110545-67-0

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 4-BROMO-3-METHOXYTHIOPHENE-2-CARBOXYLATE is used as a synthetic intermediate for the production of pharmaceuticals. Its unique structure allows for the introduction of specific functional groups onto molecules, facilitating the development of new drugs with improved therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, METHYL 4-BROMO-3-METHOXYTHIOPHENE-2-CARBOXYLATE serves as a key component in the synthesis of various agrochemicals. Its reactivity and functional group compatibility make it suitable for creating compounds with targeted pest control and crop protection capabilities.
Used in Materials Industry:
METHYL 4-BROMO-3-METHOXYTHIOPHENE-2-CARBOXYLATE is also utilized in the materials industry, where it contributes to the synthesis of advanced materials with specific properties. Its role as a building block enables the creation of materials with tailored characteristics for various applications, such as electronics, coatings, and adhesives.
Used as a Reagent in Chemical Reactions:
Beyond its applications in specific industries, METHYL 4-BROMO-3-METHOXYTHIOPHENE-2-CARBOXYLATE is employed as a reagent in chemical reactions. Its ability to introduce functional groups onto molecules makes it a valuable tool in the synthesis of a wide range of compounds, further expanding its utility in the chemical industry.

InChI:InChI=1/C7H7BrO3S/c1-10-5-4(8)3-12-6(5)7(9)11-2/h3H,1-2H3

Upstream product

• 95201-93-7 methyl 3-hydroxy-4-bromo-2-thiophenecarboxylate 
• 74-88-4 methyl iodide 
• 5118-06-9 methyl 3-hydroxy-2-thiophenecarboxylate 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 1047645-66-8 N-[2-amino-1-(phenylmethyl)ethyl]-3-(methyloxy)-4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide hydrochloride 
• 1047645-62-4 1,1-dimethylethyl [2-({[3-(methyloxy)-4-(1-methyl-1H-pyrazol-5-yl)-2-thienyl]carbonyl}amino)-3-phenylpropyl]carbamate 
• 1047644-60-9 N-[2-amino-1-(phenylmethyl)ethyl]-3-(methyloxy)-4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide 

Relevant academic research and scientific papers

Synthesis and Anticancer Activity of Thiophene-2-carboxamide Derivatives and In Silico Docking Studies

A novel series of thiophene-2-carboxamide derivatives are designed and synthesized, and their structures are confirmed by 1H and 13C NMR, and mass spectra. The synthesized compounds are evaluated for their in vitro cytotoxic activity by MTT assay. Among the tested compounds, the derivative with 4-Cl-phenyl ring exhibits potent inhibitory activity against MCF-7, K562, HepG2, and MDA-MB-231. The molecular docking study performed for the synthesized compounds against PTP1B exhibits essential key interactions.

3-Alkoxy-4-bromothiophenes: General synthesis of monomers and regio-selective preparation of two dimers

3-Alkoxy-4-bromothiophenes were synthesized in three steps from the readily available methyl 2-carboxylate-3-hydroxythiophene and two isomers of bithiophenes based on the 3-bromo-4-methoxythiophene moiety were regio-selectively prepared.

Design, synthesis, in silico and in vitro evaluation of thiophene derivatives: A potent tyrosine phosphatase 1B inhibitor and anticancer activity

A series of novel methyl 4-(4-amidoaryl)-3-methoxythiophene-2-carboxylate derivatives were designed against the active site of protein tyrosine phosphatise 1B (PTP1B) enzyme using MOE.2008.10. These molecules are also subjected for in silico toxicity prediction studies and considering their corresponding drug scores, it implied that, the molecules are promising as anticancer agents. The designed compounds were synthesized by using suitable methods and characterized. They were subjected to inhibitory activity against PTP1B and in vitro anticancer activity by MTT assay. Most of the tested compounds showed potent inhibitory activity against PTP1B, among the compounds tested, compound 5b exhibited the highest activity (IC50?=?5.25?μM) and remarkable cytotoxic activity at 0.09?μM of IC50 against the MCF-7 cell line. In addition to this, compound 5c also showed potential anticancer activity at 2.22?μM of IC50 against MCF-7 and 0.72?μM against HepG2 cell lines as well as PTP1B inhibitory activity at IC50 of 6.37?μM.

Synthesis and Anticancer Activity of Novel Urea and Thiourea Bearing Thiophene-2-carboxalate Derivatives

Abstract: A new series of urea and thiourea bearing thiophene-2-carboxalate derivatives has been designed against protein tyrosine phosphatase 1B (PTP1B) active site, synthesized and charecterized by 1H and 13C NMR, and mass spectra. The compounds have been evaluated for in vitro anticancer activity against different cancer cell lines using the MTT colorimetric assay and doxorubicin as a standard drug. Among the tested compounds, methyl 3-methoxy-4-{4-[3-(4-methoxyphenyl)thioureido]phenyl}thiophene-2-carboxylate demonstrates the highest inhibitory activity against MCF-7, K562, HepG2, MDA-MB-231, and HeLa cell lines. The new molecular structures and their interactions with PNP1B have been evaluated by docking studies.

Opioid receptor agonists and application thereof

The invention discloses compounds and salts thereof that can be used as opioid receptor ligands, a preparation method of the compounds, compositions containing the compounds, and a use of the compounds as [mu] opioid receptor agonists; the compounds are used for treatment of [mu] opioid receptor-mediated related diseases, such as pains and pain-related disorders.

Synthesis of functionalized hydroxy-thiophene motifs as amido- and sulfonamido-phenol bioisosteres

Novel highly substituted hydroxy thiophene motifs were designed and synthesized as viable amido phenol and sulfonamido phenol bioisosteres. Hydroxy group-directed regioselective bromination and palladium-catalyzed amination of thienyl bromide via Buckwald

INHIBITORS OF Akt ACTIVITY

Invented are novel thiophene compounds, the use of such compounds as inhibitors of protein kinase B activity and in the treatment of cancer and arthritis.

THIADIAZOLES AS CXC- AND CC- CHEMOKINE RECEPTOR LIGANDS

Disclosed are novel compounds of Formula (IA) and the pharmaceutically acceptable salts and solvates thereof. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and ischemia reperfusion injury, pain (e.g., acute pain, acute and chronic inflammatory pain, and neuropathic pain) using a compound of Formula (IA).

ISOTHIAZOLE DIOXIDES AS CXC- AND CC- CHEMOKINE RECEPTOR LIGANDS

Disclosed are novel compounds of the formula (IA): and the pharmaceutically acceptable salts and solvates thereof. D and E are different groups wherein one is N and the other is CR50. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and cardiac reperfusion injury, pain (e.g., acute pain, acute and chronic inflammatory pain, and neuropathic pain) using a compound of formula IA.

CXCR1 AND CXCR2 CHEMOKINE ANTAGONISTS

The present invention is directed to a compound having the general structure of formula (1) useful for the treatment, prevention or amelioration of a CXCR1 or CXCR2 chemokine-mediated disease.