57009-12-8

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 3-ACETYL-4-HYDROXYBENZOATE is used as a key intermediate in the synthesis of 2-(1-adamantyl)-4-(thio)chromenone-6-carboxylic acids, which are potent reversible inhibitors of human steroid sulfatase. These inhibitors have potential applications in the treatment of various hormonal disorders and cancers, such as breast and ovarian cancer, by modulating the activity of steroid sulfatase enzymes.
Used in Agrochemical Industry:
METHYL 3-ACETYL-4-HYDROXYBENZOATE is also utilized in the development of novel agrochemicals, such as herbicides, insecticides, and fungicides. Its unique chemical structure allows for the design of molecules with enhanced biological activity and selectivity, leading to improved crop protection and reduced environmental impact.

InChI:InChI=1/C10H10O4/c1-6(11)8-5-7(10(13)14-2)3-4-9(8)12/h3-5,12H,1-2H3

Upstream product

• 67-56-1 methanol 
• 16357-40-7 3-acetyl-4-hydroxybenzoic acid 
• 24262-66-6 methyl 4-acetoxybenzoate 
• 71407-97-1 methyl 3-acetyl-4-hydroxy-6-amino benzoate 
• 4869-46-9 1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde 
• 123-54-6 acetylacetone 
• 201230-82-2 carbon monoxide 
• 1450-75-5 5-Bromo-2-hydroxyacetophenone 
• 2345-34-8 4-acetyloxy-benzoic acid 
• 111-34-2 -butyl vinyl ether 
• 29415-97-2 methyl 3-bromo-4-hydroxybenzoate 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 90330-49-7 3-(methoxymethylene)-2,4-bis(trimethylsilyloxy)-1,4-pentadiene 
• 922-67-8 propynoic acid methyl ester 

Downstream Products

• 16357-40-7 3-acetyl-4-hydroxybenzoic acid 
• 147918-99-8 Bis-(2-acetyl-4-methoxycarbonylphenyl)-2,3-dimethoxyterephthalat 
• 147919-00-4 2,6-Bis-(2-acetyl-4-methoxycarbonylphenyl)-1,5-dimethoxynaphthalindicarboxylat 
• 71620-33-2 2-bromo-2'-hydroxy-5'-carbomethoxy-acetophenone 
• 78581-52-9 4-acetoxy-3-acetyl-benzoic acid, methyl ester 
• 147918-98-7 Bis-(2-acetyl-4-methoxycarbonylphenyl)-terephthalat 
• 750572-54-4 adamantane-1-carboxylic acid 2-acetyl-4-(methoxycarbonyl)phenyl ester 
• 71620-35-4 methyl 2-benzylidene-3(2H)-benzofuranone-5-carboxylate 
• 71620-38-7 methyl 2-(2',3',4'-trimethoxybenzylidene)-3(2H)-benzofuranone-5-carboxylate 
• 105211-75-4 3-ethyl-4-hydroxybenzoic acid 
• 65843-60-9 methyl 3-acetyl-4-(benzyloxy)benzoate 
• 160753-84-4 methyl 3-acetyl-5-bromo-4-hydroxybenzoate 
• 912968-06-0 4-trifluoromethyl-(2'-acetyl-4'-methoxycarbonyl)phenyl benzoate 
• 1296271-78-7 8-(1-(3,5-difluorophenylamino)ethyl)-2-((S)-3-methylmorpholino)-4-oxo-4H-chromene-6-carboxylic acid 

Relevant academic research and scientific papers

Benzo[d]Isoxazole compound, preparation method and applications thereof

The invention provides a benzo[d]isoxazole compound, a preparation method and applications thereof, wherein the benzo[d]isoxazole compound has novel structure, can be used as a BET bromodomain receptor inhibitor, and can effectively inhibit the bromodomai

Structure-Based Discovery and Optimization of Benzo [d] isoxazole Derivatives as Potent and Selective BET Inhibitors for Potential Treatment of Castration-Resistant Prostate Cancer (CRPC)

The bromodomain and extra-terminal (BET) family proteins have gained increasing interest as drug targets for treatment of castration-resistant prostate cancer (CRPC). Here, we describe the design, optimization, and evaluation of benzo[d]isoxazole-containing compounds as potent BET bromodomain inhibitors. Cocrystal structures of the representative inhibitors in complex with BRD4(1) provided solid structural basis for compound optimization. The two most potent compounds, 6i (Y06036) and 7m (Y06137), bound to the BRD4(1) bromodomain with Kd values of 82 and 81 nM, respectively. They also exhibited high selectivity over other non-BET subfamily members. The compounds potently inhibited cell growth, colony formation, and the expression of AR, AR regulated genes, and MYC in prostate cancer cell lines. Compounds 6i and 7m also demonstrated therapeutic effects in a C4-2B CRPC xenograft tumor model in mice. These potent and selective BET inhibitors represent a new class of compounds for the development of potential therapeutics against CRPC.

