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PubMedDate not supplied

[Activities of molecules similar to carboxyhydroxamic acid chromone-2 (sodium salt) in experimental mercury chloride poisoning; importance of the chromone cycle].

The carbo-hydroxamic-2 chromone acid (sodium salt) shows a higher protective action in vivo than in vitro against mercury chloride induced intoxications. The higher effect observed in vivo might be due to the activity itself of the chromone cycle which added up to that of the carbo-hydroxamic acid function. This latter alone appears in vitro. The antihyaluronidasic properties of this protective agent allow it to prevent the toxic substances to be diffused.

Animals↗
PubMed1992

(Aminoalkoxy)chromones. Selective sigma receptor ligands.

A series of (aminoalkoxy)chromones has been prepared, members of which bind potently (16-100 nM) at the sigma binding site and bind weakly (greater than 1000 nM) at the dopamine D2 receptor and 33 other receptors, second messenger systems, and ion channels. At the sigma receptor, the preferred position of attachment for the aminoalkoxy side chain to the chromone ring followed the rank order: 7-position greater than 5-position greater than 6-position. Chromones that contained a 2-substituent that was not coplanar with the chromone ring system showed improved binding over compounds with coplanar substituents. The most potent compound at the sigma site, 7-[[7-(4-hydroxypiperidyl)heptyl]oxy]-2-phenylchromone (74), had receptor affinities (IC50) of 16 nM at the [3H]DTG site, 19 nM at the [3H]-(+)-3-PPP site, and 4000 nM (Ki) at the dopamine D2 receptor. The most selective compound examined, 6-[[6-(4-hydroxypiperidyl)hexyl]-oxy]-2-cyclopentylchromone (58), exhibited IC50s of 51 nM at the [3H]DTG site, 55 nM at the [3H]-(+)-3-PPP site, and 21,000 nM (Ki) at the dopamine D2 receptor. Compound 44 (6-[[6-(4-hydroxypiperidyl)hexyl]oxy]-3-methylflavone, NPC 16377) was systemically effective (ip and po) in two behavioral models predictive of antipsychotic compounds and systemically active in animal models of ischemia.

Chromones↗
PubMed1990

Chromone glycosides from Schumanniophyton magnificum.

Two new chromone glycosides, schumanniofiosides A and B have been isolated from the root bark of Schumanniophyton magnificum and their structures shown to be 2-methyl-5,7-dihydroxychromone 5-O-beta-D-glucopyranoside and 2-methyl-5,7-dihydroxychromone 7-O-beta-D-glucopyranosyl-(1----2)-apiofuranoside, respectively. The structures were elucidated by a combination of spectral data and chemical degradation.

Carbohydrate Conformation↗
PubMed1979

Studies on antianaphylactic agents. 6. Synthesis of some metabolites of 6-ethyl-3-(1H-tetrazol-5-yl)chromone and their analogues.

The metabolites of 6-ethyl-3-(1H-tetrazol-5-yl)chromone (AA-344) (1), an orally effective antiallergic agent, and their analogues were synthesized to confirm the proposed structures and to determine their activity in the rat passive cutaneous anaphylaxis (PCA) test. A glucuronic acid metabolite (6) was assigned the structure 24b, 1-deoxy-1-[5-(6-ethylchromon-3-yl)tetrazol-1-yl]-beta-D-glucopyranuronate, by the comparison of 13C NMR, mass spectra, and TLC of isomeric compounds. In 13C NMR spectra, the shift difference of the tetrazole ring carbons between a pair of isomers was more remarkable than that of the glycosidic carbons. Therefore, the former is a useful criterion for distinguishing between such isomers. Some of the metabolities and analogues were active when administered intravenously, and two metabolites (2 and 3) were also effective upon oral administration.

Animals↗
PubMed1977

Antagonists of slow reacting substance of anaphylaxis. Synthesis of a series of chromone-2-carboxylic acids.

