K. M. Turdybekov

Synthesis and intramolecular heterocyclization of n-allylthiocarbamide derivatives of the alkaloids cytisine and anabasine into 1,3-thiazoline derivatives and features of their molecular structures

Allylthiourea derivatives were synthesized from the alkaloids cytisine and anabasine and allylisothiocyanate. 1,3-Thiazoline derivatives were synthesized from them via intramolecular heterocyclization using HCl and heating in a sealed ampul. The structures of the synthesized compounds were proved by IR and PMR spectroscopy, mass spectrometry, and x-ray structure analysis.

SYNTHESIS AND CRYSTAL STRUCTURE OF CYTISINO- N-(2-HYDROXYETHYL)-THIOCARBAMIDE

A thiourea derivative of the alkaloid cytisine was synthesized by reacting it with 1-propargyloxyethoxyethylisothiocyanate. It was shown that the synthesized acetal thiourea derivative underwent hydrolysis in acidic medium to cytisino-N-(2-hydroxyethyl)-thiocarbamide, the molecular structure of which was confirmed by an x-ray structure analysis.

1β,10α-Dihydroxyarglabin — A new sesquiterpene lactone fromArtemisia glabella

The new sesquiterpene lactone 1β,10α-dihydroxydihydroxyarglabin has been isolated from the epigeal part ofArtemisia glabella Kar. et Kir., and its structure has been established on the basis of spectral characteristics, independent synthesis, arglabin, and an x-ray structural investigation.

Reactions at the double bond in the epoxy group of arglabin

The interaction of arglabin, a sesquiterpene lactone of the guainane type, with peracetic acid and hydrogen chloride has been investigated. This led to the synthesis of nine compounds the structure of which have been established in the basis of spectral characteristics (IR, PMR, and mass spectra). The structures and absolute configurations of the molecules of 3α,10α-dichloro-1β,4β-dihydroxy-and 10α-chloro-1β-hydroxy-3β,4β-epoxyarglabins have been determined as 3R, 10R-dichloro-1R,4R-dihydroxy-5S,6S,7S-trans-trans-guai-11(13)-en-6,12-olide and 10R-chloro-1R-hydroxy-3S,4R-epoxy-5S,6S,7S-trans-trans-guai-11(13)-en-6,12-olide, respectively.

Molecular structure of crepidioside a and isolipidiol fromCrepis multicaulis

Crepidioside A, a guaian-like sesquiterpene lactone, is isolated fromCrepis multicaulis Ldb, and identified. The structure 15-glycoside-2-oxo-5,7α,6β(H)-guai-1(10),3(4),11(13)-trien-6,12-olide is found from an x-ray structure analysis. 8-Epi-isolipidiol is isolated fromCrepis tectorum L. Its new polymorphic crystal structure is found from an x-ray structure analysis.

Synthesis, and crystal and molecular structures of anabasinium O,O-dialkyl phosphorothioates

The synthesis has been effected of anabasinium O,O-dialkyl phosphorothioates. The crystal and molecular structures of the complex compounds obtained have been determined by the method of x-ray structural analysis. It has been established that the cations and anions of the anabasinium O,O-dialkyl phosphorothioates are combined into cyclic associates each including two anions and two cations with different conformations.

Pulchellin C and inuchinenolide C from Inula caspica

The pseudoguaianolide inuchinenolide C and the eudesmanolide pulchellin C have been isolated for the first time from the flower heads and leaves ofInula caspica Blume, and their spatial structures have been established by an x-ray structural experiment as 2α,6β-diacetoxy-6α-hydroxy-1α,7α(H),8β,10β(H)-pseudoguai-11(13)-en-8,12-olide and 2α,3β-dihydroxy-5β,7α,8α(H)-eudesma-4(15),11(13)-dien-8,12-olide, respectively.

Molecular and crystal structure of the germacranolides salonitenolide and hanphyllin

A sesquiterpene lactone of the germacrane type, salonitenolide, has been isolated for the first time from the epigeal part ofCentaurea pseudomaculosa Dobrocz (spotted centaurea) and has been identified. The structures of the germacranolides and hanphyllin have been determined by the method of x-ray structural analysis: salonitenolide is 8-hydroxy-6β,8β(H)7α(H)-germacra-1(10),4,11(13)-trien-6,12-olide and hanphyllin is 3-hydroxy-3α,7α(H),6β(H)-germacra-1(10),4,11(13)-trien-6,12-olide. It has been established that the ten-membered rings of salonitenolide and hanphyllin are of the chair-chair type,1D14,15D5. On the basis of the results of CD spectroscopy, the chiral centers in the hanphyllin molecule have been assigned the 3S, 6R, and 7S configurations.

Synthesis, steric structure, and biological activity of 5-methyl-2-(morpholin-4-ylamino)-5,6-dihydro-4H-1,3-thiazin-4-one

New 5,6-dihydro-1,3-thiazin-4-one derivatives have been synthesized by one-pot reaction of morpholin-4-amine and adamantan-1-amine with methacryloyl isothiocyanate. Structure of 5-methyl-2-(morpholin-4-ylamino)-5,6-dihydro-4H-1,3-thiazin-4-one has been determined by X-ray analysis, and its high antiradical and anti-inflammatory activity has been revealed.

Synthesis of dithiocarbamine derivatives on the matrix of cytisine, anabasine and d-pseudoephedrine alkaloids. Crystalline structure of N-cytisine dithiocarbamate ammonium salt

On the matrix of physiologically active alkaloids such as cytisine, anabasine, and d-pseudoephedrine the simplest alkaloid dithiocarbamates ammonium salts were synthesized by reaction with carbon disulfide in solution of ammonia in alcohol. Spatial structure of ammonium N-cytisine dithiocarbamate crystal hydrate was proved with X-ray diffraction analysis.