Synthetic and modified isoflavonoids

Water-soluble diethanolamine and morpholine salts of derivatives of 1,3-benzodioxole, 1,4-benzodioxane, and 1,5-benzodioxepane analogs of isoflavones have been synthesized.Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 306–312, May–June, 1998.     

Synthetic and modified isoflavonoids XVIII. Synthesis of 7-isopropoxy-substituted analogs of pseudobaptigenin

7-Isopropoxy derivatives of isoflavones have been synthesized from 1,3-benzodioxole, 1,4-benzodioxane, and 1,4-benzodioxepane analogs of pseudobaptigenin. Their structures have been confirmed by PMR.Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 365–369, May–June, 1997.     

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.     

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.Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 629–633, September–October, 1994.     

Chemistry of heteroanalogs of isoflavones

Pyrazole analogs of isoflavones were synthesized from substituted -(4-pyrazolyl)-2,4-dihydroxyacetophenones.See [1] for communication III.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1108–1111, August, 1976.     

Synthetic analogs of natural flavolignans. II. A new synthesis of benzodioxepane analogs of silandrin and hydnocarpin

Benzodioxepane analogs of chalcones have been obtained from which analogs of natural flavolignans — silandrin and hydnocarpin — have been synthesized. The PMR spectra of the new substances are given and are discussed.KIEN, Karakalpak Division, Academy of Sciences of the Republic of Uzbekistan, Nukus. Taras Shevchenko Kiev University, Ukraine. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 480–483, July–August, 1994.     

Chemistry of isoflavone heteroanalogs.

Benzodioxane analogs of chalcones were isomerized to the corresponding flavanones and isoflavones. The PMR and IR spectra of these compounds were discussed.For Communication 11, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 319–323, March, 1989.     

Chemistry of isoflavone heteroanalogs. 11. Benzodioxane analogs of chalcone,flavone, and isoflavone

Benzodioxane analogs of chalcones and their epoxides have been prepared. Different types of analogs of natural flavonolignan — silibin — have been synthesized from these compounds. The PMR spectra of the new compounds and the results of the preliminary biological testings are reported and discussed.For article 10, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 192–198, February, 1986.     

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.Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 633–636, September–October, 1994.     

Chemistry of heteroanalogs of isoflavones

Condensation of 2-pyridylacetonitrile with polyphenols gave the corresponding -(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.See [1] for communication V.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1180–1185, September, 1977.     

Chemistry of heteroanalogs of isoflavones

Thiazole analogs of natural isoflavones were synthesized, and their reactions with alkalis, phosphorus pentasulfide, and alkylating and acylating agents were studied. Data on the biological activity of the compounds are presented.     

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.Translated from Teoreticheskaya i Éksperimental'naya Khimiya, Vol. 25, No. 5, pp. 629–633, September–October, 1989.     

Synthetic analogs of natural flavolignans. IV. Synthesis of benzodioxocane analogs of silandrin and hydnocarpin

1,6-Benzodioxocane analogs of chalcones have been synthesized. From them have been obtained benzodioxocane analogs of silandrin and hydnocarpin. The PMR spectra of the substances synthesized are given and are discussed.Taras Shevchenko Kiev University, Ukraine. KIEN, Karakalpak Division, Academy of Sciences of the Republic of Uzbekistan, Nukus. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 490–493, July–August, 1994.     

Synthetic and modified isoflavonoids. I. Synthetic analogues of pseudo-baptigenin

New isoflavones derived from pseudobaptigenin containing alkyl substituents in position 6 have been synthesized. The structures of the compounds have been confirmed by PMR and IR spectroscopies.Taras Shevchenko Kiev University KIEN. and Karakalpak Division. Academy of Sciences of the Republic of Uzbekistan, Nukus. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 669–674, September–October, 1993.     

Chemistry of heteroanalogs of isoflavones

Thiazole analogs of isomeric isoflavones were synthesized from -(2,4-dimethyl-5-thiazolyl)-2-hydroxyacetophenones, and their reaction with hydrazine hydrate and alkylating and acylating agents was studied. The reaction of thiazole derivatives of 7-hydroxychromone with hydrazine hydrate proceeds with opening of the pyrone ring and subsequent cyclization of the intermediate to o-hydroxyphenylpyrazole derivatives. The reaction of hydrazine hydrate with thiazole derivatives of 5-hydroxychromone, which proceeds with retention of the pyrone ring, leads to hydrazones. The structures of the new compounds were confirmed by the PMR spectra.See [1] for communication 6.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 25–28, January, 1979.     

Synthetic analogs of natural flavolignans. V. A new synthesis of 6-halogeno-1,3-benzodioxane analogs of silandrin and hydnocarpin

6-Halogeno-1,3-benzodioxane analogs of chalcones have been synthesized by various methods. Flavanone and flavone analogs of silandrin and hydnocarpin have been obtained from them. The structures of the new flavonoids have been shown by their PMR spectra.KIEN Karakalpak Division, Academy of Sciences of the Republic of Uzbekistan, Nukus. Taras Shevchenko Kiev University, Ukraine. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 494–498, July–August, 1994.     

Modified coumarins. 14. Synthesis of 7-hydroxy-[4,3′]dichromenyl-2,2′-dione derivatives

New derivatives of 3-(2-oxochromen-4-yl)chromen-2-one, modified analogs of natural dicoumarins, were prepared from substituted coumarin-4-acetic acids.Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 358–365, September–October, 2004.     

Basicity constants of natural isoflavonoids

The basicities (pK_BH+) of 13 natural isoflavones have been determined spectrophotometrically in sulfuric acid solutions. It has been shown that the change of basicity in this series of compounds depends on the geometry of the molecules and on intramolecular effects.All-Union Scientific-Research Institute of Drug Chemistry and Technology, Khar'kov. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 773–775, November–December, 1985.     

Synthetic analogs of natural flavolignans VIII. Synthesis of 6-chloro-1,3-benzodioxane, 1,4-benzodioxane, 1,5-benzodioxepane, and 1,6-benzodioxocane analogs of 4-thioflavone

1,3-Benzodioxane, 1,4-benzodioxane, 1,5-benzodioxepane, and 1,6-benzodioxocane analogs of 4-thioflavone have been synthesized.Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 375–378, May–June, 1997.     

Synthetic and modified isoflavonoids. VII. Synthesis of benzodioxocane analogs of pseudobaptigenin

Benzodioxocane analogs of pseudobaptigenin have been synthesized, and their structures have been shown by chemical transformations and PMR spectra.Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 223–226, March–April, 1994.