21260-41-3

Usage

Uses

Used in Pharmaceutical Development:
7-Hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one is used as a pharmaceutical candidate for its potential antioxidant, anti-inflammatory, and anti-cancer properties. Its ability to combat oxidative stress, reduce inflammation, and inhibit cancer cell growth makes it a valuable asset in the development of new medications for various diseases and conditions.
Used in Nutraceutical Formulation:
In the nutraceutical industry, 7-Hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one is utilized as an active ingredient for its health-promoting benefits. Its presence in dietary supplements and functional foods can contribute to enhanced antioxidant capacity, anti-inflammatory effects, and overall wellness, supporting the maintenance of good health and potentially reducing the risk of certain diseases.
Used in Cosmetics and Personal Care Products:
7-Hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one is employed in the cosmetics and personal care industry for its potential skin health benefits. Its antioxidant and anti-inflammatory properties may contribute to improved skin condition, reduced signs of aging, and protection against environmental stressors, making it a sought-after ingredient in skincare formulations.
Used in Agricultural Applications:
In agriculture, 7-Hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one may be used as a natural pesticide or growth promoter, leveraging its bioactive properties to protect crops from diseases and pests, and to enhance plant growth and productivity. Its potential use in this industry highlights the versatility of 7-Hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one and its applications beyond the medical and pharmaceutical fields.

InChI:InChI=1/C12H10O3/c13-7-4-5-9-8-2-1-3-10(8)12(14)15-11(9)6-7/h4-6,13H,1-3H2

Upstream product

• 117071-64-4 7-hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one-imine 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 108-46-3 recorcinol 
• 2941-29-9 2-oxocyclopentanecarbonitrile 
• 124-04-9 Adipic acid 
• 627-93-0 hexanedioic acid dimethyl ester 
• 10472-24-9 methyl 2-oxocyclopentane-1-carboxylate 
• 141-28-6 diethyl adipate 
• 120-92-3 cyclopentanone 
• 24922-00-7 ethyl 3-cyclopentyl-3-oxopropionate 

Downstream Products

• 312518-97-1 7-acetonyloxy-3,4-cyclopentenecoumarin 
• 314743-56-1 7-(1-methyl-2-oxopropoxy)-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 307548-74-9 7-(1-methyl-2-oxo-2-phenylethoxy)-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 500203-98-5 7-[2-(3-methoxyphenyl)-2-oxoethoxy]-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 301309-01-3 7-(2-oxo-2-phenylethoxy)-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 312496-58-5 7-[2-(4-methylphenyl)-2-oxoethoxy]-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 307548-76-1 7-[2-(4-chlorophenyl)-2-oxoethoxy]-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 500204-18-2 7-[2-(4-bromophenyl)-2-oxoethoxy]-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 307548-75-0 7-[2-(4-fluorophenyl)-2-oxoethoxy]-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 374762-16-0 7-[2-(4-methoxyphenyl)-2-oxoethoxy]-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 314743-57-2 7-(2-oxocyclohexyloxy)-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 298207-30-4 ethyl [(4-oxo-1,2,3,4-tetrahydrocyclopenta[c]chromen-7-yl)oxy]acetate 
• 1578300-75-0 7-(4-(4-phenylpiperazin-1-yl)butoxy)-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 1578300-76-1 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2,3-dihydrocyclo-penta[c]chromen-4(1H)-one 

Relevant academic research and scientific papers

Photobiological studies of new cyclopentene-psoralens

Psoralen analogues bearing a cyclopentane ring fused to either the 4',5' double bond (compound 4) or the 3,4 double bond (compound 7) of the tricyclic furocoumarin structure were prepared. AM1 theoretical calculations performed for these compounds indicated that the electronic properties of their reactive double bonds were very similar to those of psoralen and its derivative 8-methoxypsoralen (8-MOP), though the overall molecular geometries were clearly different, particularly as regards the change in molecular curvature produced by the introduction of the cyclopentane ring. Compound 4 showed a capacity similar to that of 8-MOP to inhibit the growth of human cervix adenocarcinoma cells (HeLa) and to induce mutagenic effects, but it was definitely less phototoxic to skin than 8-MOP. Its ability to photoadd to DNA and to cross-link DNA strands was also demonstrated. Instead, compound 7 was practically devoid of biological activity and no interaction with the macromolecule could be detected. These differences in behaviour between 4 and 7 are probably due to the molecular curvature resulting from the introduction of the cyclopentane ring.

