10341-88-5

Usage

Chemical Properties

Yellow Solid

Uses

An intermediate in the preparation of PARP inhibitors.

InChI:InChI=1/C11H8O2S/c12-11(13)10-9(6-7-14-10)8-4-2-1-3-5-8/h1-7H,(H,12,13)

Upstream product

• 930-96-1 3-bromo-2-thiophenecarboxaldehyde 
• 98-80-6 phenylboronic acid 
• 124-38-9 carbon dioxide 
• 2404-87-7 3-phenylthiophene 
• 527-72-0 2-thiophenylcarboxylic acid 
• 591-50-4 iodobenzene 
• 7311-64-0 3-bromothiophene-2-carboxylic acid 
• 62353-77-9 3-iodothiophene-2-carboxylic acid methyl ester 
• 21676-89-1 methyl 3-phenylthiophene-2-carboxylate 
• 108-86-1 bromobenzene 
• 26170-85-4 3-Phenyl-2-thiophenecarboxaldehyde 
• 26137-08-6 methyl 3-bromothiophene-2-carboxylate 
• 4347-31-3 2-formylthiophene-3-boronic acid 

Downstream Products

• 873581-61-4 (3-phenyl-thiophen-2-yl)-carbamic acid tert-butyl ester 
• 1047672-37-6 1-azabicyclo[2.2.2]oct-4-yl (3-phenyl-2-thienyl)carbamate 
• 21676-89-1 methyl 3-phenylthiophene-2-carboxylate 
• 1579940-00-3 2-(3-phenyl-thiophen-2-ylcarbamoyl)-cyclopent-1-enecarboxylic acid 
• 1293280-54-2 2-(4,6-dimethylpyrimidin-2-yl)-5-[(3-phenylthiophen-2-yl)carbonyl]octahydropyrrolo[3 ,4-c]pyrrole 
• 420849-22-5 TIQ-A 

Relevant academic research and scientific papers

Towards new neuroprotective agents: Design and synthesis of 4H-thieno[2,3-c] isoquinolin-5-one derivatives as potent PARP-1 inhibitors

An excessive activation of poly(ADP-ribose) polymerase-1 (PARP-1), a nuclear enzyme able to catalyze the transfer of ADP-ribose from NAD to acceptor proteins, is involved in the progression of neuronal damage after brain insult. Potent and selective PARP-

Continuous flow synthesis of thieno[2,3-c ]isoquinolin-5(4 H)-one scaffold: A valuable source of PARP-1 inhibitors

An efficient multistep method for the continuous flow synthesis of thieno[2,3-c]isoquinolin-5(4H)-one-A (TIQ-A), an important pharmacological tool and building block for PARP-1 inhibitors, has been developed. The synthesis involves a Suzuki coupling reaction to generate 3-phenylthiophene-2-carboxylic acid which is transformed into the corresponding acyl azide and readily cyclized by a thermal Curtius rearrangement. A statistical design of experiments (DoE) was employed as a valuable support for decision-making of further experiments enabling the development of a robust and reliable protocol for large-scale preparation. As a result, the reactions are facile, safe, and easy to scale-up. The large-scale applicability of this improved flow method was tested by conducting the reactions on multigram scale to produce the desired product in high yield and quality for biopharmacological appraisals.

Visible-Light-Induced Arene C(sp 2)-H Lactonization Promoted by DDQ and tert -Butyl Nitrite

A visible-light photocatalytic aerobic oxidative lactonization of arene C(sp 2)-H bonds proceeds in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and tert -butyl nitrite (TBN). Under the optimized conditions, a range of 2-arylbenzoic acids is converted into the corresponding benzocoumarin derivatives in moderate to excellent yields. This method is characterized by its atom economy, mild reaction conditions, the use of a green oxidant and metal-free catalysis.

Ruthenium-Catalyzed C-H Arylation of Diverse Aryl Carboxylic Acids with Aryl and Heteroaryl Halides

Ruthenium ligated to tricyclohexylphosphine or di-tert-butylbipyridine catalyzes the arylation of carboxylic acids with diverse aryl halides (iodide, bromide, and triflate; aryl and heteroaryl). In addition, arylations with 2-iodophenol formed benzochromenones, carboxylate was shown to be a stronger donor than an amide, and the arylation of a pyridine carboxylate was demonstrated. Stoichiometric studies demonstrated that the added ligand is required for reaction with the electrophile but not the C-H bond.

Silver-Catalyzed C(sp2)-H Functionalization/C-O Cyclization Reaction at Room Temperature

Silver-catalyzed C(sp2)-H functionalization/C-O cyclization has been developed. The scalable reaction proceeds at room temperature in an open flask. The present method exhibits good functional-group compatibility because of the mild reaction conditions. Using a AgNO3 catalyst and a (NH4)2S2O8 oxidant in CH2Cl2/H2O solvent, various lactones are obtained in good to excellent yields. A kinetic isotope effect (KIE) study indicates that the reaction may occur via a radical process.

New non-annulated thiophenylamides

The invention provides novel compounds having the general formula (I) wherein R1, R2, R3, R4, R5, R6, R7, A, E and n are as described herein, compositions including the compounds and methods of using the compounds.

Novel quinuclidinyl heteroarylcarbamate derivatives as muscarinic receptor antagonists

Herein, we describe the synthesis and pharmacological profiles of novel quinuclidinyl heteroarylcarbamate derivatives. Among them, the quinuclidin-4-yl thiazolylcarbamate derivative ASP9133 was identified as a promising long-acting muscarinic antagonist (LAMA) showing more selective inhibition of bronchoconstriction against salivation and more rapid onset of action in a rat model than tiotropium bromide.

NON-ANNULATED THIOPHENYLAMIDES AS INHIBITORS OF FATTY ACID BINDING PROTEINI(FABP) 4 AND/OR 5

The invention provides novel compounds having the general formula (I), wherein R1, R2, R3, R4, R5, R6 , R7, A, E and n are as described herein, compositions including the compounds and methods of using the compounds.

Thieno[2,3-c]iosquinolines for use as inhibitors of parp

Heterocyclic derivatives, including derivatives of thieno[2,3-c]isoquinolin-3-one and their use in therapy as inhibitors of poly(ADP-ribose) polymers (PARP), for use in the prevention and treatment of tissue damage due to ischaemia and reperfusion, degene