1075-14-5

Upstream product

• 81536-29-0 2-mercaptocinnamic acid 
• 108-24-7 acetic anhydride 
• 254-37-5 2H-thiochromene 
• 81536-24-5 trans-3-(2-mercaptophenyl)-2-propenoic acid ethyl ester 
• 81536-21-2 ethyl 2-mercaptodihydrocinnamate 
• 102-92-1 Cinnamoyl chloride 
• 140-10-3 (E)-3-phenylacrylic acid 
• 1664-63-7 2-amino-cinnamic acid 
• 108-98-5 thiophenol 
• 70030-52-3 (E)-S-phenyl 3-phenylprop-2-enethioate 
• 7664-93-9 sulfuric acid 
• 5962-02-7 Dihydro-3,4 thio-1 coumarine 

Relevant academic research and scientific papers

A stereoselective synthetic route to (E)-α,β-unsaturated thioesters

Terminal alkynes 1 react with Cp2Zr(H)Cl (Cp = η5-C5H5) and CO to give acylzirconocene chloride derivatives 2, which are trapped with arylsulfenyl chlorides to afford (E)-α,β-unsaturated thioesters.

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.

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.

META-GUANIDINE, UREA, THIOUREA OR AZACYCLIC AMINO BENZOIC ACID DERIVATIVES AS INTEGRIN ANTAGONISTS

The present invention relates to a class of compounds represented by the Formula Ior a pharmaceutically acceptable salt thereof, whereinA ispharmaceutical compositions thereof and methods of using such compounds and compositions as alphavbeta3 antagonists.

Biotransformation of Unsaturated Heterocyclic Rings by Pseudomonas putida to Yield cis-Diols

New cis-diols metabolites of both aromatic and non-aromatic heterocyclic rings have been isolated from growing cultures of a mutant strain of the soil bacterium Pseudomonas putida (UV4) and stereochemically assigned; a novel heterocyclic cis-diol of benzothiophene, 2,3-dihydroxy-2,3-dihydrobenzothiophene is found to exist exclusively in the cis-configuration in water but equilibrates readily with the trans-isomer.