19225-02-6

Usage

Uses

Used in Pharmaceutical Industry:
Scopoletin is used as a bioactive compound for its antioxidant, anti-inflammatory, and anti-cancer properties, making it a candidate for the development of therapeutic agents targeting various diseases.
Used in Traditional Medicine:
Scopoletin is used as an analgesic and anti-spasmodic agent, leveraging its historical use in traditional medicine to alleviate pain and muscle spasms.
Used in Cosmetics Industry:
Scopoletin is used as a fragrance ingredient in perfumes and cosmetics, capitalizing on its aromatic properties to enhance the sensory experience of these products.
Used in Nutraceutical Industry:
Given its anti-microbial and anti-diabetic activities, scopoletin is used as a functional ingredient in nutraceutical products to promote health and well-being.
Used in Research and Development:
Scopoletin is utilized in research settings for investigating its potential therapeutic effects in cardiovascular diseases, neurodegenerative disorders, and skin conditions, contributing to the advancement of medical knowledge and treatment options.

InChI:InChI=1/C12H12O3/c1-2-3-8-6-12(14)15-11-7-9(13)4-5-10(8)11/h4-7,13H,2-3H2,1H3

Upstream product

• 3249-68-1 ethyl butyroyl acetate 
• 108-46-3 recorcinol 
• 36873-43-5 ethyl 2-formylpentanoate 
• 16205-90-6 ethyl 2-hexynoate 
• 4949-44-4 ethyl propanoylacetate 
• 131431-64-6 ethyl hexa-2,3-dienoate 

Downstream Products

• 104229-64-3 7-[3-(4-Phenyl-1-piperazinyl)propoxy]-4-propyl-2H-1-benzopyran-2-one 
• 96623-62-0 4'-methyl-4-propylpsoralen 
• 864838-86-8 C₁₉H₁₆O₄ 
• 307546-61-8 C₁₅H₁₆O₅ 
• 304896-86-4 2-(4-propyl-2-oxo-2H-7-chromenyloxy)acetic acid 
• 95184-94-4 7-(2-oxo-cyclohexanyloxy)-4-propyl-2H-1-benzopyran-2-one 

Relevant academic research and scientific papers

Synthesis and antioxidant activity of novel 8-formyl-4-substitued coumarins

4-Methyl-8-formyl- and 4-phenyl-8-formyl coumarins have been synthesized by Pechmann reaction using oxalic acid catalyst for the first time. 4-Propyl-7-hydroxy-, and 4-methyl-7-methoxy coumarins have also been accomplished by this catalyst for the first time. They have been characterizated by IR,1H-NMR,13C-NMR, mass and elemental analysis. Furthermore, the obtained coumarins were compared according to antioxidant activity by DPPH method.

FeCl3-catalysed ultrasonic-assisted, solvent-free synthesis of 4-substituted coumarins. A useful complement to the Pechmann reaction

The catalytic activity of FeCl3 for the synthesis of a variety of 4-substituted coumarins using high energy techniques has been investigated. The ultrasonic-assisted conditions provide a useful complement to the Pechmann reaction, affording the coumarin derivatives in excellent yields, under solvent-free conditions, in short reaction times using an inexpensive, mild and benign Lewis acid catalyst.

Investigation of the cytotoxicity of bioinspired coumarin analogues towards human breast cancer cells

Abstract: Coumarins possess a wide array of therapeutic capabilities, but often with unclear mechanism of action. We tested a small library of 18 coumarin derivatives against human invasive breast ductal carcinoma cells with the capacity of each compound to inhibit cell proliferation scored, and the most potent coumarin analogues selected for further studies. Interestingly, the presence of two prenyloxy groups (5,7-diprenyloxy-4-methyl-coumarin, 4g) or the presence of octyloxy substituent (coumarin 4d) was found to increase the potency of compounds in breast cancer cells, but not against healthy human fibroblasts. The activity of potent compounds on breast cancer cells cultured more similarly to the conditions of the tumour microenvironment was also investigated, and increased toxicity was observed. Results suggest that tested coumarin derivatives could potentially reduce the growth of tumour mass. Moreover, their use as (combination) therapy in cancer treatment might have the potential of causing limited side effects. Graphic abstract: [Figure not available: see fulltext.].

