39793-31-2

Basic information

• Product Name: 4H-THIENO[3,2-B]PYRROLE-5-CARBOXYLIC ACID
• Synonyms: 4H-THIENO[3,2-B]PYRROLE-5-CARBOXYLIC ACID;AKOS BB-9991;CHEMBRDG-BB 4012315;4H-thieno[3,2-b]pyrrole-5-carboxylic acid(SALTDATA: FREE);Thieno[2,3-b]pyrrole-5-carboxylic acid;4H-thieno[2,3-d]pyrrole-5-carboxylic acid;D-Amino Acid Oxidase Inhibitor
• CAS NO: 39793-31-2
• Molecular Formula: C₇H₅NO₂S
• Molecular Weight: 167.19
• Mol File: 39793-31-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 180 °C
• Boiling Point: 437.4°C at 760 mmHg
• Flash Point: 218.3°C
• Appearance: /
• Density: 1.609
• Vapor Pressure: 2E-08mmHg at 25°C
• Refractive Index: 1.786
• Storage Temp.: +2C to +8C
• CAS DataBase Reference: 4H-THIENO[3,2-B]PYRROLE-5-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-THIENO[3,2-B]PYRROLE-5-CARBOXYLIC ACID(39793-31-2)
• EPA Substance Registry System: 4H-THIENO[3,2-B]PYRROLE-5-CARBOXYLIC ACID(39793-31-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 22-26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 39793-31-2(Hazardous Substances Data)

Usage

Description

4H-Thieno[3,2-b]pyrrole-5-carboxylic acid is a cell-permeable thienopyrrole compound that effectively inhibits the cellular activity of transfected D-amino acid oxidase (DAO/DAAO/DAMOX/OXDA) in CHO cells. It demonstrates high potency with an IC50 against human and rat DAO of 145 and 114 nM, respectively. 4H-Thieno[3,2-b]pyrrole-5-carboxylic acid does not exhibit activity towards D-aspartate oxidase (DDO), P450 enzymes CYP3A4/2D6/3C9, or a panel of over 150 other enzymes, receptors, and ion channels.
Usage:
Used in Pharmaceutical Industry:
4H-Thieno[3,2-b]pyrrole-5-carboxylic acid is used as an inhibitor for D-amino acid oxidase (DAO) due to its high potency and selectivity. It has potential applications in the development of antipsychotic and cognitive enhancing drugs, as it can effectively inhibit DAO activity in rat brain and kidney.
Used in Research and Development:
4H-Thieno[3,2-b]pyrrole-5-carboxylic acid serves as a valuable tool in research and development for studying the role of D-amino acid oxidase in various biological processes. Its selectivity for DAO over other enzymes and receptors makes it an ideal candidate for investigating the enzyme's function and potential therapeutic targets.
Used in Drug Design and Optimization:
4H-Thieno[3,2-b]pyrrole-5-carboxylic acid's high potency and selectivity for DAO make it a promising starting point for drug design and optimization efforts. Researchers can use this compound to develop more effective and targeted therapies for conditions related to D-amino acid oxidase dysregulation.
Used in Enzyme Inhibition Studies:
4H-Thieno[3,2-b]pyrrole-5-carboxylic acid is used as a reference compound in enzyme inhibition studies, particularly for D-amino acid oxidase. Its lack of activity towards other enzymes and receptors allows researchers to better understand the specific interactions between DAO and potential inhibitors.

Synthesis Reference(s)

Journal of the American Chemical Society, 79, p. 2556, 1957 DOI: 10.1021/ja01567a053

InChI:InChI=1/C7H5NO2S/c9-7(10)5-3-6-4(8-5)1-2-11-6/h1-3,8H,(H,9,10)

Upstream product

• 82782-85-2 thieno<3,2-b>pyrrole-5-carboxylic acid methyl ester 

Downstream Products

• 82782-85-2 thieno<3,2-b>pyrrole-5-carboxylic acid methyl ester 
• 46193-76-4 ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate 
• 878657-01-3 (4H-thieno[3,2-b]pyrrol-5-yl)methanol 
• 182553-05-5 4H-thieno[3,2-b]pyrrole-5-carbonyl chloride 
• 924643-46-9 4-(4-chlorobenzyl)-4H-thieno[3,2-b] pyrrole-5-carboxylic acid 
• 1047023-77-7 ethyl 1-(4-(4-fluorobenzyl)-4H-thieno[3,2-b]pyrrole-5-carbonyl)-piperidine-4-carboxylate 
• 1163209-26-4 C₂₂H₂₃ClN₂O₃S 
• 1369487-46-6 (R)-ethyl 1-(4-(1-(4-fluorophenyl)ethyl)-4H-thieno[3,2-b]pyrrole-5-carbonyl)piperidine-4-carboxylate 
• 1369487-47-7 (S)-ethyl 1-(4-(1-(4-fluorophenyl)ethyl)-4H-thieno[3,2-b]pyrrole-5-carbonyl)piperidine-4-carboxylate 
• 903165-55-9 C₂₀H₁₉FN₂O₃S 
• 903165-63-9 C₂₀H₁₉ClN₂O₃S 
• 902901-29-5 N-benzyl-1-(4-(4-fluorobenzyl)-4H-thieno[3,2-b]pyrrole-5-carbonyl)piperidine-4-carboxamide 
• 902902-81-2 N-benzyl-1-(4-(4-chlorobenzyl)-4H-thieno[3,2-b]pyrrole-5-carbonyl)piperidine-4-carboxamide 
• 1439376-14-3 N-(3,4-diethoxyphenethyl)-4-(3-methylbenzyl)-4H-thieno[3,2-b]pyrrole-5-carboxamide trifluoroacetate 

Relevant articles and documents

Chemical Evolution of a Bacterial Proteome

We have changed the amino acid set of the genetic code of Escherichia coli by evolving cultures capable of growing on the synthetic noncanonical amino acid L-β-(thieno[3,2-b]pyrrolyl)alanine ([3,2]Tpa) as a sole surrogate for the canonical amino acid L-tryptophan (Trp). A long-term cultivation experiment in defined synthetic media resulted in the evolution of cells capable of surviving Trp→[3,2]Tpa substitutions in their proteomes in response to the 20 899 TGG codons of the E. coli W3110 genome. These evolved bacteria with new-to-nature amino acid composition showed robust growth in the complete absence of Trp. Our experimental results illustrate an approach for the evolution of synthetic cells with alternative biochemical building blocks.

Novel thienopyrrole glycogen phosphorylase inhibitors: Synthesis, in vitro SAR and crystallographic studies

Two series of novel thienopyrrole inhibitors of recombinant human liver glycogen phosphorylase a (GPa) which are effective in reducing glucose output from rat hepatocytes are described. Representative compounds have been shown to bind at the dimer interface site of the rabbit muscle enzyme by X-ray crystallography.