16979-15-0

Usage

Type of compound

Heterocyclic compound

Structure

Tricyclic structure containing a benzene ring fused to both a thiophene and an oxygen-containing heterocycle

Common uses

Building block in the synthesis of various pharmaceuticals and agrochemicals

Potential applications

a. Corrosion inhibitor
b. Photochromic material (changes color when exposed to light)
c. Organic electronics
d. Antioxidant in polymer materials

InChI:InChI=1/C8H6O3S/c9-12(10)6-5-7-3-1-2-4-8(7)11-12/h1-6H

Upstream product

• 90-02-8 salicylaldehyde 
• 49670-40-8 2-methanesulfonyloxybenzaldehyde 

Downstream Products

• 1380035-70-0 C₁₄H₁₂O₃S 

Relevant academic research and scientific papers

Deciphering the Mechanism of Human Carbonic Anhydrases Inhibition with Sulfocoumarins: Computational and Experimental Studies

The reaction mechanism of the carbonic anhydrase-mediated hydrolysis of sulfocoumarins to sulfonic acids has been investigated on an enzyme cluster model using the B3LYP hybrid density functional theory (DFT) and the QST procedure for the Transition State (TS) search. A multistep process was highlighted, with the rate-determining step identified in the initial dual nucleophilic/acidic attack of the zinc-bound hydroxide ion to the sulfocoumarin sulfur atom and to the C3=C4 double bond. The reported multi-step process, combined to SAR analysis on a new set of derivatives, highlighted unprecedented mechanistic aspects of the CA-mediated prodrug activation, which in turn possess relevant consequences to the isoforms-selective inhibition profiles reported by such a class of compounds.

Glyoxalase 1 and 2 enzyme inhibitory activity of 6-sulfamoylsaccharin and sulfocoumarin derivates

The glyoxalase enzymes represent a cellular defence system against the accumulation of cytotoxic α-oxoaldehydes leading to apoptosis. The potential of glyoxalase inhibitors to act as novel anti-cancer agents for drugresistant tumours that over-express gly

Facile synthesis of coumarin bioisosteres - 1,2-benzoxathiine 2,2-dioxides

A simple and reproducible procedure for the synthesis of bioisosteres of coumarin - 1,2-benzoxathiine 2,2-dioxide is presented. The developed method is based on the intramolecular aldol cyclization of derivatives of mesylsalicyl aldehydes in the presence

Effect of chiral diene ligands in rhodium-catalyzed asymmetric addition of arylboronic acids to α,β-unsaturated sulfonyl compounds

Asymmetric addition of arylboronic acids to α,β-unsaturated sulfonyl compounds proceeded in the presence of a rhodium catalyst coordinated with a chiral diene ligand to give high yields of the addition products with high enantioselectivity (96->99.5% ee). The diene ligand was proved to be essential for the formation of the addition products, while the use of a bisphosphine ligand mainly gave the cine-substitution product.