Bisquaternary salts of pyrrolizidine alkaloids and their derivatives

Summary ,-Bisquaternary salts of the pyrrolizidine series have been synthesized by the reaction of ,-dibromoalkanes with some products of the cleavage of pyrrolizidine alkaloids (lindelofidine, hydroxyheliotridene, and their esters).Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 77–80, January–February, 1977.     

Growth-regulating activity of bis-quaternary salts of pyrrolizidine alkaloids and the products of their transformation

The growth-regulating activity of bis-quaternary salts of the pyrrolizidine series has been studied. It has been established that they possess a retardant activity which depends on the presence of the quaternary nitrogen atom, the acid residue of the molecule, and its configuration.     

Growth-regulating activity of bis-quaternary salts of pyrrolizidine alkaloids and the products of their transformation

The growth-regulating activity of bis-quaternary salts of the pyrrolizidine series has been studied. It has been established that they possess a retardant activity which depends on the presence of the quaternary nitrogen atom, the acid residue of the molecule, and its configuration.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 802–805, November–December, 1979.     

Synthesis of some bisquaternary salts of the alkaloids loline and lolinine

Summary An investigation of the UV, IR, PMR, and mass spectra and chemical transformations of luteicine have established for it the structure of 11-hydroxy-2,13-dimethoxyhexahydro-1,13-epoxyhomoproaporphine.The structure of the base was confirmed by its partial synthesis from luteidine.V. I. Lenin Tashkent State University. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 359–363, May–June, 1976.     

Study of the conformational states of amino-alcohol derivatives of some alkaloids and bases and their protonated forms and quaternary salts

Summary 1. Salsoline, salsolidine, ephedrine, pseudoephedrine, tetrahydroquinoline, and decahydroquinoline have been condensed with ethylene oxide and the corresponding amino alcohols have been obtained.2. The conformational states and spatial structures of the compounds synthesized and their protonated forms and methiodides have been studied by IR and PMR spectroscopy. It has been shown that because of the rapid conversion of the saturated parts of the molecules of the bases and inversion processes, several stable spatial forms of the N-derivatives with quarternized nitrogen atoms exist in solutions.V. I. Lenin Tashkent State University. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 486–492, July–August, 1974.     

Isomerization of the hydrochlorides of some alkaloids of the matrine series

Conclusions The conversions of sophoridane into allomatridine and matridine, of isosophoridane into allomatridine, and of isosophoridine into sophoridine have been effected. A mechanism has been proposed for the thermal isomerization of the hydrochlorides of the quinolizidine alkaloids.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 2, pp. 96–99, 1969     

Synthesis and structure of some diazonium salts of the 1,2,4-triazole series

Diazotriazolecarboxylic acid, its methyl ester, and 3-diazonium-5-nitrophenyltriazoles have an internal salt structure. 3-Diazonium-5-methyl- and -5-phenyl-1,2,4-triazoles have been isolated as nitrates, perchlorates, and fluoroborates. All the compounds mentioned exist in strongly acid media as salts of the corresponding acid with diazo cations, but in weakly acid and neutral solutions they exist as zwitterions, formed by elimination of a proton from the imino nitrogen of the heterocycle.Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 5, pp. 705–709, May, 1970.     

The transformation products of some natural coumarins

Summary Products of the reactions of natural coumarins have been studied for the first time: the products of the reaction of osthole with a mixture of concentrated acetic and hydrochloric acid, of oxypeucedanin hydrate with acetone and thionyl chloride, and of decursinol with chromium trioxide. A total of eight new compounds not previously described in the literature has been obtained.The structures of seven of the substances have been established on the basis of their IR, PMR, and mass spectra and chemical reactions.Leningrad Sanitary-Hygienic Medical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 562–566, September–October, 1978.     

Bisquaternary derivatives of cyclobuxine-D and their biological activity

Six new bisquaternary derivatives of cyclobuxine-D have been obtained, and their biological activities have been studied.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 40 64 75. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 742–744, September–October, 1997.     

Quaternary salts of alkaloids

New biologically active quaternary salts of the alkaloids ajmaline, quinine, hyoscyamine, codeine, and strychnine were synthesized. So-called separable conformers were observed among the ajmaline derivatives. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 381–383, July–August, 2006.     

Synthesis of some 4-chlorobenzopyrylium salts and their reactions

4-Chlorobenzopyrylium and 4-chloroflavylium salts have been synthesized, and some reactions of benzopyrylium cations of this type have been studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 8, pp. 1028–1030, August, 1970.     

Synthesis of some vinyl-substituted pyrylium salts and their intermediates

The preparation of vinyl-substituted pyrylium salts and their intermediates is described. These monomers and intermediates have been derived from syntheses based on p-2-hydroxyethoxybenzaldehyde and 4-methoxypyrylium salts. Treatment of the hydroxybenzaldehyde with acetophenone gives a hydroxypyrylium intermediate which, when methacrylated, gives a pyrylium methacrylate. Methacrylation of the hydroxy-benzyldehyde followed by condensation with methylpyrylium salts gives styryl-pyrylium methacrylates. Displacement of the methoxy group in methoxypyrylium salts with ethanolamine derivatives followed by methacrylation yields a series of aminopyrylium methacrylates. The preparation of a divinylpyrylium urethane and a pyrylium-type copolymer is also described.     

Transformations of some alkaloids of the carboline series under the influence of alkali

The reaction of quaternized forms of two alkaloids of the -carboline series — harman and brevicarine — with alkali was investigated. It was established that, under the reaction conditions, the harman derivative undergoes recyclization of the pyridine part of the molecule, whereas in the analogous brevicarine derivative the pyridine ring does not undergo transformations.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 530–533, April, 1985.     

Investigation of the lability of the conformations of some alkaloids of the quinolizidine series

Summary The IR and NMR spectra of lupinine, epilupinine, and a series of other alkaloids of the quinolizidine series have been studied.It has been shown that the inhibition of the inversion processes in the molecules of the alkaloids in the solid phase is revealed in a change in the nature of the absorption in the 500–1200 cm^2–1 region.V. I. Lenin Tashkent State University. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 49–54, January, 1971.