Novel C7-substituted coumarins as selective monoamine oxidase inhibitors: Discovery, synthesis and theoretical simulation

There is a continued need to develop new selective human monoamine oxidase (hMAO) inhibitors that could be beneficial for the treatment of neurological diseases. However, hMAOs are closely related with high sequence identity and structural similarity, which hinders the development of selective MAO inhibitors. “Three-Dimensional Biologically Relevant Spectrum (BRS-3D)” method developed by our group has demonstrated its effectiveness in subtype selectivity studies of receptor and enzyme ligands. Here, we report a series of novel C7-substituted coumarins, either synthesized or commercially purchased, which were identified as selective hMAO inhibitors. Most of the compounds demonstrated strong activities with IC50 values (half-inhibitory concentration) ranging from sub-micromolar to nanomolar. Compounds, FR1 and SP1, were identified as the most selective hMAO-A inhibitors, with IC50 values of 1.5 nM (selectivity index (SI) 50 of 18 nM and 15 nM (SI > 2.74 and SI > 2.82). Docking calculations and molecular dynamic simulations were performed to elucidate the selectivity preference and SAR profiles.

Synthesis of Novel Anti-inflammatory Psoralen Derivatives?-?Structures?with?Distinct?Anti-Inflammatory?Activities

As a continuum to our work with coumarins, 12 psoralens were synthesized and evaluated for their anti-inflammatory activity. Psoralens were prepared in three steps; at first, 7-hydroxycoumarins were synthesized by von Pechmann condensation and then converted to 7-(2-oxopropoxy)coumarins. In the final step, a fused furan ring was introduced in an intramolecular ring-formation reaction. Based on a SciFinder search, two out of the 12 synthesized psoralen derivatives (compounds 9 and 12) were found to be novel. The derivatives displayed anti-inflammatory activity by suppressing iNOS and IL-6 expression, but their mechanism of action seemed to be dependent on the substitution. Compound 6 with propyl side chain inhibited NF-κB mediated transcription, while compound 10 with a phenyl substituent down-regulated iNOS expression in a posttranscriptional manner. The results introduce psoralen derivatives as promising anti-inflammatory compounds with potential for treatment of conditions involving iNOS and/or IL-6-mediated adverse responses.

Method for the diagnosis of lysosomal storage diseases

The present invention relates to a method for the diagnosis of a lysosomal storage disease (LSD) in a subject which is based on determining the activity of lysosomal enzymes with the help of 4-alkyl umbelliferyl derivatives. The present invention further relates to said 4-alkyl umbelliferyl derivatives for use in the diagnosis of an LSD, and a kit for the diagnosis of an LSD.

BENZOPYRONE DERIVATIVE AND USE THEREOF

The present invention relates to the field of pharmaceutical chemistry, and in particular, to a benzopyrone derivative and a use thereof. The benzopyrone derivative is compound having a structure of formula (I) or a pharmaceutically acceptable salt thereof. It has been found by experiments that, this type of compounds is useful in prevention or treatment of neuropsychical diseases.

Synthesis and biological investigation of coumarin piperazine (piperidine) derivatives as potential multireceptor atypical antipsychotics

The discovery and synthesis of potential and novel antipsychotic coumarin derivatives, associated with potent dopamine D2, D3, and serotonin 5-HT1A and 5-HT2A receptor properties, are the focus of the present article. The most-promising derivative was 7-(4-(4-(6-fluorobenzo[d]isoxazol-3-yl)-piperidin-1-yl)butoxy) -4-methyl-8-chloro-2H-chromen-2-one (17m). This derivative possesses unique pharmacological features, including high affinity for dopamine D2 and D3 and serotonin 5-HT1A and 5-HT2A receptors. Moreover, it possesses low affinity for 5-HT2C and H1 receptors (to reduce the risk of obesity associated with chronic treatment) and hERG channels (to reduce the incidence of torsade des pointes). In animal models, compound 17m inhibited apomorphine-induced climbing behavior, MK-801-induced hyperactivity, and the conditioned avoidance response without observable catalepsy at the highest dose tested. Further, fewer preclinical adverse events were noted with 17m compared with risperidone in assays that measured prolactin secretion and weight gain. Acceptable pharmacokinetic properties were also noted with 17m. Taken together, 17m may constitute a novel class of drugs for the treatment of schizophrenia.

Synthesis of substituted coumarins via Bronsted acid mediated condensation of allenes with substituted phenols or anisoles

Coumarins were obtained from the condensation of electron-rich arenes with allenes in the presence of TfOH in good yield. Depending on the substituent pattern of allenes employed, the general synthetic method of 4-substituted and 3,4-disubstituted 3-arylc

Synthesis and anti-inflammatory effects of a series of novel 7-hydroxycoumarin derivatives

A number of 7-hydroxycoumarins have been synthesised by Pechmann cyclisation using differently substituted resorcinols employing perchloric acid as the condensing agent. All the compounds have been characterised by analytical and spectroscopic methods. The anti-inflammatory properties were tested with LPS-induced inflammation in J774 macrophages. Expression of iNOS and COX-2 was determined by Western blot, NO by nitrite assay and IL-6 by ELISA analyses. Fifteen of the tested 7-hydroxycoumarins also inhibited IL-6 production but none of them had any major inhibitory effect on COX-2 expression.