Isoflavone Analogs Research Articles

Potent Antioxidative Isoflavones Isolated from Soybeans Fermented with Aspergillus saitoi.

Two potent antioxidative isoflavones were isolated from soybeans fermented with Aspergillus saitoi by silica gel column chromatography and preparative HPLC, using ODS column, or in addition, Toyopearl HW-40 column chromatography. The purified AS-13 and AS-9B compounds were identified as 8-hydroxydaidzein (8-OHD) and 8-hydroxygenistein (8-OHG), respectively, by MS, and (1)H-NMR, (13)C-NMR and HMBC spectra. These isoflavones, which have an o-dihydroxy structure between the 7- and 8-position, each exhibited significantly stronger antioxidative activity than daidzein and genistein in both oil and lipid/aqueous systems. Furthermore, the antioxidative activity and the content of each isoflavone analog in soybeans with different fermentation periods were investigated. It is suggested from these results that AS-13 and AS-9B were produced from daidzein and genistein, respectively, by hydroxylation at the 8-position of each isoflavone structure. In addition, it is concluded that these isoflavones were also the principal antioxidants in potent antioxidative soybeans fermented with A. saitoi.

Chemistry of modified flavonoids. XVIII. Thiazole analogs of isoflavones. Homologous and isomeric series

Homologous and isomeric series of thiazole derivatives of isoflavones were produced on the basis of α-(4-methyl-2-thiazolyl)-2-hydroxyacetophenones. A study of α-(4-methyl-2-thiazoyl)-2-hydroxyacetophenones by PMR spectroscopy showed that these compounds exist in most nonpolar and low polarity organic solvents exclusively in the ketone form, but in dimethyl sulfoxide solution both the ketone and enol forms are observed in various ratios. A simple and effective preparative method of synthesis of homologs of 3-(2-diazolyl)-chromones was developed, and their alkylation at the phenolic hydroxyl was studied. Data of biological tests of the compounds synthesized are presented.

Synthetic and modified isoflavonoids XV. Interaction of synthetic analogs of isoflavones with hydrazine hydrate and its derivatives

The reactions of 1,3-benzodioxolane, 1,4-benzodioxane, and 1,5-benzodioxepane analogs of isoflavones with hydrazine derivatives have been studied. It has been found that under the action of hydrazines the new isoflavones recyclize into 3,4-diarylpyrazones. Their structures have been confirmed by their PMR spectra.

Synthetic and modified isoflavonoids XVI. The interaction of synthetic isoflavone analogs with hydroxylamine

Under the action of hydroxylamine, 1,3-benzodioxolane, 1,4-benzodioxane, and 1,5-benzodioxepane analogs of isoflavones recyclize into 5-(2-hydroxyphenyl)isoxazole derivatives. Their structures have been shown by their PMR spectra.

Synthetic and modified isoflavonoids XIV. Mannich bases and their salts in a series of synthetic isoflavone analogs

Mannich bases and their hydrochlorides have been obtained from 1,3-benzodioxolane, 1,4-benzodioxane, and 1,5-benzodioxepane analogs of pseudobaptigenin. The PMR spectra of the compounds obtained are given and are discussed.

Chemistry of heteroanalogs of isoflavones 14. Isoxazole analogs of isoflavones

Isoxazole analogs of isoflavones have been synthesized by the cyclization of α-(3-isoxazolyl)-2-hydroxyacetophenones. Their alkylation, acylation, and electrophilic substitution reactions, and reactions with binucleophiles have been studied. 3-(3-Isoxazolyl)-7-methoxychromones are rearranged selectively into 2-aminochromone derivatives by the action of hydroxylamine as a result of a double recyclization and are recyclized into pyrazole derivatives by hydrazine. Preparations with hypolipidemic, anabolic, hypoglycemic, and antiarrhythmic action are found among the derivatives of 3-(3-isoxazolyl)chromones.

