Modified coumarins. 22. Synthesis of N-coumarinyloxyacetyl derivatives of cytisine

N-Acetyl derivatives of cytisine modified by coumarins were synthesized. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 110–113, March–April, 2006.     

Thiazole and benzothiazole derivatives of cytisine

Several new derivatives were prepared by reacting N-1(5-R-thiazol-2-yl)-2-chloroacetamides and N-1(6-R-benzothiazol-2-yl)chloroacetamides with cytisine. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 379–380, July–August, 2006.     

1,2,4-Thiadiazole derivatives of cytisine

Several new derivatives were prepared by reaction of 3-alkylthio-5-chloroacetamido-1,2,4-thiadiazoles with cytisine.Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 479–480, November–December, 2004.This revised version was published online in April 2005 with a corrected cover date.     

Modified coumarins. 20. Furocoumarin derivatives of cytisine

Cytisine derivatives modified by furocoumarins were synthesized using activated esters. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 230–232, May–June, 2006.     

Synthesis and biological activity of N-benzyl derivatives of cytisine

The reductive alkylation of cytisine by various aromatic aldehydes was studied. Preliminary pharmacological investigations of the synthesized compounds were performed. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 373–378, July–August, 2006.     

Aminomethylation of cytisine by 3-hetaryl-7-hydroxycoumarins

8-Aminomethyl derivatives of 7-hydroxycoumarins were prepared by reaction of methylene-bis-cytisine and substituted 7-hydroxycoumarins. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 145–148, March–April, 2007.     

Aminomethylation of cytisine by 3-hetaryl-7-hydroxychromones

8-Aminomethyl derivatives of 7-hydroxychromones were prepared by reaction of methylene-bis-cytisine with substituted 7-hydroxychromones. The structures of the synthesized compounds were investigated using NMR spectroscopy. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 237–241, May–June, 2007.     

Modified coumarins. 25. <Emphasis Type="Italic">N</Emphasis>-acyl cytisine derivatives containing a coumarin fragment

New modified cytisine derivatives were prepared by acylation with coumarin-3-acetic acids. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 10–13, January–February, 2007.     

Synthesis of N-aminoglycosides of the alkaloid cytisine

A series of new N-aminoglycosides of the alkaloid cytisine based on industrially available monosaccharides D-glucose, D-galactose, D-xylose, and L-arabinose was synthesized and characterized. The optimal methods for condensing and isolating the products were found. The structures and position of cytisine in the glycosides were proved by PMR spectroscopy. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 596–597, November–December, 2008.     

Reaction of cytisine with formalin

The reaction of cytisine with formalin in various solvents was studied. Methylene-bis-cytisine was produced in addition to the expected N-methylolcytisine in all solvents except acetone, in which N-(3-oxobutyl)cytisine was produced. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 579–580, November–December, 2006.     

Synthesis and biological activity of <Emphasis Type="Italic">N</Emphasis>-(2-hydroxyethyl)cytisine derivatives

Derivatives of N-(2-hydroxyethyl)cytisine, N-(2-hydroxypropyl)-, N-(2-hydroxy-2-(1-adamantyl)ethyl)-, and N-(2-hydroxy-2-phenylethyl)cytisine, were synthesized by reduction of N-(2-oxopropyl)-, N-(2-oxo-2-(1-adamantyl)ethyl)-and N-(2-oxo-2-phenylethyl)cytisine with metal hydrides. The antiarrhythmic and analgesic activities of the prepared compounds were investigated. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 157–162, March–April, 2007.     

Parallel solid-phase synthesis of novel 3,7-diazabicyclo[3.3.1]nonane derivatives starting from natural alkaloid cytisine

A parallel solid-phase synthesis of combinatorial library of 436 amides of 4-(3,7-diorganyl-3,7-diazabicyclo[3.3.1]nonan-2-yl)butanoic acid has been accomplished starting from natural alcaloid (−)-cytisine. A five-step liquid-phase synthesis resulted in the conversion of cytisine to 7-benzyl-3-[(9H-fluoren-9-yl)methyl]-substituted acids, which were further diversified with the use of solid-phase technology on the acid-susceptible amine resins. The combinatorial library obtained is intended for a discovery of new physiologically active compounds. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1964–1970, September, 2008.     

Chemical modification of plant alkaloids. I. Aminomethylation of barbituric acid derivatives by cytisine

Reaction of cytisine with 1-mono- and 1,3-disubstituted 5-arylmethylbarbituric acids in the presence of formaldehyde results in aminomethylation of C-5 to form the corresponding 5-cytisylmethylbarbituric acids. The structures of the products are found using PMR spectroscopy and mass spectrometry. 1-Phenyl-5-(2,4-dimethoxybenzyl)-5-cytisylmethylbarbituric acid is obtained as a mixture of two steroisomers in an approximately 21 ratio.I. I. Mechnikov St. Petersburg State Medical Academy, 195067, St. Petersburg, Piskarevskii pr., 47; 2) ZAO Interbioscreen, 142432, Chernogolovka, Moscow District, Institutskii pr. 8. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 152–156, March–April, 2000.     

Modified coumarins. 21. Synthesis of neoflavones produced by Marila pluricostata and their derivatives

Natural neoflavones 5-hydroxy-8,8-dimethyl-4-phenyl-9,10-dihydropyrano[2,3-f]chromen-2-one and 5-hydroxy-8,8-dimethyl-6-propionyl-4-phenyl-9,10-dihydropyrano[2,3-f]chromen-2-one and their derivatives were synthesized. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 107–109, March–April, 2006.     

Thermochemistry of some cytisine derivatives

The enthalpies of solution of cytisine derivatives (phosphoric acid cytiside dimethyl ester, cytisinovinyloxyethylaminothiourea) in 96% ethanol at various dilutions were determined by isothermal calorimetry. Equations describing the dependences ΔH _s ⁰ = f(m ^1/2) (m is the molal concentration) were obtained. The standard enthalpies of solution, combustion, melting, and formation (at 298.15 K) of the compounds were calculated.     

Synthesis and biological activity of anabasine and cytisine derivatives of monothiooxamides

Monothiooxamides were synthesized by the reaction of chloroacetamides with elemental sulfur and cyclic amines in the presence of triethylamine. The compounds were tested for fungicidal and aphicidal activity.     

Reaction of diphenylphosphinoylallene derivatives of cytisine

Diphenylphosphinoylallenes containing a ClCH₂ group were synthesized, and their reaction with cytisine was studied. It was shown that the reaction involves exclusives as nucleophilic substitution of chlorine in the chloromethyl group. The synthesized conjugates of cytisine with diphenylphosphinoylallene derivatives are of interest as potential agonists of nicotinic acetylcholine neuroreceptors (nAChRs).     

Thermodynamic properties of cytisine dithiocarbamate derivatives

The heat of solution in water and the heat capacity in the range 173 K-T _m of triethylammonium, sodium, and potassium dithiocarbamates derived from cytisine were studied by calorimetry. The heats of combustion and melting and the standard enthalpies of formation of the compounds were calculated.     

低聚苯醚链系列化合物的醚化

在相转移催化剂PEG-600存在下,利用2-((2-甲氧基)乙氧基)氯乙烷和低聚苯醚链反应,合成双醚化的产物;与此相对应,利用2-(氯乙氧基)乙醇和低聚苯醚链反应,只生成单醚化的产物。所有的产物都经过1H-NMR,MS及元素分析表征。