A series of substituted chromone-2-carboxylic acids was synthesized and tested as antagonists of SRS-A induced contractions of isolated guinea pig ileum. This work led to the discovery of sodium 7-[3-(4-acetyl-3hydroxy-2-propylphenoxy)-2-hydroxypropoxy]-4-oxo-8-propyl-4H-1-benzopyran-2-carboxylate (FPL 55712) which is the first reported specific antagonist of SRS-A. Some structural requirements for biological activity within this series are discussed.

Animals↗
PubMed1975

Synthesis of ethyl 6-substituted-chroman- and -chromone-2-carboxylates. A comparative structure-activity study employing the 6-phenyl and phenoxy analogs in the triton hyperlipidemic rat model.

To explore the effect of lipophilicity on antilipidemic activity in the Triton WR-1339 induced hyperlipidemic rat model we synthesized the 6-cyclohexyl, phenyl, and phenoxy analogs of ethyl chroman-2-carboxylate. Results obtained were analyzed in light of the biological activity observed for the 6-chloro-substituted and unsubstituted chromans, the 6-chlorochroman-4-one ester, and the 6-chloro-, phenyl-, and phenoxychromone esters. The suggestion is made that chromones likely exert their antilipidemic effects by a somewhat different set of mechanisms than do the chromans and clofibrate. Whereas the 6-chlorochromanone ester is inactive, the 6-chlorochromone ester is active in both normal and hyperlipidemic Sprague-Dawley rats. The major differential effect was observed for ethyl 6-cyclohexylchroman-2-carboxylate which did not lower cholesterol levels but returned triglyceride levels to normal in hyperlipidemic rats.

Animals↗
PubMed1979

Antiallergic action of 6-ethyl-3-(1h-tetrazol-5-YL) chromone (AA-344) on immediate hypersensitivity reaction in rats.

A newly synthesized compound, 6-ethyl-3-(1H-tetrazol-5-yl)chromone (AA-344) given intravenously or orally inhibited considerably the 72-hr passive cutaneous anaphylaxis (72-hr PCA) induced by IgE in rats. The antiallergic action of AA-344 was neither due to the antihistamine or antiserotonin effect nor was it mediated via adrenergic mechanisms. The results obtained in a double sensitization with two IgE antibodies suggest that AA-344 may not impair antigen-antibody combination but probably prevents the release of chemical mediators including histamine. This assumption was supported by observation that AA-344 inhibited a reduction in the skin histamine content caused by the 72-hr PCA, without effect on the compound 48/80-induced histamine reduction. AA-344 also partially inhibited the IgGa-mediated 3-hr PCA in rats. These results indicate that the inhibitory action of AA-344 on the immediate hypersensitivity reactions is due to prevention of the release of chemical mediators from the mast cells, by acting on some process in sequential events leading to the mediator release following antigen-antibody combination.

Adrenalectomy↗
PubMed1979

Inhibitory action of 6-ethyl-3-(1H-tetrazol-5-YL)chromone (AA-344) on IgE, IgGa- or chemical agent-induced histamine release from isolated rat mast cells.

The antiallergic action of 6-ethyl-3-(1H-tetrazol-5-yl)chromone (AA-344) was studied on isolated rat peritoneal mast cells. AA-344 clearly inhibited the IgE-mediated release of histamine caused by various concentrations of antigen and the 50% inhibitory concentration was 0.1 microM. On the IgGa-mediated release of histamine, a peak inhibition of AA-344 was observed at 10 microM. The histamine release induced by chemical agents such as concanavalin A, dextran and compound 48/80 was depressed by AA-344 at the range of 0.1--1 mM. The results obtained in this study indicate that the antiallergic action of AA-344 is due to selective inhibition on the immunological release of the chemical mediator from mast cells.

Animals↗
PubMed1979

Effect of 6-ethyl-3-(1H-tetrazol-5-yl)chromone (AA-344) on the immediate and delayed hypersensitivity reactions.

