7312-11-0

Basic information

• Product Name: METHYL 5-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLATE
• Synonyms: METHYL 5-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLATE;5-Bromo-benzothiophene-2-carboxylic acid;5-BROMO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER;Benzo[b]thiophene-2-carboxylic acid, 5-broMo-, Methyl ester;5-BroMobenzothiophene-2-carboxylic Acid Methyl Ester;Methyl 5-BroMobenzo[b]thiophen-2-carboxylate;Methyl 5-BroMobenzo[b]thiophene-2- carboxylate;3T-1185
• CAS NO: 7312-11-0
• Molecular Formula: C₁₀H₇BrO₂S
• Molecular Weight: 271.13
• Product Categories: Aromatics;Heterocycles;Sulfur & Selenium Compounds
• Mol File: 7312-11-0.mol

Chemical Properties

• Melting Point: 110 °C
• Boiling Point: 358.9 °C at 760 mmHg
• Flash Point: 170.8 °C
• Appearance: /
• Density: 1.622 g/cm³
• Vapor Pressure: 2.47E-05mmHg at 25°C
• Refractive Index: 1.663
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: METHYL 5-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 5-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLATE(7312-11-0)
• EPA Substance Registry System: METHYL 5-BROMO-1-BENZOTHIOPHENE-2-CARBOXYLATE(7312-11-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 7312-11-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 5-bromo-1-benzothiophene-2-carboxylate is used as a key intermediate in the synthesis of new derivatives of (heterocycle-tetrahydropyridine)-(piperazinyl)-1-alkanone and (heterocycle-dihydropyrrolidine)-(piperazinyl)-1-alkanone. These derivatives have been identified as potential p75 neurotrophin receptor ligands, which can be utilized for the treatment of various neurological and neurodegenerative diseases.
Methyl 5-bromo-1-benzothiophene-2-carboxylate's unique structure and functional groups make it a valuable building block for the development of novel therapeutic agents. By targeting the p75 neurotrophin receptor, these derivatives have the potential to modulate cellular signaling pathways and provide therapeutic benefits for patients suffering from neurological and neurodegenerative conditions, such as Alzheimer's disease, Parkinson's disease, and multiple sclerosis.

InChI:InChI=1/C10H7BrO2S/c1-13-10(12)9-5-6-4-7(11)2-3-8(6)14-9/h2-5H,1H3

Upstream product

• 2365-48-2 Methyl thioglycolate 
• 93777-26-5 5-bromo-2-fluorobenzaldehyde 
• 4923-87-9 5-bromobenzo[b]thiophene 
• 124-38-9 carbon dioxide 
• 74-88-4 methyl iodide 

Downstream Products

• 7312-10-9 5-bromo-1-benzothiophene-2-carboxylic acid 
• 146137-90-8 methyl 5-iodobenzo[b]thiophene-2-carboxylate 
• 924869-09-0 methyl 5-(4-methoxyphenyl)benzo[b]thiophene-2-carboxylate 
• 154649-85-1 methyl 5-phenylbenzo[b]thiophene-2-carboxylate 
• 1252780-49-6 5-phenylbenzo[b]thiophene-2-carboxylic acid 
• 1252780-50-9 3-fluoro-5-phenyl-benzo[b]thiophene-2-carboxylic acid 
• 1252781-80-8 3-fluoro-5-phenyl-benzo[b]thiophene-2-carbonyl chloride 
• 1373524-56-1 (3S)-N-{1-[(3-Fluoro-5-phenyl-1-benzothiophen-2-yl)carbonyl]azetidin-3-yl}-1-(phenylcarbonyl)pyrrolidin-3-amine 
• 907945-15-7 5-(4-chlorophenyl)benzo[b]thiophene-2-carboxylic acid 
• 907945-17-9 5-(4-trifluoromethylphenyl)benzo[b]thiophene-2-carboxylic acid 

Relevant articles and documents

Design, synthesis, and biological activity evaluation of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives as broad-spectrum antifungal agents

To discover antifungal compounds with broad-spectrum and stable metabolism, a series of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives was designed and synthesized. Compounds A30-A34 exhibited excellent broad-spectrum antifungal activity against Candida albicans with MIC values in the range of 0.03–0.5 μg/mL, and against Cryptococcus neoformans and Aspergillus fumigatus with MIC values in the range of 0.25–2 μg/mL. In addition, compounds A31 and A33 showed high metabolic stability in human liver microsomes in vitro, with the half-life of 80.5 min and 69.4 min, respectively. Moreover, compounds A31 and A33 showed weak or almost no inhibitory effect on the CYP3A4 and CYP2D6. The pharmacokinetic evaluation in SD rats showed that compound A31 had suitable pharmacokinetic properties and was worthy of further study.

