5751-82-6

Usage

Chemical Properties

Colorless to light yellow liquid

InChI:InChI=1/C7H7ClO2S/c1-2-10-7(9)5-3-4-6(8)11-5/h3-4H,2H2,1H3

Upstream product

• 24065-33-6 5-Chlorothiophene-2-carboxylic acid 
• 64-17-5 ethanol 
• 2873-18-9 5-bromo-2-chlorothiophene 
• 1609-47-8 diethyl dicarbonate 
• 75-03-6 ethyl iodide 
• 6310-09-4 2-acetyl-5-chlorothiophene 
• 3437-95-4 2-Iodothiophene 
• 56-23-5 tetrachloromethane 
• 1003-09-4 2-bromothiophene 
• 96-43-5 2-thienyl chloride 
• 42518-98-9 5-chlorothiophene-2-carbonyl chloride 

Downstream Products

• 351983-31-8 5-chloro-2-thiophenecarboxylic acid hydrazide 
• 202336-16-1 5-chlorothiophene-2-carboxamidine hydrochloride 
• 89640-03-9 ethyl 5‐chloro‐4‐nitrothiophene‐2‐carboxylate 
• 943780-16-3 (S)-5-(4-aminophenylthio)-4-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)-N-(2-phenylpropyl)thiophene-2-carboxamide 
• 943780-19-6 ethyl 5-(4-(((9H-fluoren-9-yl)methoxy)carbonylamino)phenylthio)-4-aminothiophene-2-carboxylate 
• 943780-18-5 ethyl 5-(4-(((9H-fluoren-9-yl)methoxy)carbonylamino)phenylthio)-4-nitrothiophene-2-carboxylate 
• 943780-21-0 5-(4-aminophenylthio)-4-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)thiophene-2-carboxylic acid 
• 943780-17-4 ethyl 5-(4-aminophenylthio)-4-nitrothiophene-2-carboxylate 
• 1007578-47-3 ethyl 5-(3-{[2,2-bis(ethyloxy)ethyl]oxy}phenyl)-2-thiophene carboxylate 
• 1007578-70-2 5-{3-[(2-Chloroethyl)oxy]phenyl}-2-thiophenecarboxamide 
• 1007578-72-4 5-(3-Hydroxyphenyl)-2-thiophenecarboxamide 
• 1007578-71-3 ethyl 5-{3-[(2-oxoethyl)oxy]phenyl}-2-thiophenecarboxylate 
• 130562-97-9 4,5-dichloro-2-thiophenecarboxylic acid ethyl ester 
• 74168-69-7 5-chloro-2-thiophenemethanol 

Relevant academic research and scientific papers

4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-β-lactamase inhibitors

In Gram-negative bacteria, the major mechanism of resistance to β-lactam antibiotics is the production of one or several β-lactamases (BLs), including the highly worrying carbapenemases. Whereas inhibitors of these enzymes were recently marketed, they only target serine-carbapenemases (e.g. KPC-type), and no clinically useful inhibitor is available yet to neutralize the class of metallo-β-lactamases (MBLs). We are developing compounds based on the 1,2,4-triazole-3-thione scaffold, which binds to the di-zinc catalytic site of MBLs in an original fashion, and we previously reported its promising potential to yield broad-spectrum inhibitors. However, up to now only moderate antibiotic potentiation could be observed in microbiological assays and further exploration was needed to improve outer membrane penetration. Here, we synthesized and characterized a series of compounds possessing a diversely functionalized alkyl chain at the 4-position of the heterocycle. We found that the presence of a carboxylic group at the extremity of an alkyl chain yielded potent inhibitors of VIM-type enzymes with Ki values in the μM to sub-μM range, and that this alkyl chain had to be longer or equal to a propyl chain. This result confirmed the importance of a carboxylic function on the 4-substituent of 1,2,4-triazole-3-thione heterocycle. As observed in previous series, active compounds also preferentially contained phenyl, 2-hydroxy-5-methoxyphenyl, naphth-2-yl or m-biphenyl at position 5. However, none efficiently inhibited NDM-1 or IMP-1. Microbiological study on VIM-2-producing E. coli strains and on VIM-1/VIM-4-producing multidrug-resistant K. pneumoniae clinical isolates gave promising results, suggesting that the 1,2,4-triazole-3-thione scaffold worth continuing exploration to further improve penetration. Finally, docking experiments were performed to study the binding mode of alkanoic analogues in the active site of VIM-2.

