Experimental studies of charge density distribution in the crystals of cytisine and N-methylcytisine. Inside the Fake Tobacco

Owczarzak, Agata; Grześkiewicz, Anita M.; Kubicki, Maciej

doi:10.1007/s11224-017-0972-5

Cited by 10 publications

(5 citation statements)

References 27 publications

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“…As a result, the addition of any groups has not led to the conjugation of a nitrogen lone electron pair with electrons from these groups. Thus, the electronic configuration of the N12 atom has been pyramidal in molecules of nitromethylcytisine [ 17 ] and cytisine [ 18 ] without the corresponding conjugation. The sum of bond angles has been 333.7 and 338.3°, respectively.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Properties and Spatial Structure of 4-[(3,5-Dimethyl-1,2-oxazol-4-yl)sulfonyl]cytisine

Ibraev

Нуркенов

Rakhimberlinova

et al. 2022

Plants

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This article has studied the synthesis of a new derivative of the known alkaloid cytisine contained in the seeds of plants of Cytisus laburnum L. and Thermopsis lanceolata R.Br., both of the Lugiminosae family. The new compound has been obtained from two biologically active compounds, such as isoxazole and cytisine. It has been demonstrated that the reaction led to the single-stage method under very mild conditions to obtain 4-[(3,5-dimethyl-1,2-oxazol-4-yl)sulfonyl]cytisine. This class of compounds is promising for obtaining the new biologically active compounds. This article has examined, in detail, a structure with using the 1H and 13C NMR and two-dimensional NMR spectroscopy of COSY (1H-1H), HMQC (1H-13C) and HMBC (1H-13C). As a result, the homo- and heteronuclear spin-spin couplings should be established. The X-ray diffraction analysis has determined the spatial structure of a new derivative based on the cytisine alkaloid. Thus, its hemorheological activity has been studied.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Properties and Spatial Structure of 4-[(3,5-Dimethyl-1,2-oxazol-4-yl)sulfonyl]cytisine

Ibraev

Нуркенов

Rakhimberlinova

et al. 2022

Plants

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show abstract

“…As a result, the addition of any groups has not lead to conjugation of nitrogen lone electron pair with electrons of these groups. Thus, the electronic configuration of N12 atom has been pyramidal in molecules of nitromethylcytisine [17] and cytisine [18] without the corresponding conjugation. The sum of bond angles has been 333.7 and 338.3°, respectively.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Properties and Spatial Structure of 4-[(3,5-dimethyl-1,2-oxazol-4-yl)sulfonyl]cytisine

Ibraev¹,

Nurkenov²,

Rakhimberlinova³

et al. 2022

Preprint

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This article has been studied the synthesis of a new derivative of the known alkaloid cytisine contained in the seeds of plants of Cytisus laburnum L. and Thermopsis lanceolata R.Br., both of the Lugiminosae family. The new compound has been obtained from two biologically active compounds such as isoxazole and cytisine. It has been demonstrated that the reaction led to the single-stage method under very mild conditions to obtain some 4-[(3,5-dimethyl-1,2-oxazole-4-yl)sulfonyl]amides. This class of compounds is promising to obtain the new biologically active compounds. This article has examined in detail a structure with using the 1H and 13C NMR and two-dimensional NMR spectroscopy of COSY (1H-1H), HMQC (1H-13C) and NMVS (1H-13C). As a result, the homo- and heteronuclear spin-spin couplings should be established. The X-ray diffraction analysis has determined the spatial structure of a new derivative based on cytisine alkaloid. Thus, its hemorheological activity has been studied.

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“…Iodides and triodides are shown as spheres of van der Waals radii. of the A ring was found to be positively charged (Owczarzak et al, 2017).…”

Section: Dicationsmentioning

confidence: 98%

Different cationic forms of (–)-cytisine in the crystal structures of its simple inorganic salts

2018

Self Cite

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The crystal structures of 13 simple salts of cytisine, an alkaloid isolated from the seeds of Laburnum anagyroides, have been determined, namely cytisinium (6‐oxo‐7,11‐diazatricyclo[7.3.1.02,7]trideca‐2,4‐dien‐11‐ium) bromide, C11H15N2O+·Br−, cytisinium iodide, C11H15N2O+·I−, cytisinium perchlorate, C11H15N2O+·ClO4−, cytisinium iodide triiodide, C11H15N2O+·I−·I3−, cytisinium chloride monohydrate, C11H15N2O+·Cl−·H2O, cytisinium iodide monohydrate, C11H15N2O+·I−·H2O, cytisinium nitrate monohydrate, C11H15N2O+·NO3−·H2O, hydrogen dicytisinium tribromide, C22H31N4O23+·3Br−, hydrogen dicytisinium triiodide, C22H31N4O23+·3I−, hydrogen dicytisinium triiodide diiodide, C22H31N4O23+·I3−·2I−, hydrogen dicytisinium bis(triiodide) iodide, C22H31N4O23+·2I3−·I−, cytisinediium (6‐oxidaniumylidene‐7,11‐diazatricyclo[7.3.1.02,7]trideca‐2,4‐dien‐11‐ium) bis(perchlorate), C11H16N2O2+·2ClO4−, and cytisinediium dichloride trihydrate, C11H16N2O2+·2Cl−·3H2O. Cytisine has two potential protonation sites, i.e. the N atom of the piperidine ring and the carbonyl O atom of the pyridone ring. Three forms of the cytisinium cation were identified, namely the monocation, which is always protonated at the N atom, the dication, which utilizes both protonation sites, and the third form, which contains two cytisine moieties connected by very short and linear O…H…O hydrogen bonds, with an O…O distance of approximately 2.4 Å. This third form may therefore be regarded as a 3+ species, or sesqui‐cation, and is observed solely in the salts with bromide, iodide or triiodide (heavier halogen) anions. The cation is quite rigid and all 19 cytisinium fragments in the studied series have very similar conformations. The crystal structures are determined mainly by Coulombic interactions and hydrogen bonds, and the latter form is determined by different networks. Additionally, some anion–π and lone‐pair…π secondary interactions are identified in almost all of the crystal structures. Hirshfeld surface analysis generally confirms the role of different interactions in the determination of the crystal architecture.

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Experimental studies of charge density distribution in the crystals of cytisine and N-methylcytisine. Inside the Fake Tobacco

Cited by 10 publications

References 27 publications

Synthesis, Properties and Spatial Structure of 4-[(3,5-Dimethyl-1,2-oxazol-4-yl)sulfonyl]cytisine

Synthesis, Properties and Spatial Structure of 4-[(3,5-Dimethyl-1,2-oxazol-4-yl)sulfonyl]cytisine

Synthesis, Properties and Spatial Structure of 4-[(3,5-dimethyl-1,2-oxazol-4-yl)sulfonyl]cytisine

Different cationic forms of (–)-cytisine in the crystal structures of its simple inorganic salts

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