21587-39-3

Usage

Uses

Used in Pharmaceutical Research:
1-(5-Methoxy-2-benzofuranyl)ethanone is used as a research chemical for studying the effects of psychoactive substances on the central nervous system. Its structural and functional similarities to MDMA make it a valuable tool in understanding the mechanisms of action and potential therapeutic applications of entactogens.
Used in Forensic Toxicology:
In forensic toxicology, MBDB is utilized for the identification and analysis of controlled substances in biological samples. Its detection in post-mortem cases or drug-related incidents aids in determining the cause of death or intoxication, providing crucial evidence for legal proceedings.
Used in Drug Policy and Regulation:
1-(5-Methoxy-2-benzofuranyl)ethanone is used as a reference substance in the development and implementation of drug policy and regulation. Its classification as a controlled substance helps inform public health and safety measures, guiding the enforcement of drug laws and the management of substance abuse.

InChI:InChI=1/C11H10O3/c1-7(12)11-6-8-5-9(13-2)3-4-10(8)14-11/h3-6H,1-2H3

Upstream product

• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 78-95-5 chloroacetone 

Downstream Products

• 1292843-01-6 (4,6-dibromo-2-ethyl-5-hydroxybenzofuran-3-yl)(4-methoxyphenyl)methanone 
• 1292842-98-8 (3,5-dibromo-4-hydroxyphenyl)(2-ethyl-5-hydroxybenzofuran-7-yl)methanone 
• 1292842-97-7 (3,5-dibromo-4-hydroxyphenyl)(2-ethyl-5-methoxybenzofuran-7-yl)methanone 
• 1292842-96-6 (3,5-dibromo-4-hydroxyphenyl)(2-ethyl-5-hydroxybenzofuran-4-yl)methanone 
• 1292842-95-5 (3,5-dibromo-4-hydroxyphenyl)(2-ethyl-5-methoxybenzofuran-4-yl)methanone 
• 1001092-00-7 (3,5-dibromo-4-hydroxyphenyl)(2-ethyl-5-hydroxybenzofuran-3-yl)methanone 
• 1292842-94-4 (3,5-dibromo-4-hydroxyphenyl)(2-ethyl-5-methoxybenzofuran-3-yl)methanone 
• 1292842-85-3 (2-ethyl-5-methoxybenzofuran-7-yl)(4-hydroxyphenyl)methanone 
• 1292842-87-5 (2-ethyl-5-hydroxybenzofuran-7-yl)(4-hydroxyphenyl)methanone 
• 1292842-86-4 (2-ethyl-5-hydroxybenzofuran-7-yl)(4-methoxyphenyl)methanone 
• 1292842-83-1 (2-ethyl-5-hydroxybenzofuran-4-yl)(4-methoxyphenyl)methanone 
• 1292842-82-0 (2-ethyl-5-methoxybenzofuran-4-yl)(4-hydroxyphenyl)methanone 
• 1292842-84-2 (2-ethyl-5-hydroxybenzofuran-4-yl)(4-hydroxyphenyl)methanone 
• 90908-68-2 (2-ethyl-5-hydroxybenzofuran-3-yl)(4-hydroxyphenyl)methanone 

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.

Discovery of Potent Protease-Activated Receptor 4 Antagonists with in Vivo Antithrombotic Efficacy

In an effort to identify novel antithrombotics, we have investigated protease-activated receptor 4 (PAR4) antagonism by developing and evaluating a tool compound, UDM-001651, in a monkey thrombosis model. Beginning with a high-throughput screening hit, we identified an imidazothiadiazole-based PAR4 antagonist chemotype. Detailed structure-activity relationship studies enabled optimization to a potent, selective, and orally bioavailable PAR4 antagonist, UDM-001651. UDM-001651 was evaluated in a monkey thrombosis model and shown to have robust antithrombotic efficacy and no prolongation of kidney bleeding time. This combination of excellent efficacy and safety margin strongly validates PAR4 antagonism as a promising antithrombotic mechanism.

Biologically Active Heterocyclic Hybrids Based on Quinazolinone, Benzofuran and Imidazolium Moieties: Synthesis, Characterization, Cytotoxic and Antibacterial Evaluation

