330555-71-0

Basic information

• Product Name: 3-AMINO-5-BROMO-BENZOFURAN-2-CARBOXYLIC ACID ETHYL ESTER
• Synonyms: 3-AMINO-5-BROMO-BENZOFURAN-2-CARBOXYLIC ACID ETHYL ESTER;AKOS BBS-00006196;Ethyl 3-amino-5-bromo-1-benzofuran-2-carboxylate;ethyl 3-amino-5-bromobenzofuran-2-carboxylate;3-amino-5-bromo-2-Benzofurancarboxylic acid ethyl ester
• CAS NO: 330555-71-0
• Molecular Formula: C11H10BrNO3
• Molecular Weight: 284.11
• Mol File: 330555-71-0.mol

Chemical Properties

• Melting Point: 155-157°
• Appearance: /
• CAS DataBase Reference: 3-AMINO-5-BROMO-BENZOFURAN-2-CARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-5-BROMO-BENZOFURAN-2-CARBOXYLIC ACID ETHYL ESTER(330555-71-0)
• EPA Substance Registry System: 3-AMINO-5-BROMO-BENZOFURAN-2-CARBOXYLIC ACID ETHYL ESTER(330555-71-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 330555-71-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-AMINO-5-BROMO-BENZOFURAN-2-CARBOXYLIC ACID ETHYL ESTER is employed as a key intermediate in organic synthesis for the production of various chemical compounds. Its unique structure allows for versatile reactions and modifications, making it a valuable component in the synthesis of specialty chemicals and complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 3-AMINO-5-BROMO-BENZOFURAN-2-CARBOXYLIC ACID ETHYL ESTER is used as a building block for the development of new drugs. Its distinctive molecular features, including the benzofuran ring and the bromine and amino substituents, offer opportunities for the design of novel therapeutic agents with potential applications in treating various diseases and medical conditions.
Used in Drug Development:
3-AMINO-5-BROMO-BENZOFURAN-2-CARBOXYLIC ACID ETHYL ESTER is utilized as a precursor in the synthesis of pharmaceutical compounds, contributing to the discovery and development of new drugs. Its chemical properties and structural elements can be leveraged to create molecules with specific biological activities, enhancing the therapeutic potential of drug candidates in clinical research and development.
Used in Material Science:
3-AMINO-5-BROMO-BENZOFURAN-2-CARBOXYLIC ACID ETHYL ESTER may also find applications in the field of material science, where its unique chemical structure could be employed to develop new materials with specialized properties. These materials could have uses in various industries, including electronics, coatings, and advanced composites, where novel properties are sought to meet specific performance requirements.

Upstream product

• 611-20-1 salicylonitrile 
• 1761-61-1 5-bromosalicyclaldehyde 
• 40530-18-5 5-bromo-2-hydroxybenzonitrile 
• 105-36-2 ethyl bromoacetate 
• 39786-34-0 ethyl 2-(2-cyanophenoxy)acetate 
• 328009-03-6 (4-bromo-2-cyanophenoxy)acetic acid ethyl ester 

Downstream Products

• 1277185-69-9 C₁₇H₁₄BrN₃O₂ 
• 1277185-70-2 C₁₇H₁₃BrClN₃O₂ 
• 1277185-71-3 C₁₇H₁₃Br₂N₃O₂ 
• 1277185-72-4 C₁₈H₁₆BrN₃O₃ 
• 1277185-73-5 C₁₇H₁₂BrCl₂N₃O₂ 
• 1277185-74-6 C₁₉H₁₂BrN₃O₃ 
• 1277185-75-7 C₁₉H₁₁BrClN₃O₃ 
• 1277185-76-8 C₁₉H₁₁Br₂N₃O₃ 
• 1277185-77-9 C₂₀H₁₄BrN₃O₄ 
• 1277185-78-0 C₁₉H₁₀BrCl₂N₃O₃ 

Relevant articles and documents

Nucleotide competing reverse transcriptase inhibitors: Discovery of a series of non-basic benzofurano[3,2-d]pyrimidin-2-one derived inhibitors

A HTS screen led to the identification of a benzofurano[3,2-d]pyrimidin-2- one core structure which upon further optimization resulted in 1 as a potent HIV-1 nucleotide competing reverse transcriptase inhibitor (NcRTI). Investigation of the SAR at N-1 allowed significant improvements in potency and when combined with the incorporation of heterocycles at C-8 resulted in potent analogues not requiring a basic amine to achieve antiviral activity. Additional modifications at N-1 resulted in 33 which demonstrated excellent antiviral potency and improved physicochemical properties.

