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Results for “Chromones”

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At least 55 records · Page 3Linked to original sources
PubMed2004

Anti-AIDS agents. 60. Substituted 3'R,4'R-di-O-(-)-camphanoyl-2',2'-dimethyldihydropyrano[2,3-f]chromone (DCP) analogues as potent anti-HIV agents.

Synthesis of positional isomers is a commonly used technique in drug design. Accordingly, based on prior SAR studies of 3'R,4'R-di-O-(S)-camphanoyl-(+)-cis-khellactone (DCK, 1) analogues, a series of mono- and disubstituted chromone derivatives of 3'R,4'R-di-O-(-)-camphanoyl-2',2'-dimethyldihydropyrano[2,3-f]chromone (DCP, 4) were designed and synthesized. Together with 1 and 4-methyl DCK (2), all newly synthesized DCP analogues (4-21) were screened for anti-HIV-1 activity against a non-drug-resistant strain in H9 lymphocytes and a multiple reverse transcriptase (RT) inhibitor-resistant strain in the MT4 cell line. Several DCP analogues (4, 5, 7, 8, 13, and 17) exhibited extremely high anti-HIV activity in the non-drug-resistant strain assay, with EC(50) values ranging from 0.00032 to 0.0057 microM and remarkable therapeutic indexes (TI) ranging from 5.6 x 10(3) to 1.16 x 10(5), which were similar to those of 2 (EC(50) 0.0059 microM, TI > 6.6 x 10(3)) and better than those of 1 (EC(50) 0.049 microM, TI > 328). Even more promisingly, some DCP analogues also showed activity against a multi-RT inhibitor-resistant strain, HIV-1 RTMDR1, whereas most DCK analogues did not. The most significant compound was 8, with an EC(50) value of 0.06 microM and TI of 718 against the multi-RT inhibitor-resistant HIV-1 strain. Compounds 9 and 10 also showed good activity with an EC(50) value of 0.14 microM, and TIs of 272 and >111, respectively. 2-Ethyl DCP (8) exhibited the best anti-HIV activity in both assays. Further development of 8-related compounds as clinical trial candidates is warranted.

Anti-HIV Agents↗
PubMed2006

Neuroprotective 2-(2-phenylethyl)chromones of Imperata cylindrica.

Bioactivity-guided fractionation of the methanolic extract of the rhizomes of Imperata cylindrica afforded a new compound, 5-hydroxy-2-(2-phenylethyl)chromone (1), together with three known compounds, 5-hydroxy-2-[2-(2-hydroxyphenyl)ethyl]chromone (2), flidersiachromone (3), and 5-hydroxy-2-styrylchromone (4). Among these four compounds, 1 and 2 showed significant neuroprotective activity against glutamate-induced neurotoxicity in primary cultures of rat cortical cells.

Adrenal Cortex↗
PubMed2005

Sesquiterpene chromones from Ferula fukanensis and their nitric oxide production inhibitory effects.

Five new sesquiterpene chromone derivatives, fukanefurochromones A-E (1-5), were isolated from a 80% aqueous methanol extract of the roots of Ferula fukanensis. The structures were elucidated on the basis of spectroscopic evidence, especially heteronuclear multiple-bond connectivity (HMBC) and high-resolution MS. The sesquiterpene chromone derivatives inhibited nitric oxide (NO) production and inducible NO synthase (iNOS) gene expression by a murine macrophage-like cell line (RAW 264.7), which was activated by lipopolysaccharide (LPS) and recombinant mouse interferon-gamma (IFN-gamma).

Chromones↗
PubMedDate not supplied

Novel chromones from Spathelia sorbifolia.

Three new chromones, namely 10-(2',3'-dihydroxy-3'-methylbutanyl)-spatheliachromen, 10-(1',2',3'-trihydroxy-3'-methylbutanyl)spatheliachromen, and 6-(3'-hydroxy-3'-methyl-trans-but-1'-enyl)-O-methylisospatheliachrome n were isolated from the 10% aqueous MeOH extract of the twigs and leaves of Spathelia sorbifolia, together with five known chromones. Compound 2, the known spatheliabischromen, and 5-O-methylsorbifolin showed cytotoxicity against 9PS cells in culture.

Acetylation↗
PubMed1997

Granulosin, a new chromone from Galipea granulosa.

A novel chromone, granulosin (1), has been isolated from the bark of Galipea granulosa. The extract of the bark, as well as granulosin (1), exhibited lethality in the brine shrimp test. The structure of granulosin (1) as 2-propyl-7,8-(methylenedioxy)chromone was established via spectroscopic analysis.

Animals↗
PubMed2000

Luteolin, a compound with adenosine A(1) receptor-binding activity, and chromone and dihydronaphthalenone constituents from Senna siamea.

