414864-00-9

Usage

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

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

Downstream Products

• 866323-14-0 belinostat 

Relevant academic research and scientific papers

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.

Green synthetic method of belinostat

The invention belongs to the technical field of pharmaceutical chemicals, and particularly relates to a green synthetic method of belinostat. The method comprises the following steps of taking water as a solvent, and enabling the salt of hydroxylamine to react with an alkali compound to obtain a free hydroxylamine solution; adding a compound I into the free hydroxylamine solution to react, addingacid after completing the reaction to adjust a pH value to 2-9, separating out solid, filtering, and washing by using water to obtain the belinostat. According to the synthetic method, the use of a large quantity of an organic solvent is avoided, the operation is simple and convenient, the reaction route is short, the cost is low, the water is taken as a solvent and is pollution-free and environmentally friendly, and the reaction yield and the purity of target products are improved, so that the belinostat is more suitable for the requirement for industrialized production on a large scale.

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.

A method for preparing belli department he isomer (by machine translation)

The present invention provides a kind of he belli department method for preparing cis-isomer, the method uses 3-phenyl amino sulfonyl benzald as the starting material, by Wittig condensation reaction, hydrolysis, chlorinated reaction, condensation reaction and Belinostat azanol Belinostat isomer mixture, mixture in the content of the cis-isomer Belinostat than the prior art is greatly improved. The reaction to obtain the isomer mixture Belinostat Belinostat and efficient process for preparing liquid-phase chromatography of the opposite phase separation and purification, gradient elution get purity 99% of the material above Belinostat check the requirements of the impurity in a vertebrate Belinostat isomer. (by machine translation)