104093-04-1

Basic information

• Product Name: 2-(7-Hydroxy-2-oxo-2H-chromen-3-yl)acetic acid
• Synonyms: 2-(7-Hydroxy-2-oxo-2H-chromen-3-yl)acetic acid
• CAS NO: 104093-04-1
• Molecular Formula: C11H8O5
• Molecular Weight: 220.17822
• Mol File: 104093-04-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(7-Hydroxy-2-oxo-2H-chromen-3-yl)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(7-Hydroxy-2-oxo-2H-chromen-3-yl)acetic acid(104093-04-1)
• EPA Substance Registry System: 2-(7-Hydroxy-2-oxo-2H-chromen-3-yl)acetic acid(104093-04-1)

Safety Data

• Hazardous Substances Data: 104093-04-1(Hazardous Substances Data)

Usage

Derivative of coumarin

umbelliferone acetic acid
Commonly found in plants such as citrus fruits
Antioxidant and anti-inflammatory properties

Potential therapeutic effects

ability to inhibit the growth of certain types of cancer cells and potential use as a treatment for diabetes and other metabolic disorders
Used in the development of novel pharmaceutical drugs due to its interesting pharmacological properties.

Upstream product

• 108-30-5 succinic acid anhydride 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 150-90-3 sodium succinate 
• 108-46-3 recorcinol 

Relevant articles and documents

PSORALEN DERIVATIVES AS NON-PEPTIDIC INHIBITORS OF CHYMOTRYPSIN-LIKE ACTIVITY OF THE IMMUNOPROTEASOME

This invention relates to new inhibitors of chymothrypsin-like activity of the immunoproteasome (inhibitors of β5? or LMP7 subunit) with the general formula (I), where substituents are described in patent description. Compounds can be in the form of pure enantiomers or as racemic mixtures, or in the form of pharmaceutically acceptable salts. The present invention relates to the use of these inhibitors for the treatment of diseases where immunoproteasome activity is increased.

Nonpeptidic Selective Inhibitors of the Chymotrypsin-Like (β5 i) Subunit of the Immunoproteasome

Elevated expression of the immunoproteasome has been associated with autoimmune diseases, inflammatory diseases, and various types of cancer. Selective inhibitors of the immunoproteasome are not only scarce, but also almost entirely restricted to peptide-based compounds. Herein, we describe nonpeptidic reversible inhibitors that selectively block the chymotrypsin-like (β5i) subunit of the human immunoproteasome in the low micromolar range. The most potent of the reversibly acting compounds were then converted into covalent, irreversible, nonpeptidic inhibitors that retained selectivity for the β5i subunit. In addition, these inhibitors discriminate between the immunoproteasome and the constitutive proteasome in cell-based assays. Along with their lack of cytotoxicity, these data point to these nonpeptidic compounds being suitable for further investigation as β5i-selective probes for possible application in noncancer diseases related to the immunoproteasome.

Microwave assisted one pot synthesis of 7-substituted 2-(2-oxo-2H-chromen-3-yl)acetic acids as precursors of new anti-tumour compounds

Perkin condensation with subsequent intramolecular lactonisation as one pot syntheses of 2-(2-oxo-2H-chromen-3-yl)acetic acids VIIa-Xa has been studied. The required acids VIIa-Xa were prepared as precursors of recently discovered compounds possessing antineoplastic activities. Syntheses of VIIa-Xa were carried out using para substituted 2-hydroxybenzaldehydes II-VI, succinic acid anhydride, sodium succinate under thermal or microwave conditions. Significant shortening of the reaction time under microwave irradiation was observed (18-50 min instead of 1.5-5 h of heating). Microwave assisted reactions proceeded more smoothly to give higher yield of the required products VIIa-Xa (31-61 %) compared to those under classical thermal conditions e.g. 21.8 % for IXa (Hurenkamp et al., 2007). Seven reaction by-products were isolated and determined as 2H,2′H-3,3′-bichromene-2,2′-diones VIIb-Xb and (E)-3-(2-hydroxystyryl)-2H-chromen-2-ones VIIc-IXc.