ChemInform Abstract: Synthesis as well as Molecular and Crystal Structure of O,O‐Dimethyl N‐Cytisinylamidophosphate.

Газалиев, А. М.; Турдыбеков, К. М.; Lindeman, S. V.; Struchkov, Yu. T.; Tuleuov, B. I.; Zhurinov, M. Zh.

doi:10.1002/chin.199411224

Cited by 3 publications

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“…The bond lengths and angles in the cytisine skeleton of 3 are normal and close to the corresponding values in N-methylcytisine [7], N-cyanmethylcytisine [8], and O,O-dimethyl-N-cytisinylamidophosphate [9]. The exceptions were the bond angles around N12.…”

Section: And a M Gazalievsupporting

confidence: 63%

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Synthesis and crystal structure of cytisino-N-(2-hydroxyethyl)-thiocarbamide

et al. 2009

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Section: And a M Gazalievsupporting

confidence: 63%

“…Cell constants and intensities of 1798 reflections were measured on an automated fourcircle Bruker P4 diffractometer (λ MoKα-radiation, graphite monochromator). The crystals were monoclinic, a = 7.3546(7), b = 13.0173 (9), c = 7.9229(5) Å, V = 696.15(9) Å 3 , Z = 2 (C 14 H 18 N 2 O 2 ), d calc = 1.328 cm 3 , space group P2 1 .…”

Section: Methodsmentioning

confidence: 99%

Synthesis and crystal structure of cytisino-N-(2-hydroxyethyl)-thiocarbamide

et al. 2009

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“…The bond lengths and angles of this compound were found to be close to standard values [9]. The cytisine unit is rather rigid and virtually unaltered, which has been in previously studied molecules [10][11][12]. The dihidropyridine ring is planar to within 0.009 Å.…”

supporting

confidence: 70%

Synthesis of n-aminoglycosides derived from alkaloid cytisine, their biological activity and crystal structure of N-(β-D-galactopyranosyl)cytisine

Кулаков

Нуркенов

Турдыбеков

et al. 2010

Chem Heterocycl Comp

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Optimal conditions were found for the synthesis of a number of new N-aminoglycosides of the alkaloid cytisine, using commercially available monosaccharides, namely, D-glucose, D-galactose, D-xylose, and L-arabinose. X-ray structural analysis indicated an absolute -anomeric configuration of N-(-D-galactopyranosyl)cytisine in the crystalline state. The comparative cytotoxicity of cytisine and some of its N-aminoglycosides was determined.

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“…The bond lengths and bond angles in the cytisine fragment of III have their standard values and approach those found for N-methylcytisine [7], N-cyanomethylcytisine [8], and O,O-dimethyl N-cytisinylamidophosphate [9]. Exceptions are the bond angles at N 12 .…”

supporting

confidence: 66%

“…The melting points were determined on a Boetius melting point apparatus. Thin-layer chromatography was per- (7), b = 13.0173 (9), c = 7.9229(5) Å; V = 696.15(9) Å 3 ; Z = 2; d calc = 1.328 g/cm 3 ; space group P2 1 . The calculations involved 1675 independent reflections with I > 2σ(I).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of N-{2-[1-(prop-2-yn-1-yloxy)ethoxy]ethyl}-cytisinecarbothioamide and steric structure of its hydrolysis product, N-(2-hydroxyethyl)cytisinecarbothioamide

et al. 2010

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The reaction of 2-[1-(prop-2-yn-1-yloxy)ethoxy]ethyl isothiocyanate with alkaloid cytisine gave the corresponding thiourea derivative which was subjected to partial hydrolysis on heating in boiling aqueous ethanol or complete hydrolysis in the presence of a catalytic amount of an acid. The structure of the hydrolysis product, N-(2-hydroxyethyl)cytisinecarbothioamide, was proved by X-ray analysis.Thiourea derivatives constitute an important group of sulfur-containing organic compounds that are widely used in organic synthesis, as well as in industry, agriculture, and medicine. Most thiourea derivatives exhibit pharmacological activity, in particular antituberculous, antitumor, anti-inflammatory, antimicrobial, antiulcer, and other kinds of activity [1,2]. Thiourea derivatives are generally synthesized by reaction of isothiocyanates with amines. Reactions of various isothiocyanates with such alkaloids as cytisine and anabasine and ephedrine derivatives were studied previously [3][4][5]. Among the series of isothiocyanates, of specific interest is 2-vinyloxyethyl isothiocyanate which is a highly reactive difunctional synthon possessing unique synthetic potential, including the potentials of vinyl ethers and isothiocyanates. 2-[1-(Prop-2-yn-1-yloxy)ethoxy]ethyl isothiocyanate (I) was synthesized by electrophilic addition of prop-2-yn-1-ol at the double C=C bond of 2-vinyloxyethyl isothiocyanate in the presence of trifluoroacetic acid as catalyst according to the procedure reported in [6]. Acetal I opens wide prospects in the synthesis of more complex thiourea derivatives which undoubtedly attract interest from the viewpoint of design of new biologically active compounds.On the basis of isothiocyanate I and physiologically active alkaloid cytisine we synthesized N-{2-[1-(prop-2-yn-1-yloxy)ethoxy]ethyl}cytisinecarbothioamide (II) (Scheme 1). The reaction followed the generally

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ChemInform Abstract: Synthesis as well as Molecular and Crystal Structure of O,O‐Dimethyl N‐Cytisinylamidophosphate.

Cited by 3 publications

References 0 publications

Synthesis and crystal structure of cytisino-N-(2-hydroxyethyl)-thiocarbamide

Synthesis and crystal structure of cytisino-N-(2-hydroxyethyl)-thiocarbamide

Synthesis of n-aminoglycosides derived from alkaloid cytisine, their biological activity and crystal structure of N-(β-D-galactopyranosyl)cytisine

Synthesis of N-{2-[1-(prop-2-yn-1-yloxy)ethoxy]ethyl}-cytisinecarbothioamide and steric structure of its hydrolysis product, N-(2-hydroxyethyl)cytisinecarbothioamide

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