19075-59-3

Usage

Uses

Used in Pharmaceutical Industry:
Benzo[b]thiophene-2-carboxylic acid, 7-bromo-, is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique chemical properties and structural features make it a valuable component in the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
Benzo[b]thiophene-2-carboxylic acid, 7-bromois also utilized in the synthesis of agrochemicals, contributing to the development of effective pesticides, herbicides, and other agricultural chemicals. Its unique properties allow for the creation of innovative and efficient products in this field.
Used in Material and Dye Development:
Benzo[b]thiophene-2-carboxylic acid, 7-bromo-, is employed in the development of new materials and dyes, thanks to its distinctive chemical characteristics. Its potential applications in this area include the creation of novel pigments, coatings, and other materials with specific properties.
Used in Environmental Research:
The presence of Benzo[b]thiophene-2-carboxylic acid, 7-bromo-, in nature and its potential environmental impact are subjects of ongoing research and study. Understanding its behavior in the environment and its interactions with other compounds can provide valuable insights for environmental protection and management.

InChI:InChI=1/C9H5BrO2S/c10-6-3-1-2-5-4-7(9(11)12)13-8(5)6/h1-4H,(H,11,12)

Upstream product

• 149947-15-9 3-bromo-2-fluorobenzaldehyde 
• 2365-48-2 Methyl thioglycolate 
• 1072-85-1 o-fluorobromobenzene 
• 1355171-39-9 ethyl 7-bromobenzo[b]thiophene-2-carboxylate 
• 550998-53-3 methyl 7-bromobenzo[b]thiophene-2-carboxylate 

Downstream Products

• 547766-28-9 7-Bromo-1-benzothiophen-2-amine 
• 1423-61-6 7-bromobenzo(b)thiophene 
• 634904-48-6 N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-(3-{[(2-methoxyethyl)(methyl)amino]carbonyl}phenyl)-1-benzothiophene-2-carboxamide hydrochloride 
• 634904-45-3 N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-(3-{[ethyl(methyl)amino]carbonyl}phenyl)-1-benzothiophene-2-carboxamide hydrochloride 
• 634903-65-4 N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-[4-(dimethylamino)phenyl]-1-benzothiophene-2-carboxamide hydrochloride 
• 791060-90-7 N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-(3-{[(2-methoxyethyl)(methyl)amino]carbonyl}phenyl)-1-benzothiophene-2-carboxamide 
• 765269-10-1 N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-(3-{[ethyl(methyl)amino]carbonyl}phenyl)-1-benzothiophene-2-carboxamide 
• 750569-34-7 N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-[4-(dimethylamino)phenyl]-1-benzothiophene-2-carboxamide 
• 634904-54-4 N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-{3-[(cyclohexylcarbonyl)amino]phenyl}-1-benzothiophene-2-carboxamide hydrochloride 
• 634904-49-7 N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-(3-{[(3-ethoxypropyl)amino]carbonyl}phenyl)-1-benzothiophene-2-carboxamide hydrochloride 
• 634904-53-3 N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-{3-[(cyclopentylcarbonyl)amino]phenyl}-1-benzothiophene-2-carboxamide hydrochloride 
• 634903-86-9 N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-[3-(4-morpholinylcarbonyl)phenyl]-1-benzothiophene-2-carboxamide hydrochloride 
• 634904-55-5 N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-{3-[(tetrahydro-2-furanylcarbonyl)amino]phenyl}-1-benzothiophene-2-carboxamide hydrochloride 
• 634903-80-3 N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-[4-(4-morpholinylcarbonyl)phenyl]-1-benzothiophene-2-carboxamide hydrochloride 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of benzo[b]thiophene 1,1-dioxide derivatives as potent STAT3 inhibitors

