23136-39-2

Usage

Uses

Used in Organic Synthesis:
2-ACETYL-5-NITROBENZO[B]FURAN is used as a building block in organic synthesis for the creation of various complex organic molecules. Its unique structure, including the acetyl and nitro groups, allows for versatile chemical reactions and modifications, contributing to the synthesis of new compounds with potential applications in various fields.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-ACETYL-5-NITROBENZO[B]FURAN is used as a starting material or intermediate in the development of pharmaceutical compounds. Its structural features may provide opportunities for the design of new drugs with specific therapeutic properties. The acetyl and nitro groups can be further functionalized or modified to explore its potential in drug discovery and optimization processes.
Used in Chemical Research:
2-ACETYL-5-NITROBENZO[B]FURAN is also utilized in chemical research to study the properties and reactivity of nitro-substituted benzofuran derivatives. Understanding its chemical behavior can contribute to the advancement of knowledge in organic chemistry and potentially lead to the discovery of new synthetic methods or applications.

InChI:InChI=1/C10H7NO4/c1-6(12)10-5-7-4-8(11(13)14)2-3-9(7)15-10/h2-5H,1H3

Upstream product

• 1646-26-0 1-(benzo[b]furan-2-yl)ethanone 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 97-51-8 5-Nitrosalicylaldehyde 
• 70726-17-9 (2-hydroxy-5-nitrobenzyl)triphenylphosphine chloride 
• 5704-66-5 pyruvoyl chloride 
• 78-95-5 chloroacetone 
• 2973-19-5 2-hydroxy-5-nitrobenzyl chloride 
• 598-31-2 1-bromoacetone 
• 67-64-1 acetone 

Downstream Products

• 98873-72-4 2-ethyl-3-4'-hydroxybenzoyl-5-nitrobenzofuran 
• 90908-76-2 2-ethyl-3-4'-methoxybenzoyl-5-nitrobenzofuran 
• 29735-83-9 2-ethyl-3-4'-hydroxybenzoyl-3',5'-diiodo-5-nitrobenzofuran 
• 1206485-67-7 2-tosyloxy-1-(5-nitrobenzofuran-2-yl)ethanone 

Relevant academic research and scientific papers

Synthesis and Anti-Cholinesterase Activity of Novel Glycosyl Benzofuranylthiazole Derivatives

Abstract: A new series of glycosyl benzofuranylthiazole derivatives were designed, synthesized, characterized, and evaluated as potential candidates to treat Alzheimer’s disease. The compounds have been synthesized by the cyclocondensation of glycosyl thiourea with a variety of 2-(bromoacetyl)benzofurans. The reaction conditions have been optimized, and good yields (79–95%) have been obtained. The synthesized compounds showed different degrees of cholinesterase inhibitory activity.

Synthesis and bioactivity of novel C2-glycosyl benzofuranylthiazoles derivatives as acetylcholinesterase inhibitors

A new series of C2-glycosyl benzofuranylthiazole derivatives was synthesised by the further cyclization of glycosyl thiourea and 2-(bromoacetyl)-benzofuran via Hantzsch’s method. The corresponding 2-(bromoacetyl)-benzofuran derivatives were obtained by the reaction from various salicylaldehydes, and the glycosyl thiourea was prepared through a series of steps from D-Glucosamine. The acetylcholinesterase-inhibitory activities of the products were tested by Ellman’s method. The most active compounds were subsequently evaluated for the 50% inhibitory concentration values. N-(1,3,4,6-tetra-O-benzyl-2-deoxy-β-D-glucopyranosyl)-4-(5-methoxy-benzofuran-2-yl)-1,3-thiazole-2-amine possessed the best acetylcholinesterase-inhibition activity with a 50% inhibitory concentration of 2.03 ± 0.26 μM.

Design, synthesis and biological evaluation of benzofuran appended benzothiazepine derivatives as inhibitors of butyrylcholinesterase and antimicrobial agents

A series of bezofuran appended 1,5-benzothiazepine compounds 7a–v was designed, synthesized and evaluated as cholinesterase inhibitors. The biological assay experiments showed that most of the compounds displayed a clearly selective inhibition for butyrylcholinesterase (BChE), while a weak or no effect towards acetylcholinesterase (AChE) was detected. All analogs exhibited varied BChE inhibitory activity with IC50 value ranging between 1.0 ± 0.01 and 72 ± 2.8 μM when compared with the standard donepezil (IC50, 2.63 ± 0.28 μM). Among the synthesized derivatives, compounds 7l, 7m and 7k exhibited the highest BChE inhibition with IC50 values of 1.0, 1.0 and 1.8 μM, respectively. The results from a Lineweaver-Burk plot indicated a mixed-type inhibition for compound 7l with BChE. In addition, docking studies confirmed the results obtained through in vitro experiments and showed that most potent compounds bind to both the catalytic anionic site (CAS) and peripheral anionic site (PAS) of BChE active site. The synthesized compounds were also evaluated for their in vitro antibacterial and antifungal activities. The results indicated that the compounds possessed a broad spectrum of activity against the tested microorganisms and showed high activity against both gram positive and gram negative bacteria and fungi.