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.

HDAC inhibitor and preparation method and application thereof

The present invention discloses a compound represented by a formula I, a stereoisomer thereof, and a pharmaceutically acceptable salt thereof. The invention further relates to a pharmaceutical composition containing the compound shown in the formula I and application of the compound in preparation of HDAC inhibitor drugs. The compound or the pharmaceutical composition thereof can be used for treating cell proliferation diseases, autoimmune diseases, inflammation, neurodegenerative diseases or viral diseases.

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.

Direct Carboxylation of Electron-Rich Heteroarenes Promoted by LiO-tBu with CsF and [18]Crown-6

We herein demonstrate that the combination of LiO-tBu, CsF, and [18]crown-6 efficiently promotes the direct C?H carboxylation of electron-rich heteroarenes (benzothiophene, thiophene, benzofuran, and furan derivatives). A variety of functional groups, including methyl, methoxy, halo, cyano, amide, and keto moieties, are compatible with this system. The reaction proceeds via the formation of a tert-butyl carbonate species.

Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?

The syntheses and antiplasmodial activities of various substituted aminoquinolines coupled to an adamantane carrier are described. The compounds exhibited pronounced in vitro and in vivo activity against Plasmodium berghei in the Thompson test. Tethering a fluorine atom to the aminoquinoline C(3) position afforded fluoroaminoquinolines that act as intrahepatocytic parasite inhibitors, with compound 25 having an IC50 = 0.31 μM and reducing the liver load in mice by up to 92% at 80 mg/kg dose. Screening our peroxides as inhibitors of liver stage infection revealed that the tetraoxane pharmacophore itself is also an excellent liver stage P. berghei inhibitor (78: IC50 = 0.33 μM). Up to 91% reduction of the parasite liver load in mice was achieved at 100 mg/kg. Examination of tetraoxane 78 against the transgenic 3D7 strain expressing luciferase under a gametocyte-specific promoter revealed its activity against stage IV-V Plasmodium falciparum gametocytes (IC50 = 1.16 ± 0.37 μM). To the best of our knowledge, compounds 25 and 78 are the first examples of either an 4-aminoquinoline or a tetraoxane liver stage inhibitors.

GEMINAL SUBSTITUTED QUINUCLIDINE AMIDE COMPOUNDS AS AGONISTS OF ALPHA-7 NICOTINIC ACETYLCHOLINE RECEPTORS

The present invention relates to novel geminal substituted quinuclidine amide compounds, and pharmaceutical compositions of the same, that are suitable as agonists or partial agonists of α7- nAChR, and methods of preparing these compounds and compositions, and the use of these compounds and compositions in methods of maintaining, treating and/or improving cognitive function. In particular, methods of administering the compound or composition to a patient in need thereof, for example a patient with a cognitive deficiency and/or a desire to enhance cognitive function, that may derive a benefit therefrom.

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.

Novel 2-Carbonylbenzo[b]thiophene 1,1-Dioxide Derivatives as Potent Inhibitors of STAT3 Signaling Pathway

Signal transducer and activator of transcription 3 (STAT3) is considered to be an attractive therapeutic target for cancer therapy. In this study, a series of 2-carbonylbenzo[b]thiophene 1,1-dioxide derivatives (CBT) were designed to inhibit the STAT3 SH2 domain phosphorylation site Try 705. We demonstrated that incorporation of basic flexible groups through amide bond linkage to benzo[b]thiophene 1,1-dioxide (BTP) achieved compounds with higher antiproliferative potency than BTP itself. The most potent compound 6o, as indicated from luciferase reporter gene assay, inhibited the STAT3 pathway by decreasing the phosphorylation level of STAT3 Tyr705, while the phosphorylation level of other upstream tyrosine kinases in this pathway was not significantly inhibited. Compound 6o was also shown to trigger ROS generation and accumulation, thus consequently attributed partially to the observed cell apoptosis. This study provided important structural information for the development of inhibitors targeting the STAT3 pathway.

INHIBITORS OF HISTONE DEACETYLASE

The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.