17720-60-4

Usage

Preparation

Preparation by reaction of p-hydroxyphenylacetic acid with resorcinol in the presence of boron trifluoride etherate under argon on a water bath for 1 h (98%), at 100° for 1 h (70%) or for 15 min (40%).

InChI:InChI=1/C14H12O4/c15-10-3-1-9(2-4-10)7-13(17)12-6-5-11(16)8-14(12)18/h1-6,8,15-16,18H,7H2

Upstream product

• 156-38-7 4-hydroxyphenylacetate 
• 108-46-3 recorcinol 
• 14191-95-8 4-cyanomethylphenol 
• 487-49-0 1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone 
• 140-53-4 p-chlorobenzyl cyanide 
• 67804-60-8 1-(2,4-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanone 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 111797-19-4 3-(2,4-dimethoxy-phenyl)-2-(4-methoxy-phenyl)-3-oxo-propionic acid ethyl ester 

Downstream Products

• 33871-32-8 7-acetoxy-3-(4-acetoxy-phenyl)-2-methyl-chromen-4-one 
• 57023-42-4 2-Carboxy-7,4'-dihydroxyisoflavone 
• 272463-67-9 2-Ethoxycarbonyl-7,4'-dihydroxyisoflavone 
• 486-66-8 daidzein 
• 130064-21-0 1-(2-hydroxy-4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)-2-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)ethanone 
• 171973-40-3 2-hydroxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl 4'-hydroxybenzyl ketone 
• 77316-88-2 7,4'-dihydroxy-2-methylisoflavone 
• 148356-24-5 5-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 17238-05-0 dihydrodaidzein 
• 112182-89-5 7,4'-diethoxymethoxyisoflavanone 
• 112182-88-4 4,4'-diethoxymethoxy-α-hydroxymethyl-2-hydroxydesoxybenzoin 
• 3682-01-7 daidzein diacetate 
• 552-66-9 daidzin 
• 1206192-96-2 4-(4-hydroxyphenethyl)benzene-1,3-diol 

Relevant academic research and scientific papers

Structure–activity relationship of phytoestrogen analogs as ERα/β agonists with neuroprotective activities

A set of isoflavononid and flavonoid analogs was prepared and evaluated for estrogen receptor α (ERα) and ERβ transactivation and anti-neuroinflammatory activities. Structure–activity relationship (SAR) study of naturally occurring phytoestrogens, their metabolites, and related isoflavone analogs revealed the importance of the C-ring of isoflavonoids for ER activity and selectivity. Docking study suggested putative binding modes of daidzein 2 and dehydroequol 8 in the active site of ERα and ERβ, and provided an understanding of the promising activity and selectivity of dehydroequol 8. Among the tested compounds, equol 7 and dehydroequol 8 were the most potent ERα/β agonists with ERβ selectivity and neuroprotective activity. This study provides knowledge on the SAR of isoflavonoids for further development of potent and selective ER agonists with neuroprotective potential.

Water-in-oil skin-whitening skin care lotion and preparation method thereof

The invention discloses a water-in-oil skin-whitening skin care lotion. The water-in-oil skin-whitening skin care lotion comprises the following components in parts by weight of 26-29 parts of camellia oil, 18-23 parts of grape seed oil, 22-25 parts of squalane, 2-3 parts of an oxidation resisting skin whitening agent, 4-6 parts of emulsifying wax, 8-16 parts of distilled water, 11-14 parts of a hydrating agent, and 1-2 parts of a surfactant. The prepared oxidation-resisting skin whitening agent contains sulphadiazine, has certain properties of resisting bacteria and inhibiting bacteria, can effectively realize efficacy of sterilizing and diminishing inflammation of skin care products, can effectively restrain breeding of bacteria, can realize antiseptic effects, can further reduce addition of preservatives in the lotion, can effectively reduce burden to skin, and can further effectively solve the problems that in the preparation process of conventional skin care products, the preservative is directly added to the skin care products to achieve the antibacterial effect, but the added preservative can easily increase the burden to skin, and the preservative has definite stimulability, so that more crowds have intolerance to the prepared skin care lotion.