As a member of the signal transducer and activator of transcription (STAT) family, STAT3 plays a critical role in several biological pathways such as cell proliferation, migration, survival, and differentiation. Due to abnormal continuous activation in tumors, inhibition of STAT3 has emerged as an attractive approach for the treatment of various cancer cells. Herein, we report a series of novel STAT3 inhibitors based on benzo[b]thiophene 1,1-dioxide scaffold and evaluated their anticancer potency. Among them, compound 8b exhibited the best activity against cancer cells. Compound 8b induced apoptosis and blocked the cell cycle. Meanwhile, 8b reduced intracellular ROS content and caused the loss of mitochondrial membrane potential. Further research revealed that 8b significantly blocked STAT3 phosphorylation and STAT3-dependent dual-luciferase reporter gene experiments showed that compound 8b has a marked inhibition of STAT3-mediated Firefly luciferase activity. Molecular modeling studies revealed compound 8b occupied the pocket well with the SH2 domain in a favorable conformation.

Discovery of fluorescent coumarin-benzo[b]thiophene 1, 1-dioxide conjugates as mitochondria-targeting antitumor STAT3 inhibitors

STAT3 has been extensively studied as a potential antitumor target. Though studies on regulating STAT3 mainly focus on the inhibition of STAT3 phosphorylation at Tyr705 residue, the phosphorylation at Ser727 residue of STAT3 protein is also closely associated with the mitochondrial import of STAT3 protein. N, N-diethyl-7-aminocoumarin is a fluorescent mitochondria-targeting probe. In this study, a series of STAT3 inhibitors were developed by connecting N, N-diethyl-7-aminocoumarin fluorophore with benzo [b]thiophene 1, 1-dioxide moiety. All designed compounds displayed potent anti-proliferative activity against cancer cells. The representative compound 7a was mainly accumulated in mitochondria visualized by its fluorescence. STAT3 phosphorylation was inhibited by compound 7a at both Tyr705 and Ser727 residues. Compound 7a inhibited STAT3 phosphorylation whereas had no influence on the phosphorylation levels of STAT1, JAK2, Src and Erk1/2, indicating good selectivity of compound 7a. Moreover, compound 7a down-regulated the expression of STAT3 target genes Bcl-2 and Cyclin D1, increased ROS production and remarkably reduced the mitochondrial membrane potential to induce mitochondrial apoptotic pathway. Furthermore, compound 7a in vivo suppressed breast cancer 4T1 implanted tumor growth. Taken together, these results highlighted that compound 7a might be a promising mitochondria-targeting STAT3 inhibitor for cancer therapy.

Antagonizing STAT3 activation with benzo[b]thiophene 1, 1-dioxide based small molecules

STAT3 is an attractive therapeutic target for cancer therapy. However, due to low potency or poor druggability, none of its inhibitors are clinically available. Herein, a series of aminobenzo[b]thiophene 1, 1-dioxides with good drug-likeness properties were designed, synthesized and evaluated as STAT3 inhibitors. Most of them exhibited higher antitumor activity than the small-molecule STAT3 inhibitor, Stattic. Compound 15 was the most potent and had an IC50range in 0.33–0.75?μM in various cancer cell lines. The overexpressed and IL-6 induced phosphorylation levels of STAT3 were both inhibited by 15 without influencing the phosphorylation levels of the upstream kinases Src and Jak2. 15 also suppressed the expressions of STAT3 downstream gene, Bcl-2. 15 effectively increased the ROS levels of cancer cells, induced cancer cell apoptosis and abolished the colony formation ability of cancer cells without affecting bypass kinase p-Erk. Furthermore, 15 in?vivo induced significant antitumor responses, and exhibited less toxicity than Doxorubicin. Together, this study described a class of new STAT3 inhibitors as antitumor agents.

