1914-60-9

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Dihydro-1-benzofuran-2-carboxylic acid is used as a starting material for the synthesis of (dihydro)benzofuran-2-carboxylic acid N-(substituted)phenylamide derivatives. These derivatives have shown potential as anticancer agents, making 2,3-Dihydro-1-benzofuran-2-carboxylic acid an important component in the development of novel treatments for cancer.
The compound's role in the synthesis of anticancer agents highlights its significance in the pharmaceutical industry, where it contributes to the creation of new drugs that can help combat various types of cancer.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 24, p. 495, 1987 DOI: 10.1002/jhet.5570240236

InChI:InChI=1/C9H8O3/c10-9(11)8-5-6-3-1-2-4-7(6)12-8/h1-4,8H,5H2,(H,10,11)

Upstream product

• 496-41-3 Benzofuran-2-carboxylic acid 
• 90-02-8 salicylaldehyde 
• 108-95-2 phenol 
• 1746-13-0 allyl phenyl ether 
• 66158-96-1 2-hydroxymethyl-1H-2,3-dihydrobenzofuran 
• 1745-81-9 o-Allylphenol 
• 41873-61-4 ethyl (2-formylphenoxy)acetate 
• 43119-53-5 ethyl 2,3-dihydro-1-benzofuran-2-carboxylate 
• 111080-49-0 o-(ethoxycarbonylmethoxy)benzyl chloride 
• 111080-48-9 ethyl 2-[2-(hydroxymethyl)phenoxy]acetate 

Downstream Products

• 885069-03-4 5-bromo-2,3-dihydro-1-benzofuran-2-carboxylic acid 
• 66673-50-5 Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-3-(S)-2,3-dihydro-benzofuran-2-yl-3-oxo-propenyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 66673-51-6 Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-3-(R)-2,3-dihydro-benzofuran-2-yl-3-oxo-propenyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 66673-52-7 Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-(S)-3-(S)-2,3-dihydro-benzofuran-2-yl-3-hydroxy-propenyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 66673-54-9 Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-(S)-3-(R)-2,3-dihydro-benzofuran-2-yl-3-hydroxy-propenyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 66673-53-8 Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-(R)-3-(S)-2,3-dihydro-benzofuran-2-yl-3-hydroxy-propenyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 66673-55-0 Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-(R)-3-(R)-2,3-dihydro-benzofuran-2-yl-3-hydroxy-propenyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 

Relevant academic research and scientific papers

Green Organocatalytic Synthesis of Dihydrobenzofurans by Oxidation-Cyclization of Allylphenols

A green and cheap protocol for the synthesis of dihydrobenzofurans via an organocatalytic oxidation of o -allylphenols is presented. The use of 2,2,2-trifluoroacetophenone and H 2 O 2 as the oxidation system, leads to a highly useful synthetic method, where a variety of substituted o -allylphenols were cyclized in high yields..

Design, synthesis, and biological evaluation of benzofuran- and 2,3-dihydrobenzofuran-2-carboxylic acid N-(substituted)phenylamide derivatives as anticancer agents and inhibitors of NF-κB

With the aim of developing novel scaffolds as anticancer agents and inhibitors of NF-κB activity, 60 novel benzofuran- and 2,3-dihydrobenzofuran-2-carboxylic acid N-(substituted)phenylamide derivatives (1a-s, 2a-k, 3a-s, and 4a-k) were designed and synthesized from the reference lead compound KL-1156, which is an inhibitor of NF-κB translocation to the nucleus in LPS-stimulated RAW 264.7 macrophage cells. The novel benzofuran- and 2,3-dihydrobenzofuran-2-carboxamide derivatives exhibited potent cytotoxic activities (measured by the sulforhodamine B assay) at low micromolar concentrations against six human cancer cell lines: ACHN (renal), HCT15 (colon), MM231 (breast), NUGC-3 (gastric), NCI-H23 (lung), and PC-3 (prostate). In addition, these compounds also inhibited LPS-induced NF-κB transcriptional activity. The +M effect and hydrophobic groups on the N-phenyl ring potentiated the anticancer activity and NF-κB inhibitory activity, respectively. However, according to the results of structure-activity relationship studies, only benzofuran-2-carboxylic acid N-(4′-hydroxy)phenylamide (3m) was the lead scaffold with both an outstanding anticancer activity and NF-κB inhibitory activity. This novel lead scaffold may be helpful for investigation of new anticancer agents that act through inactivation of NF-κB.

ANTIPARASITIC AGENTS

The present invention relates to compounds of the formula (I) and pharmaceutically acceptable salts thereof, compositions containing such compounds and the uses of such compounds as antiparasitic agents.

Fused bicyclic carboxamide derivatives and methods of their use

Fused bicyclic carboxamide derivatives are disclosed. Pharmaceutical compositions containing the compounds and methods for their use are also disclosed.

Further structure-activity relationships in the series of tropanyl esters endowed with potent antinociceptive activity

Several analogs of the α-tropanyl esters of 2-(4-chlorophenoxy)butyric acid (SM21) and 2-phenylthiobutyric acid (SM32), endowed with potent antinociceptive and cognition enhancing activity, were synthesized, aimed at obtaining more potent and safe drug candidates. Variation of the acyl moiety, as well as the conformational restriction of atropine to give the α-tropanyl ester of 2,3-dihydrobenzofurane-3-carboxylic acid (18), practically abolished activity. In the case of 18, the antimuscarinic activity was also severely affected by the conformation restrain. On the contrary, conformational restriction of phenoxybutyric and phenylthiobutyric acid derivatives to give the α-tropanyl ester of 2,3-dihydro-benzofurane-2-carboxylic acid and 2,3-dihydro-benzothiophene-2-carboxylic acid, afforded potent analgesic drugs that unfortunately were too toxic to be reliable drug candidates. A series of related esters of benzofurane-3-carboxylic acid and benzothiophene-3-carboxylic acid were also studied and found to be potent but toxic analgesics.