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

New 2,6-dialkyl-substituted isoflavone analogues of the natural isoflavone pseudobaptigenin have been synthesized. Their structures have been confirmed by IR and PMR spectroscopies.Taras Shevchenko University, KIEN. Karakalpak Division. Academy of Sciences of the Republic of Uzbekistan. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 674–677, September–October, 1993.     

Synthetic and modified isoflavonoids. XIII. Synthesis of analogues of fujikinin

Analogues of a natural isoflavone glycoside — fujikinin — have been synthesized. Their structures have been confirmed by their PMR spectra.Taras Shevenko Kiev University: KIEN, Karakalpak Division, Academy of Sciences of the Republic of Uzbekistan, Nukus. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 347–351, May–June, 1994.     

Synthetic and modified isoflavonoids XVII. Interaction of synthetic analogs of isoflavones with guanidine

Under the influence of guanidine, 1,3-benzodioxolane, 1,4-benzodioxane, and 1,5-benzodioxepane analogs of isoflavone are converted into 2-aminopyrimidine derivativesTranslated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 636–640, September–October, 1994.     

A new isoflavonostilbene from the heartwood of Maackia amurensis

A new isoflavonostilbene which has been called maackiasin has been isolated from an ethanolic extract of the heartwood ofMaackia amurensis and its structure has been established by spectral methods. The maackiasin molecule is constructed of fragments of the isoflavone retusin and of 3,3,4,5-tetrahydroxystilbene linked by a diether bond. The dioxane grouping connecting the two fragments is constructed from the hydroxyls at C-7 and C-8 of the isoflavone and the vinyl grouping of the stilbene. Maackiasin is the first representative of a new type of natural polyphenols.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 39–42, January–February, 1986.     

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.     

Photophysics of Genistein isoflavone: Solvent and concentration effects studied by UV–visible spectroscopy and theoretical simulation

Genistein isoflavone is shown to exist in two different conformations which are the 90° completely twisted geometry and the 50° less twisted one. Specific interactions with the solvent cage as well as self-association processes seem shifting the isoflavone from the perpendicular conformation towards the less twisted one. The theoretical simulation, using analytical atom–atom pair potential, predicts a self-dimer in a slipped non-sandwich, face to river, perpendicular structure. From the UV–visible photophysics investigations it is revealed that monomeric species cannot exist alone even at very low solute concentration (10⁻⁶ M), the self-association process occurs already in this concentration range.     

Synthetic and modified isoflavonoids. II. Synthesis of new 2,6-dialkyl-substituted analogues of pseudobaptigenin

New 2,6-dialkyl-substituted isoflavone analogues of the natural isoflavone pseudobaptigenin have been synthesized. Their structures have been confirmed by IR and PMR spectroscopies.     

Phenolic compounds of Ononis arvensis the structure of onogenin

Summary From the roots ofOnonis arvensis L. a new isoflavone has been isolated with mp 213–214° C which has been called onogenin. On the basis of the results of a study of its UV, IR, NMR, and mass spectra, the structure of 7-hydroxy-6-methoxy-3,4-methylenedioxyisoflavanone is proposed for onogenin.Khar'kov State Pharmaceutical Institute. Khar'kov Scientific-Research Institute of Pharmaceutical Chemistry. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 354–357, May–June, 1975.     

Synthesis of 7-O-β-D-glucopyranosides of isoflavones and their heterocyclic analogues

The products of the interaction of -acetobromoglucose with 2,4,5-trihydroxyphenyl benzyl ketone and 2,4-dihydroxyphenyl 4-hydroxybenzyl ketone and also with their heterocyclic analogues, which are present completely or partially in the enolic form, have been investigated. It has been shown that in this reaction a tetra-O-acetylglucosyl residue is added at the 4-OH hydroxy group of the phenyl residue of the ketone. The compounds obtained have been converted into isoflavone 7-O-glucosides by the action of the vilsmeier reagent or acetoformic anhydride.Taras Shevchenko Kiev University. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 220–227, March–April, 1993.     

X-ray structural investigation of gossypol and its derivatives. VIII. A new class of inclusion compounds based on dianilinegossypol

Summary The existence of a new class of ICs based on DAGP has been established. Single crystals have been obtained and the crystallographic characteristics of 15 ICs of this GP derivative have been determined.A. S. Sadykov Institute of Bioorganic Chemistry, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 666–669, September–October, 1988.     