Activity-guided fractionation led to the isolation of luteolin (1) from the leaves of Senna siamea (syn. Cassia siamea). This compound was found to be an antagonist at the adenosine A(1) receptor with a K(i) value in the low micromolar range. Four additional nonactive compounds (2-5) were also isolated, and their structures were elucidated. One compound was identified as cassia chromone (5-acetonyl-7-hydroxy-2-methylchromone) (2). Three other compounds are new, and they were identified as 5-acetonyl-7-hydroxy-2-hydroxymethyl-chromone (3), 4-(trans)-acetyl-3,6,8-trihydroxy-3-methyldihydronaphthalenone (4), and 4-(cis)-acetyl-3,6,8-trihydroxy-3-methyldihydronaphthalenone (5).

Chromones↗
PubMedDate not supplied

A new chromone from Cassia nodosa.

A new chromone named as 5,4'-dihydroxy-7-methyl 3-benzyl chromone (1) along with three known flavonoid compounds as unsubstituted flavone, kaempferol-3-o-rhamnoside and quercetin-3-o-arabinoside have been isolated from the leaves of Cassia nodosa. Their structures have been established by means of chemical and spectral evidences (IR, UV, 1H-NMR, 13C-NMR and mass spectra).

Cassia↗
PubMed1986

A double-blind crossover study of the effect of a chromone carboxylic acid, FPL 52694, on overnight fasting gastric acid secretion.

The chromone FPL 52694 is a preparation thought to act by stabilizing mast cell membranes, thus reducing free histamine in the gastric mucosa. The effect of FPL 52694 on overnight gastric secretion was tested in 15 dyspeptic individuals in a double-blind crossover study. Each individual received the chromone preparation or placebo for 1 week. After each of the treatment periods gastric secretion was collected after 6 h of fasting by continuous suction for 8 h during the night. A significant reduction of the total acid secretion was observed after active drug compared with placebo administration, mean reduction being 17% (median, 23%). No difference was observed between 30-min and 60-min periods. FPL 52694 had no significant effect on pepsin, intrinsic factor (IF) or volume secretion. The difference in the effect on pepsin and acid secretion, reflected in a significant increase in the pepsin to acid ratio, indicates that intrinsic histamine, similarly to extrinsic histamine, has a specific effect on parietal cells. The difference in effect on acid and IF secretion indicates that intrinsic histamine not only has a specific effect on parietal cells but also has different effects on the secretory substances contained in this cell. Since IF was not reduced by the use of FPL 52694, it may be that this substance will not influence vitamin B12 metabolism.

Adolescent↗
PubMed1982

Metabolism and excretion of a chromone carboxylic acid (FPL 52757) in various animal species.

1. The disposition of the chromone carboxylic acid (FPL 52757) in several species has been investigated. The compound is extensively metabolized by hydroxylation in rat, mouse, ferret, squirrel monkey, cynomolgus monkey, rabbit, hamster, stumped-tailed macaque and baboon (e.g. 50-100% in rat, cynomolgus monkey and squirrel monkey). 2. The plasma clearance of the chromone in rat, rabbit and squirrel monkey was 138, 44 and 59 ml/kg per h respectively. Plasma clearance by the dog was slower (13 ml/kg per h) and due mainly to elimination of unchanged compound. 3. As the dog is particularly susceptible to FPL 52757-induced hepatotoxicity the parent compound may be responsible. Species which clear the compound rapidly compared with the dog did not show a hepatotoxic response. 4. Although metabolism occurs in man the clearance is still slow (15 ml/kg per h) and may be one reason for human susceptibility to a mild hepatotoxic effect with the compound.

Animals↗
PubMed2004

Optical and surface morphological properties of polarizing films fabricated from a chromonic dye by the photoalignment technique.

The inherent chromonic lyotropic liquid crystalline properties of a dye have been manipulated to fabricate multi-axial micropolarizing thin films by means of the photoalignment technique. The dye aqueous solution is deposited on a photopatterned polymer film to result in the macroscopic alignment of the dye molecules, followed by drying at ambient temperature. The solid polarizing dye layers thus produced exhibit very a high contrast ratio and degree of polarization in the region of visible light. Addition of a small amount of surfactant to the dye solution is a prerequisite for the generation of a nematic chromonic phase and for the formation of homogeneous thin dye layers on the polymer film. The correlation between the optical and surface morphological properties of the dye layers is discussed.

Coloring Agents↗
PubMed2004

Conformational analysis of the biflavanoid GB2 and a polyhydroxylated flavanone-chromone of Cratoxylum neriifolium.

Three compounds, namely the interesting biflavanonol GB-2(naringenin 1-3, 11-8-dihydroquercetin, 1), 1-4',1-5,11-5,1-7,11-7-pentahydroxyflavanone(l-3,11-8)chromone [naringenin-(3 -8) 5,7-dihydroxychromone, 21 and stigmasterol, have been isolated from the leaves of Cratoxylum neriifolium Kurz. Compounds 1 and 2 show rotameric behavior due to the presence of a single bond between the highly substituted flavanone and flavanonol part and the flavanone and chromone part, respectively. Complete NMR spectral assignments of 1 and 2 have been done at 27 C and 90 C for the first time followed by a study of conformational behavior at room temperature by ROESY.

