25001-57-4

Usage

Uses

Used in Pharmaceutical Industry:
Justicidin A is used as an anti-inflammatory agent for its potential to alleviate inflammatory conditions by modulating cytokine production and suppressing the activation of NF-κB.
Used in Oncology:
Justicidin A is used as a cytotoxic and anti-tumor agent for its potential in cancer therapy, targeting the inhibition and control of tumor growth.
Used in Drug Development:
Justicidin A is used as a lead compound in drug development for its pharmacological properties, which may contribute to the creation of novel therapeutic agents for various diseases and conditions.

InChI:InChI=1/C22H18O7/c1-24-16-7-12-13(8-17(16)25-2)21(26-3)14-9-27-22(23)20(14)19(12)11-4-5-15-18(6-11)29-10-28-15/h4-8H,9-10H2,1-3H3

Upstream product

• 186581-53-3 diazomethane 
• 22055-22-7 diphyllin 
• 74-88-4 methyl iodide 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 103477-58-3 2-(2-bromo-4,5-dimethoxyphenyl)-1,3-dioxolane 
• 175883-67-7 diethyl 1-(3',4'-methylenedioxyphenyl)-4-hydroxy-6,7-dimethoxy-naphthalene-2,3-dicarboxylate 
• 70461-33-5 2-bromo-4,5-dimethoxybenzaldehyde dimethyl acetal 
• 58-55-9 theophylline 
• 74-83-9 methyl bromide 
• 4687-37-0 ethyl 3,4-dimethoxybenzoylacetate 
• 16900-54-2 3-(3,4-methylenedioxyphenyl)propynoic acid ethyl ester 
• 1621253-11-9 9-(benzo[d][1,3]dioxol-5-yl)-6,7-dimethoxy-1-oxo-1,3-dihydronaphtho[2,3-c]furan-4-yl t-butylcarbonate 
• 1621253-10-8 9-[(tert-butoxycarbonyl)oxy]-6,7-dimethoxy-3-oxo-1,3-dihydronaphtho[2,3-c]furan-4-yl trifluoromethanesulfonate 
• 1621253-09-5 tert-butyl (9-hydroxy-6,7-dimethoxy-1-oxo-1,3-dihydronaphtho[2,3-c]furan-4-yl)carbonate 

Relevant academic research and scientific papers

13C NMR SPECTRA OF ARYLNAPHTHALENE LIGNANS

The 13C NMR spectra have been investigated of a number of arylnaphthalene lignans of plant origin: daurinol and its acetyl derivative and reduction product, justicidin A, justicidin B and its reduction product and the diacetyl derivative of the reduction product, and diphyllin and its acetate.The values of the chemical shifts of the carbon atoms in the spectra of the compounds investigated and the nature of their change according to structural factors are discussed and an assignment is made of the resonance lines in the spectra.The characteristics of the spectrumof one compound are used as models for others.The parameters of the 13C NMR spectra of a number of naphthalene derivatives are also used.On the basis of the results of the assignment of the signals, difference values of the chemical shifts of the carbon atoms in the series of compounds investigated have been determined.Using the experimental results as a background, some examples taken from the literature of investigations of the 13C NMR spectra of related compounds have been analyzed.

Cytotoxic arylnaphthalide lignan glycosides from the aerial parts of Phyllanthus taxodiifolius

The arylnaphthalide lignan glycosides, taxodiifoloside (1), cleistanthoside A (2), cleistanthin A (3) and cleistanthin A methyl ether (4), together with a triterpene, glochidone (5), have been isolated from the aerial parts of Phyllanthus taxodiifolius. The structures were established using spectral and chemical methods. Compounds 3 and 4, as well as the derivatives 2a and 3a exhibited potent cytotoxic activities with GI50 values in the range of 10-7-10-9 M in five cultured mammalian cancer cell lines while the new compound 1 showed moderate activity (GI50 in the order of 10-6 M). Compounds 2 and 5 were inactive in all tested cell lines. Georg Thieme Verlag KG Stuttgart.

