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.     

Mass-spectrometric investigation of some new derivatives of the alkaloid lupinine

The mass spectra of some new derivatives of lupinine have been studied with the use of the spectra of metastable ions. On the basis of the results of an investigation of DADI spectra it has been shown that in the formation of low-mass quinolizidine ions the ions with m/z 152–150 are of considerable importance.A. S. Sadykov Institute of Biororganic Chemistry, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 508–512, July–August, 1990.     

Synthesis and anticholinesterase properties of new derivatives of lupinine and elipulinine

Esters of lupinine and epilupinine have been obtained by their acylation with isovaleroyl, cinnamoyl, trichloroacetyl, and trimethylacetyl chlorides. The methiodide derivatives of these esters have been investigated in reactions with the blood cholinesterases of warm-blooded animals. The interaction has a reversible nature, and the inhibition of the activity of the enzyme is both quantitative and qualitative in dependence on the structure of the acid taken and the conformational properties of the lupinine epimers.A. S. Sadykov Institute of Bioorganic Chemistry, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 64–67, January–February, 1991.     

Novel quinine,lupinine, and anabasine derivatives containing dithiophosphinate groups

A three-component, atom-economic reaction between natural quinine, lupinine, or anabasine, secondary phosphines, and elemental sulfur occurs under mild conditions to yield previously unknown optically active dithiophosphinates.     

Synthesis of organophosphorus derivatives of lupinine and epilupinine and their interaction with cholinesterases

Conclusions Some esters of O-alkyl methylphosphonic acid and thioesters of O-alkyl methylthiophosphonic acid derived from the alkaloids lupinine and epilupinine have been prepared. These were found to be reversible competitive inhibitors of acetylcholinesterase and butyrylcholinesterase.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 650–654, March, 1987.     

Synthesis and anticholinesterase activites of a number of derivatives of the alkaloid lupinine

A series of new lupinine derivatives and their methiodides has been synthesized. It has been shown that they are powerful reversible inhibitors of acetylcholinesterase and butyrylcholinesterase.A. S. Sadykov Institute of Bioorganic Chemistry, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 513–515, July–August, 1990.     

Synthesis of organophosphorus derivatives of lupinine and solasodine and investigation of their cholinergic activities

The synthesis of lupinine O-(dialkyl phosphate)s and of solasodine O-(diethyl phosphate) has been achieved under the conditions of phase-transfer catalysis-and their antienzyme activities have been studied.     

Preparation of lupinine esters

Conclusions A number of lupinine esters and their methiodides were synthesized.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 728–730, March, 1972.     

Synthesis of organophosphorus derivatives of lupinine and solasodine and investigation of their cholinergic activities

The synthesis of lupinine O-(dialkyl phosphate)s and of solasodine O-(diethyl phosphate) has been achieved under the conditions of phase-transfer catalysis-and their antienzyme activities have been studied.Institute of Organic Synthesis and Coal Chemistry, Kazakhstan Academy of Sciences, Karaganda. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 541–542, September–October, 1992.     

Synthesis and characterization of some derivatives of lupinine and aminolupinine. Collision induced dissociation mass spectrometry studies of protonated molecules

Some ester, amide and thioether derivatives of lupinine, aminolupinine and bromolupinine were synthesized and characterized in order to search biologically active compounds. The protonated molecules were studied by tandem mass spectrometry using collision induced dissociation (CID) technique in order to find out how different structural features and functional groups in different quinolizidine derivatives influence fragmentation behavior. Some theoretical calculations were also made to clarify the conformations of neutral and protonated molecules, to reveal the fragmentation routes and the product ions obtained. The functional groups clearly directed the fragmentations although the typical fragments for lupinine were still observed in all the cases. Theoretical calculations were in agreement with observed fragmentations and greatly helped interpretation of the CID spectra.     

Synthesis of the lupinine ester of betulonic acid

The lupinine ester and 3-oxime of betulonic acid were prepared for the first time.Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 467–468, November–December, 2004.This revised version was published online in April 2005 with a corrected cover date.     

Synthesis of lupinine esters and their interaction with cholinesterases

A number of lupinine esters of carboxylic acids and their hydrochlorides and methiodides have been synthesized. It has been shown that these compounds are reversible inhibitors of human blood erythrocyte acetylcholinesterase and horse blood serum butyryl cholinesterase. Noncompetitive inhibitors of these enzymes 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 Prirodnykh Soedinenii, No. 1, pp. 75–79, January–February, 1990.     

New isatin derivatives

The review compiles published data on the synthesis and biological action of new isatin derivatives containing in their composition additional oxygen, nitrogen, or sulfur heterocycles.     

New derivatives of N-nitrosamines

Two new derivatives are proposed for determination of nitrosamines by GLC. One is formed by reaction with di(2-chloroethyl) phosphochloridate and the other by reaction with m-trifluorotoluene sulphonyl chloride.