23046-02-8

Usage

Uses

Used in Scientific Research:
5-METHOXY-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID is used as a chemical intermediate for the synthesis of various compounds in scientific research. Its unique structure allows it to be a valuable building block in the development of new molecules with potential applications in different fields.
Used in Industrial Applications:
5-METHOXY-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID is employed as a raw material in the production of certain industrial chemicals. Its presence in the synthesis process contributes to the creation of new compounds that can be used in various industries, such as pharmaceuticals, materials science, and chemical manufacturing.
Used in Pharmaceutical Development:
5-METHOXY-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID is used as a potential candidate for drug development. Its chemical structure may offer opportunities for the design of new therapeutic agents, particularly in the area of medicinal chemistry, where it could be utilized to create novel drugs with specific pharmacological properties.
Note: Due to the limited information provided about the specific uses, hazards, and toxicity of 5-METHOXY-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID, it is essential to conduct comprehensive studies to explore its properties and applications further. This will help in understanding its potential benefits and risks, as well as its suitability for various applications.

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

Upstream product

• 1010456-51-5 (2Z)-2-mercapto-3-(3-methoxyphenyl)-2-propenoic acid 
• 91715-52-5 β-(3-methoxyphenyl)-α-mercaptoacryIic acid 
• 19492-99-0 methyl 5-methoxylbenzo[b]thiophene-2-carboxylate 
• 105728-90-3 2-fluoro-5-methoxybenzaldehyde 
• 40862-88-2 5-methoxybenzo[b]thiophene-2-carboxylic acid ethyl ester 

Downstream Products

• 1010456-27-5 C₁₈H₁₅F₃N₂O₄S₂ 
• 19492-99-0 methyl 5-methoxylbenzo[b]thiophene-2-carboxylate 
• 20532-30-3 5-methoxybenzothiophene 

Relevant academic research and scientific papers

Development of Selective Clk1 and -4 Inhibitors for Cellular Depletion of Cancer-Relevant Proteins

In cancer cells, kinases of the Clk family control the supply of full-length, functional mRNAs coding for a variety of proteins essential to cell growth and survival. Thus, inhibition of Clks might become a novel anticancer strategy, leading to a selective depletion of cancer-relevant proteins after turnover. On the basis of a Weinreb amide hit compound, we designed and synthesized a diverse set of methoxybenzothiophene-2-carboxamides, of which the N-benzylated derivative showed enhanced Clk1 inhibitory activity. Introduction of a m-fluorine in the benzyl moiety eventually led to the discovery of compound 21b, a potent inhibitor of Clk1 and -4 (IC50 = 7 and 2.3 nM, respectively), exhibiting an unprecedented selectivity over Dyrk1A. 21b triggered the depletion of EGFR, HDAC1, and p70S6 kinase from the cancer cells, with potencies in line with the measured GI50 values. In contrast, the cellular effects of congener 21a, which inhibited Clk1 only weakly, were substantially lower.

5-methoxybenzothiophene-2-Carboxamides as inhibitors of Clk1/4: Optimization of selectivity and cellular potency

Clks have been shown by recent studies to be promising targets for cancer therapy, as they are considered key regulators in the process of pre-mRNA splicing, which in turn affects every aspect of tumor biology. In particular, Clk1 and -4 are overexpressed in several human tumors. Most of the potent Clk1 inhibitors reported in the literature are non-selective, mainly showing off-target activity towards Clk2, Dyrk1A and Dyrk1B. Herein, we present new 5-methoxybenzothiophene-2-carboxamide derivatives with unprecedented selectivity. In particular, the introduction of a 3,5-difluoro benzyl extension to the methylated amide led to the discovery of compound 10b (cell-free IC50 = 12.7 nM), which was four times more selective for Clk1 over Clk2 than the previously published flagship compound 1b. Moreover, 10b showed an improved growth inhibitory activity with T24 cells (GI50 = 0.43 μM). Furthermore, a new binding model in the ATP pocket of Clk1 was developed based on the structure-activity relationships derived from new rigidified analogues.

Benzo[b]thiophene-2-carboxamide derivatives as potent urotensin-II receptor antagonists

Members of a series of benzo[b]thiophene-2-carboxamide derivatives, possessing an N-(1-(3-bromo-4-(piperidin-4-yloxy)benzyl)piperidin-4-yl) group, were synthesized and evaluated as urotensin-II receptor antagonists. The results show that these substances have potent UT binding affinities. Observations made in a systematic SAR investigation of the effects of a variety of substituents (R1and R2) at the 5- and 6-positions in the benzo[b]thiophene-2-carboxamide moiety on UT binding affinities led to identification of the 5-cyano analog 7f as a highly potent UT antagonist with an IC50value of 25?nM. Despite having a good metabolic stability, 7f is a potent inhibitor of CYP isozyme and displays an unsuitable PK profile.

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.

Hydroxybenzothiophene ketones are efficient pre-mRNA splicing modulators due to dual inhibition of Dyrk1A and Clk1/4

Dysregulated usage of pre-mRNA splicing sites contributes to the progression of cancer, neurodegenerative diseases, and viral infections. Serine/arginine-rich (SR) proteins play major roles in the splice site recognition and are largely regulated by phosp

CHEMILUMINESCENT COMPOSITIONS, METHODS, ASSAYS AND KITS FOR OXIDATIVE ENZYMES

Chemiluminescent compositions, methods, assays and kits for oxidative enzymes are described. Further disclosed are dioxetane compounds of the form: 0-0 ΛR R R T (i) where R can independently be any branched alkyl or cycloalkyl group which provides stabili

NOVEL INHIBITORS OF BETA-LACTAMASE

This invention provides novel β-lactamase inhibitors of the aryl- and heteroarylsulfonamidomethylphosphonate monoester class having nitrogen-based cations or quarternary ammonium groups. The compounds inhibit three classes of β-lactamases and synergize the antibacterial effects of β-lactam antibiotics (e.g., imipenem and ceftazidime) against those micro-organisms normally resistant to the β-lactam antibiotics as a result of the presence of the β-lactamases. Formula (I) or pharmaceutically acceptable salt thereof.

Design, synthesis and evaluation of trifluoromethane sulfonamide derivatives as new potent and selective peroxisome proliferator-activated receptor α agonists

Starting from the structure of 5, a two-step strategy was applied to identify a new generation of trifluoromethane sulfonamides as potent PPARα agonists. Synthesis, in vitro and in vivo evaluation of the most potent compound are reported.