60598-68-7

Usage

Class

Belongs to the class of organic compounds known as benzothiophenes, which are fused benzene and thiene rings

Classification

Also classified as a carboxamide

Molecular weight

268.36 g/mol

Melting point

225-227°C

Potential uses

May have potential uses in pharmaceuticals, agrochemicals, or materials science due to its structural features

Upstream product

• 108-94-1 cyclohexanone 
• 62-53-3 aniline 
• 621-03-4 cyanoacetanilide 
• 89733-13-1 α-cyclohexylidenecyanoacetanilide 

Downstream Products

• 85930-49-0 N-(3-Phenylcarbamoyl-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)-malonamic acid ethyl ester 
• 1246527-86-5 3-N-phenyl-4,5-tetramethylene thieno-[2,3-d][1,2,3]-triazin-4(3H)-one 
• 142465-23-4 1-hydroxy-4-phenyl-6,7,8,9-tetrahydro<1,2,4>triazolo<4,3-a>benzothieno<3,2-e>pyrimidin-5(4H)-one 
• 142465-24-5 1-Amino-4-phenyl-6,7,8,9-tetrahydro-4H-10-thia-2,3,4,10b-tetraaza-cyclopenta[a]fluoren-5-one 
• 142465-26-7 1-benzoylamino-4-phenyl-6,7,8,9-tetrahydro<1,2,4>triazolo<4,3-a>benzothieno<3,2-e>pyrimidin-5(4H)-one 
• 142465-16-5 2-(N-benzoyl)hydrazino-3-phenyl-6,7,8,9-tetrahydrobenzothieno<2,3-d>pyrimidin-4-one 
• 142465-27-8 1,4-diphenyl-6,7,8,9-tetrahydro<1,2,4>triazolo<4,3-a>benzothieno<3,2-e>pyrimidin-5(4H)-one 
• 142465-21-2 1-Ethyl-4-phenyl-6,7,8,9-tetrahydro-4H-10-thia-2,3,4,10b-tetraaza-cyclopenta[a]fluoren-5-one 
• 142465-14-3 2-azido-3-phenyl-5,6,7,8-tetrahydrobenzothieno<2,3-d>pyrimidin-4(3H)-one 
• 142465-22-3 1-mercapto-4-phenyl-6,7,8,9-tetrahydro<1,2,4>triazolo<4,3-a>benzothieno<3,2-e>pyrimidin-5(4H)-one 
• 142465-19-8 1-methyl-4-phenyl-6,7,8,9-tetrahydrobenzo[4,5]thieno[3,2-e][1,2,4]triazolo[4,3-a]pyrimidine-5(4H)-one 
• 142465-17-6 4-phenyl-6,7,8,9-tetrahydro-<1>benzothieno<3,2-e><1,2,4>triazolo<4,3-a>pyrimidin-5(4H)-one 
• 142465-12-1 2-hydrazinyl-3-phenyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one 
• 27285-14-9 2-Hydroxy-3-phenyl-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 

Relevant academic research and scientific papers

Barium aluminate nano-powders efficient catalyst for the synthesis of novel benzo[b]thiophene, thieno[2,3-c]thiopyran and thieno[2,3-c]pyridine derivatives

Uniform nanopowders of barium aluminate (BaAl2O4) can be synthesized by a facile solution reaction at room temperature using barium and aluminum salts and 2-aminoethanol as a precipitating agent. The asprepared sample showed a good reactivity in the synthesis of benzo[b]thiophene, thieno[2,3-c]thiopyran and thieno[2,3-c]pyridine derivatives. Comparatively the method is efficient and eco-friendly, and finally, a range of compounds with variable functionalities in excellent yield can be achieved.

Substituted 2-Acylaminocycloalkylthiophene-3-carboxylic Acid Arylamides as Inhibitors of the Calcium-Activated Chloride Channel Transmembrane Protein 16A (TMEM16A)

Transmembrane protein 16A (TMEM16A), also called anoctamin 1 (ANO1), is a calcium-activated chloride channel expressed widely mammalian cells, including epithelia, vascular smooth muscle tissue, electrically excitable cells, and some tumors. TMEM16A inhibitors have been proposed for treatment of disorders of epithelial fluid and mucus secretion, hypertension, asthma, and possibly cancer. Herein we report, by screening, the discovery of 2-acylaminocycloalkylthiophene-3-carboxylic acid arylamides (AACTs) as inhibitors of TMEM16A and analysis of 48 synthesized analogs (10ab-10bw) of the original AACT compound (10aa). Structure-activity studies indicated the importance of benzene substituted as 2- or 4-methyl, or 4-fluoro, and defined the significance of thiophene substituents and size of the cycloalkylthiophene core. The most potent compound (10bm), which contains an unusual bromodifluoroacetamide at the thiophene 2-position, had IC50 of ～30 nM, ～3.6-fold more potent than the most potent previously reported TMEM16A inhibitor 4 (Ani9), and >10-fold improved metabolic stability. Direct and reversible inhibition of TMEM16A by 10bm was demonstrated by patch-clamp analysis. AACTs may be useful as pharmacological tools to study TMEM16A function and as potential drug development candidates.

New approaches for the synthesis of thiophene derivatives with antitumor activities

TETRAHYDROBENZO[B]THIOPHENE derivatives 3a,b and 5a,b were synthesized followed by the alkylation of some derivatives. The antitumor evaluation of the newly synthesized products against three cancer cell lines, namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) was recorded. Some of the synthesized compounds show high inhibitory effects.

Synthesis of some 3-substituted amino-4,5-tetramethylene thieno[2,3-d][ 1,2,3]-triazin-4(3H)-ones as potential antimicrobial agents

A series of 3-Substituted amino-4,5-tetramethylene thieno[2,3-d] [1,2,3]-triazine-4(3H)-ones have been synthesized and characterized by UV,IR, 1H NMR, elemental and mass spectral analysis. The title compounds were evaluated for their antimicrobial activit

Uses of 4, 5, 6, 7-tetrahydrobenzo[b]thiophene derivatives in heterocyclic synthesis: Synthesis of pyrazol, pyrimidine and pyridazine derivatives with antimicrobial activities

THE 2-DAIZO-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide coupled with either malononitrile or ethyl cyanoacetate to give the hydrazo derivatives 4a and 4b, respectively. The latter products underwent hetero-cyclization to give pyrazole, pyrimidine an

Microwave-assisted synthesis of 2-amino-thiophene-3-carboxylic derivatives under solvent-free conditions

Under microwave irradiation and solvent-free conditions, cyanoacetates (cyanoacetamides) react with ketones and sulphur in the presence of a small amount of morpholine to give 2-amino-thiophene-3-carboxylic derivatives. In particular, tetrahydro-benzo[b]thiophene-3-carboxylic acid N-aryl amides were synthesized in high yields of 84-95%. Copyright Taylor & Francis, Inc.

Synthesis and local anaesthetic activity of some 2-aminoacetylamino-3-carbetoxy/anilido-4,5,6,7-tetrahydro-benzothiophenes

Twenty new 2-substituted aminoacetylamino-3-carbetoxy/anilido-4,5,6,7-tetrahydrobenzothiophenes (4a-4t) have been synthesised with a view to studying the effect of structural modification of carticaine (B) on the local anaesthetic activity and evaluated by Sollman's method as well as Bulbring and Wajda method using lignocaine hydrochloride as a standard.All the tested compounds show moderate to good activity and 4a has been found to be the most active drug comparable to the standard.