29682-12-0

Usage

Uses

Used in Pharmaceutical Industry:
4'-Benzyloxy-2'-hydroxyacetophenone is used as an intermediate compound for the synthesis of various pharmaceutical products. Its chemical structure allows for the creation of new drugs with potential therapeutic benefits.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4'-Benzyloxy-2'-hydroxyacetophenone serves as a key building block for the development of novel chemical compounds. Its unique structure enables the formation of new molecules with specific properties and applications.
Used in Research and Development:
4'-Benzyloxy-2'-hydroxyacetophenone is utilized as a research compound in various scientific studies. Its properties and reactivity make it an interesting subject for exploring new chemical reactions and understanding the underlying mechanisms.
Used in Cosmetics Industry:
In the cosmetics industry, 4'-Benzyloxy-2'-hydroxyacetophenone may be used as an ingredient in the formulation of various beauty products. Its chemical properties could contribute to the development of innovative products with enhanced performance and efficacy.
Used in Material Science:
4'-Benzyloxy-2'-hydroxyacetophenone can be employed in the development of new materials with specific properties. Its unique structure and reactivity can be harnessed to create materials with improved characteristics for various applications.

Preparation

Preparation by reaction of resacetophenone, with benzyl chloride, in the presence of potassium carbonate in refluxing acetone.

InChI:InChI=1/C15H14O3/c1-11(16)14-8-7-13(9-15(14)17)18-10-12-5-3-2-4-6-12/h2-9,17H,10H2,1H3

Upstream product

• 855287-16-0 7-benzyloxy-2,2,4-trimethyl-2H-chromene 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 506-96-7 Acetyl bromide 
• 22877-01-6 2,4-bis(benzyloxy)acetophenone 
• 3769-41-3 3-Benzyloxyphenol 
• 64-19-7 acetic acid 
• 66447-10-7 1-[4-(benzyloxy)-2-(methoxymethoxy)phenyl]ethanone 
• 5706-85-4 2-hydroxy-1-(4-hydroxyphenyl)ethan-1-one 
• 42059-48-3 acetic acid 4-acetyl-3-hydroxyphenyl ester 
• 108-46-3 recorcinol 
• 100-51-6 benzyl alcohol 
• 1024-41-5 benzyl tosylate 

Downstream Products

• 34176-17-5 1-(4-(benzyloxy)-2,5-dihydroxyphenyl)ethan-1-one 
• 101097-87-4 1-(4-benzyloxy-2-hydroxy-5-nitro-phenyl)-ethanone 
• 56923-49-0 bis-(5-acetyl-2-benzyloxy-4-hydroxy-phenyl)-sulfide 
• 98314-70-6 2-(2-acetyl-5-(benzyloxy) phenoxy)acetic acid ethyl ester 
• 855606-02-9 (6-benzyloxy-3-methyl-benzofuran-2-yl)-(4-methoxy-phenyl)-ketone 
• 102706-13-8 2-(2-acetyl-5-benzyloxy-phenoxy)-benzoic acid 
• 70239-64-4 (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(4-(benzyloxy)-2-hydroxyphenyl)prop-2-en-1-one 
• 96755-09-8 (E)-1-(4-Benzyloxy-2-hydroxy-phenyl)-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-propenone 
• 34128-24-0 1-(4-benzyloxy-2-hydroxyphenyl)-1,3-butanedione 
• 56879-12-0 1-(4-(benzyloxy)-2-methoxyphenyl)ethanone 
• 79566-30-6 7-benzyloxy-1-benzopyran-4-one 
• 152609-99-9 2-(4-chlorobutoxy)-4-(phenyl-methoxy)acetophenone 
• 74372-56-8 (E)-1-(4-Benzyloxy-2-hydroxy-phenyl)-3-(3,4-bis-benzyloxy-phenyl)-propenone 
• 261529-75-3 7-(benzyloxy)-2-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one 

Relevant academic research and scientific papers

Demonstrating Ligandability of the LC3A and LC3B Adapter Interface

Autophagy is the common name for a number of lysosome-based degradation pathways of cytosolic cargos. The key components of autophagy are members of Atg8 family proteins involved in almost all steps of the process, from autophagosome formation to their selective fusion with lysosomes. In this study, we show that the homologous members of the human Atg8 family proteins, LC3A and LC3B, are druggable by a small molecule inhibitor novobiocin. Structure-activity relationship (SAR) studies of the 4-hydroxy coumarin core scaffold were performed, supported by a crystal structure of the LC3A dihydronovobiocin complex. The study reports the first nonpeptide inhibitors for these protein interaction targets and will lay the foundation for the development of more potent chemical probes for the Atg8 protein family which may also find applications for the development of autophagy-mediated degraders (AUTACs).