Effects of 6-ethyl-3-(1H-tetrazol-5-yl)chromone (AA-344) on the experimental models of the type I-IV allergic reactions were studied in comparison with those of disodium cromoglycate (DSCG), dexamethasone and other agents. AA-344 showed inhibitory effects on the homologous passive cutaneous anaphylaxis and the passive systemic anaphylaxis in guinea pigs. However, it had only a slight or little effect on the Forssman shock in guinea pigs, the complete-dependent cytolysis of mast cells in rats, the Arthus reaction in guinea pigs and the tuberculin reaction and the contact sensitivity in mice. DSCG was less effective, using these experimental models. Dexamethasone showed a suppressive effect on the type III and IV allergic reactions. The results indicate that AA-344 selectively suppresses the type I allergic reaction.

Animals↗
PubMed1979

Peroral chromones. A new way to treat allergic rhinitis?

Disodium chromoglycate (DSCG) is well documented in the topical treatment of allergic rhinitis. Its use does not lead to any major side effects. FPL 57579 is a new chromone compound which is well absorbed after oral administration. In a clinical trial, patients with allergic rhinitis underwent a nasal challenge before and after ingestion of FPL 57579. the effect on nasal airway resistance (NAR) was determined by rhinomanometry. In all cases there was a smaller increase in NAR after the intake of FPL 57579.

Administration, Oral↗
PubMed1992

Synthesis and in vitro activity of alkylaminoalkyloxy chromones on protoscoleces of Echinococcus multilocularis (Cestoda).

Twelve derivatives with alkylaminoalkyloxy chromone structures were synthesized and tested upon protoscoleces of Echinococcus multilocularis metacestode kept alive in vitro. Assays were performed with protoscoleces attached to the germinal layer in open and in closed vesicles. Compounds IVb and IIIe at the concentration of 0.1 mmol.L-1 killed 50% of the protoscoleces in open vesicles in 48 hours and compound IVb killed 100% of the protoscoleces in open vesicles within 96 hours at the same concentration. In closed vesicles after four days compound IVb killed all protoscoleces, compounds IIIe and IVd half of them, whereas in the controls all protoscoleces were alive. Trifluoperazine (TFP) was the reference compound; none of the new compounds showed better activity than TFP.

Animals↗
PubMed1979

[Chemical and pharmacological research on pyran derivatives. XII. Bis-(beta-chloroethyl)amino-substituted chromones and benzochromones].

By the reaction of phenols or naphthols with N,N-bis-(beta-methoxyethyl)ethoxycarbonylacetamide in the presence of phosphorus oxychloride the preparation of bis-(beta-methoxyethyl)amino substituted chromones or benzochromones was achieved. Treatment of these compounds with hydriodic acid at 95 degrees and then with thionyl chloride gave rise to the formation of the corresponding bis-(beta-chloroethyl)amino derivatives. When beta-naphthols reacted with N-ethoxycarbonylacetylmorpholine 1-oxo-3-morpholino-1H-naphtho[2,1-b]pyrans were obtained. These compounds as well as the corresponding 3-bis-(beta-methoxyethyl)amino derivatives afforded 1-oxo-3-bis-(beta-iodoethyl)amino-1H-naphtho[2,1-b]pyrans by treatment with hydriodic acid at reflux. The latter compounds were also easily transformed into 3-bis-(beta-chloroethyl)amino derivatives by reaction with phosphorus oxychloride in N,N-dimethylformamide. Pharmacological screening of some of the compounds described indicated no tumor-inhibiting activity.

Animals↗
PubMed1979

Clinical trial of a new chromone compound for systemic treatment of atopic dermatitis.

In a double-blind group comparative study, 14 adults with atopic dermatitis were treated systemically for 6 weeks with a new anti-allergic chromone compound (FPL 57787) 6 mg four times a day. A similar group of 13 adults was given placebo. Both groups improved during the trial in all the clinical assessments without significant differences, but there was a tendency to a decreased use of local treatment (hydrocortisone butyrate) in the active group during the trial. There were no drug-related complaints, but one patient in the active group had transiently elevated liver enzyme levels. Further investigations are warranted.

Administration, Topical↗