342372-36-5

Basic information

• Product Name: 3-[4-(3,4-Dimethoxyphenylsulfonamido)phenyl]-2-propenohydroxamic acid
• Synonyms: PX-117794
• CAS NO: 342372-36-5
• Molecular Formula: C₁₇H₁₈N₂O₆S
• Molecular Weight: 378.40681
• Mol File: 342372-36-5.mol

Chemical Properties

• CAS DataBase Reference: 3-[4-(3,4-Dimethoxyphenylsulfonamido)phenyl]-2-propenohydroxamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[4-(3,4-Dimethoxyphenylsulfonamido)phenyl]-2-propenohydroxamic acid(342372-36-5)
• EPA Substance Registry System: 3-[4-(3,4-Dimethoxyphenylsulfonamido)phenyl]-2-propenohydroxamic acid(342372-36-5)

Safety Data

• Hazardous Substances Data: 342372-36-5(Hazardous Substances Data)

Upstream product

• 637-57-0 p-nitrocinnamic acid methyl ester 
• 23095-31-0 3,4-dimethoxybenzene-1-sulfonyl chloride 
• 66417-26-3 methyl (2E)-3-(4-aminophenyl)acrylate 
• 501682-95-7 3-[4-(3,4-Dimethoxy-benzenesulfonylamino)-phenyl]-acrylic acid 
• 333320-72-2 3,4-dimethoxy-N-(4-iodophenyl)benzenesulfonamide 
• 540-37-4 p-aminoiodobenzene 

Relevant articles and documents

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.

Polymer-assisted, multi-step solution phase synthesis and biological screening of histone deacetylase inhibitors

The polymer-assisted solution phase synthesis (PASP) of an array of histone deacetylase (HDAc) inhibitors is described. HDAc inhibitors have considerable potential as new anti-proliferative agents. Selected compounds were shown to inhibit both human endothelial cell proliferation, and the formation of tubules (neovascularisation) in an in vitro model of angiogenesis.

Development of potential antitumor agents. Synthesis and biological evaluation of a new set of sulfonamide derivatives as histone deacetylase inhibitors

A series of sulfonamide hydroxamic acids and anilides have been synthesized and studied as histone deacetylase (HDAC) inhibitors that can induce hyperacetylation of histones in human cancer cells. The inhibition of HDAC activity represents a novel approach for intervening in cell cycle regulation. The lead candidates were screened in a panel of human tumor and normal cell lines. They selectively inhibit proliferation, cause cell cycle blocks, and induce apoptosis in human cancer cells but not in normal cells. The structure-activity relationships, the antiproliferative activity, and the in vivo efficacy are described.

Design and synthesis of a novel class of histone deacetylase inhibitors.

Histone deacetylase inhibitors (HDACs) have emerged as a novel class of antiproliferative agents. Utilizing structure-based design, the synthesis of a series of sulfonamide hydroxamic acids is described. Further optimization of this series by substitution of the terminal aromatic ring yielded HDAC inhibitors with good in vitro and in vivo activities.