Anabasine and cytisine derivatives as reversible cholinesterase inhibitors

A number of analogs of acetyl--methylcholine, containing residues of the alkaloids anabasine and cytisine as cyclic ammonium groupings, have been synthesized. The structures of the substances obtained have been confirmed by their IR and PMR spectra and the result of elementary analysis. The kientic parameters of the interaction of the compounds synthesized with acetylcholinesterase (ACE) of human blood erythrocytes and with butylcholinesterase (BuCE) of horse blood serum have been investigated. All the substances synthesized proved to be reversible inhibitors of ACE and BuCE.Institute of Bioorganic Chemistry, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 97–100, January–February, 1988.     

Synthesis of a number of derivatives of alkaloids and of nitrogen-containing heterocycles and their anticholinesterase activities

N-Methyl- and N-phenylcarbamates based on a number of alkaloids and nitrogen-containing heterocycles have been synthesized, and they have proved to be weak irreversible inhibitors of acetylcholinesterase and butyrylcholinesterase. It has been shown that the choline fragments of the above-mentioned carbamates and their -methylcholine analogs are reversible inhibitors of both cholinesterases and make a substantial contribution to the anticholinesterase activity. Selective inhibitors of ACE and BuCE have been found among the compounds synthesized.A. S. Sadykov Institute of Bioorganic Chemistry, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodynkh Soedinenii, No. 6, pp. 825–831, November–December, 1988.     

Synthesis and antienzyme activity of 2-OXO-2SR-4-methyl-1,3,2-dioxaphosphorinanes containing salsoline,salsolidine, cytisine,and decahydroquinoline residues

New derivatives of 2-oxo-4-methyl-1,3,2-dioxaphosphorinane containing residues of salsoline, salsolidine, cytisine, and decahydroquinoline have been synthesized, and their antienzyme activities have been investigated. The new compounds are irreversible inhibitors of the ACNE, BuChE, and CBE of warm-blooded animals and of insects: the antienzyme activities of the compounds depend substantially on the structure of the alkaloid component of the inhibitor molecule.A. S. Sadykov Institute of Biorganic Chemistry, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 62 70 71. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 572–575, July–August, 1996. Original article submitted October 4, 1995.     

Synthesis of some bis(2-morpholino-1-methylethyl) esters of carboxylic acids and study of their interaction with the cholinesterases of warm-blooded animals

The bis(2-morpholino-1-methylethyl) esters of glutaric, adipic, azelaic, and sebacic acids have been synthesized, and their dihydrochlorides and dimethiodides have been obtained. The structures of the compounds obtained have been shown by their IR and PMR spectra. The interaction of the compounds synthesized with the acetylcholineresterase (ACE) of human blood erythrocytes and the butyrylcholinesterase (BuCE) of horse blood serum have been investigated. All the bis-esters are reversible competitive inhibitors of ACE and BuCE, while the dimethiodides exhibit specificity of their action with respect to ACE.Institute of Bioorganic Chemistry, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 239–243, March–April, 1998.     

Synthesis, structure, and anticholinesterase activity of some organophosphorus derivatives of anabasine

Anabasine derivatives based on methylphosphonothoic acid have been synthesized. It has been shown by PMR spectroscopy that in solution O-alkyl O-[-(anabasin-1-yl)ethyl] methylphosphonothioates exist in two stereomeric forms, which is due to the influence of the optically active anabasine residue. It has been shown that these compounds are competitive reversible inhibitors of acetylcholinesterase and of butyrylcholinesterase.Institute of Bioorganic Chemistry of the Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 561–565, July–August, 1987.     

Complexes of copper with 14–18-membered macrocyclic tetraaza ligands and their participation in oscillating chemical reactions

A number of copper complexes have been synthesized with 14–18-membered tetraaza macrocyclic ligands having six methyl groups and two double bonds located in the cis position relative to the metal ion. These compounds have been investigated by means of ESR spectrometry and electronic and IR spectroscopy. It has been shown that the size of the macroring does not have any great influence on the magnitudes of the spectral parameters. It has been found that these copper complexes can be oxidized by potassium bromate in an oscillatory regime.Translated from Teoreticheskaya i Éksperimental'naya Khimiya, Vol. 22, No. 1, pp. 59–64, January–February, 1986.     

Geometry and mesomorphic properties of new schiff bases containing thiazole ring

New liquid-crystalline azomethines — 2-(4-alkoxybenzylideneamino)-4-(3-nitrophenylamino)thiazoles —displaying nematic mesomorphism at 42–137°C have been synthesized. The structure of these compounds was studied by the MNDO LCAO MO method. A correlation was found between the geometric parameters and liquid crystal properties.Bashkir State University, 450074 Ufa, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1242–1248, September, 1999.     

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.     

Synthesis of N-[methyl-(O-alkyl)phosphinyloxyethyl]piperidines and their methiodides

Conclusions A number of N-[methyl-(O-alkyl)phosphinyloxyethyl]piperidines and their methiodides was synthesized. The compounds are potential cholinesterase inhibitors.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1900–1901, August, 1974.     