Clusiaceae↗
PubMed1994

[7-fluoro-4-chromone-3-sulfur compounds].

The novel 7-fluoro-4-chromone-3-sulfur compounds 5-12 were synthesized from the sulfinic acid 4, which can be obtained from the enaminone 3 and thionyl chloride. Especially the Flosequinane-like sulfoxide 12 was prepared and the vasodilating activity was evaluated in isolated ring segments of rat aorta.

Animals↗
PubMed2003

Structural characterization of chromone C-glucosides in a toxic herbal remedy.

Two novel compounds, 8-C-D-glucopyranosyl-7-hydroxy-5-methylchromone-2-carboxylic acid and a 2-O'-p-coumaroyl derivative thereof, were identified in a herbal tea that caused severe vomiting in a South African patient who had taken the traditional remedy to clean his stomach. For structural characterization, electrospray (ES) ionization in combination with collision-induced dissociation (CID) and tandem mass spectrometry (MS/MS) were used, as well as UV and nuclear magnetic resonance (NMR) spectroscopy. Specific ions or neutral losses generated under conditions of ES-MS/CID/MS permitted the establishment of structural features such as the free carboxyl group, the C-hexosidic part and the p-coumaroyl group. NMR spectroscopy was necessary to support the structure of the chromone-type aglycone and the glucosidic parts. Since the compounds are structurally related to aloesin and aloeresin A, which are chemotaxonomic markers of Aloe species, and have not been previously reported, we propose that they were formed by oxidative degradation during preparation of the herbal tea from an Aloe species or during its storage.

Chromatography, High Pressure Liquid↗
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↗
PubMed2006

Specificities of acetoxy derivatives of coumarins, biscoumarins, chromones, flavones, isoflavones and xanthones for acetoxy drug: protein transacetylase.

The earlier work carried out in our laboratory led to the identification of a novel rat liver microsomal enzyme termed as acetoxy drug: protein transacetylase (TAase), catalyzing the transfer of acetyl group from polyphenolic acetates (PA) to functional proteins. In this paper, we have reported the comparison of the specificities of acetoxy derivatives of coumarins, biscoumarins, chromones, flavones, isoflavones and xanthones with special reference to the phenyl moiety/bulky group on the pyran ring of PA. The results clearly indicated that compounds having phenyl moieties, when used as the substrates, resulted in a significant reduction of TAase catalyzed activity. The alteration in TAase catalyzed activation of NADPH cytochrome c reductase and inhibition of benzene-induced micronuclei in bone marrow cells by PA were in tune with their specificities to TAase.

Acetylation↗
PubMed2005

Synthesis, structure, infrared and fluorescence spectra of new rare earth complexes with 6-hydroxy chromone-3-carbaldehyde benzoyl hydrazone.

A novel 6-hydroxy chromone-3-carbaldehyde benzoyl hydrazone ligand and its four complexes, [LnL2(NO3)2]NO3 [Ln = Eu(1), Sm(2), Tb(3), Dy(4)], were synthesized. The complexes were characterized by the elemental analyses, molar conductivity and IR spectra. The crystal and molecular structure of Sm(III) complex was determined by single-crystal X-ray diffraction: crystallized in the triclinic system, space group P-1, Z = 1, a = 11.037(4) A, b = 14.770(5) A, c = 15.032(7) A, alpha = 60.583(4), beta = 75.528(7), gamma = 88.999(4), R1 = 0.0349. The fluorescence properties of complexes in the solid state and in the organic solvent were studied in detail, respectively. Under the excitation of ultraviolet light, strong red fluorescence of solid europium complex was observed. But the green fluorescence of solid terbium complex was not observed. These observations show that the ligand favor energy transfers to the emitting energy level of Eu3+. Some factors that influence the fluorescent intensity were also discussed.

Chromones↗
PubMed1999

N,N-dialkylaminosubstituted chromones and isoxazoles as potential anti-inflammatory agents.

The ability of some N,N-dialkylaminosubstituted chromones and isoxazoles to inhibit the protein kinase C (PKC) dependent signal transduction pathway was tested. As a cellular model, human neutrophils stimulated with either phorbol myristate acetate (PMA) or formylmethionine-leucine-phenylalanine (f-MLF) were used. The efficiency of the compounds was established by their capacity to reduce the O2- production by activated human neutrophils. Compounds carrying a 3-bis(2-methoxyethyl)amino group, a substituent found active in previously tested tricyclic compounds, do not show significant anti-PKC activity in this study. On the other hand, substitution with a 1-piperidinyl group leads all tested compounds to a high biological activity against stimulated neutrophils.

Anti-Inflammatory Agents, Non-Steroidal↗