90110-32-0

Usage

Preparation

Preparation by reaction of acetic acid on 4-chlororesorcinol with zinc chloride at 145° (Nencki reaction) (31%).

Upstream product

• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 95-88-5 4-Chlororesorcinol 
• 108-24-7 acetic anhydride 
• 625-60-5 ethyl thioacetate 
• 373-61-5 boron trifluoride diacetate 
• 2161-86-6 2,4-diacetylphloroglucinol 
• 108-22-5 Isopropenyl acetate 
• 2466-76-4 N-Acetylimidazole 
• 64-19-7 acetic acid 

Downstream Products

• 705963-54-8 1-[2,4-bis(benzyloxy)-5-chlorophenyl]ethan-1-one 
• 1361551-76-9 5-chloro-4-O-(propargyl)resacetophenone 
• 1522361-70-1 (E)-1-(2,4-bis(allyloxy)-5-chlorophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 1522361-80-3 (E)-1-(5-chloro-2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one 
• 1522361-81-4 (E)-1-(5-chloro-2,4-dihydroxyphenyl)-3-(2,4-dihydroxyphenyl)prop-2-en-1-one 
• 1522361-82-5 (E)-1-(5-chloro-2,4-dihydroxyphenyl)-3-(2,4-dimethoxyphenyl)prop-2-en-1-one 
• 1522361-83-6 (E)-1-(5-chloro-2,4-dihydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 
• 1522361-84-7 (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(5-chloro-2,4-dihydroxyphenyl)prop-2-en-1-one 
• 1522361-71-2 (E)-3-(4-(allyloxy)phenyl)-1-(2,4-bis(allyloxy)-5-chlorophenyl)prop-2-en-1-one 
• 1522361-72-3 (E)-1-(2,4-bis(allyloxy)-5-chlorophenyl)-3-(3,4-bis(allyloxy)phenyl)prop-2-en-1-one 
• 1522361-73-4 (E)-1-(2,4-bis(allyloxy)-5-chlorophenyl)-3-(2,4-bis(allyloxy)phenyl)prop-2-en-1-one 
• 1522361-74-5 (E)-1-(2,4-bis(allyloxy)-5-chlorophenyl)-3-(2,4-dimethoxyphenyl)prop-2-en-1-one 
• 1522361-76-7 (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(2,4-bis(allyloxy)-5-chlorophenyl)prop-2-en-1-one 
• 1522361-78-9 (E)-1-(5-chloro-2,4-dihydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 

Relevant academic research and scientific papers

2-OXO-5H-CHROMENO[4,3-B]PYRIDINES FOR USE IN THE TREATMENT OF HEPATITIS B

The present invention discloses compounds according to Formula (I), wherein R1, R2a, R2b, R3, R4, and R5 are as defined herein. The present invention relates to compounds, methods for their production, pharmaceutical compositions comprising the same, and methods of treatment using the same, for the prophylaxis and/or treatment of diseases involving hepatitis B by administering the compound of the invention.

Thioesters as Acyl Donors in Biocatalytic Friedel-Crafts-type Acylation Catalyzed by Acyltransferase from Pseudomonas Protegens

Functionalization of aromatic compounds by acylation has considerable significance in synthetic organic chemistry. As an alternative to chemical Friedel-Crafts acylation, the C-acyltransferase from Pseudomonas protegens has been found to catalyze C?C bond formation with non-natural resorcinol substrates. Extending the scope of acyl donors, it is now shown that the enzyme is also able to catalyze C?S bond cleavage prior to C?C bond formation, thus aliphatic and aromatic thioesters can be used as acyl donors. It is worth to mention that this reaction can be performed in aqueous buffer. Identifying ethyl thioacetate as the most suitable acetyl donor, the products were obtained with up to >99 % conversion and up to 88 % isolated yield without using additional base additives; this represents a significant advancement to prior protocols.

Biocatalytic Friedel–Crafts Acylation and Fries Reaction

The Friedel–Crafts acylation is commonly used for the synthesis of aryl ketones, and a biocatalytic version, which may benefit from the chemo- and regioselectivity of enzymes, has not yet been introduced. Described here is a bacterial acyltransferase which can catalyze Friedel–Crafts C-acylation of phenolic substrates in buffer without the need of CoA-activated reagents. Conversions reach up to >99 %, and various C- or O-acyl donors, such as DAPG or isopropenyl acetate, are accepted by this enzyme. Furthermore the enzyme enables a Fries rearrangement-like reaction of resorcinol derivatives. These findings open an avenue for the development of alternative and selective C?C bond formation methods.

