866323-87-7

Usage

Uses

Used in Pharmaceutical Industry:
2-Propenoic acid, 3-[3-[(phenylamino)sulfonyl]phenyl]-, (2E)is used as a pharmaceutical agent for its ability to protect β cells from cytokine-induced apoptosis. This makes it a potential candidate for the development of treatments targeting conditions such as diabetes, where β cell preservation is crucial for maintaining glucose homeostasis.
Additionally, as a metabolite of Belinostat, a histone deacetylase 3 selective inhibitor, it may also have potential applications in the treatment of various diseases where histone deacetylase 3 plays a significant role, such as cancer and neurodegenerative disorders. Further research is needed to explore its therapeutic potential in these areas.

Upstream product

• 2905-24-0 3-Bromobenzenesulfonyl chloride 
• 1159834-58-8 ethyl (E)-3-(3-(chlorosulfonyl)phenyl)prop-2-enoate 
• 125872-97-1 ethyl (E)-3-(3-aminophenyl)acrylate 
• 621-19-2 (E)-ethyl 3-(3-nitrophenyl)acrylate 
• 99-61-6 3-nitro-benzaldehyde 
• 62-53-3 aniline 
• 53460-88-1 3-formylbenzenesulfonyl chloride 
• 4657-12-9 sodium hydroxy(phenyl)methanesulfonate 
• 100-52-7 benzaldehyde 
• 936-51-6 2-phenyl-1,3-dioxolane 
• 405058-55-1 3-formyl-N-phenylbenzene-1-sulfonamide 
• 141-82-2 malonic acid 
• 610801-83-7 methyl (2E)-3-[3-(chlorosulfonyl)phenyl]prop-2-enoate 
• 866323-86-6 methyl (2E)-3-{3-[(phenylamino)sulfonyl]phenyl}prop-2-enoate 

Downstream Products

• 866323-14-0 belinostat 

Relevant academic research and scientific papers

COMPOUNDS AND METHODS FOR TREATING CANCER

Substituted cinnamamide compounds and analogs, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or ameliorate cancer are provided.

Biocompatible Boron-Containing Prodrugs of Belinostat for the Potential Treatment of Solid Tumors

Despite promising therapeutic utilities for treatment of hematological malignancies, histone deacetylase inhibitor (HDACi) drugs have not proven as effective in the treatment of solid tumors. To expand the clinical indications of HDACi drugs, we developed novel boron-containing prodrugs of belinostat (2), one of which efficiently releases active 2 through a cascade of reactions in cell culture and demonstrates activities comparable to 2 against a panel of cancer cell lines. Importantly, prodrug 7 is more efficacious than belinostat in vivo, not only inhibiting the growth of tumor but also reducing tumor volumes in an MCF-7 xenograft tumor model owing to its superior biocompatibility, which suggests its clinical potential in the treatment of solid tumors.

NOVEL PROCESS FOR THE PREPARATION OF BELINOSTAT

The present invention provides a novel and commercially viable process with high yield for the preparation of (E)-N-hydroxy-3-(3-phenylsulfamoyl-phenyl)-acrylamide, also known as Belinostat (I). The invention also provides process for purification and nov

Synthesis method of belinostat

The invention discloses a synthesis method of belinostat. The method comprises the following steps: by using benzoic acid as an initial material, performing six reaction steps of chlorosulfonation, aniline condensation, reduction, oxidation, Witting-Horner condensation and hydrolysis, acylating chlorination and hydroxylamine condensation to prepare a target compound. The initial material benzoic acid of the method is cheap and easy to obtain, the sulfonylation and acylating chlorination reaction are realized through one step, the preparation time is shortened, and the yield is improved. In the oxidation process, an oxidizing reagent which is cheap and does not contains metal ion is adopted so that the active ingredients easily achieve the requirement of heavy metal ion limitation, and the pollution to the environment is reduced. All reaction intermediates of the method are solid and can be purified through a salt formation or recrystallization method, the time-consuming and labor-consuming column chromatography purification is avoided, and the method is suitable for industrial production.

The Development of an Effective Synthetic Route of Belinostat

A practical synthetic route of belinostat is reported. Belinostat was obtained via a five-step process starting from benzaldehyde and including addition reaction with sodium bisulfite, sulfochlorination with chlorosulfonic acid, sulfonamidation with aniline, Knoevenagel condensation, and the final amidation with hydroxylamine. Key to the strategy is the preparation of 3-formylbenzenesulfonyl chloride using an economical and practical protocol. The main advantages of the route include inexpensive starting materials and acceptable overall yield. The scale-up experiment was carried out to provide 169 g of belinostat with 99.6% purity in 33% total yield.

METHODS OF SYNTHESIS OF CERTAIN HYDROXAMIC ACID COMPOUNDS

The present invention pertains to the general field of chemical synthesis, and more particularly to methods for the synthesis of certain hydroxamic acid compounds, and in particular, (E)-N-hydroxy-3-(3-phenylsulfamoyl-phenyl)-acrylamide, also known as PXD

Novel sulfonamide derivatives as inhibitors of histone deacetylase

Inhibition of the enzyme histone deacetylase (HDAC) is emerging as a novel approach to the treatment of cancer. A series of novel sulfonamide derivatives were synthesized and evaluated for their ability to inhibit human HDAC. Compounds were identified which are potent enzyme inhibitors, with IC 50 values in the low nanomolar range against enzyme obtained from HeLa cell extracts, and with antiproliferative effects in cell culture. Extensive characterization of the structure - activity relationships of this series identified key requirements for activity. These include the direction of the sulfonamide bond and substitution patterns on the central phenyl ring. The alkyl spacer between the aromatic head group and the sulfonamide functionality also influenced the HDAC inhibitory activity. One of these compounds, m11.1, also designated PXD101, has entered clinical trials for solid tumors and haematological malignancies.

Carbamic acid compounds comprising a sulfonamide linkage as hdac inhibitors

This invention pertains to certain active carbamic acid compounds which inhibit HDAC activity and which have the following formula: (I) A is an aryl group; Q1 is a covalent bond or an aryl leader group; J is a sulfonamide linkage selected from: —S (═O)2NR1— and —NR1S(═O)2—; R1 is a sulfonamido substituent; and, Q2 is an acid leader group; with the proviso that if J is —S(═O)2NR1—, then Q1 is an aryl leader group; and pharmaceutically acceptable salts, solvates, amides, esters, ethers, chemically protected forms, and prodrugs thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit HDAC, and, e.g., to inhibit proliferative conditions, such as cancer and psoriasis.