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ETHYL 5-NITROBENZOFURAN-2-CARBOXYLATE is a derivative of benzofuran-2-carboxylic acid, a heterocyclic compound with a benzene ring fused to a furan ring. It is known for its pharmacological activities, including acting as a selective adenosine A2A receptor antagonist, anti-inflammatory agent, and local anesthetic.

69604-00-8

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69604-00-8 Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 5-NITROBENZOFURAN-2-CARBOXYLATE is used as a DNA-binding group for its ability to mimic natural antitumor agents such as duocarmycin and netropsin. This makes it a promising candidate for the development of novel anticancer drugs.
Used in Medicinal Chemistry Research:
As a derivative of benzofuran-2-carboxylic acid, ETHYL 5-NITROBENZOFURAN-2-CARBOXYLATE is used in medicinal chemistry research to explore its potential as a selective adenosine A2A receptor antagonist, anti-inflammatory agent, and local anesthetic. Its unique structural features and pharmacological properties make it a valuable compound for the development of new therapeutic agents.

Check Digit Verification of cas no

The CAS Registry Mumber 69604-00-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,9,6,0 and 4 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 69604-00:
(7*6)+(6*9)+(5*6)+(4*0)+(3*4)+(2*0)+(1*0)=138
138 % 10 = 8
So 69604-00-8 is a valid CAS Registry Number.
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

69604-00-8 Well-known Company Product Price

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  • Aldrich

  • (678716)  Ethyl5-nitrobenzofuran-2-carboxylate  97%

  • 69604-00-8

  • 678716-5G

  • 1,316.25CNY

  • Detail

69604-00-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl 5-Nitrobenzofuran-2-Carboxylate

1.2 Other means of identification

Product number -
Other names Ethyl 5-nitro-1-benzofuran-2-carboxylate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

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More Details:69604-00-8 SDS

69604-00-8Relevant articles and documents

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

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, (2018/04/01)

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)

Synthetic method for vilazodone intermediate ethyl 5-(1-piperazinyl)-2-benzofuran-2-carboxylate

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Paragraph 0032-0034, (2018/03/01)

The invention relates to a synthetic method for a vilazodone intermediate, i.e., ethyl 5-(1-piperazinyl)-2-benzofuran-2-carboxylate. The key vilazodone intermediate ethyl 5-(1-piperazinyl)-2-benzofuran-2-carboxylate as shown in a formula I is prepared with 6-nitrocoumarin as a starting raw material through addition, ring opening, intramolecular ring closure, nitro reduction, piperazine ring preparation, etc. The synthetic method is simple in synthetic route, high in the yield of target products and suitable for industrial scale-up production.

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

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Paragraph 0147; 0148; 0149; 0150, (2017/07/26)

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.

PROCESS FOR THE PREPARATION OF VILAZODONE HYDROCHLORIDE AND ITS AMORPHOUS FORM

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Paragraph 0124, (2015/03/31)

The present invention relates to an improved process for the preparation of vilazodone Hydrochloride and a process for preparation of novel pure amorphous form of vilazodone hydrochloride.

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

Reddy, Kummetha Indrasena,Srihari, Konduri,Renuka, Janupally,Sree, Komanduri Shruthi,Chuppala, Aruna,Jeankumar, Variam Ullas,Sridevi, Jonnalagadda Padma,Babu, Kondra Sudhakar,Yogeeswari, Perumal,Sriram, Dharmarajan

, p. 6552 - 6563 (2015/02/18)

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.

Design, synthesis, biological evaluation of substituted benzofurans as DNA gyraseB inhibitors of Mycobacterium tuberculosis

Renuka, Janupally,Reddy, Kummetha Indrasena,Srihari, Konduri,Jeankumar, Variam Ullas,Shravan, Morla,Sridevi, Jonnalagadda Padma,Yogeeswari, Perumal,Babu, Kondra Sudhakar,Sriram, Dharmarajan

, p. 4924 - 4934 (2014/10/16)

DNA gyrase of Mycobacterium tuberculosis (MTB) is a type II topoisomerase and is a well-established and validated target for the development of novel therapeutics. By adapting the medium throughput screening approach, we present the discovery and optimization of ethyl 5-(piperazin-1-yl) benzofuran-2- carboxylate series of mycobacterial DNA gyraseB inhibitors, selected from Birla Institute of Technology and Science (BITS) database chemical library of about 3000 molecules. These compounds were tested for their biological activity; the compound 22 emerged as the most active potent lead with an IC50 of 3.2 ± 0.15 μM against Mycobacterium smegmatis DNA gyraseB enzyme and 0.81 ± 0.24 μM in MTB supercoiling activity. Subsequently, the binding of the most active compound to the DNA gyraseB enzyme and its thermal stability was further characterized using differential scanning fluorimetry method.

Facile microwave-assisted synthesis of substituted benzofuran derivatives

Liu, Junqiang,Mi, Chenggen,Tang, Xuemei,Cao, Yuan,Li, Zicheng,Huang, Wencai

, p. 2083 - 2090 (2014/05/06)

A series of benzofuran derivatives have been synthesized by use of a microwave-assisted process. Substituted or unsubstituted ?- hydroxyacetophenone and salicylaldehyde reacted with ethyl bromoacetate, ω-bromoacetophenone, or chloroacetone under the action of potassium carbonate in DMF to yield substituted benzofuran derivatives. Compared with conventional heating, this microwave-assisted synthetic process has the advantages of more convenient operation, shorter reaction time, and higher yield.

PROCESS FOR THE PREPARATION OF VILAZODONE HYDROCHLORIDE AND ITS AMORPHOUS FORM

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Page/Page column 23, (2013/11/05)

The present invention relates to an improved process for the preparation of vilazodone Hydrochloride and a process for preparation of novel pure amorphous form of vilazodone hydrochloride.

Synthesis and CYP24A1 inhibitory activity of N-(2-(1H-imidazol-1-yl)-2- phenylethyl)arylamides

Aboraia, Ahmed S.,Yee, Sook Wah,Gomaa, Mohamed Sayed,Shah, Nikhil,Robotham, Anna C.,Makowski, Bart,Prosser, David,Brancale, Andrea,Jones, Glenville,Simons, Claire

experimental part, p. 4939 - 4946 (2010/09/10)

A series of N-(2-(1H-imidazol-1-yl)-2-phenylethyl)arylamides were prepared, using an efficient three- to five-step synthesis, and evaluated for their inhibitory activity against human cytochrome P450C24A1 (CYP24A1) hydroxylase. Inhibition ranged from IC50 0.3-72 μM compared with the standard ketoconazole IC50 0.52 μM, with the styryl derivative (11c) displaying enhanced activity (IC50 = 0.3 μM) compared with the standard, providing a useful preliminary lead for drug development.

EP2 RECEPTOR AGONISTS

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Page/Page column 145, (2008/06/13)

A compound of Formula (I) or a salt, solvate and chemically protected form thereof, wherein: R5 is an optionally substituted C5-20 aryl or C4-20 alkyl group; A is selected from the group consisting of Formulae (Ai), (Aii), (Aiii) D is selected from Formulae (Di), (Dii), (Diii), (Div), (Dv) B is selected from the group consisting of Formulae (Bi), (Bii), (Biii), (Biv) (Bv).

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