Identification of Interleukin-8-Reducing Lead Compounds Based on SAR Studies on Dihydrochalcone-Related Compounds in Human Gingival Fibroblasts (HGF-1 cells) in Vitro

Background: In order to identify potential activities against periodontal diseases, eighteen dihydrochalcones and structurally related compounds were tested in an established biological in vitro cell model of periodontal inflammation using human gingival fibroblasts (HGF-1 cells). Methods: Subsequently to co-incubation of HGF-1 cells with a bacterial endotoxin (Porphyromonas gingivalis lipopolysaccharide, pgLPS) and each individual dihydrochalcone in a concentration range of 1 μM to 100 μM, gene expression of interleukin-8 (IL-8) was determined by qPCR and cellular interleukin-8 (IL-8) release by ELISA. Results: Structure–activity analysis based on the dihydrochalcone backbone and various substitution patterns at its aromatic ring revealed moieties 20,4,40,60-tetrahydroxy 3-methoxydihydrochalcone (7) to be the most effective anti-inflammatory compound, reducing the pgLPS-induced IL-8 release concentration between 1 μM and 100 μM up to 94%. In general, a 2,4,6-trihydroxy substitution at the A-ring and concomitant vanilloyl (4-hydroxy-3-methoxy) pattern at the B-ring revealed to be preferable for IL-8 release inhibition. Furthermore, the introduction of an electronegative atom in the A,B-linker chain led to an increased anti-inflammatory activity, shown by the potency of 4-hydroxybenzoic acid N-vanillylamide (13). Conclusions: Our data may be feasible to be used for further lead structure designs for the development of potent anti-inflammatory additives in oral care products.

Design, synthesis, and biological activity of a novel series of benzofuran derivatives against oestrogen receptor-dependent breast cancer cell lines

A docking study of a novel series of benzofuran derivatives with ERα was conducted. In this study, we report the synthesis of a novel series of benzofuran derivatives and evaluation of their anticancer activity in vitro against MCF-7 human breast cancer cells, as well as their potential toxicity to ER-independent MDA-MB-231 breast cancer cells, human renal epithelial HEK-293 cells, and human immortal keratinocytes (HaCaT cells) by using the MTT colorimetric assay. The screening results indicated that the target compounds exhibited anti-breast cancer activity. The target compound 2-benzoyl-3-methyl-6-[2-(morpholin-4-yl)ethoxy]benzofuran hydrochloride (4e) exhibited excellent activity against anti-oestrogen receptor-dependent breast cancer cells and low toxicity. The preliminary structure-activity relationships of the target benzofuran derivatives have been summarised. In conclusion, the novel benzofuran scaffold may be a promising lead for the development of potential oestrogen receptor inhibitors.

Design, synthesis and anti-TMV activities of novel chromone derivatives containing dithioacetal moiety

Thirty-five novel chromone derivatives containing dithioacetal moiety were designed, synthesized, and their anti-TMV activities were evaluated through half-leaf method. The results showed compound c23 illustrates highly curative, protective and inactivating activities against TMV at 500 mg/L, with the values of 68.8%, 58.8%, 86.0% respectively, which were superior to that of Ribavirin (42.3%, 49.8%, 68.4%, respectively) and similar to that of Ningnanmycin (59.4%, 52.4%, 88.4%, respectively). The EC50 value of inactivating activities of compound c23 is 9.3 mg/L, which was better than that of Ribavirin (135.2 mg/L), and equivalent to that of Ningnanmycin (8.8 mg/L). Furthermore, compound c23 can destroy the integrity of TMV-CP, resulting in reduced infectivity of TMV. Meanwhile, compound c23 can combine with TMV protein coat and hydrolyze TMV protein coat to impact the process of self-assembling of TMV, with the association constant (Kd) 4.5 mg/L. This finding suggests that chromone derivatives containing dithioacetal moiety can be used as new antiviral agent.

MODULATORS OF STIMULATOR OF INTERFERON GENES (STING)

The present invention relates to compounds of formula (I) and salts, stereoisomers, tautomers or N-oxides thereof that are useful as modulators of STING (Stimulator of Interferon Genes). The present invention further relates to the compounds of formula (I) for use as a medicament and to a pharmaceutical composition comprising said compounds.