Cytotoxic and antimicrobial agents structurally based on quinazolinone, benzofuran and imidazole pharmacophores, have been designed and synthesized. Spectral (IR, 1H-NMR) and elemental analysis data established the structures of these novel 3-[1-(1-benzofuran-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)ethyl]-1-methyl-1H-imidazol-3-ium chloride hybrid derivatives. All the synthesized compounds were evaluated for in?vitro cytotoxicity and antimicrobial activities. Cytotoxic evaluation using MTT assay revealed that compounds 12c, 12g and 12i exhibited significant cytotoxicity with IC50 values 1, 1, and 0.57?μm on this cell line, respectively. Biological activity of the synthesized compounds as antibacterial agent were also evaluated against three Gram-negative (Escherichia coli, Pseudomonas aeruginosa and Salmonella typhi), three Gram-positive (Staphylococcus aureus, Bacillus subtilis and Listeria monocitogenes) and one yeast-like fungi (Candida albicans) strains. All compounds 12a?–?12i showed slightly higher activity against Gram-positive bacteria than the Gram-negative one. Among the nine new compounds screened, 3-[1-(5-bromo-1-benzofuran-2-yl)-2-(6-chloro-4-oxoquinazolin-3(4H)-yl)ethyl]-1-methyl-1H-imidazol-3-ium chloride (12e) has pronounced higher antimicrobial activity against all tested strains. These results demonstrated potential importance of molecular hybridization in the development of new lead molecules with major cytotoxicity and antimicrobial activity.

PROBES FOR IMAGING HUNTINGTIN PROTEIN

Provided are imaging agents comprising a compound of Formula I, or a pharmaceutically acceptable salt thereof, and methods of their use. Formula (I)

NEW ARYLALKENYLPROPARGYLAMINE DERIVATIVES EXHIBITING NEUROPROTECTIVE ACTION FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES

The invention relates to novel arylalkenylpropargylamine derivatives of general formula (I) or enantiomers or diastereomers thereof or salts, optionally pharmaceutically acceptable salts, or solvates of any of these. The compounds can be used in treating or preventing a disease or condition in a mammal related to monoamine oxidase dysfunction, especially in neurodegenerative diseases, e.g. Parkinson's disease, Alzheimer's disease or Huntington's disease.

A novel, facile approach to frondosin B and 5-epi-liphagal via a new [4 + 3]-cycloaddition

A new [4 + 3]-cycloaddition between benzofuran allylic alcohols and dienes, promoted by camphorsulfonic acid, has been identified. A novel strategy which used this cycloaddition as a key step has been developed for the synthesis of 6,7,5-tricyclic skeleta

DEVELOPING POTENT URATE TRANSPORTER INHIBITORS: COMPOUNDS DESIGNED FOR THEIR URICOSURIC ACTION

A compound represented by the general Formula (I): a pharmaceutically acceptable salt or ester thereof, a solvate thereof, a chelate thereof, a non-covalent complex thereof, a pro-drug thereof, a deuterated radio-labeled analog thereof, and mixtures of any of the foregoing, wherein: A - K are individually selected from carbon or nitrogen; X = -O, -NR1,or -S; R1-11 are individually selected from the group consisting of-H, C1-C6 alkyl, C6-C aryl, substituted C6-C14 aryl, C1-C14-alkoxy, halogen, hydroxyl, carboxy, cyano, C1-C6-alkanoyloxy, C1-C6-alkylthio, C1-C6-alkylsulfonyl, trifluoromethyl, hydroxy, C2-C6-alkoxycarbonyl, C2-C6-alkanoylamino, -O-R12, S-R12,-SO2-Ri2, -NHSO2R12 and -NHCO2R12, wherein R12 is phenyl, naphthyl, or phenyl or naphthly substituted with one to three groups selected from C1-C6-alkyl, C6-C10 aryl,C1-C6-alkoxy and halogen, and C4-C20 hydroxyheteroaryl wherein the heteroatoms are selected from the group consisting of sulfur, nitrogen, and oxygen.

Developing potent human uric acid transporter 1 (hURAT1) inhibitors

The kidneys are a vital organ in the human body. They serve several purposes including homeostatic functions such as regulating extracellular fluid volume and maintaining acid-base and electrolyte balance and are essential regarding the excretion of metabolic waste. Furthermore, the kidneys play an important role in uric acid secretion/reabsorption. Abnormalities associated with kidney transporters have been associated with various diseases, such as gout. The current study utilized Xenopus oocytes expressing human uric acid transporter 1 (hURAT1; SLC22A12) as an in vitro method to investigate novel compounds and their ability to inhibit 14C-uric acid uptake via hURAT1. We have prepared and tested a series of 2-ethyl-benzofuran compounds and probed the hURAT1 in vitro inhibitor structure-activity relationship. As compared to dimethoxy analogues, monophenols formed on the C ring showed the best in vitro inhibitory potential. Compounds with submicromolar (i.e., IC 50 1000 nM) inhibitors were prepared by brominating the corresponding phenols to produce compounds with potent uricosuric activity.

Total Synthesis and Determination of the Absolute Configuration of Frondosin B

Two concise syntheses of (+/-)-frondosin B (1), an interleukin-8 receptor antagonist, have been achieved from commercially available 5-methoxysalicylaldehyde. The seven-membered ring in ketone 33, the common intermediate for both syntheses, was built by a