Pharmaceutical Industry:
Belinostat (PXD101) is used as a therapeutic agent in the pharmaceutical industry for the treatment of specific types of cancer, including hematological malignancies and solid tumors associated with peripheral T-cell lymphoma (PTCL). Its role as an HDAC inhibitor makes it a valuable asset in the fight against cancer, offering a targeted approach to treatment.

Synthesis

Commercially available 3-bromobenzenesulfonyl chloride (41) was reacted with aniline in the presence of aqueous sodium carbonate to deliver sulfonamide 42 in 94% yield. Next, this aryl bromide was subjected to a Heck reaction involving ethyl acrylate to give rise to cinnamate ester 43, which was immediately saponified under basic conditions and acidic workup to furnish the corresponding acid 44. This acid was activated as the corresponding acid chloride prior to subjection to hydroxylamine under basic conditions to form the hydroxamic acid, which was then recrystallized from an 8:1 ethanol/water mixture in the presence of a catalytic amount of sodium bicarbonate to furnish crystalline belinostat (VI) in 87% overall yield from acid 44.

InChI:InChI=1/C15H14N2O4S/c18-15(16-19)10-9-12-5-4-8-14(11-12)22(20,21)17-13-6-2-1-3-7-13/h1-11,17,19H,(H,16,18)/b10-9+

Upstream product

• 62-53-3 aniline 
• 20677-52-5 3-chlorobenzenesulphonic acid 
• 412268-99-6 C₁₆H₁₅NO₄S 
• 866324-02-9 methyl 3-[(phenylamino)sulfonyl]benzenecarboxylate 
• 2565-10-8 sodium 3-(methoxycarbonyl)benzenesulfonate 
• 17625-03-5 m-sulfobenzoic acid, monosodium salt 
• 405058-54-0 3-(hydroxymethyl)-N-phenylbenzenesulfonamide 
• 412269-00-2 C₁₅H₁₃NO₄S 
• 405058-55-1 3-formyl-N-phenylbenzene-1-sulfonamide 

Downstream Products

• 866323-14-0 belinostat 

Relevant articles and documents

Method for preparing belinostat

The invention discloses a method for preparing belinostat. The method comprises the following steps: carrying out an amidation reaction by taking m-chlorobenzene sulfonic acid and phenylamine as raw materials so as to obtain 3-chloro-N-benzenesulfonanilide; carrying out a Heck reaction by taking 3-chloro-N-benzenesulfonanilide and ethyl acrylate as raw material so as to obtain 3-ethyl acrylate-N-benzenesulfonanilide; carrying out a hydroxylation reaction by taking 3-ethyl acrylate-N-benzenesulfonanilide and hydroxylamine hydrochloride as raw materials, thereby obtaining the belinostat. The method for preparing belinostat provided by the invention is cheap and readily available in raw materials, convenient and simple in operation, novel in route, green and environmental-friendly, the yieldis high, and the prepared belinostat is high in purity.

A he belli department is suitable for industrial production of synthetic method

The invention provides an improved belinostatsynthesis method. According to the method, sodium m-carboxyl benzenesulfonate is taken as a starting material, and belinostat is prepared through six steps of esterification, acylation and aniline condensation, reduction, oxidation, Wittig-Horner condensation and hydrolysis as well as acylation and hydroxylamine condensation. With the adoption of the method, the production time is shortened, the reaction yield is increased, the production safety is enhanced, the environmental pollution is reduced, and the method is more suitable for industrial production.