52122-86-8

Usage

Preparation

Obtained by partial demethylation of 2,5-dimethoxyphenyl benzyl ketone, ? with hydriodic acid in acetic acid on a water bath for 2 h ; ? with hydrobromic acid in acetic acid, first at 0°, then at reflux for 6 h ..

Upstream product

• 103-82-2 phenylacetic acid 
• 123-31-9 hydroquinone 
• 103-80-0 phenylacetyl chloride 
• 1146443-78-8 N,2,5-trimethoxy-N-methylbenzamide 
• 150-78-7 1,4-dimethoxybezene 
• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 106-51-4 p-benzoquinone 
• 76246-92-9 1-(2,5-dimethoxy)-2-phenyl-1-ethanone 
• 2785-98-0 2,5-dimethoxybenzoic acid 

Downstream Products

• 32684-57-4 6-hydroxy-3-phenyl-4H-chromen-4-one 
• 1352307-40-4 4-methyl-2-(4-((S)-2-((R)-3-methylpyrrolidin-1-yl)propoxy)phenyl)-3-phenyl-2H-chromen-6-ol hydrochloride 
• 32684-58-5 6-methoxy-3-phenyl-4H-chromen-4-one 

Relevant academic research and scientific papers

A concise synthesis of 2-alkenyl-3-phenyl-4H-chromen-4-ones via novel C-C bond formation using sulfone as potential intermediate

A new methodology has been designed for the synthesis of some non-natural 2-alkenyl-3-phenyl-4H-chromen-4-ones of potential biological importance. The strategy makes use of appropriately substituted heteroaryl sulfone as the potent intermediate. An ambide

Identification of an Orally Bioavailable Chromene-Based Selective Estrogen Receptor Degrader (SERD) That Demonstrates Robust Activity in a Model of Tamoxifen-Resistant Breast Cancer

About 75% of breast cancers are estrogen receptor alpha (ER-α) positive, and women typically initially respond well to antihormonal therapies such as tamoxifen and aromatase inhibitors, but resistance often emerges. Fulvestrant is a steroid-based, selective estrogen receptor degrader (SERD) that both antagonizes and degrades ER-α and shows some activity in patients who have progressed on antihormonal agents. However, fulvestrant must be administered by intramuscular injections that limit its efficacy. We describe the optimization of ER-α degradation efficacy of a chromene series of ER modulators resulting in highly potent and efficacious SERDs such as 14n. When examined in a xenograft model of tamoxifen-resistant breast cancer, 14n (ER-α degradation efficacy = 91%) demonstrated robust activity, while, despite superior oral exposure, 15g (ER-α degradation efficacy = 82%) was essentially inactive. This result suggests that optimizing ER-α degradation efficacy in the MCF-7 cell line leads to compounds with robust effects in models of tamoxifen-resistant breast cancer derived from an MCF-7 background.

Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging

Starting from 7-hydroxyisoflavones, we developed a new class of fluorescent scaffolds, 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs, MW ～ 205.19, λab ～ 350 nm, λem ～ 450 nm) via a trial and error process. AMHCs have the advantages of being a small molecular moiety, having strong fluorescence in basic buffers, reasonable solubility and stability, non-toxicity, and are conveniently linked to pharmacophores. AMHCs were successfully used in fluorescence microscopy imaging of cells and tissues. This journal is

A direct route to acylhydroquinones from α-keto acids and α- carboxamido acids

The reaction of quinones with in situ generated acyl- or carboxamido radicals provides a direct rome to the synthesis of acylhydroquinones not accessible by the photochemical reaction of quinones with aldehydes.

Process for the preparation of ketone compounds

The invention relates to an improved, large scale process for the preparation of compounds of formula (I) STR1 wherein R is halogen atom or hydroxyl, R2 is hydrogen atom or hydroxyl, R3 and R4 are hydrogen or alkoxy having

Expedient Synthesis of Polyhydroxyisoflavones

A general and direct synthesis of polyhydroxy isoflavones (3-phenyl-4H-1-benzopyran-4-ones) starting from the corresponding unprotected phenols and arylacetic acids is described.The aryl rings may carry additional alkyl, methoxy and/or halogeno groups.Intermediate polyhydroxydeoxybenzoins (1,2-diphenylethanones) can also be isolated in good yields.

Synthesis of Some Arylated Quinones

1,3-Dihydroxy-2-phenylanthraquinone has been synthesized by reaction of 2-phenylacetyl-1,4-naphthoquinone with 1,1-dimethoxyethene and subsequent intramolecular condensation.It has also been obtained by Diels-Alder cycloaddition.Some arylated benzo- and naphthoquinones have been synthesized by the Meerwein reaction.