69604-00-8

Basic information

• Product Name: ETHYL 5-NITROBENZOFURAN-2-CARBOXYLATE
• Synonyms: ethyl 5-nitro-1-benzofuran-2-carboxylate;2-Benzofurancarboxylicacid, 5-nitro-, ethyl ester;5-Nitrobenzofuran-2-carboxylic acid ethyl esther;Vilazodone INT 1;Ethyl 5-nitrobenzofuran-2-carboxylate 97%;5-Nitrobenzofuran-2-carboxylic acid methyl ester;ETHYL 5-NITROBENZO[B]FURAN-2-CARBOXYLATE;ETHYL 5-NITROBENZOFURAN-2-CARBOXYLATE
• CAS NO: 69604-00-8
• Molecular Formula: C₁₁H₉NO₅
• Molecular Weight: 235.19
• Product Categories: Esters;Fused Ring Systems;Benzofurans;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 69604-00-8.mol
• Article Data: 15

Chemical Properties

• Melting Point: 150 °C
• Boiling Point: 377.58°C (rough estimate)
• Flash Point: 171.3 °C
• Appearance: Light yellow to light brown powder
• Density: 1.362
• Vapor Pressure: 2.34E-05mmHg at 25°C
• Refractive Index: 1.4950 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: slightly sol. in Acetone
• CAS DataBase Reference: ETHYL 5-NITROBENZOFURAN-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 5-NITROBENZOFURAN-2-CARBOXYLATE(69604-00-8)
• EPA Substance Registry System: ETHYL 5-NITROBENZOFURAN-2-CARBOXYLATE(69604-00-8)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 69604-00-8(Hazardous Substances Data)

Usage

Uses

Deriatives of benzofuran-2-carboxylic acid are known for exhibiting various pharmacological activities such as selective adenosine A2A receptor antagonists, anti-inflammatory agents and local anaesthe tics. Benzofuran-2-carboxylic acids bearing benzoyl nitrogen such as Ethyl 5-Nitrobenzofuran-2-carboxylate, are used as DNA-binding groups, where the these structural subunits mimic natural antitumor agents such as duocarmycin and netropsin.

InChI:InChI=1/C11H9NO5/c1-2-16-11(13)10-6-7-5-8(12(14)15)3-4-9(7)17-10/h3-6H,2H2,1H3

Upstream product

• 3199-61-9 ethyl coumarilate 
• 685-87-0 Diethyl 2-bromomalonate 
• 97-51-8 5-Nitrosalicylaldehyde 
• 50396-49-1 3-(2-hydroxy-5-nitrophenyl)acrylic acid 
• 64-17-5 ethanol 
• 10242-12-3 5-nitrobenzofuran-2-carboxylic acid 
• 2725-81-7 6-nitrocoumarin 
• 90-02-8 salicylaldehyde 
• 105-36-2 ethyl bromoacetate 
• 75-03-6 ethyl iodide 
• 51336-43-7 2-formyl-4-nitrophenoxyacetic acid ethyl ester 

Downstream Products

• 163521-20-8 5-(piperazin-1-yl)benzofuran-2-carboxylic acid ethyl ester 
• 53020-42-1 5-hydroxybenzofuran-2-carbonitrile 
• 916737-84-3 5-aminobenzofuran-2-carbonitrile 
• 183288-46-2 5-(1-piperazinyl)benzofuran-2-carboxamide 
• 90322-48-8 (5-nitro-1-benzofuran-2-yl)methanol 
• 10242-12-3 5-nitrobenzofuran-2-carboxylic acid 

Relevant articles and documents

[...] intermediate synthetic method (by machine translation)

The invention relates to a [...] intermediate synthesis method, in order to 6 - nitro coumarin as the starting the raw materials, through ring-opening, the ring in the molecule, esterification, reduction, paipai qin link other steps, to obtain key [...] middle style I compound 5 - (1 - piperazinyl) - 2 - benzofuran - 2 - carboxylic acid ethyl ester. The invention synthetic route is simple, the target product yield is relatively high, and is suitable for industrial scale production. (by machine translation)

Pyrimidine heterocyclic compounds, pyrimidine heterocyclic compound salts, and preparation method and application thereof

The invention provides pyrimidine heterocyclic compounds, pyrimidine heterocyclic compound salts, and a preparation method and application thereof. According to the pyrimidine heterocyclic compounds provided by the invention, specific Rq is selected, so that the obtained compounds have favorable drug resistance and long half life when being used as the medicine for treating or preventing HIV. The compounds have the advantages of high activity, low toxicity and high stability.

An efficient synthesis and biological screening of benzofuran and benzo[d]isothiazole derivatives for Mycobacterium tuberculosis DNA GyrB inhibition

A series of twenty eight molecules of ethyl 5-(piperazin-1-yl)benzofuran-2-carboxylate and 3-(piperazin-1-yl)benzo[d]isothiazole were designed by molecular hybridization of thiazole aminopiperidine core and carbamide side chain in eight steps and were screened for their in vitro Mycobacterium smegmatis (MS) GyrB ATPase assay, Mycobacterium tuberculosis (MTB) DNA gyrase super coiling assay, antitubercular activity, cytotoxicity and protein-inhibitor interaction assay through differential scanning fluorimetry. Also the orientation and the ligand-protein interactions of the top hit molecules with MS DNA gyrase B subunit active site were investigated applying extra precision mode (XP) of Glide. Among the compounds studied, 4-(benzo[d]isothiazol-3-yl)-N-(4-chlorophenyl)piperazine-1-carboxamide (26) was found to be the most promising inhibitor with an MS GyrB IC50 of 1.77 ± 0.23 μM, 0.42 ± 0.23 against MTB DNA gyrase, MTB MIC of 3.64 μM, and was not cytotoxic in eukaryotic cells at 100 μM. Moreover the interaction of protein-ligand complex was stable and showed a positive shift of 3.5 °C in differential scanning fluorimetric evaluations.