TBAI/TBHP mediated oxidative cross coupling of ketones with phenols and carboxylic acids: Direct access to benzofurans

TBAI/TBHP mediated oxidative cross coupling of phenols and carboxylic acids with ketones has been reported under metal-free, base free, solvent free conditions enabling environmentally benign synthesis of aryloxyketones, acyloxy ketones and benzofurans. Phenoxyketones and acyloxylcarbonyl compounds were synthesized in good to high yields, where as benzofurans were synthesized in moderate yields. This method is operationally simple, works under mild conditions, using commercially available as well as inexpensive TBAI and an oxidant TBHP.

Potential of aryl-urea-benzofuranylthiazoles hybrids as multitasking agents in Alzheimer's disease

New benzofuranylthiazole derivatives containing the aryl-urea moiety were synthesized and evaluated in vitro as dual acetylcholinesterase (AChE)-butyrylcholinesterase (BuChE) inhibitors. In addition, the cupric reducing antioxidant capacities (CUPRAC) and ABTS cation radical scavenging abilities of the synthesized compounds were assayed. The result showed that all the synthesized compounds exhibited inhibitory activity on both AChE and BuChE with 1-(4-(5-bromobenzofuran-2-yl)thiazol-2-yl)-3-(2-fluorophenyl)urea (e25, IC50 value of 3.85 1/4M) and 1-(4-iodophenyl)-3-(4-(5-nitrobenzofuran-2-yl)thiazol-2-yl)urea (e38, IC50 value of 2.03 1/4M) as the strongest inhibitors against AChE and BuChE, respectively. Compound e38 was 8.5-fold more potent than galanthamine. The selectivity index of e25 and e38 was 2.40 and 0.37 against AChE and BuChE, respectively. Compound e2, e4 and e11 (IC50 Combining double low line 0.2, 0.5 and 1.13 1/4M, respectively) showed a better ABTS cation radical scavenging ability than the standard quercetin (IC50 Combining double low line 1.18 1/4M). Best poses of compounds e38 on BuChE and e25 on AChE indicate that the thiazole ring and the amidic moiety are important sites of interaction with both ChEs. In addition, the benzofuran ring and phenyl ring are anchored to the side chains of both enzymes by €-€(pi-pi) interactions.

One-pot synthesis of novel symmetric 1,5-di(benzofuran-2-yl)-3-(4- substituted-aryl)-pentane-1,5-dione derivatives

Salicylaldehyde and its substituted derivatives on reaction with bromoacetone under basic condition in ethanol afford corresponding benzofuran derivatives 1a-d. The compounds 1a-d on treatment with different para substituted aromatic aldehydes in presence of base and minimum amount of acetonitrile upon grinding at room temperature gives corresponding α,β-unsaturated carbonyl compounds by crossed aldol condensation, which further undergo Michael addition with 2-acetyl benzofuran to give a new class of symmetric 1,5-di(benzofuran-2-yl)-3-(4-substituted-aryl)-pentane-1,5- dione derivatives 2a-p in one step. The structures of all the newly synthesized compounds have been established by spectral studies.

Facile microwave-assisted synthesis of substituted benzofuran derivatives

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.

Optically active 1-(benzofuran-2-yl)ethanols and ethane-1,2-diols by enantiotopic selective bioreductions

Enantiotopic selective reduction of 1-(benzofuran-2-yl)ethanones 1a-d, 1-(benzofuran-2-yl)-2-hydroxyethanones 4a-c and 2-acetoxy-1-(benzofuran-2-yl)ethanones 3a-c was performed by baker's yeast for preparation of optically active (benzofuran-2-yl)carbinols [(S)-5a-d, (S)-6a-c and (R)-6a-c, enantiomeric excess from 55 to 93% ee].

New Syntheses of 2-Acylbenzofurans, 2-Acylindoles, 2-Indolylcarboxylates, and 2-Quinolones by Intramolecular Wittig Reaction

The title compounds are obtained by intramolecular Wittiig reaction of 2-(α-ketoacyloxy)-, 2-(α-ketoacylamino)-, or 2-benzyltriphenylphosphonium salts, respectively.

Antibacterial activity and polarographic half-wave reduction potential of 2-nitrobenzo[b]furans

The antibacterial activities of a series of 2-nitrobenzo[b]furan derivatives against St. aureus, B. subtilis, E. coli, Sal. typhimurium, Sal. enteritidis, Sh. flexneri, Pr. vulgaris or Ps. aeruginosa were determined in vitro. Most of the compounds showed