Synthesis of (3-(2-aminopyrimidin-4-yl)-4-hydroxyphenyl)phenyl methanone analogues as inhibitors of vascular endothelial growth factor receptor-2 kinase

Angiogenesis is critical for tumor growth and mediated mainly by vascular endothelial growth factor (VEGF) signaling. Inhibition of the VEGF signaling pathway has emerged as one of the promising approaches for cancer therapy. VEGF receptor 2 (VEGFR-2) is

Imidazole-containing condensed tricyclic compound and application thereof

The invention discloses an imidazole-containing condensed tricyclic compound adopting the structure as shown in the formula (I) or pharmaceutically acceptable salts, stereisomers or prodrug molecules thereof. The imidazole-containing condensed tricyclic compound has the IDO1 activity regulation function, can enhance T-cell activation through blocking immune checkpoints IDO1, is used for treating IDO1-mediated immunosuppression, and therefore, can become an effective medicine for treating malignant tumors. When used together with checkpoint protein anti-body drugs or other anti-cancer drugs, the imidazole-containing condensed tricyclic compound can enhance the anti-cancer effect. Meanwhile, the imidazole-containing condensed tricyclic compound has the potential of effectively treating IDO1 abnormity related immunosuppressive diseases and has a high application value.

Discovery of (R)-8-(1-(3,5-difluorophenylamino)ethyl)- N, N -dimethyl-2-morpholino-4-oxo-4 H -chromene-6-carboxamide (AZD8186): A potent and selective inhibitor of PI3Kβ and PI3Kδ for the treatment of PTEN-deficient cancers

Several studies have highlighted the dependency of PTEN deficient tumors to PI3Kβ activity and specific inhibition of PI3Kδ has been shown activity against human B-cell cancers. We describe the discovery and optimization of a series of 8-(1-anilino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxamides as PI3Kβ/δ inhibitors, which led to the discovery of the clinical candidate 13, also known as AZD8186. On the basis of the lower lipophilicity of the chromen-4-one core compared to the previously utilized pyrido[1,2-a]pyrimid-4-one core, this series of compounds displayed high metabolic stability and suitable physical properties for oral administration. Compound 13 showed profound pharmacodynamic modulation of p-Akt in PTEN-deficient PC3 prostate tumor bearing mice after oral administration and showed complete inhibition of tumor growth in the mouse PTEN-deficient PC3 prostate tumor xenograft model. 13 was selected as a clinical candidate for treatment of PTEN-deficient cancers and has recently entered phase I clinical trials.

HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

CHROMENONE COMPOUNDS AS PI 3 -KINASE INHIBITORS FOR THE TREATMENT OF CANCER

The invention concerns chromenone compounds of Formula I; or pharmaceutically-acceptable salts thereof, wherein each of R1, R2, R3, R4, R5, n and R6 has any of the meanings defined hereinbe

CHROMENONE DERIVATIVES

The invention concerns chromenone compounds of Formula I; or pharmaceutically-acceptable salts thereof, wherein each of R1, R2, R3, R4, R5, n and R6 has any of the meanings defined hereinbe

Enantioselective total synthesis and absolute configuration of the alleged structure of crassinervic acid

An enantioselective synthesis of the structure reported for the natural antifungal compound, (-)-crassinervic acid (1), has been achieved starting from geraniol and p-hydroxybenzoic acid. The key chirality-inducing step is a Sharpless asymmetric epoxidation of an allylic alcohol, on the basis of which the S configuration can be assigned to the (-) natural enantiomer. The discrepancies between the spectroscopic data for synthetic and natural crassinervic acid cast some doubts on the structure assigned to the natural compound. A possible revised structure is discussed.

CHROMENONE DERIVATIVES

The invention concerns chromenone derivatives of Formula I or a pharmaceutically-acceptable salts thereof, wherein each of R1, R2, R3, R4, R5, R6, R7, R8, n and R9 has any of the meanings defined hereinbefore in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use in the treatment of cell proliferative disorders.