CONDENSED TRICLYCLIC COMPOUNDS AS INHIBITORS OF HIV REPLICATION

Compounds of formula (I) and pharmaceutical compositions thereof: wherein A1 A2 and A3 are each independently selected from the group consisting of N and CR3, wherein R1 is an optionally substituted heterocyclyl or an optionally substituted -(C1-6)alkyl-heterocyclyl, R2 is an optionally substituted aryl or an optionally subsisted heteroaryl, R4 is an optionally substituted aryl, an optionally substituted heterocyclyl or an optionally substituted heteroaryl, useful as an inbitor of HIV replication.

Identification and characterization of a novel HIV-1 nucleotide-competing reverse transcriptase inhibitor series

Several groups have recently reported on the identification of nucleotide-competing reverse transcriptase inhibitors (NcRTIs), a new class of RT inhibitors. NcRTIs reversibly inhibit binding of the incoming nucleotide to the RT active site but do not act

Synthesis of some pyrazole incorporated benzofurans and their antiinflammatory activity

The reaction of 5-bromosalicylaldehyde 1 with hydroxylamine hydrochloride gave 5-bromosalicylonitrile 2 which upon condensation with ethyl chloroacetate followed by cyclization gave ethyl 3-amino-5-bromo-1-benzofuran-2-carboxylate 4. The compound 4 on treatment with hydrazine hydrate in ethanol gave 3-amino-5-bromo-1-benzofuran-2-carbohydrazide 5 which further on reaction with various substituted acetophenones in abs ethanol in presence of catalytic quantity of hydrochloric acid furnished corresponding hydrazones 6a-e. The title compounds 7a-e were synthesized by the reaction of 6a-e with Vilsmerier-Haack reagent. The structures of all synthesized compounds were established using analytical and spectral data. 6a-e and 7a-e have been evaluated for antiinflammatory activities.

INHIBITORS OF HIV REPLICATION

Compounds of formula (I): wherein R1, R2, A1, A2, A3, A4, X and Y are as defined herein, are useful as inhibitors of HIV replication.

Synthesis and anti-microbial activities of oxadiazoles, thiadiazoles and triazoles containing 5-bromo-3-amino benzofuran nucleus from 5-bromosalicylonitrile

5-Bromosalicylonitrile 2 has been prepared from 5-Bromosalicylladehyde 1 and hydroxylamine hydrochloride, which on further treatment with ethyl chloroacetate gave ethyl 5-bromo-3-amino-2-benzofurancarboxylate 4. The resulting compound 4 was treated with hydrazine hydrate in boiling ethanol gave the hydrazide compound 5. The resulting hydrazide was reacted with substituted aryl isothiocyanates and offered thiosemicarbazide compounds 6-9. 5Bromo-3-amino-2+--benzofurothiosemicarbazides underwent cyclization with different reagents under different reaction conditions to furnish benzofuran derivatives possessing oxadiazoles, triazoles and thiadiazoles 10-21 respectively. The structures of all the compounds have been assigned by elemental analysis and spectral studies. The synthesized compounds were screened for their antimicrobial and antifungal activities.

Syntheses of 3-acetoacetylaminobenzo[b]furan derivatives having cysteinyl leukotriene 2 receptor antagonistic activity

Novel 3-acetoacetylaminobenzo[b]furan derivatives having a modified triene system at the 3-position were synthesized starting with 3-aminobenzo[b]furans. The enol isomers, 3-[(3-hydroxybul-2-enonyl)amino]benzo[b]furans (1), of the 3-acetoacetylaminobenzo[b]furans were obtained as stable isomers owing to formation of a hydrogen bonding between the enol hydroxyl group and the amidocarbonyl group. The planarity of the C-2 substituent through the C-3 side chain suggested the existence of a modified conjugational triene system in the enol compound. Cysteinyl leukotriene 1 and 2 receptor antagonistic activities for these compounds were evaluated. 2-(4-Cyanobenzoyl or ethoxycarbonyl)-3-[(2-cyano-3-hydroxybut-2-enonyl)amino]benzo[e]furans (15g, 15o, 15u) were moderately active.

Preparation of 3-acetoacetylaminobenzo[b]furan derivatives with cysteinyl leukotriene receptor 2 antagonistic activity.

Novel 3-acetoacetylaminobenzo[b]furan derivatives with a modified triene system at the 3-position were prepared through acylation of the 3-aminobenzo[b]furans with 5-methylisoxazole-4-carboxylic acid chloride followed by basic cleavage of the isoxazole ring and several of these compounds showed moderate cysteinyl leukotriene receptor 2 antagonistic activity.