Phenotypic Prioritization of Diphyllin Derivatives That Block Filoviral Cell Entry by Vacuolar (H+)-ATPase Inhibition

Many viruses use endosomal pathways to gain entry into cells and propagate infection. Sensing of endosomal acidification is a trigger for the release of many virus cores into the cell cytosol. Previous efforts with inhibitors of vacuolar ATPase have been shown to block endosomal acidification and affect viral entry, albeit with limited potential for therapeutic selectivity. In this study, four novel series of derivatives of the vacuolar ATPase inhibitor diphyllin were synthesized to assess their potential for enhancing potency and anti-filoviral activity over cytotoxicity. Derivatives that suitably blocked cellular entry of Ebola pseudotyped virus were further evaluated as inhibitors of endosomal acidification and isolated human vacuolar ATPase activity. Several compounds with significant increases in potency over diphyllin in these assays also separated from cytotoxic doses in human cell models by >100-fold. Finally, three derivatives were shown to be inhibitors of replication-competent Ebola viral entry into primary macrophages with similar potencies and enhanced selectivity toward antiviral activity.

Patentiflorin A Analogs as Antiviral Agents

The present disclosure relates to patentiflorin A analogs that are useful as antivirals, such as anti-HIV, anti-coronaviral, anti-Ebola viral, and anti-influenza viral agents and methods of use thereof.

ARYLNAPHTHALENE COMPOUNDS AS VACUOLAR-ATPASE INHIBITORS AND THE USE THEREOF

Ebola virus and Marburg virus are filoviruses and are responsible for outbreaks that cause up to 90% fatality, including the recent outbreak in West Africa that has resulted in over 11,000 deaths. The present disclosure generally relates to novel arylnaphthalene compounds as a vacuolar-ATPase inhibitor that are useful for the treatment of various viral infections, including those infections caused by filoviruses. Pharmaceutical composition matters and methods of use are within the scope of this invention.

An Optimized and General Synthetic Strategy To Prepare Arylnaphthalene Lactone Natural Products from Cyanophthalides

A simple method for the preparation of arylnaphthalene lactone natural products was developed and used to synthesize diphyllin (10), justicidin A (12), cilinaphthalide B (13), taiwanin E (15), chinensinaphthol (16), taiwanin E methyl ether (17), chinensin

Silver(I)-Catalyzed Regioselective Construction of Highly Substituted α-Naphthols and Its Application toward Expeditious Synthesis of Lignan Natural Products

A novel route has been developed for regioselective synthesis of highly substituted α-naphthols, binaphthols, and anthracenol through silver(I) catalyzed C(sp3)-H/C(sp)-H, C(sp2)-H/C(sp)-H functionalization of β-ketoesters and alkyne

METHOD FOR PREPARATION OF JUSTICIDIN A DERIVATIVES OF ARYLNAPHTHALENE LIGNAN STRUCTURE

The present disclosure relates to a novel method for preparing an arylnaphthalene lignan compound. In synthesis of arylnaphthalene lignan compounds and derivatives according to the present disclosure, a naphthalene backbone may be constructed first and an

Hindered rotation in arylnaphthalene lignans

Many arylnaphthalene lignans show biological activity and although few of them contain stereogenic centers, they may nevertheless be chiral if there is hindered rotation about the aryl-naphthalene bond. A relatively high barrier to rotation may give rise to separable rotational enantiomers (atropisomers) which might have quite different pharmacological properties. In order to investigate this possibility we have synthesized the natural products justicidin A, justicidin B, retro-helioxanthin, retro-justicidin B, and helioxanthin as well as four other arylnaphthalenes lignan analogs. We have studied the aryl-naphthalene rotational barrier in these compounds by dynamic NMR and HPLC and find barriers to rotation ranging from 16.9 to 21.5 kcal/mol. This translates to half-lives for individual atropisomers of less than 10 min at room temperature. The experimentally found barriers are compared to those obtained from molecular orbital calculations.

Justicidin insecticidal and antiviral compounds

A natural lignan of the 1-aryl-2-napthoic acid type and related compounds are disclosed. The compounds correspond to the formula STR1 and exhibit both insecticidal and antiviral activity.