332099-42-0

Basic information

• Product Name: ETHYL 3-METHYL-4H-THIENO[3,2-B]PYRROLE-5-CARBOXYLATE
• Synonyms: ETHYL 3-METHYL-4H-THIENO[3,2-B]PYRROLE-5-CARBOXYLATE
• CAS NO: 332099-42-0
• Molecular Formula: C10H11NO2S
• Molecular Weight: 209.26484
• Mol File: 332099-42-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ETHYL 3-METHYL-4H-THIENO[3,2-B]PYRROLE-5-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 3-METHYL-4H-THIENO[3,2-B]PYRROLE-5-CARBOXYLATE(332099-42-0)
• EPA Substance Registry System: ETHYL 3-METHYL-4H-THIENO[3,2-B]PYRROLE-5-CARBOXYLATE(332099-42-0)

Safety Data

• Hazardous Substances Data: 332099-42-0(Hazardous Substances Data)

Upstream product

• 637-81-0 ethyl-2-azidoacetate 
• 616-44-4 3-Methylthiophene 
• 68-12-2 N,N-dimethyl-formamide 
• 6030-36-0 4-methylthiophene-2-carbaldehyde 

Downstream Products

• 332099-44-2 3-Methyl-4H-thieno[3,2-b]pyrrole-5-carboxylic acid 

Relevant articles and documents

Thieno[3,2-b]pyrrole-5-carboxamides as New Reversible Inhibitors of Histone Lysine Demethylase KDM1A/LSD1. Part 1: High-Throughput Screening and Preliminary Exploration

Lysine specific demethylase 1 KDM1A (LSD1) regulates histone methylation and it is increasingly recognized as a potential therapeutic target in oncology. We report on a high-throughput screening campaign performed on KDM1A/CoREST, using a time-resolved fluorescence resonance energy transfer (TR-FRET) technology, to identify reversible inhibitors. The screening led to 115 hits for which we determined biochemical IC50, thus identifying four chemical series. After data analysis, we have prioritized the chemical series of N-phenyl-4H-thieno[3, 2-b]pyrrole-5-carboxamide for which we obtained X-ray structures of the most potent hit (compound 19, IC50 = 2.9 μM) in complex with the enzyme. Initial expansion of this chemical class, both modifying core structure and decorating benzamide moiety, was directed toward the definition of the moieties responsible for the interaction with the enzyme. Preliminary optimization led to compound 90, which inhibited the enzyme with a submicromolar IC50 (0.162 μM), capable of inhibiting the target in cells.

FLUORO-SUBSTITUTED INHIBITORS OF D-AMINO ACID OXIDASE

This invention provides novel inhibitors of the enzyme D-amino acid oxidase as well as pharmaceutical compositions including the compounds of the invention. The invention also provides methods for the treatment and prevention of neurological disorders, such as neuropsychiatric and neurodegenerative diseases, as well as pain, ataxia and convulsion. The compounds of the invention have the general structure: wherein A is NH or S. Q is a member selected from CR1 and N. X and Y are members independently selected from O, S, CR2, N and NH. R1, R2 and R4 are members independently selected from H and F, provided that at least one member selected from R1, R2 and R4 is F. R6 is a member selected from O?X+ and OH, wherein X+ is a positive ion, which is a member selected from inorganic positive ions and organic positive ions.

Preparation and biological evaluation of indole, benzimidazole, and thienopyrrole piperazine carboxamides: Potent human histamine H4 antagonists

Three series of H4 receptor ligands,- derived from indoly-2-yl-(4-methyl-piperazin-1-yl)-methanones, have been synthesized and their structure-activity relationships evaluated for activity at the H 4 receptor in competitive binding and functional assays. In all cases, substitution of small lipophilic groups in the 4 and 5-positions led to increased activity in a [3H]histamine radiolabeled ligand competitive binding assay. In vitro metabolism and initial pharmacokinetic studies were performed on selected compounds leading to the identification of indole 8 and benzimidazole 40 as potent H4 antagonists with the potential for further development. In addition, both 8 and 40 demonstrated efficacy in in vitro mast cell and eosinophil chemotaxis assays.

Heterocyclic compounds

Certain thienopyrrolyl and furanopyrrolyl compounds are disclosed as useful to treat or prevent disorders and conditions mediated by the histamine H4 receptor, including allergic rhinitis.

Use of glycogen phosphorylase inhibitors

The invention provides methods of treating prophylactically an individual in whom Type 2 diabetes mellitus has not yet presented, but in whom there is an increased risk of developing such condition, which methods comprise administering to an individual in need thereof an effective amount of a glycogen phosphorylase inhibitor; effective amounts of a glycogen phosphorylase inhibitor and a non-glycogen phosphorylase inhibiting anti-diabetic agent; or effective amounts of a glycogen phosphorylase inhibitor and an anti-obesity agent. The invention further provides methods of treating prophylactically an individual in whom Type 2 diabetes mellitus has not yet presented, but in whom there is an increased risk of developing such condition, which methods comprise administering to an individual in need thereof a pharmaceutical composition comprising effective amounts of a glycogen phosphorylase inhibitor and a non-glycogen phosphorylase inhibiting anti-diabetic agent; or effective amounts of a glycogen phosphorylase inhibitor and an anti-obesity agent.

Bicyclic pyrrolyl amides as glycogen phosphorylase inhibitors

This invention relates to compounds of Formula I or stereoisomers, pharmaceutically acceptable salts or prodrugs thereof or a pharmaceutically acceptable salts of the prodrugs. This invention also relates to pharmaceutical compositions comprising a compou