50551-58-1

Usage

Chemical Properties

yellow crystals

InChI:InChI=1/C12H12O4/c1-3-15-12(13)10-7-8-5-4-6-9(14-2)11(8)16-10/h4-7H,3H2,1-2H3

Upstream product

• 64-17-5 ethanol 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 105-39-5 chloroacetic acid ethyl ester 
• 70076-67-4 2-ethoxycarbonylmethoxy-3-methoxybenzaldehyde 
• 621-59-0 isovanillin 
• 105-36-2 ethyl bromoacetate 
• 685-87-0 Diethyl 2-bromomalonate 

Downstream Products

• 75566-54-0 2-hydroxymethyl-7-methoxy-benzofuran 
• 4790-79-8 7-methoxybenzofuran-2-carboxylic acid 

Relevant academic research and scientific papers

Novel tacrine–benzofuran hybrids as potential multi-target drug candidates for the treatment of Alzheimer’s Disease

Pursuing the widespread interest on multi-target drugs to combat Alzheimer′s disease (AD), a new series of hybrids was designed and developed based on the repositioning of the well-known acetylcholinesterase (AChE) inhibitor, tacrine (TAC), by its coupling to benzofuran (BF) derivatives. The BF framework aims to endow the conjugate molecules with ability for inhibition of AChE (bimodal way) and of amyloid-beta peptide aggregation, besides providing metal (Fe, Cu) chelating ability and concomitant extra anti-oxidant activity, for the hybrids with hydroxyl substitution. The new TAC-BF conjugates showed very good activity for AChE inhibition (sub-micromolar range) and good capacity for the inhibition of self- and Cu-mediated Aβ aggregation, with dependence on the linker size and substituent groups of each main moiety. Neuroprotective effects were also found for the compounds through viability assays of neuroblastoma cells, after Aβ1-42 induced toxicity. Structure-activity relationship analysis provides insights on the best structural parameters, to take in consideration for future studies in view of potential applications in AD therapy.

Polysubstituted Pyrimidines as mPGES-1 Inhibitors: Discovery of Potent Inhibitors of PGE2 Production with Strong Anti-inflammatory Effects in Carrageenan-Induced Rat Paw Edema

We report an extensive structure-activity relationship optimization of polysubstituted pyrimidines that led to the discovery of 5-butyl-4-(4-benzyloxyphenyl)-6-phenylpyrimidin-2-amine, and its difluorinated analogue. These compounds are sub-micromolar inh

Synthesis and AChE inhibitory activity of N-glycosyl benzofuran derivatives

Six N-glycosyl benzofuran derivatives were synthesized by the catalysis of organic bases and condensation agents. The benzofuran derivatives were obtained by the reaction of various salicylaldehydes in acetone, and then hydrolyzed to the corresponding carboxylic acids. Finally, the target compounds were synthesized by acylation and the reaction conditions were optimized. The acetylcholinesterase (AChE) inhibitory activity of the desired compounds was tested using Ellman's method. Most of the compounds showed acetylcholinesterase-inhibition activity; N-(2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)benzofuran-2-carbxamide (5a) showed the best acetylcholinesterase inhibition, with an inhibitory rate of 84%.

Development of coumarin–benzofuran hybrids as versatile multitargeted compounds for the treatment of Alzheimer’s Disease

Alzheimer’s disease (AD), the most common cause of dementia, is a neurodegenerative disorder characterized by progressive deterioration of memory and cognition. The evidenced multifactorial nature of AD has been considered the main reason for the absence of cure so far. Therefore, the development of novel hybrids to treat the disease is very much essential. Focusing on this, a novel series of coumarin–benzofuran hybrids have been designed and screened as anti-Alzheimer’s disease agents. The strategy is to obtain an effective mimetic of donepezil, which is acetylcholinesterase inhibitor. Herein, the two main scaffolds namely coumarin and benzofuran are known pharmacophore moieties and we have performed their molecular design, pharmacokinetic descriptor studies for drug-likeliness. Further, in vitro studies such as antioxidant capacity, acetylcholinesterase (AChE) inhibition and amyloid-β (Aβ) self-aggregation inhibition have also been performed. Most importantly, these studies revealed that the newly synthesized hybrids can be versatile and promising drug-like moieties as efficient anti-AD agents.