Anti-influenza activity of monoterpene-containing substituted coumarins

Compounds simultaneously carrying the monoterpene and coumarin moieties have been tested for cytotoxicity and inhibition of activity against influenza virus A/California/07/09 (H1N1)pdm09. The structure of substituents in the coumarin framework, as well as the structure and the absolute configuration of the monoterpenoid moiety, are shown to significantly influence the anti-influenza activity and cytotoxicity of the compounds under study. The compounds with a bicyclic pinane framework exhibit the highest selectivity indices (the ratios between the cytotoxicity and the active dose). The derivative of (?)-myrtenol 15c, which is characterized by promising activity, low cytotoxicity, and synthetic accessibility, has the greatest potential among this group of compounds. It exhibited the highest activity when added to the infected cell culture at early stages of viral reproduction.

Nano-BFn/cellulose: a bio-based nano-catalyst for synthesis of bio-active 7-hydroxycoumarins

Nano-BFn/cellulose as a modified bio-based nano-catalyst has been synthesized from nanocellulose and boron triflouride via very simple steps. This novel nano-catalyst exhibited many advantages in the synthesis of 7-hydroxycoumarins such as good

Monoterpene-containing substituted coumarins as inhibitors of respiratory syncytial virus (Rsv) replication

Respiratory syncytial virus (RSV) is a critical cause of infant mortality. However, there are no vaccines and adequate drugs for its treatment. We showed, for the first time, that O-linked coumarin–monoterpene conjugates are effective RSV inhibitors. The most potent compounds are active against both RSV serotypes, A and B. According to the results of the time-of-addition experiment, the conjugates act at the early stages of virus cycle. Based on molecular modelling data, RSV F protein may be considered as a possible target.

Coumarin-dithiocarbamate hybrids as novel multitarget AChE and MAO-B inhibitors against Alzheimer's disease: Design, synthesis and biological evaluation

A series of new coumarin-dithiocarbamate hybrids were designed and synthesized as multitarget agents for the treatment of Alzheimer's disease. Most of them showed potent and clearly selective inhibition towards AChE and MAO-B. Among these compounds, compound 8f demonstrated the most potent inhibition to AChE with IC50 values of 0.0068 μM and 0.0089 μM for eeAChE and hAChE, respectively. Compound 8g was identified as the most potent inhibitor to hMAO-B, and it is also a good and balanced inhibitor to both hAChE and hMAO-B (0.114 μM for hAChE; 0.101 μM for hMAO-B). Kinetic and molecular modeling studies revealed that 8g was a dual binding site inhibitor for AChE and a competitive inhibitor for MAO-B. Further studies indicated that 8g could penetrate the BBB and exhibit no toxicity on SH-SY5Y neuroblastoma cells. More importantly, 8g did not display any acute toxicity in mice at doses up to 2500 mg/kg and could reverse the cognitive dysfunction of scopolamine-induced AD mice. Overall, these results highlighted 8g as a potential multitarget agent for AD treatment and offered a starting point for design of new multitarget AChE/MAO-B inhibitors based on dithiocarbamate scaffold.

Preparation of a novel, efficient, and recyclable magnetic catalyst, γ-Fe2O3@HAp-Ag nanoparticles, and a solvent- and halogen-free protocol for the synthesis of coumarin derivatives

In this protocol, Ag supported on the hydroxyapatite-core–shell magnetic γ-Fe2O3nanoparticles (γ-Fe2O3@HAp-Ag NPs) as a novel, efficient, and magnetically recyclable catalyst is synthesized, and characterized by transmission electron microscopy (TEM), scanning electron microscopy (SEM), Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), and vibrating sample magnetometry (VSM). The use of the catalyst is described in the synthesis of coumarin derivatives by the Pechmann condensation of various phenols with β-ketoesters under solvent- and halogen-free conditions at 80?°C. This novel and inexpensive method offers advantages, such as recyclability simple experimental protocol, short reaction time, minimal work-up procedure, and excellent yields of products, together with desirable, eco-friendly, green aspects by avoiding toxic elements and solvents, and ease of recovery from the reaction mixture using an external magnet.