Atropo-isomerism and abnormal temperature dependence of paramagnetic shifts in 1H NMR spectra of heterocyclic analogs of isoflavones in the presence of lanthanide chelates

It has been found that spatially hindered analogs of isoflavones can occur as a mixture of atropo-isomers, which is conveniently detected by using optically active lanthanide shift reagents. It is shown that on lowering the temperature the individual shifts of the signals of the isoflavone protons can either increase or decrease. The observed anomalies are attributed to changes in the predominant conformations of the molecules as the temperature is varied.

ChemInform Abstract: Glucosides of Thiazole Isoflavone Analogs.

Chemischer InformationsdienstVolume 17, Issue 30 Natural Products ChemInform Abstract: Glucosides of Thiazole Isoflavone Analogs. V. P. KHILYA, V. P. KHILYASearch for more papers by this authorV. G. PIVOVARENKO, V. G. PIVOVARENKOSearch for more papers by this authorF. S. BABICHEV, F. S. BABICHEVSearch for more papers by this author V. P. KHILYA, V. P. KHILYASearch for more papers by this authorV. G. PIVOVARENKO, V. G. PIVOVARENKOSearch for more papers by this authorF. S. BABICHEV, F. S. BABICHEVSearch for more papers by this author First published: July 29, 1986 https://doi.org/10.1002/chin.198630317Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume17, Issue30July 29, 1986 RelatedInformation

Synthesis of analogs of natural isoflavones from 2,4-dihydroxydeoxybenzoins

A number of analogs of natural isoflavones have been synthesized. The starting materials were 2,4-dihydroxydeoxybenzoins obtained under modified conditions of the Houben-Hoesch reaction. The yields of the isoflavones synthesized were 63–69%. All the analogs of natural flavones possess a pronounced hypolipidemic action.

Chemistry of heteroanalogs of isoflavones. 9. Reaction of thiazole analogs of isoflavones with nucleophilic and electrophilic reagents

Thiazole analogs of isoflavones and their 4-thioxo derivatives undergo recyclization to pyrazole derivatives and isomeric isoxazoles under the influence of hydrazine, methylhydrazine, phenylhydrazine, and hydroxylamine. A new group enters the 8 position or two groups simultaneously enter the 6 and 8 positions of the chromone ring in electrophilic substitution reactions. Data from the PMR spectra and on the biological activity are presented and discussed.

Chemistry of heteroanalogs of isoflavones. 8. Reaction of benzofuran analogs of isoflavones and their 4-thioxo derivatives with hydroxylamine and hydrazine

A number of 3-(2-benzofuryl)-6-ethylchromones and their 4-thioxo derivatives were synthesized, and the action of hydroxylamine and hydrazine on them was investigated. Isomeric 3 (5)-(o-hydroxyphenyl) isoxazoles were obtained in the reaction with hydroxylamine. The predominant formation of one or the other isomer depends on the character of the substituents in the 2 and 4 positions of the chromone. The reaction of chromones with hydrazine leads to o-hydroxyphenylpyrazoles. The compounds obtained were characterized by their IR, UV, and PME spectra.

Synthesis and biological activity of furan, pyridine, and benzimidazole analogs of isoflavones

Synthesis and biological activity of furan, pyridine, and benzimidazole analogs of isoflavones

Chemistry of heteroanalogs of isoflavones

Condensation of 2-pyridylacetonitrile with polyphenols gave the corresponding α-(2-pyridyl)-acetophenones, which were converted to the pyridine analogs of natural isoflavones and to 3-pyridylchromones with methyl, trifluoromethyl, and ethoxycarbonyl groups in the 2 position. The antimicrobial activity of 3-pyridylchromones and their reaction with alkylating and acylating agents and phosphorus pentasulfide were investigated.

Synthesis and biological activity of thiazole analogs of isoflavones

Synthesis and biological activity of thiazole analogs of isoflavones

Synthesis and properties of heterocyclic analogs of isoflavones

The condensation of cyanomethyl derivatives of furan and benzofuran with di- and trihydric phenols has given the corresponding 2,4-dihydroxy- and 2,4,6-trihydroxy-α-heterylacetophenones. The latter have been converted by reaction with acid anhydride, ethoxalyl chloride, and trifluoroacetic anhydride into 3-heterylchromones with methyl, trifluoromethyl, and ethoxycarbonyl groups in position 2.