Synthetic studies on selective adenosine A2A receptor antagonists: Synthesis and structure-activity relationships of novel benzofuran derivatives

A series of benzofuran derivatives were prepared to study their antagonistic activities to the A2A receptor. Replacement of the ester group of the lead compound 1 with phenyl ring improved the PK profile, while modifications of the amide moiety

NOVEL HETEROCYCLIC COMPOUNDS USEFUL FOR THE TREATMENT OF INFLAMMATORY AND ALLERGIC DISORDERS: PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

The present invention relates to novel Phosphodiesterase type 4 (PDE4) inhibitors of the formula (1) and analogs, tautomers, enantiomers, a diasteromers, regioisomers, stereoisomers, polymorphs, pharmaceutically acceptable salts, appropriate N-oxides, pharmaceutically acceptable solvates thereof and the pharmaceutical compositions containing them which are useful in the treatment of allergic and inflammatory diseases including asthma, chronic bronchitis, atopic dermatitis, urticaria, allergic rhinitis, allergic conjunctivitis, vernal conjunctivitis, eosinophilic granuloma, psoriasis, rheumatoid arthritis, septic shock, ulcerative colitis, Crohn's disease, reperfusion injury of the myocardium and reperfusion injury of the brain, chronic glomerulonephritis, endotoxic shock and adult respiratory distress syndrome.

NOVEL HETEROCYCLIC COMPOUNDS USEFUL FOR THE TREATMENT OF INFLAMMATORY AND ALLERGIC DISORDERS

The present invention relates to novel Phosphodiesterase type 4 (PDE4) inhibitors of the formula (1) and analogs, tautomers, enantiomers, diasteromers, regioisomers, stereoisomers, polymorphs, pharmaceutically acceptable salts, appropriate N-oxides, pharm

P(MeNCH2CH2)3N: An efficient catalyst for the synthesis of substituted ethyl benzofuran-2-carboxylates

A superior method for the synthesis of substituted ethyl benzofuran-2-carboxylates in 80-99% yields from substituted 2-formylphenoxy ethylcarboxylates using 0.4 equiv of commercially available P(MeNCH2CH2)3N at 70 °C for 3 hours is described.

Benzimidazole compounds as bradykinin antagonists

PCT No. PCT/JP95/01478 Sec. 371 Date Feb. 3, 1997 Sec. 102(e) Date Feb. 3, 1997 PCT Filed Jul. 25, 1995 PCT Pub. No. WO96/04251 PCT Pub. Date Feb. 15, 1996This invention relates to a heterocyclic compound of the formula: wherein a group of the formula: is a group of the formula: etc., X is O, S or N-R5, R1 is lower alkyl, etc., R5 is hydrogen, lower alkyl, etc., R2 is hydrogen, halogen, lower alkyl, etc., R3 is halogen, lower alkyl, etc., R4 is amino optionally having suitable substituent(s), and A is lower alkylene, and a salt thereof, to processes for preparation thereof, and to a pharmaceutical composition comprising the same for the prevention and/or the treatment of bradykinin or its analogues mediated diseases in human being or animals.

Microwave-assisted preparation of benzo[b]furans under solventless phase-transfer catalytic conditions

Condensation of salicylaldehyde and its derivatives with various esters of chloroacetic acids in the presence of tetrabutylammonium bromide (TBAB) leads to the synthesis of benzo[b]furans by a solventless phase-transfer catalytic (PTC) reaction under microwave irradiation. (C) 2000 Elsevier Science Ltd.