3986-98-9

Usage

InChI:InChI=1/C9H6OS/c11-9-6-5-7-3-1-2-4-8(7)10-9/h1-6H

Upstream product

• 614-60-8 o-Coumaric acid 
• 91-64-5 coumarin 
• 1745-81-9 o-Allylphenol 
• 5703-63-9 3,4-dihydro-2H-[1]benzopyran-2-thione 
• 74-88-4 methyl iodide 
• 119-84-6 C₆H₄(CH₂CH₂C(O)O) 
• 12086-84-9 benzothiaferrole 

Downstream Products

• 77509-74-1 o-hydroxycinnamic acid thiopiperidide 
• 3937-40-4 triphenyl arsine sulfide 
• 75424-92-9 2-[1-(4-Chloro-phenyl)-meth-(Z)-ylidene]-2H-chromene 
• 75424-89-4 2-[1-Phenyl-meth-(Z)-ylidene]-2H-chromene 
• 2963-66-8 2-(2'-Hydroxyphenyl)benzimidazole 
• 224300-20-3 2-<2-(2-hydroxyphenyl)vinyl>-4H-3,1-benzothiazine 
• 91-64-5 coumarin 
• 224300-40-7 C₃₄H₂₈N₂O₂S₂ 
• 940292-81-9 2H-chromen-2-one N-benzylthiosemicarbazone 
• 231290-32-7 4-Nitro-benzoic acid chromen-(2E)-ylidene-hydrazide 
• 5841-45-2 chromen-2-one benzoylhydrazone 
• 5841-39-4 2H-1-benzopyran-Δ²-α-malononitrile 
• 92-45-5 3-chloro-2H-chromen-2-one 

Relevant academic research and scientific papers

New chemotypes acting as isozyme-selective carbonic anhydrase inhibitors with low affinity for the offtarget cytosolic isoform II

Considering phenols and coumarins as lead molecules for obtaining non-sulfonamide inhibitors of carbonic anhydrases (CAs, EC 4.2.1.1), we screened a large number of compounds possessing diverse chemotypes, but structural features which resemble the two chemical classes. Here we report an investigation of such derivatives which do not significantly inhibit CA II, but show interesting inhibition profiles against other isozymes. Pyridine-N-oxide-2-thiophenol, thiobenzoic acid, thimerosal, two oximes derived from a six-membered-ring lactone and from coumarin; 2-hydroxyquinoline and coumaphos, were investigated as inhibitors of CA I-XIV. All these compounds did not inhibit CA II, whereas the two oximes and 2-hydroxyquinoline were low nanomolar inhibitors of CA I, IX, XII, XIII and XIV, showing a very different inhibition profile compared to sulfonamides and sulfamates. Some other compounds showed low micromolar inhibition of other isoforms of interest, such as CA VA/VB, CA VI and VII. This study demonstrates that a rather wide range of structures show low nanomolar - micromolar inhibitory activity against many CA isozymes, without inhibiting significantly the offtarget isoform CA II.

Thioxocoumarins Show an Alternative Carbonic Anhydrase Inhibition Mechanism Compared to Coumarins

A series of coumarins and the corresponding 2-thioxocoumarines were prepared and tested for their inhibition profiles against four physiologically relevant human carbonic anhydrases (hCAs, EC 4.2.1.1), isoforms hCA I, II, IX, and XII. The X-ray crystal structure of 6-hydroxy-2-thioxocoumarin bound to hCA II revealed an unprecedented and unexpected inhibition mechanism for this new class of inhibitors when compared to isostructural coumarins. Unlike coumarins which are hydrolyzed by the esterase CA activity to the corresponding 2-hydroxy-cinnamic acid derivatives, the 2-thioxocoumarin was observed intact when bound to hCA II, with its exo-sulfur atom anchored to the zinc-coordinated water molecule, whereas the scaffold establishing favorable contacts with amino acid residues from the active site. This inhibition mechanism is very different from the one observed for hydrolyzed coumarins, which occlude the entrance of the active site cavity. This versatility in the binding mode of coumarins/thioxocoumarins has important consequences for the design of isoform-selective CA inhibitors, some of which are in clinical use or clinical development for various pathologies, among which glaucoma, edema, epilepsy, neuropathic pain, and hypoxic tumors.

Modification of organic compounds with Lawesson's reagent

Application in organic synthesis of Lawesson's reagent, 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide, provides a possibility to replace an oxygen atom for a sulfur atom in the carbonyl group of ketones, esters, amides, in ether group, and also either to induce a rearrangement of the initial structure of organic compounds with or without inclusion of sulfur atoms or to lead to the formation of various types of organophosphorus compounds. The formed organosulfur compounds exhibit a wide range of biological action.

CARBONIC ANHYDRASE INHIBITORS WITH ANTIMETASTATIC ACTIVITY

Compositions for the treatment of cancer comprising coumarin and thiocoumarin derivatives of Formulas I- XII are disclosed. Said derivatives preferentially inhibit carbonic anhydrase IX and XII (which are associated with hypoxic and metastatic tumours) over inhibiting carbonic anhydrase I and II activity. The compositions therefore are suited for treatment of hypoxic or metastatic cancers due to this selective mechanism of action.

P4S10/dimethicone tandem: Efficient reagent for thionation of various aromatic amides and esters

Organosulfur compounds are valuable because of their rich and varied chemistry especially in biological field. We report a new and efficient way for thionation of various aromatic amides and esters using P4S 10/ dimethicone tandem. The ease of handling and higher yield makes this protocol economical.

Synthesis and application of a fluorous Lawesson's reagent: Convenient chromatography-free product purification

A fluorous analogue of Lawesson's reagent for thionation of carbonyl compounds has been developed and its use demonstrated on a series of amides, esters, and ketones. The separation of the Lawesson's reagent-derived byproducts can be achieved by a simple fluorous solid-phase extraction.

Microwave-accelerated solvent-free synthesis of thioketones, thiolactones, thioamides, thionoesters, and thioflavonoids

Formula presented An expeditious, solvent-free, and high yield conversion of ketones, flavones, isoflavones, lactones, amides, and esters to the corresponding thio analogues is described utilizing Lawesson's reagent in a process that circumvents the use of dry solvents and excess of the reagent.

Synthesis and reactions of 4H-3,1-benzothiazines

This study is directed towards the synthesis of the pyrrolo[1,2- a]indole skeleton which is the essential ring system of the active antitumor miomycins. To this end a number of fused heterocycles such as benzothiazines, benzoxazines, indoles and quinolines were synthesized. The structures of the new compounds were assigned by ir, 1H nmr and ms-data.

Conversion of Esters and Lactones to Ethers via Thionoesters and Thionolactones Using Reductive Radical Desulfurization

Various thionoesters and thionolactones are readily reduced into the corresponding ethers in high isolated yields by radical desulfuurization with organotin hydrides and Et3B under mild reaction conditions.

Reaction of thionolactones with zinc enolate: New synthesis of vinylogous carbonates

Reaction of various thionolactones, prepared from the lactones and Lawesson's reagent, with methyl bromozinc-acetate afforded the corresponding vinylogous carbonates in good yields under mild conditions.