Synthetic and modified isoflavonoids. XI. Synthesis of analogues of maxima isoflavone A and xanthocercin

Analogues of maxima isoflavone A and of xanthocercin containing benzodioxolane, benzodioxane, and benzodioxepane fragments in rings A and B of isoflavone have been synthesized. The structures of the compounds obtained have been confirmed by analytical and spectral characteristics.KIEN, Karakalpak Division, Academy of Sciences of the Republic of Uzbekistan, Nukus. Taras Shevchenko Kiev University. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 337–343, May–June, 1994.     

Luminescence properties of 5-oxazolone derivatives containing a pyrazoline ring

New difluorophors have been synthesized containing both 2-phenyl-4-benzyliden-5-oxazolone and 1,3,5-tri-aryl-2-pyrazoline fragments. A study was carried out on the effect of the structure of these compounds on their spectroluminescence properties in solvents of different polarity. Positive solvatofl uorochromy was detected. The use of these compounds as luminescent dyes for polymers was proposed taking account of their solvatofuorochromic effects.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 407–410, March, 1994.     

Synthesis and pharmacology of some diisoquinoline alkaloids

A number of tetrahydrodiisoquinoline alkaloids has been synthesized by various routes. Some connections between the chemical structures of the compounds obtained and their pharmacological effects have been found.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 343–350, May–June, 1979.     

Characteristic and spectroscopic properties of the Schiff-base model compounds

Two series of conjugated aromatic imines (Schiff-base model compounds) with different central groups and various side-group substitutions have been synthesized and characterized by elemental analysis, differential scanning calorimetry (DSC) technique, hydrogen nuclear magnetic resonance (¹H NMR), Fourier transform infrared (FTIR) and ultra-violet and visible light (UV–vis) spectroscopy measurements. The UV–vis absorption of solutions of these compounds in dimethylacetamid (DMA), chloroform and methanol was investigated in the optical range from 240 to 450 nm, where two distinct absorption bands: at 250–280 and 315–360 nm with the different level of absorption have been observed. The influence of compound molecular structure and polarity of solvent on the absorption spectra and the possible optical transitions have been discussed. Structure of diamines in the azomethine models fundamentally affected their spectroscopic properties and conjugation of π-electrons.     

In vitro biosynthesis,isolation, and activities of nuclear glycoproteins

It has been shown by HPLC, electrophoresis, etc., that, in vitro, the nuclei of neurons of rabbit and cow brains synthesize two glycoproteins (M 25–30 kDa and 10–15 kDa). The influence of some neurotropic compounds on the kinetics of the nuclear protein synthesis has been investigated. New inhibitors of this biosynthesis have been found.A. S. Sadykov Institute of Bioorganic Chemistry, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax 627071. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 112–118, January–February, 1994.     

Synthesis of 4-chloro-7-dialkylaminocoumarins

A series of 4-chloro-7-dialkylaminocoumarins has been synthesized by heating m-diethylaminophenol, m-N-piperidinophenol, m-N-morpholinophenol, and 8-hydroxyjulolidine, respectively, with malonic acids in the presence of excess phosphorus oxychloride. The feasibility of preparing other 4-substituted 7-aminocoumarins from these 4-chloro derivatives has been demonstrated using as an example the reactions of 4-chloro-7-diethylaminocoumarins with sodium ethoxide, hydrazine, and dibutylamine. The spectral and luminescence characteristics of these newly synthesized compounds have been investigated.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 830–835, June, 1990.     

Ge-substituted germatranes and their mass spectra

Conclusions The previously unknown Ge-substituted germatranes have been synthesized. The mass spectra of these compounds have been studied, and paths for their dissociative ionization are proposed.Translated fron Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1846–1849, August, 1979.     

New phosphorylated derivatives of anabasine and of lupinine,and their anticholinesterase properties

A series of new phosphorylated esters of anabasine, lupinine, and piperidine differing by the nature of the alkyl radicals attached to the phosphorus atom has been synthesized. The results of investigations of the antiesterase properties of the compounds in relation to the acetylcholinesterase of human blood erythrocytes and of the turnip moth and the carboxylesterase of porcine kidney have shown a selectivity of their action in relation to the insect enzyme and a substantially lower activity towards esterases of warm-blooded animals.A. S. Sadykov Institute of Bioorganic Chemistry, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax 627071. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 66–70, January–February, 1994.     

Synthesis and three-dimensional structure of 4-hydroxy-4-methyl-3-chloro-6-alkyltetrahydropyrans

A method has been developed for the preparation of 4-hydroxy-4-methyl-3-chloro-6-alkyltetrahydropyrans based on the cycloalkylation of 4-hydroxy-2-methyl-3-chloro-1-butene with aldehydes. Dehydrochlorination of these compounds furnished the corresponding oxiranes of the tetrahydropyran series. The chlorine atoms in these newly synthesized chlorotetrahydropyranols have been found to favor equatorial positions.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1457–1460, November, 1986.     

Synthetic analogs of natural flavolignans IX. Synthesis of 3-amino-substituted analogs of hydnocarpin

New 3-amino-substituted chromones with 1,3-benzodioxan and 1,4-benzodioxan nuclei in position 2 have been synthesized. The structures of the compounds obtained have been confirmed by their PMR spectra.Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 178–181, March–April, 1999.     

Phytoecdysteroids of plants of the genusSilene XVI. 5α-sileneoside E FromSilene brahuica

Derivatives of derrusnin and also its benzodioxane and benzodioxepane analogs have been synthesized. The structures of the compounds obtained have been confirmed by spectral studies.Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 226–230, March–April, 1994.