19354-50-8

Usage

Uses

Used in Organic Synthesis:
3-Methoxybenzo[b]thiophene-3-carboxylic acid is used as a building block in organic synthesis for the creation of various complex organic molecules. Its unique structure and reactivity make it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-methoxybenzo[b]thiophene-3-carboxylic acid is used as a key intermediate in the development of new drugs. Its chemical properties allow for the formation of diverse drug candidates with potential therapeutic applications.
Used in Materials Science:
3-Methoxybenzo[b]thiophene-3-carboxylic acid is utilized in materials science for the development of novel materials with specific properties. Its incorporation into polymers or other materials can lead to enhanced performance characteristics, such as improved stability, conductivity, or optical properties.

InChI:InChI=1/C10H8O3S/c1-13-8-6-4-2-3-5-7(6)14-9(8)10(11)12/h2-5H,1H3,(H,11,12)

Upstream product

• 606-27-9 methyl 2-nitrobenzoate 
• 2365-48-2 Methyl thioglycolate 
• 19354-51-9 methyl 3-methoxybenzothiophene-2-carboxylate 
• 4892-02-8 Methyl thiosalicylate 
• 5556-20-7 ethyl 3-hydroxybenzothiophene-2-carboxylate 
• 147-93-3 Thiosalicylic acid 
• 13134-76-4 methyl 3-hydroxybenzo[b]thiophene-2-carboxylate 
• 394-35-4 methyl 2-fluorobenzoate 
• 21815-91-8 3-chlorobenzo[b]thiophen-2-carbonyl chloride 
• 140-10-3 (E)-3-phenylacrylic acid 

Relevant academic research and scientific papers

Annulation of eight-to ten-membered oxaza rings to the benzo[b]thiophene system by intramolecular nucleophilic displacement

Concise synthetic routes to 2H-benzo[b]thieno[3,2-b][1,5]oxazocin-6(3H)- one, and the new benzo[b]thieno[3,2-b][1,5]oxazonin-7(2H)-one and 2H-benzo[b]thieno[3,2-b][1,5]oxazecin-8(3H)-one systems, have been developed based on intramolecular nucleophilic displacement in the key ring forming step.

Benzothiophene-2-carboxamide derivatives as SENPs inhibitors with selectivity within SENPs family

The SUMO (small ubiquitin-related modifier)-specific proteases (SENPs) are responsible for the cleavage of SUMO from its target proteins, thus play important roles in the dynamic SUMOylation and deSUMOylation processes. SENPs are related to a variety of human diseases including cancer and represent a new class of potential therapeutic targets with mechanism of action that is likely to be different from that of current clinically used drugs. However, potent inhibitors that are selective within the SENPs family members still remain a challenge due to their high homology. In order to demonstrate the feasibility of developing selective inhibitors within the SENPs family, we chose SENP1/2/5 as representatives, aiming to identify inhibitors with selectivity among the members. Starting from a hit compound ZCL951 from virtual screening, a series of benzothiophene-2-carboxamide inhibitors were designed based on the protein structures of SENP1, 2, and 5. First, an unoccupied hydrophobic pocket was first identified which led to IC50 as low as 0.56 μM. Furthermore, the ethylacetate 77 gave both submicromolar inhibitory activity and 33-fold selectivity for SENP2 versus SENP5. They are the most potent and selective nonpeptidic inhibitor reported so far for the SENPs family, as far as we are aware. Their structure-activity relationship was also discussed.

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.

METHOD FOR PROMOTING PLANT GROWTH

The present invention provides a method for promoting plant growth, which comprises treating a plant with at least one compound selected from a group consisting of a compound represented by the following Formula (1): and an agriculturally acceptable salt thereof, provided that a method for promoting plant growth which comprises treating plants with a compound corresponding to any one of the following (1) to (5) and an agriculturally acceptable salt thereof is excluded: (1) 4-(Trifluoromethyl)benzo[b]thiophene-2-carboxylic acid, (2) 5-(Trifluoromethyl)benzo[b]thiophene-2-carboxylic acid, (3) 6-(Trifluoromethyl)benzo[b]thiophene-2-carboxylic acid, (4) 7-(Trifluoromethyl)benzo[b]thiophene-2-carboxylic acid, and (5) Benzo[b]thiophene-2-carboxylic acid.

ORTHO-ANTHRANILAMIDE DERIVATIVES AS ANTI-COAGULANTS

This invention is directed to compounds of formula (III): STR1 wherein B, C, D, E, R 1, R 2 and R 3 are disclosed herein. These compounds are disclosed as being useful as anti-coagulants.

PHARMACEUTICAL COMPOUNDS

Compounds of the formula: STR1 in which each R 1 is hydrogen, C 1-4 alkyl, C 1-4 alkoxy, halogen or nitro, and n is 0, 1, 2 or 3, R 2 is hydrogen, C 1-4 alkyl or C 2-4 alkenyl, R. sup.3 and R. sup.4 are each hydrogen, C 1-4 alkyl, optionally substituted phenyl or C. sub.6-9 cycloalkyl optionally substituted by 1 to 4 C 1-4 alkyl groups, R 5 is optionally substituted phenyl, tetrahydronaphthyl, phthalimido, saccharinyl, glutaramido, C 6-10 cycloalkyl optionally substituted with 1 to 4 C. sub.1-4 alkyl groups or a phenyl group, or C. sub.4-9 heterosubstituted cycloalkyl optionally substituted with 1 to 4 alkyl groups, x is 1, 2 or 3, y is 0 or 1 and z is 0, 1, 2 or 3; and salts thereof.The compounds are indicated for use in the treatment of disorders of the central nervous system.

Anti-inflammatory and analgesic 3-hydroxybenzo[b]thiophene derivatives, compositions, and method of use therefor

3-Hydroxybenzo[b]thiophene derivatives, such as 2-aralkyl, 2-alkyl and 2-alkenyl-3-hydroxybenzo[b]-thiophenes, were prepared by, among other methods, ring closure of 2-(2-carboxy-phenylthio)-α-substituted acetic acids. These compounds are found to be useful in the treatment of pain, fever, inflammation, arthritic conditions, asthma, allergic disorders, skin diseases, cardiovascular disorders, psoriasis, inflammatory diseases and other prostaglandin and/or leukotriene mediated diseases.

3-Alkoxy-thianapthene-2-carboxamides

The 3-alkoxy-thianaphthene-2-carboxamides of this invention are effective for the treatment of mammals afflicted with emesis. When administered to dogs in dosages of 250 μg/kg, compounds of this invention give 100% protection against vomiting normally induced by subcutaneous administration of apomorphine. The compounds of this invention also favorably modify behavior disturbances in mammals.