Addressing the Glycine-Rich Loop of Protein Kinases by a Multi-Facetted Interaction Network: Inhibition of PKA and a PKB Mimic

Protein kinases continue to be hot targets in drug discovery research, as they are involved in many essential cellular processes and their deregulation can lead to a variety of diseases. A series of 32 enantiomerically pure inhibitors was synthesized and tested towards protein kinase A (PKA) and protein kinase B mimic PKAB3 (PKA triple mutant). The ligands bind to the hinge region, ribose pocket, and glycine-rich loop at the ATP site. Biological assays showed high potency against PKA, with Ki values in the low nanomolar range. The investigation demonstrates the significance of targeting the often neglected glycine-rich loop for gaining high binding potency. X-ray co-crystal structures revealed a multi-facetted network of ligand-loop interactions for the tightest binders, involving orthogonal dipolar contacts, sulfur and other dispersive contacts, amide-π stacking, and H-bonding to organofluorine, besides efficient water replacement. The network was analyzed in a computational approach.

NOVEL SUBSTITUTED CONDENSED PYRIMIDINE COMPOUNDS

Novel substituted condensed pyrimidine compounds of general formula (I) in which the chemical groupings, substituents and indices are as defined in the description, and to their use as medicaments, in particular as medicaments for the treatment of conditions and diseases that can be treated by inhibition of the PDE4 enzyme.

Direct conversion of aromatic ketones to arenecarboxylic esters via carbon-carbon bond-cleavage reactions

Aromatic methyl ketones, ss-keto esters, and trifluoromethyl-l,3- diketones can be directly converted to arene-carboxylic esters via carbon-carbon bond cleavage of pyridinium iodide intermediates in the presence of copper(II) oxide, iodine, pyridine, and potassium carbonate in alcoholic media. The advantages of the present method in terms of good yields, mild reaction conditions, and inexpensive reagents should make this protocol a valuable alternative to the existing methods.

Synthesis of 2-thiophenecarboxylic and 2,5-thiophenedicarboxylic acid esters via the reaction of thiophenes with the CCl4-ROH reagent in the presence of vanadium, iron, and molybdenum catalysts

2-Thiophenecarboxylic and 2,5-thiohenedicarboxylic acid esters were synthesized via the reaction of thiophene with the CCl4-ROH-catalyst system, with a total yield of 44-85%. A possible reaction scheme includes the successive steps of alkylation of thiophene with carbon tetrachloride, leading to 2-trichloromethylthiophene, and alcoholysis of the product giving the corresponding 2-thiophenecarboxylate. The best catalysts for this reaction are VO(acac)2, Fe(acac)3, and Mo(CO)6.

A simple and facile carboxylation method and its application for synthesis of liquid crystals

Sonication of a mixture of magnesium powder, 1,2-dibromoethane, aryl bromide and diethyl dicarbonate in THF followed by treatment with BF 3·OEt2 at room temperature afforded aryl ester with reasonable yield. A series of aryl bromides were investigated and transformed to their corresponding aryl esters under the reaction conditions.

Phosphorylamides, their preparation and use

A phosphorylamide derivative represented by the general formula (I): STR1 wherein R represents an amino group that may be substituted, or a salt thereof, possesses potent antibacterial activity against Helicobacter bacterium, especially Helicobacter pylori, and is useful for prevention or treatment of digestive diseases caused by Helicobacter bacterium, solely or in combination with an antacid or an acid secretion inhibitor.