Bisindoles. 18. Some electrophilic substitution reactions in the 1,2-di(indol-5-yl)ethane series

A quantum-chemical calculation has been made and the laws of the electron-density distribution in the molecule of 1,2-di(indol-5-yl)ethane have been determined. The electrophilic substitution reactions most characteristic for it have been studied.For communications 15–17, see [1–3].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 73–77, January, 1984.     

A mass-spectrometric study of insect pheromones. II. Epoxy compounds

The mass spectra of epoxy compounds have been studied and the positions of the epoxy rings and their configurations have been shown.V. I. Lenin Tashkent State University. A. S. Sadykov Institute of Bioorganic Chemistry, Uzbekistan Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 130–135, January–February, 1992.     

Flavonoids of Thermopsis alterniflora

Summary From the lipophilic fraction of the substances from the herbage ofThermopsis alterniflora we have isolated a molecular compound of two flavonoids, one of which has been identified as chrysoeriol, while the second, with the composition C₁₆H₁₂O₅, mp 274–275°C, is a new isoflavone which we have called teralin. On the basis of spectral characteristics and the products of alkaline fusion, we have proposed for it the structure of 4,7-dihydroxy-2-methoxyisoflavone.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 140–144, March–April, 1975.     

Composition of the essential oil ofSalvia garedzhii. Terpenoids and sesquiterpene hydrocarbons

The composition of the terpenoid and sesquiterpene hydrocarbon fraction ofSalvia garedzhii has been studied by chromato-mass spectrometry. A total of 19 compounds have been identified and a provisional assignment of another 6 components has been made.K. A. Timiryazev Moscow Agricultural Academy. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 720–722, November–December, 1984.     

Preparation and reactions of isoflavone heteroanalogs (a review)

Methods for preparation of 3-hetarylchromones, which are isoflavone heteroanalogs, and the reactions of these compounds with either preservation or opening of the pyrone ring are reviewed.Taras Shevchenko Kiev University, 252033 Kiev, Ukraine. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 3–23, January, 1999     

Plant polysaccharides VII. Polysaccharides ofMorus and their hypoglycemic activity

Water-soluble polysaccharides, pectin substances, and hemicelluloses have been isolated fromMorus leaves, and their qualitative and quantitative compositions have been determined. The polysaccharides obtained by extraction with hot water have been investigated for hypoglycemic activity. A polysaccharide fromMorus alba proved to have the highest sugar-lowering activity.Materials presented at the IInd International Symposium of the Chemistry of Natural Compounds.Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 789–791, November–December, 1997.     

Diterpenoids ofPulicaria salviifolia. I. Structures of salvin and salvinin

Two new diterpenoids of the clerodane series — salvin and salvinin — have been isolated from the epigeal part ofPulicaria salviifolia Bgl. in Mem. A structure and a most probable stereochemistry are proposed.Presented at the VIIth Indo-Soviet Symposium on the Chemistry of Natural Compounds [16].Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 201–205, March–April, 1985.     

Crystal structure of organosilicon compounds. LXIV. Structure of four unsaturated cyclocarbosilanes

An x-ray structural investigation of four permethylcyclocarbosilanes, whose heterocycles are formed by –Si–CH₂–CH₂–, –Si–CH=CH–, and –Si–CC– fragments, has been carried out. Strong distortions of some bond lengths and bond angles (caused by the shortness of the Si...Si distances between the neighboring Si atoms and the absence of intermolecular contancts with the participation of atoms of the heterocycles), which attest to statistical disordering of the molecules in the crystals, whose character could be established unequivocally for three of the compounds, have been observed in all the structures.For part LXIII, see [1].A. N. Nesmeyanov Institute of Organometallic Compounds, Academy of Sciences of the USSR. Translated from Zhurnal Strukturnoi Khimii, Vol. 32, No. 2, pp. 116–124, March–April, 1991.     

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.     

Search for methods of synthesizing 1,9,10-trimethoxy-2,3-methylenedioxyaporphine. I

Several possible methods of obtaining 4-methoxy-2,3-methylenedioxybenzaldehyde have been considered. A method ensuring the synthesis of this aldehyde with a yield of 35–40% has been developed which consists in the bromination of isovanillin followed by the replacement of the halogen by a hydroxy group and methylation. A number of substituted benzylidene- and benzyltetrahydroisoquinolines have been synthesized. It has been shown that the irradiation of these substances leads to N-dealkylation accompanied by oxidative processes.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, Vol. 6, pp. 818–823, November–December, 1985.