Acyl Donors and Additives for the Biocatalytic Friedel–Crafts Acylation

The Friedel–Crafts acylation is a broadly applied reaction that can be conducted using various types of catalyst. However, a biocatalytic alternative has only been reported recently. In this study, the scope of acetyl donors is described, showing that, in addition to vinyl acetate derivatives, phenyl esters are also suitable donors. Furthermore, it was found that various amines enhance the reaction, whereby the effect do not seem to be correlated to the pH but to the structure of the donor. For instance, 1,4-diazabicyclo[2.2.2]octane (DABCO) turned out to be a viable alternative to imidazole; however the former performed best at pH 9.85, whereas the latter performed best at pH 8.3.

RadH: A Versatile Halogenase for Integration into Synthetic Pathways

Flavin-dependent halogenases are useful enzymes for providing halogenated molecules with improved biological activity, or intermediates for synthetic derivatization. We demonstrate how the fungal halogenase RadH can be used to regioselectively halogenate a range of bioactive aromatic scaffolds. Site-directed mutagenesis of RadH was used to identify catalytic residues and provide insight into the mechanism of fungal halogenases. A high-throughput fluorescence screen was also developed, which enabled a RadH mutant to be evolved with improved properties. Finally we demonstrate how biosynthetic genes from fungi, bacteria, and plants can be combined to encode a new pathway to generate a novel chlorinated coumarin “non-natural” product in E. coli.

Phenyl 1, 2 - isoxazole or phenyl 1, 2 - pyrazole compound and use thereof (by machine translation)

The invention discloses the following formula of phenyl 1, 2 - different oxazole or 1, 2 - pyrazole compounds with use. Through the biological activity tests show that, the compound inhibiting heat shock protein 90 activity. Therefore, the invention phenyl 1, 2 - different oxazole or 1, 2 - pyrazole compounds can be used as a heat shock protein 90 inhibitor for the treatment of cancer. (by machine translation)

New chalcone compound or pharmaceutically acceptable salt thereof having inhibitory activity on Hsp90 and medical use thereof

The present invention relates to a novel chalcone compound or pharmaceutically acceptable salt thereof having inhibitory activity on Hsp90, and to medical use thereof. The charcone compound: has an excellent effect of inhibiting Hsp90; induces decomposition of Hsp90 client protein, which causes cancer or neurodegenerative diseases; and thus can be advantageously used for a pharmaceutical product or health-promotional food for treating or preventing Hsp90-mediated diseases such as cancer or neurodegenerative diseases. The chalcone compound or the pharmaceutically acceptable salt is represented by Chemical Formula 1 below.

Discovery of potent N-(isoxazol-5-yl)amides as HSP90 inhibitors

HSP90 is ubiquitously overexpressed in a broad spectrum of human cancers and has been recognized as an attractive target for cancer treatment. Here, we described the fragment screening, synthesis and structure-activity relationship studies of small molecule inhibitors with 4,5-diarylisoxazole scaffold targeting HSP90. Among them, the compound N-(3-(2,4-dihydroxy-5-isopropylphenyl)-4-(4-((4-morpholinopiperidin-1-yl)methyl)phenyl)isoxazol-5-yl)cyclopropanecarboxamide (108) showed high affinity for binding to HSP90 (FP binding assay, IC50 Combining double low line 0.030 μM) and inhibited the proliferation of various human cancer cell lines with averaging GI50 about 88 nM. Compound 108 exhibited its functional inhibition of HSP90 by depleting key signaling pathways and concomitantly elevating of HSP70 and HSP27 in U-87MG cells. Further in vivo studies showed that compound 108 strongly suppressed the tumor growth of human glioblastoma xenograft model U-87MG with T/C Combining double low line 18.35% at 50 mg/kg q3w/2.5w. Moreover, compound 108 also exhibited good pharmacokinetic properties. Together, our study implicates that compound 108 is a promising candidate of HSP90 inhibitor and is currently advanced to preclinical study.

Discovery of hybrid Hsp90 inhibitors and their anti-neoplastic effects against gefitinib-resistant non-small cell lung cancer (NSCLC)

Heat shock protein 90 (Hsp90) represents an attractive cancer therapeutic target due to its role in the stabilization and maturation of many oncogenic proteins. We have designed a series of hybrid Hsp90 inhibitors by connecting the resorcinol ring of VER-

5-PHENYL-ISOXAZOLE-3-CARBOXAMIDES MODULATING HSP90 WITH ANTITUMORAL ACTIVITIES

The present invention relates to formula I compounds having antitumoural activities through, as one possible biological target, the molecular chaperone heat shock protein 90 (Hsp90) inhibition. The invention includes the use of such compounds in medicine,