A Direct Synthesis of 2-(ω-Carboxyalkyl)isoflavones from ortho-Hydroxylated Deoxybenzoins

As part of a program focused on the development of new antineoplastic agents based on scaffolds found in natural products, we explored the isoflavone family as potential enzyme inhibitors. We required biotin-modified isoflavones to identify potential biological targets, and we selected the C-2 position in isoflavones as an attachment site for an alkyl group bearing a terminal carboxylic acid to which we could attach a biotin derivative. The base-catalyzed condensation of 2,4-dihydroxy-substituted deoxybenzoins with cyclic anhydrides mediated by a combination of triethylamine and 1,8-diazabicyclo[5.4.0]undec-7-ene led to an efficient synthesis of the desired 2-(ω-carboxyalkyl)isoflavones with functional groups at C-5, 6 and 7 and with various substituents in the C-3 phenyl group.

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.

TREATMENT OF HOT FLUSHES, VASOMOTOR SYMPTOMS, AND NIGHT SWEATS WITH SEX STEROID PRECURSORS IN COMBINATION WITH SELECTIVE ESTROGEN RECEPTOR MODULATORS

Novel methods for reduction or elimination of the incidence of hot flushes, vasomotor symptoms, and night sweats while decreasing the risk of acquiring breast, uterine or endometrial cancer and furthermore having beneficial effect by inhibiting the develo

TREATMENT OF MALE ANDROGEN DEFICIENCY SYMPTOMS OR DISEASES WITH SEX STEROID PRECURSOR COMBINED WITH SERM

Novel methods for prevention, reduction or elimination of the incidence of male androgen deficiency symptoms or diseases including male hypogonadism-associated symptoms and diseases associated with low serum testosterone and/or low DHEA or low total andro

COMBINATIONS OF BENZOPYRAN COMPOUNDS, COMPOSITIONS AND USES THEREOF

This invention relates to a method of treating a disorder modulated, mediated or affected by the estrogen receptor in a subject comprising administering to the subject a specific benzopyran (in the form of a mixture of S-C2 and R-C2 diastereomers or its pure S-diastereomer) in combination with an agent selected from the group consisting of an mTOR inhibitor, a CDK 4/6 inhibitor, a PI3 Kinase inhibitor, a taxane, an antimetabolite, and an antitumor antibiotic.

SUBSTITUTED BENZOPYRAN COMPOUNDS, COMPOSITIONS AND USES THEREOF

Benzopyran compounds with anti-estrogenic activity are provided as Formula I, II, III, IV, V, VI, VII, VIII, IX, X, XI, XII, XIII, XIV, XV, XVI, XVII and XVIII. These compounds are useful for the treatment or prevention of a variety of conditions that are modulated through the estrogen receptor in mammals including humans.

NOVEL BENZOPYRAN COMPOUNDS, COMPOSITIONS AND USES THEREOF

Benzopyran compounds with strong anti-estrogenic activity and essentially no estrogenic activity are provided, which are OP- 1038, which is 3-(4-hydroxyphenyl)-4-methyl-2-(4-{2-[(3R)-3-methylpyrrolidin-l-yl]ethoxy}phenyl)-2H-chromen-7-ol, and OP-1074, which is (2S)-3-(4-hydroxyphenyl)-4-methyl-2-(4-{2-[(3R)-3-methylpyrrolidin- 1 -yl]ethoxy}phenyl)-2H-chromen-7-ol. OP-1074 is a pure anti-estrogen when tested in the agonist mode and a complete anti-estrogen when tested in the antagonist mode. These compounds are useful for the treatment or prevention of a variety of conditions that are modulated through the estrogen receptor in mammals including humans.

In vitro study of isoflavones and isoflavans as potent inhibitors of human 12- and 15-lipoxygenases

In this study, we have investigated 16 isoflavone and isoflavan derivatives as potential inhibitors of human lipoxygenase (platelet 12-lipoxygenase, reticulocyte 15-lipoxygenase-1, and epithelial 15-lipoxygenase-2). The flavonoid baicalein, a known lipoxygenase inhibitor, was used as positive control. Four compounds, 6,7-dihydroxy-3′-chloroisoflavone (1c), 7-hydroxy-8-methyl-4′-chloroisoflavan (5a), 7,8-dihydroxy-4′-methylisoflavan (5b), and 7,8-dihydroxy-3′-methylisoflavan (5c), were effective inhibitors of 12-lipoxygenases and 15-lipoxygenase-1 with IC50's i values in the range of 0.3-3 μm.