1-Benzofuran-2-yl(phenyl)methanone

Base Information

• Chemical Name: 1-Benzofuran-2-yl(phenyl)methanone
• CAS No.: 6272-40-8
• Molecular Formula: C15H10 O2
• Molecular Weight: 222.243
• NSC Number: 37429
• UNII: H1OLK6F7UX
• DSSTox Substance ID: DTXSID10211802
• Nikkaji Number: J81.172F
• Wikidata: Q83086782
• ChEMBL ID: CHEMBL1342446
• Mol file: 6272-40-8.mol

Synonyms:6272-40-8;1-Benzofuran-2-yl(phenyl)methanone;2-benzoylbenzofuran;benzofuran-2-yl(phenyl)methanone;Methanone, 2-benzofuranylphenyl-;2-benzoyl-1-benzofuran;H1OLK6F7UX;Ketone, 2-benzofuranyl phenyl;NSC-37429;2-benzoylbenzo(b)furan;2-benzoylbenzo[b]furan;2-benzofuranylphenylMethanone;Benzofuran-2-yl-phenyl-methanone;NSC37429;NSC 37429;2-benzoylbenzo[b]furane;Benzofuran, 2-benzoyl-;UNII-H1OLK6F7UX;TimTec1_001490;Oprea1_104896;Oprea1_386384;CBDivE_000085;MLS000029627;SCHEMBL3263663;CHEMBL1342446;DTXSID10211802;HMS1538D16;HMS2282O24;2-BENZOFURANYL PHENYL KETONE;MFCD00540083;SC5130;STK049466;1-Benzofuran-2-yl(phenyl)methanone #;AKOS000491122;CCG-200177;NCGC00026084-02;10J-537S;SMR000009134;CS-0062608;A914831;AE-641/00404052;Z31308547;F0486-2420

Chemical Property of 1-Benzofuran-2-yl(phenyl)methanone

Chemical Property:

• Melting Point: 91°C
• Refractive Index: 1.6600 (estimate)
• Boiling Point: 360°C (estimate)
• Density: 1.1404 (rough estimate)
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 222.068079557
• Heavy Atom Count: 17
• Complexity: 281

Purity/Quality:

97% ^*data from raw suppliers

Benzofuran-2-yl(phenyl)methanone 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)C2=CC3=CC=CC=C3O2
• General Description: 2-Benzoylbenzofuran (also known as 2-benzofuranyl phenyl ketone or NSC 37429) is a structural scaffold investigated for its potential as an adenosine A1 and/or A2A receptor antagonist, with relevance in neurological therapeutics such as Parkinson’s disease. Derivatives of this compound, particularly methoxy-substituted variants, have been synthesized and evaluated for receptor binding affinity, cytotoxicity, and drug-like properties, demonstrating its utility as a lead structure for further optimization in medicinal chemistry.

Technology Process of 1-Benzofuran-2-yl(phenyl)methanone

There total 52 articles about 1-Benzofuran-2-yl(phenyl)methanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

salicylaldehyde (90-02-8) + α-bromoacetophenone (70-11-1) → 2-benzoylbenzofuran (6272-40-8)

Guidance literature:

With potassium carbonate; In acetone; for 20h; Inert atmosphere; Reflux;

DOI:10.1021/jo202060k

Reference yield: 94.0%

1-phenyl-2-(p-tolylsulfonyloxy)ethanone (7257-94-5) + salicylaldehyde (90-02-8) → 2-benzoylbenzofuran (6272-40-8)

Guidance literature:

With potassium fluoride on basic alumina; at 130 ℃; for 0.05h;

DOI:10.1039/a807563h

Reference yield: 91.0%

(benzofuran-2-yl)phenylmethanol (27052-21-7) → 2-benzoylbenzofuran (6272-40-8)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1039/a703305b

upstream raw materials:

salicylaldehyde

α-bromoacetophenone

1-benzofurane

benzenecarbothioamide

Downstream raw materials:

α,α-diphenyl-2-benzofuranmethanol

1-benzofurane

2-benzylbenzofuran

(benzofuran-2-yl)phenylmethanol

Refernces

Synthesis and evaluation of methoxy substituted 2-benzoyl-1-benzofuran derivatives as lead compounds for the development adenosine A1 and/or A2A receptor antagonists

10.1016/j.bioorg.2019.103459

The research focuses on the synthesis and evaluation of methoxy substituted 2-benzoyl-1-benzofuran derivatives as potential adenosine A1 and/or A2A receptor antagonists, which are relevant for the treatment of neurological conditions such as Parkinson’s disease. The study involved the synthesis of fourteen derivatives through a base-mediated Rap-Stoermer condensation reaction, utilizing reactants like 2-hydroxybenzaldehydes and 2-halogen substituted acetophenones. The synthesized compounds were then subjected to radioligand binding assays to determine their affinities for adenosine A1 and A2A receptors, using rat brain membranes and specific radioligands. Additionally, the compounds were evaluated for cytotoxicity using the resazurin assay on Vero cells and assessed for their pharmacokinetic properties and drug-likeness through in silico methods, specifically using the SwissADME web tool. The experiments aimed to establish structure-activity relationships and identify lead compounds suitable for optimization.