220180-55-2

Usage

Uses

Used in Scientific Research:
4-Fluoro-Benzo[b]thiophene-2-carboxylic Acid Methyl Ester is used as a research compound for studying its chemical properties and potential applications in various fields.
Used in Organic Synthesis:
4-Fluoro-Benzo[b]thiophene-2-carboxylic Acid Methyl Ester is used as an intermediate in the synthesis of more complex organic molecules, contributing to the development of new compounds with potential applications in various industries.

InChI:InChI=1/C10H7FO2S/c1-13-10(12)9-5-6-7(11)3-2-4-8(6)14-9/h2-5H,1H3

Upstream product

• 437-81-0 2,6-difluorobenzaldehyde 
• 2365-48-2 Methyl thioglycolate 
• 310466-37-6 4-fluoro-1-benzothiophene-2-carboxylic acid 
• 67-56-1 methanol 
• 372-18-9 1,3-Difluorobenzene 

Downstream Products

• 957059-61-9 (4-fluoro-benzo[b]thiophen-2-yl)-methanol 
• 310466-37-6 4-fluoro-1-benzothiophene-2-carboxylic acid 
• 310466-38-7 4-fluorobenzo[b]thiophene 

Relevant academic research and scientific papers

Enantioselective Synthesis of Five-Membered-Ring Atropisomers with a Chiral Rh(III) Complex

Axially chiral atropisomeric compounds are widely applied in asymmetric catalysis and medicinal chemistry, and efficient methods for their synthesis are in high demand. This applies in particular to atropisomers derived from five-membered aromatic rings because their lower barrier for rotation among the biaryl axis limits their asymmetric synthesis. We report here an enantioselective C-H functionalization method using our chiral RhJasCp complex for the synthesis of the biaryl atropisomer types that can be accessed from three different five-membered-ring heterocycles.

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.

Design and development of cyclometalated ruthenium complexes containing thiophenyl-pyridine ligand for dye-sensitized solar cells

Two new cyclometalated ruthenium sensitizers NC102 (1) and NC103 (2), where the two NCS- ligands of the N3 analog were replaced with the 2-thiophen-2-yl-pyridine and 2-benzo[b]thiophen-2-yl-pyridine ligands, respectively, were designed and synthesized for dye-sensitized solar cell applications. The effects of these two ligands on the photophysical behavior of ruthenium complexes were investigated by their optical, electrochemical, and photovoltaic properties. The sensitizer NC103 (2) with the fluoride substitution in the ligand exhibited the best cell performance with a short-circuit current (Jsc) of 9.45 mA/cm2, an open-circuit voltage (V oc) of 630 mV, and a fill factor (FF) of 0.71, giving an overall power conversion efficiency of (η) 4.22% under simulated AM 1.5 irradiation.

COLD MENTHOL RECEPTOR-1 ANTAGONISTS

The invention is directed to TRPM8 antagonists of Formula (I). More specifically, the present invention relates to certain novel compounds, methods for preparing compounds, compositions, intermediates and derivatives thereof and methods for treating TRPM8-mediated disorders. Pharmaceutical and veterinary compositions and methods of treating pain and various other disease states or conditions using compounds of the invention are also described.

COLD MENTHOL RECEPTOR-1 ANTAGONISTS

The invention is directed to TRPM8 antagonists of Formula (I). More specifically, the present invention relates to certain novel compounds, methods for preparing compounds, compositions, intermediates and derivatives thereof and methods for treating TRPM8-mediated disorders. Pharmaceutical and veterinary compositions and methods of treating pain and various other disease states or conditions using compounds of the invention are also described.

COLD MENTHOL RECEPTOR-1 ANTAGONISTS

The invention is directed to TRPM8 antagonists of Formula (I). More specifically, the present invention relates to certain novel compounds, methods for preparing compounds, compositions, intermediates and derivatives thereof and methods for treating TRPM8-mediated disorders. Pharmaceutical and veterinary compositions and methods of treating pain and various other disease states or conditions using compounds of the invention are also described.

4-Substituted (benzo[b]thiophene-2-carbonyl)guanidines as novel Na +/H+ exchanger isoform-1 (NHE-1) inhibitors

A series of 4-substituted (benzo[b]thiophene-2-carbonyl)guanidines was synthesized and evaluated for the NHE-1 inhibitory activity and cardioprotective efficacy both in vitro and in vivo. Several analogs exhibited a strong inhibition on NHE-1, and which was generally well correlated with their cardioprotective efficacy. Especially the 4-nitro 20 and cyano 50 compounds excellently improved the cardiac function and reduced infarct size against ischemia/reperfusion injury.

Telomerase inhibitors

Methods and compositions for treating cancer and other diseases in which inhibition of telomerase activity can ameliorate disease symptoms or prevent or treat the disease relate to compounds characterized by the following structure: STR1 and their pharmaceutically acceptable salts. Y is selected from the group consisting of oxygen, sulfur, sulfonyl, sulfinyl, and --NR7 --. R1 is --TR8, where T is --C(X1)-- or --SO2 --, and R8 is selected from the group consisting of --OR9, --NHNHSO2 R9, --NHNHC(X2)OR9, --NR9 R10, --NHNHC(X2)NR9 R10, --NHCR9 R10 C(X2)NR11 R12, --NHC(X2)NR9 R10, and the piperazinyl moiety shown below: STR2 where n is 0 or 1, and Qn, for n=1, is --SO2 --, --C(X2)-- or --C(X2)NR10 --. R2 -R6 are selected independently from the group consisting of hydrogen, alkyl, aryl, hydroxyl, alkoxyl, aryloxyl, aralkoxyl, halogen, cyano, nitro, alkylcarbamido, arylcarbamido, dialkylcarbamido, diarylcarbamido, alkylarylcarbamido, alkylthiocarbamido, arylthiocarbamido, dialkylthiocarbamido, diarylthiocarbamido, alkylarylthiocarbamido, amino, alkylamino, arylamino, dialkylamino, diarylamino, arylalkylamino, aminocarbonyl, alkylaminocarbonyl, arylaminocarbonyl, dialkylaminocarbonyl, diarylaminocarbonyl, arylalkylaminocarbonyl, alkylcarbonyloxy, arylcarbonyloxy, carboxyl, alkoxycarbonyl, aryloxycarbonyl, sulfo, alkylsulfonylamido, arylsulfonylamido, alkylsulfonyl, arylsulfonyl, alkylsulfinyl, and arylsulfinyl. X1 and X2 are selected independently from the group consisting of oxygen, and sulfur. R7 -R12 are selected independently from the group consisting of hydrogen, alkyl, aryl, aralkyl, heterocycle, and heterocyclealkyl.

UROKINASE INHIBITORS

Disclosed are benzothiophene and thienothiophene derivatives useful for inhibiting urokinase activity.