30992-66-6

Usage

Uses

Used in Organic Synthesis:
4-Hydroxy-7-benzyloxycoumarin is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows it to be a versatile building block for the development of new molecules with potential applications in various fields, such as pharmaceuticals, agrochemicals, and materials science.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Hydroxy-7-benzyloxycoumarin is used as a starting material for the synthesis of drug candidates. Its chemical properties enable the formation of new compounds with potential therapeutic effects, making it a valuable asset in the discovery and development of novel medications.
Used in Agrochemical Industry:
4-Hydroxy-7-benzyloxycoumarin is also utilized in the agrochemical industry for the synthesis of bioactive compounds with potential applications as pesticides, herbicides, or insecticides. Its unique structure allows for the development of new molecules with improved efficacy and selectivity, contributing to more sustainable agricultural practices.
Used in Materials Science:
In the field of materials science, 4-Hydroxy-7-benzyloxycoumarin is employed in the synthesis of advanced materials with specific properties. Its chemical structure can be used to create new polymers, coatings, or composites with unique characteristics, such as improved stability, enhanced mechanical properties, or tailored optical properties.

Upstream product

• 1983-81-9 4,7-dihydroxycoumarin 
• 100-39-0 benzyl bromide 
• 29682-12-0 1-[4-(benzyloxy)-2-hydroxyphenyl]ethanone 
• 105-58-8 Diethyl carbonate 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 

Downstream Products

• 69076-12-6 7-(benzyloxy)-4-hydroxy-3-nitro-2H-chromen-2-one 
• 1983-81-9 4,7-dihydroxycoumarin 
• 19839-21-5 3-Benzyloxy-5,8,10,12-tetraoxa-benzo[a]cyclopenta[h]fluoren-6-one 
• 1983-72-8 medicagol 
• 882870-12-4 3-benzyloxy-8,9-dihydroxy-benzo[4,5]furo[3,2-c]chromen-6-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).

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.

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.

NEW ANTIBACTERIAL COMPOUNDS

The present invention relates to novel antibacterial compounds, pharmaceutical compositions containing them and their use as antimicrobials.

Defining a minimum pharmacophore for simocyclinone D8 disruption of DNA gyrase binding to DNA

The increasing occurrence of drug-resistant bacterial infections in the clinic has created a need for new antibacterial agents. Natural products have historically been a rich source of both antibiotics and lead compounds for new antibacterial agents. The natural product simocyclinone D8 (SD8) has been reported to inhibit DNA gyrase, a validated antibacterial drug target, by a unique catalytic inhibition mechanism of action. In this work, we have used a deconstruction-reconstruction approach to prepare analogs of the coumarin subunit of SD8 and evaluated their ability to disrupt binding of the DNA gyrase enzyme to DNA in a surface plasmon resonance assay. This has led to a minimum pharmacophore required for disruption of binding. Springer Science+Business Media 2014.

Fine molecular tuning at position 4 of 2H-chromen-2-one derivatives in the search of potent and selective monoamine oxidase B inhibitors

The effects on the inhibition potencies of monoamine oxidase isoforms A (MAO-A) and B (MAO-B) depending upon changes in the physicochemical properties (size, shape, H-bonding, lipophilicity, etc.) of substituents at the C4 position of 2H-chromen-2-one derivatives were extensively investigated, and the results significantly added to our knowledge on this class of MAO inhibitors. All the 67 examined compounds showed high MAO-B selectivity, some of them achieving potency in the low nanomolar range. In particular, the 7-metachlorobenzyloxy-4- oxyacetamido-2H-chromen-2-one (entry 62) showed single digit nanomolar MAO-B potency (IC50 = 3.1 nM) and high selectivity over the MAO-A isoform (selectivity ratio = 7244). The great variety of the investigated substituents at C4 of the 2H-chromen-2-one nucleus, combined with binding models generated from docking studies carried out on selected compounds, allowed us to shed light on the main molecular requirements for potent and selective MAO-B inhibition, highlighting the dominant role of the steric effects. Interestingly, many of the designed substituents could be metabolically related to each other (e.g., CH3/CH2OH/CHO/COOH; NH2/NHCH3, NHAc), and therefore the results obtained may help in predicting the in vivo activity of some putative metabolites of lead MAO-B inhibitors.

Inhibition of monoamine oxidases by functionalized coumarin derivatives: Biological activities, QSARs, and 3D-QSARs

A large series of coumarin derivatives (71 compounds) were tested for their monoamine oxidase A and B (MAO-A and MAO-B) inhibitory activity. Most of the compounds acted preferentially on MAO-B with IC50 values in the micromolar to low-nanomolar range; high inhibitory activities toward MAO-A were also measured for sulfonic acid esters. The most active compound was 7-[(3,4-difluorobenzyl)oxy]-3,4-dimethylcoumarin, with an IC50 value toward MAO-B of 1.14 nM. A QSAR study of 7-X-benzyloxy meta-substituted 3,4-dimethylcoumarin derivatives acting on MAO-B yielded good statistical results (q2 = 0.72, r2 = 0.86), revealing the importance of lipophilic interactions in modulating the inhibition and excluding any dependence on electronic properties. CoMFA was performed on two data sets of MAO-A and MAO-B inhibitors. The GOLPE procedure, with variable selection criteria, was applied to improve the predictivity of the models and to facilitate the graphical interpretation of results.

Photoactive coumarin derivatives

A new class of 3,4-dihydrocoumarin derivatives which are useful as photoactive compounds in a wide variety of applications including photoresists and other opto-electronic applications are disclosed and claimed. Preferred embodiments include ether, ester, carbonate, and sulfonate derivatives of 5-hydroxy, 6-hydroxy, and 7-hydroxy-3-diazo-4-oxo-3,4-dihydrocoumarins. These compounds exhibit very high photosensitivity in the deep ultraviolet (DUV) region (ca. 250 nm), and therefore, are useful as photoactive compounds in DUV photoresist formulations.

Process for preparing photoactive coumarin derivatives

Novel processes for the preparation of a new class of coumarin derivatives, which are useful as photoactive compounds in a wide variety of applications including photoresists and other opto-electronic applications, are disclosed and claimed. The process involves a multi-step synthetic method for the preparation of ether, ester, carbonate, or sulfonate derivative of 5-hydroxy, 6-hydroxy, or 7-hydroxy-3-diazo-4-oxo-3,4-dihydrocoumarin starting from the corresponding dihydroxyacetophenone. The compounds formed from the process of the present invention exhibit very high photosensitivity in the deep ultraviolet (DUV) region (ca. 250 nm), and therefore, are useful as photoactive compounds in DUV photoresist formulations.