Design, synthesis and QSAR study of 2′-hydroxy-4′-alkoxy chalcone derivatives that exert cytotoxic activity by the mitochondrial apoptotic pathway

Eleven 4′-alkoxy chalcones were synthesized and biologically evaluated for their antiproliferative activity against four human tumor cell lines (PC-3, MCF-7, HF-6, and CaSki). Compounds 3a-3d and 3f were selective against PC-3, with IC50 values ranging from 8.08 to 13.75 μM. In addition, chalcones 3a-3c did not affect the normal fibroblasts BJ cells. The most active and selective compounds were further evaluated for their effect on the progression of cell cycle in PC-3 cells, and chalcones 3a and 3c induced a G2/M phase arrest. Furthermore, it was found that these three chalcones induced the mitochondrial apoptotic pathway by regulating Bax and Bcl-2 transcripts and by increasing caspase 3/7 activation. Otherwise, the QSAR model indicates that the double bond of the α,β-unsaturated carbonyl, as well as the planar structure geometry, are important to the biological activity of the synthetized chalcones. Based on these studies, it was concluded that withdrawing substituents in ring A, decrease the antiproliferative activity. This is related to the possible mechanism of action of these compounds, where a Michael addition needs to take place in order to be a potent anticancer agent.

6-[2-hydroxyl-3-(alkylamino)propoxy]benzofuran compound and application thereof

The invention belongs to the technical field of medicines and relates to a 6-[2-hydroxyl-3-(alkylamino)propoxy]benzofuran compound and an application thereof. The 6-[2-hydroxyl-3-(alkylamino)propoxy]benzofuran compound comprises a stereoisomer and pharmacologically applicable salt of the compound and has the general structural formula shown in the description, wherein R is shown in the claims andspecification. The 6-[2-hydroxyl-3-(alkylamino)propoxy]benzofuran compound and the pharmacologically applicable salt-additive salt of the compound can be mixed with an existing medicine for use or used alone to be applied to a medicine for treating spastic diseases of vascular smooth muscle.

One-pot two-step synthesis of 3-iodo-4-aryloxy coumarins and their Pd/C-catalyzed annulation to coumestans

An efficient protocol for the synthesis of various coumestans from the intramolecular annulation of 3-iodo-4-aryloxy coumarins through C-H activation has been developed. When 3-iodo-4-aryloxy coumarins were treated with 10% Pd/C (0.3 mol% Pd) in the presence of sodium acetate, the corresponding coumestans were produced in good to excellent yield. Reusability of the palladium catalyst was investigated in up to three consecutive cycles and it was found that the yield of the reaction was almost unaltered. Sequential iodination and O-arylation of 4-hydroxy coumarins leading to the 3-iodo-4-aryloxy coumarins were also achieved in a one-pot two-step process starting from aryl iodides in high yield. Pivalic acid was revealed to be the most effective additive for the later method to produce 3-iodo-4-phenoxy coumarins. Different functional groups bearing electron-donating as well as withdrawing groups are also tolerant to the reaction conditions.

A rapid, solvent-free deprotection of methoxymethyl (MOM) ethers by pTSA; An eco-friendly approach

Background: Ease of preparation and alkaline stability of methoxymethyl (MOM) makes it an important hydroxyl protecting group. A number of methods are available for the deprotection of MOM. Though the methods are good in general, they use solvents, require prolonged reaction time and tedious work up. A solvent free, solid phase, fast deprotection of MOM has been developed and is the major theme of this paper. Methods: A mixture of MOM protected compounds and pTSA is triturated in a mortar (5 min) and left at room temperature for 30 min. On addition of water (4°C), pTSA, methanol and formaldehyde dissolved leaving the products as precipitates. Results: A series of different MOM ethers were deprotected by this method in good to excellent yield (85-98%). The compatibility of MOM in the presence of other protections such as methoxyl, benzyl, ester, amide, allyl and lactone was also established. Acetate protection is not stable under these conditions. Conclusion: An efficient, selective and high yielding deprotection MOM groups by pTSA under solvent free condition is described. The process is environment friendly since no solvent was used in the deprotection process. The reaction conditions are mild and should be useful for the deprotection of MOM derivatives of complex and labile molecules.

AUTOPHAGY INHIBITORS

A compound, which is a) a tetrahydrotriazine derivative of the formula (I), a tautomer, a pharmaceutically acceptable salt, a solvate or hydrate thereof, were the symbols have the meanings given in the description, or b) a coumarin derivative of the formula (II), a tautomer, a pharmaceutically acceptable salt, solvate or hydrate thereof, were the symbols have the meanings given in the description, is useful in a therapeutical method for inhibiting autophagy in a cell and for the treatment of cancer.