New inhibitors of tyrosyl-DNA phosphodiesterase I (Tdp 1) combining 7-hydroxycoumarin and monoterpenoid moieties

A number of derivatives of 7-hydroxycoumarins containing aromatic or monoterpene substituents at hydroxy-group were synthesized based on a hit compound from a virtual screen. The ability of these compounds to inhibit tyrosyl-DNA phosphodiesterase I (Tdp 1), important target for anti-cancer therapy, was studied for the first time. It was found that the 7-hydroxycoumarin derivatives with monoterpene pinene moiety are effective inhibitors of Tdp 1 with the most active derivative (+)-25c with IC50value of 0.675?μM. This compound has low cytotoxicity (CC50?>100?μM) when tested against human cancer cells which is crucial for presupposed application in combination with clinically established anticancer drugs. The ability of the new compounds to enhance the cytotoxicity of camptothecin, an established topoisomerase 1 poison, was demonstrated.

Phosphate tricyclic coumarin analogs as steroid sulfatase inhibitors: Synthesis and biological activity

In the present work, we report convenient methods for the synthesis and biological evaluation of phosphate tricyclic coumarin derivatives as potential steroid sulfatase inhibitors. The described synthesis includes the straightforward preparation of 7-hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one, 3-hydroxy-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one and 3-hydroxy-8,9,10,11-tetrahydro-7H-cyclohepta[c]chromen-6-one modified with various phosphate moieties. The inhibitory effects of the synthesized compounds were tested on STS isolated from human placenta as well as the MCF-7, MDA-MB-231 and MDA-MB-435S cancer cell lines. Most of the new STS inhibitors possessed IC50 values between 21 to 159 μM. In the course of our investigation, the largest inhibitory effects in the STS enzyme assays were observed for the three compounds 9p, 9r and 9s, with IC50 values of 36.4, 37.8 and 21.5 μM, respectively (IC50 value of 1.0 μM for the 665-COUMATE used as a reference). The compound 9r, exhibited the highest potency against MCF-7, an estrogen receptor positive (ER+) cell line, with a GI50 value of 24.7 μM. The structure-activity relationships of the synthesized coumarin derivatives with the STS enzyme are discussed.

ALICYCLIC[C] BENZOPYRONE DERIVATIVES AND USES THEREOF

Disclosed are alicyclic[c]benzopyrone derivatives and use thereof. The alicyclic[c]benzopyrone derivatives are compounds represented by formula I or their salts. The present compounds not only significantly improve high activity induced by MK-801, but also effectively improve clambering symptom induced by Apomorphine and do not cause EPS within effective dose. These in vitro targets and in vivo pharmacological models are closely related to diseases of the nervous system caused by dopamine dysfunction, especially schizophrenia. Therefore the present compounds can be used for the treatment of central nervous system diseases, especially schizophrenia. ED50 is lower and effect is stronger in two animal models i.e. high activity induced by MK-801 and clambering symptom induced by Apomorphine, while ED50 is higher and therapeutic index is greater in animal models of catalepsy.

ALICYCLIC[C]BENZOPYRONE DERIVATIVES AND USES THEREOF

Disclosed are alicyclic[c]benzopyrone derivatives and use thereof. The alicyclic[c]benzopyrone derivatives are compounds represented by formula I or their salts. The present compounds not only significantly improve high activity induced by MK-801, but also effectively improve clambering symptom induced by Apomorphine and do not cause EPS within effective dose. These in vitro targets and in vivo pharmacological models are closely related to diseases of the nervous system caused by dopamine dysfunction, especially schizophrenia. Therefore the present compounds can be used for the treatment of central nervous system diseases, especially schizophrenia. ED50 is lower and effect is stronger in two animal models i.e. high activity induced by MK-801 and clambering symptom induced by Apomorphine, while ED50 is higher and therapeutic index is greater in animal models of catalepsy.