5556-20-7

Usage

Uses

Used in Pharmaceutical Synthesis:
Ethyl 3-hydroxybenzo[b]thiophene-2-carboxylate is utilized as an intermediate in the synthesis of various pharmaceuticals due to its unique chemical structure, which allows for the creation of a wide range of medicinal compounds.
Used in Organic Chemistry Research:
In the realm of organic chemistry, ethyl 3-hydroxybenzo[b]thiophene-2-carboxylate serves as a key component in research, enabling the exploration of new chemical reactions and the development of novel organic compounds.
Used in Material Science:
Ethyl 3-hydroxybenzo[b]thiophene-2-carboxylate is also applied in material science, where its properties are harnessed to develop new materials with specific characteristics, potentially contributing to advancements in various industries.
Each of these applications takes advantage of the compound's distinctive features, solidifying its role as a versatile and essential chemical in contemporary scientific and industrial processes.

Upstream product

• 17927-88-7 2-(phenylsulfonyl)benzo[d]isothiazol-3(2H)-one 
• 141-97-9 ethyl acetoacetate 
• 105-53-3 diethyl malonate 
• 52140-90-6 4-hydroxy-3-nitro-1-thioumarin 
• 64-17-5 ethanol 
• 4892-02-8 Methyl thiosalicylate 
• 19602-82-5 2,2'-dithiodibenzoic acid dichloride 
• 3950-02-5 2-chlorosulfenylbenzoyl chloride 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 1190582-62-7 2-benzoyl-2-ethoxycarbonylbenzo[b]thiophen-3(2H)-one 
• 36943-39-2 2-(phenylthio)benzaldehyde 
• 120571-35-9 ethyl 1-benzyl-2,3-dihydro-3-oxobenzothiophene-1-oxide-2-carboxylate, inner salt 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 105-36-2 ethyl bromoacetate 

Downstream Products

• 1416051-61-0 tert-butyl 4-((2-(ethoxycarbonyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate 
• 1416051-64-3 tert-butyl 4-((2-((benzyloxy)carbonyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate 
• 1416051-67-6 benzyl 3-(piperidin-4-yloxy)benzo[b]thiophene-2-carboxylate 
• 1416051-66-5 tert-butyl 4-((2-(((3-methoxybenzyl)oxy)carbonyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate 
• 19354-51-9 methyl 3-methoxybenzothiophene-2-carboxylate 
• 722517-00-2 3-benzyloxy-5-methoxy-1-benzo[b]thiophene-2-carboxylic acid 
• 19354-50-8 3-methoxy-1-benzothiophene-2-carboxylic acid 

Relevant academic research and scientific papers

Accepting the Invitation to Open Innovation in Malaria Drug Discovery: Synthesis, Biological Evaluation, and Investigation on the Structure-Activity Relationships of Benzo[b]thiophene-2-carboxamides as Antimalarial Agents

Malaria eradication is a global health priority, but current therapies are not always suitable for providing a radical cure. Artemisinin has paved the way for the current malaria treatment, the so-called Artemisinin-based Combination Therapy (ACT). However, with the detection of resistance to ACT, innovative compounds active against multiple parasite species and at multiple life stages are needed. GlaxoSmithKline has recently disclosed the results of a phenotypic screening of an internal library, publishing a collection of 400 antimalarial chemotypes, termed the “Malaria Box”. After analysis of the data set, we have carried out a medicinal chemistry campaign in order to define the structure-activity relationships for one of the released compounds, which embodies a benzothiophene-2-carboxamide core. Thirty-five compounds were prepared, and a description of the structural features responsible for the in vitro activity against different strains of P. falciparum, the toxicity, and the metabolic stability is herein reported.

NOVEL COMPOUNDS AND THEIR USE IN THERAPY

The invention provides compounds which inhibit N-myristoyltransferase and are selective for protozoal N-myristoyltransferase and, consequently suitable to treat microbial infections, including viral and fungal infections, and protozoan infections such as malaria, leishmaniasis and sleeping sickness.

Discovery of novel and ligand-efficient inhibitors of plasmodium falciparum and plasmodium vivax N-myristoyltransferase

N-Myristoyltransferase (NMT) is an attractive antiprotozoan drug target. A lead-hopping approach was utilized in the design and synthesis of novel benzo[b]thiophene-containing inhibitors of Plasmodium falciparum (Pf) and Plasmodium vivax (Pv) NMT. These inhibitors are selective against Homo sapiens NMT1 (HsNMT), have excellent ligand efficiency (LE), and display antiparasitic activity in vitro. The binding mode of this series was determined by crystallography and shows a novel binding mode for the benzothiophene ring.

A simple route to benzo[b]thiophenes: Sulfanylation-acylation of C-H acids with 2-(chlorosulfanyl)benzoyl chloride

A convenient procedure for the preparation of 2,2-disubstituted benzo[b]thiophen3(2H)-ones and 2-substituted 3-hydroxybenzo[b]thiophenes from β-diketones, β-keto- and β-cyanoesters, and β-cyanoketones, diethyl malonate, malonitrile, and anthrone has been

As many as six tandem reactions in one step! Unprecedented formation of highly functionalized benzothiophenes

A novel reaction pathway involving 1,3-diketones and 2,2′- dithiodibenzoylchloride that gives access to benzothiophenes with spiroketal, lactone, carbonyl, hydroxyl and carboxylic acid functionalities is discussed. The Royal Society of Chemistry 2009.

ANTIDIABETIC COMPOUNDS COMPRISING BENZOFURAN AND BENZOTHIOPHENE DERIVATIVES

The invention relates to compounds of the general formula (I) in which R1, R2, R3, R4, R5, R6 and X are as defined in Claim 1. These compounds can be used in the treatment of pathologies associated with insulin resistance syndrome.

Rhodium carbenoid mediated cyclisations. Part 6. Synthesis of cyclic sulphoxonium ylides

Treatment of diazo sulphoxides with rhodium(11) acetate gives stable five- and six- membered cyclic sulphoxonium ylides.

Synthesis of 4,10-dihydro-4,10-dioxo-1H[1]benzothiopyrano[3,2-b]pyridine and 7-oxo-7,13-dihydro[1]benzothiopyrano[2,3-b]-1,5-benzodiazepine

3-Amino-4H-1-benzothiopyran-4-one (3-aminothiochromone) was easily prepared by reaction of 3-bromothiochromen-4-one with sodium azide in methanol-water. Condensation of 3-aminothiochromone with diethyl ethoxymethylenemalonate and with dimethyl acetylenedicarboxylate gave intermediates, which were thermally cyclized to give 4,10-dihydro-4,10-doxo-1H[1]benzothiopyrano[3,2-b]pyridinecarboxylates. 3-Formyl-thiochromone was condensed with o-phenylenediamine to give 7-oxo-7,13-dihydro[1]benzothiopyrano[2,3-b]-1,5-benzodiazepine.