39604-80-3

Usage

Preparation

Preparation by partial benzylation of 2,4-dihydroxy-phenyl benzyl ketone, ? with benzyl chloride in the presence of potassium carbonate in refluxing acetone; ? with benzyl bromide in the presence of potassium carbonate in refluxing acetone or in the presence of potassium hydroxide at r.t. for 24 h (29%).

Upstream product

• 3669-41-8 1-(2,4-dihydroxyphenyl)-2-phenylethanone 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 103-80-0 phenylacetyl chloride 
• 108-46-3 recorcinol 
• 100-51-6 benzyl alcohol 

Downstream Products

• 4253-05-8 7-benzyloxy-3-phenyl-chromen-4-one 
• 26200-05-5 7-benzyloxy-isoflavanone 
• 3669-41-8 1-(2,4-dihydroxyphenyl)-2-phenylethanone 
• 95832-52-3 5-C-benzyl-2,4-dihydroxydesoxybenzoin 
• 95832-51-2 3-C-benzyl-2,4-dihydroxydesoxybenzoin 
• 143286-80-0 1-(4-Benzyloxy-2-hydroxy-phenyl)-2-phenyl-ethanone oxime 
• 746640-15-3 3-phenyl-7-(phenylmethoxy)-2-[(pyridin-4-ylmethyl)thio]-4H-1-benzopyran-4-one 
• 869800-99-7 7-(naphthalen-1-ylmethoxy)-3-phenyl-2-(pyridin-4-ylmethylsulfanyl)-chromen-4-one 
• 869801-00-3 7-(naphthalen-2-ylmethoxy)-3-phenyl-2-(pyridin-4-ylmethylsulfanyl)-chromen-4-one 
• 869801-08-1 7-(biphenyl-4-ylmethoxy)-3-phenyl-2-(pyridin-4-ylmethylsulfanyl)-chromen-4-one 

Relevant academic research and scientific papers

Biocatalytic acylation studies on novel 3-aryl-3-hydroxymethyl-2, 3-dihydro-4H-1-benzopyran-4-ones

(±)-3-Aryl-3-hydroxymethy1-2,3-dihydro-4H-1-benzopyran-4-ones have been synthesized in four steps starting with the coupling of resorcinol with corresponding phenylacetic acid leading to the formation of 2,4-dihydroxyphenyl aryl ketones, which upon monome

Heteroaryl-containing isoflavones as aromatase inhibitors

Compounds and methods useful for treating and prevention of cancer, particularly hormone-dependent breast cancer. Provided are compounds of formula I: wherein X is selected from O, N, S, SO, SO2, and S(CH2)n, wherein n=1-1

Lead optimization of 7-benzyloxy 2-(4′-pyridylmethyl)thio isoflavone aromatase inhibitors

Aromatase, the enzyme responsible for estrogen biosynthesis, is a particularly attractive target in the treatment of hormone-dependent breast cancer. The synthesis and biological evaluation of a series of 2-(4′-pyridylmethyl)thio, 7-alkyl- or aryl-substit

Synthesis and aromatase inhibitory activity of novel pyridine-containing isoflavones

Aromatase, a cytochrome P450 hemoprotein that is responsible for estrogen biosynthesis by conversion of androgens into estrogens, has been an attractive target in the treatment of hormone-dependent breast cancer. As a result, a number of synthetic steroidal or nonsteroidal aromatase inhibitors have been successfully developed. In addition, there are several classes of natural products that exert potent activities in aromatase inhibition, with the flavonoids being most prominent. Previous studies have exploited flavone and flavanone scaffolds for the development of new aromatase inhibitors. In this paper, we describe the design, synthesis, and biological evaluation of a novel series of 2-(4′-pyridylmethyl)thioisoflavones as the first example of synthetic isoflavone-based aromatase inhibitors.

Synthese von 4-Alkoxy-2-hydroxyphenylketoximen als Metallextraktions-Reagenzien

The C-Acylation (Friedel-Crafts reaction) of resorcinol with aluminium chloride, the monoetherification in 4-position of the resulting 2,4-dihydroxyphenylketones, and the preparation of oximes (8, 9, 10, 11) from this ketones were investigated.The compounds obtained are characterized by elemental analysis, and the i.r., u.v. and 1H-n.m.r. spectra are discussed.Solubility data of some oximes are determined in water, octane and toluene.The extraction properties for copper-(II)-and iron-(III)-ions are measured by isotope methods in relation to the extragent structure, the extraction time and the pH-range.

A Study of α-C-Benzylation of 2-Hydroxydesoxybenzoins

Benzylation of three 2-hydroxy-methoxydesoxybenzoins (1a, 1b and 1c) with benzyl chloride (1 mol) in the presence of potassium iodide, potassium carbonate and acetone under dry refluxing conditions for 6 hr affords only α-C-benzyl derivatives (2a, 2b and 2c, repectively) without any O-benzylation in yields from 34 to 54percent.But, in the presence of a more polar solvent DMF under similar conditions O-benzylation also occurs giving a mixture of products.Benzylation of 2,4-dihydroxydesoxybenzoin (5) with benzyl bromide in acetone medium reveals that 4-O-benzylation is the first step followed by α-C-benzylation or O-benzylation; further no aromatic benzylation occurs.Finally it has been found that the yield of α-C-benzylated product increases up to 71percent if a non-polar solvent THF is used in the presence of sodium hydride.

Aromatic Benzylation: Part VI - Some More Experiments on Nuclear Benzylation of 2,4-Dihydroxydesoxybenzoin and Synthesis of C-Benzylated Isoflavones

2,4-Dihydroxydesoxybenzoin (1a) reacts with benzyl bromide in the presence of MeOH-KOH at room temperature to give 4-benzyl ether (1b) (31.4percent yield), 3-C-benzyl derivative (2a, 12.2percent), 5-C-benzyl derivative (3a, 2.8percent), 3,5-di-C-benzyl derivative (4a, 1.4percent) and 3-C-benzyl-4-benzyl ether (2b, 0.7percent).The desoxybenzoins 2a, 3a and 4a have also been converted into the corresponding C-benzylated isoflavones (5a, 5b and 5c).