N-(piperidin-4-yl)benzo[b]thiophenecarboxamide derivatives, preparation method therof, and pharmaceutical composition for use in preventing or treating Urotensin-Ⅱ receptor activity related diseases containing the same as an active ingredient

The present invention relates to N-(piperidin-4-yl)benzo[b]thiophenecarboxamide derivatives, a manufacturing method thereof, and a pharmaceutical composition for preventing or treating urotensin-II receptor activity-related diseases comprising the same as an active ingredient. The N-(piperidin-4-yl)benzo[b]thiophenecarboxamide derivatives can be usefully used for preventing or treating urotensin-II receptor activity-related diseases such as congestive heart failure, ischemic heart, myocardial infarction, cardiomegaly, fibrosis cordis, coronary artery disease, arteriosclerosis, hypertension, asthma, renal failure, diabetes, vasculitis, neurodegenerative disease, stroke, pain, depressive disorder, psychosis, cancer, etc., by acting as an antagonist with respect to a urotensin-II receptor.COPYRIGHT KIPO 2016

A novel α2/α4 subtype-selective positive allosteric modulator of nicotinic acetylcholine receptors acting from the C-tail of an α subunit

Positive allosteric modulators (PAMs) of nicotinic acetylcholine receptors (nAChR) are important therapeutic candidates as well as valuable research tools. We identified a novel type II PAM, (R)-7-bromo-N-(piperidin-3-yl)benzo[b]thiophene-2-carboxamide (Br-PBTC), which both increases activation and reactivates desensitized nAChRs. This compound increases acetylcholine-evoked responses of α2 and α4 nAChRs but is without effect on α3 or α6 nAChRs ( indicates the presence of other nAChR subunits). Br-BPTC acts from the C-terminal extracellular sequences of α4 subunits, which is also a PAM site for steroid hormone estrogens such as 17β-estradiol. Br-PBTC is much more potent than estrogens. Like 17β-estradiol, the non-steroid Br-PBTC only requires one α4 subunit to potentiate nAChR function, and its potentiation is stronger with more α4 subunits. This feature enables Br-BPTC to potentiate activation of (α4β2)(α6β2)β3 but not (α6β2)2β3 nAChRs. Therefore, this compound is potentially useful in vivo for determining functions of different α6 nAChR subtypes. Besides activation, Br-BPTC affects desensitization of nAChRs induced by sustained exposure to agonists. After minutes of exposure to agonists, Br-PBTC reactivated short term desensitized nAChRs that have at least two α4 subunits but not those with only one. Three α4 subunits were required for Br-BPTC to reactivate long term desensitized nAChRs. These data suggest that higher PAM occupancy promotes channel opening more efficiently and overcomes short and long term desensitization. This C-terminal extracellular domain could be a target for developing subtype or state-selective drugs for nAChRs.

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.

BENZOTHIOPHENE UREA, BENZOFURANE UREA, AND INDOLE UREA, AND USE OF THE SAME AS ALPHA-7 ACHR AGONISTS

The invention relates to novel benzothiophene urea, benzofurane urea, and indole urea, and to the use thereof for producing medicaments for the treatment and/or prophylaxis of diseases and for improving perception, concentration power, learning capacity and/or memory retention.

2-HETEROARYL CARBOXAMIDES

The invention relates to the novel 2-heteroaryl carboxamides according to formula (I), wherein R1 represents 1-aza-bicyclo [2.2.2]oct-3-yl, which is optionally replaced via the nitrogen atom by a group selected from the family C1-C4 alkyl, benzyl and oxy, A represents oxygen or sulfur, the ring B represents benzo or pyrido that are optionally replaced by the groups from the family of halogen, cyano, formyl, trifluoromethyl, trifluoromethoxy, nitro, amino, C1-C6 alkyl and C1-C6 alkoxy, E represents C=C, aryl and heteroaryl, wherein aryl and heteroaryl may be replaced by groups from the family of halogen, cyano, trifluoromethyl, trifluoromethoxy, nitro, amino, C1-C6 alkoxy and C1-C6 alkyl, and to the solvents, salts or solvents of salts of said compounds. The invention also relates to the use of said compounds in the production of drugs for the treatment and/or the prophylaxis of diseases and for improving perception, power of concentration, learning power and/or retentiveness of memory.