238749-53-6

Basic information

• Product Name: ethyl 4H-pyrrolo[2,3-d][1,3]thiazole-5-carboxylate
• Synonyms: ethyl 4H-pyrrolo[2,3-d][1,3]thiazole-5-carboxylate
• CAS NO: 238749-53-6
• Molecular Formula: C8H8N2O2S
• Molecular Weight: 196.22632
• Mol File: 238749-53-6.mol

Chemical Properties

• Boiling Point: 352.9±22.0 °C(Predicted)
• Appearance: /
• Density: 1.411±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 11.53±0.30(Predicted)
• CAS DataBase Reference: ethyl 4H-pyrrolo[2,3-d][1,3]thiazole-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4H-pyrrolo[2,3-d][1,3]thiazole-5-carboxylate(238749-53-6)
• EPA Substance Registry System: ethyl 4H-pyrrolo[2,3-d][1,3]thiazole-5-carboxylate(238749-53-6)

Safety Data

• Hazardous Substances Data: 238749-53-6(Hazardous Substances Data)

Upstream product

• 1003-32-3 thiazole-5-carboxaldehyde 
• 1007389-04-9 ethyl 2-azido-3-(thiazol-5-yl)acrylate 

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.

Structural Optimizations of Thieno[3,2-b]pyrrole Derivatives for the Development of Metabolically Stable Inhibitors of Chikungunya Virus

Chikungunya virus (CHIKV) is a re-emerging vector-borne alphavirus, and there is no approved effective antiviral treatment currently available for CHIKV. We previously reported the discovery of thieno[3,2-b]pyrrole 1b that displayed good antiviral activit

The discovery of fused pyrrole carboxylic acids as novel, potent d-amino acid oxidase (DAO) inhibitors

The 'NMDA hypofunction hypothesis of schizophrenia' can be tested in a number of ways. DAO is the enzyme primarily responsible for the metabolism of d-serine, a co-agonist for the NMDA receptor. We identified novel DAO inhibitors, in particular, acid 1, which demonstrated moderate potency for DAO in vitro and ex vivo, and raised plasma d-serine levels after dosing ip to rats. In parallel, analogues were prepared to survey the SARs of 1.

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.

SUBSTITUTED THIENOPYRROLE CARBOXYLIC ACID AMIDES, PYRROLOTHIAZOLE CARBOXYLIC ACID AMIDES, AND RELATED ANALOGS AS INHIBITORS OF CASEIN KINASE I

The present invention discloses and claims compounds of formula (I) and formula (II), as inhibitors of human casein kinase Iε and methods for using said compounds for treating central nervous system diseases and disorders including mood disorders and slee

Bicyclic pyrrole derivatives as MCP-1 inhibitors

A pharmaceutical composition comprising a compound of formula (I): or a pharmaceutically acceptable salt, ester or amide thereof, which is an inhibitor of monocyte chemoattractant protein-1 and wherein A and B together form an optionally substituted 5-member aromatic ring which includes at least one heteroatom; R1is an optionally substituted aryl or heteroaryl ring; R2is selected from a range of organic groups including carboxy, and R3is hydrogen, or a range of organic groups; in combination with a pharmaceutically acceptable carrier. Certain compounds of formula (I) are novel and these form a further aspect of the invention.