A5090938831- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Analytical Chemistry and Chromatography
- Botanical Research and Chemistry
- Nicotinic Acetylcholine Receptors Study
- Synthesis and Biological Evaluation
- Chemical Synthesis and Analysis
- Chemical synthesis and alkaloids
- Synthesis and Reactions of Organic Compounds
- Alkaloids: synthesis and pharmacology
- Fluorine in Organic Chemistry
- Plant and fungal interactions
- Molecular spectroscopy and chirality
- Agriculture, Plant Science, Crop Management
- Asymmetric Synthesis and Catalysis
- Receptor Mechanisms and Signaling
- Botany and Plant Ecology Studies
- Synthesis and Characterization of Pyrroles
- Biochemical Analysis and Sensing Techniques
- Synthesis and Reactivity of Heterocycles
- Psychedelics and Drug Studies
- Neuropeptides and Animal Physiology
- Photochemistry and Electron Transfer Studies
- Advanced Chemical Sensor Technologies
- Carbohydrate Chemistry and Synthesis
Adam Mickiewicz University in Poznań
2010-2025
National Institute on Alcohol Abuse and Alcoholism
2008
National Institutes of Health
2003-2008
National Institute on Drug Abuse
2008
Derivatives of squaric acid are valuable building blocks with promising applications in the investigation various bioactivities. In this study, we focus on squaramides functionalized (-)-cytisine moiety, an alkaloid known for its bioactivity as a nicotinic acetylcholine receptor agonist and application nicotine addiction treatment. Reactions cytisine-monosquarate several amines, such ammonia, propargylamine, morpholine, led to formation novel conjugates cytisine-squaramides. Additionally,...
Chiroptical spectroscopy usually requires theoretically computed spectra to assist in the elucidation of absolute configuration samples for which experimental have been recorded. Due inherently different nature these two types spectra, perfect agreement is quasi impossible. Several methods exist quantify degree similarity between but rather limited work has done evaluate robustness theory and experiment. In this work, a novel method described determine statistical significance numerical...
In the isomeric series of 12 racemic topologically rigid N-methyl analogues oxide-bridged phenylmorphans, all but two racemates, ortho- and para-b-oxide-bridged phenylmorphans 20 12, have remained to be synthesized. The b-isomers were very difficult synthesize because highly strained 5,6-trans-fused ring junction that had formed. Our successful strategy required functionalization position para (or ortho) a fluorine atom on aromatic using an electron-withdrawing nitro group activate fluorine....
The synthesis of the ortho- and para-e isomers in oxide-bridged 5-phenylmorphan series rigid tetracyclic compounds was accomplished via rac-5-(2-fluoro-5-nitrophenyl)-2-methyl-2-azabicyclo[3.3.1]nonan-9β-ol ((±)-10), an intermediate containing aromatic nitro-activated fluorine atom. atom used as leaving group for formation strained trans-fused 5,6-ring system rac-(1α,4aα,9aα)-1,3,4,9a-tetrahydro-2-methyl-6-nitro-2H-1,4a-propanobenzofuro[2,3-c]pyridine ((±)-11), although preference cis ring...
The N-phenethyl analogues of (1R*,4aR*,9aS*)-2-phenethyl-1,3,4,9a-tetrahydro-2H-1,4a-propanobenzofuro[2,3-c]pyridin-6-ol and 8-ol (1R*,4aR*,9aR*)-2-phenethyl-1,3,4,9a-tetrahydro-2H-1,4a-propanobenzofuro[2.3-c]pyridin-6-ol 8-ol, the ortho- (43) para-hydroxy e- (20), f-oxide-bridged 5-phenylmorphans (53 26) were prepared in racemic enantiomerically pure forms from a common precursor, quaternary salt 12. Optical resolutions accomplished by formation with suitable chiral acids or preparative...
Abstract (–)‐Cytisine and its derivatives are promising alkaloids in the development of new drugs for treatment disorders central nervous system (CNS). Electron ionization (EI) mass spectral fragmentations cytisine (1), N ‐methylcytisine (2), ‐ethylcytisine (3), ‐acetylcytisine (4), ‐propionylcytisine (5) ‐benzoylcytisine (6) have been investigated. Detailed fragmentation pathways identified all significant ions, including a few characteristic fragment ions. The principal routes compounds...
The crystal structures of three 3-halogeno derivatives 13N-substituted cytisine have been determined by X-ray diffraction. two 13-acetyl substituted compounds, 3-bromo (1) and 3-iodo (2) are isostructural, with the isostructurality index as high 99%. They both crystallize in monoclinic P21 space group, unit cell parameters a = 8.4709(10) Å, b 9.2266(12) c 8.6051(10) β 98.528(11)º 8.2322(6) 9.1724(7) 8.5494(6) 98.181(7)º (2). In turn, 3-bromo-13-t-butyl-carbonate derivative (3) crystallizes...
Spectral and photophysical properties of (-)-cytisine (the compound used as a smoking cessation aid potential drug in Alzheimer's Parkinson's diseases) were investigated. The two conformers cytisine, whose presence the S0 state has been earlier proved by NMR IR methods well theoretical calculation, nonpolar n-hexane show rarely observed prompt fluorescence from S1(n,π*) excited state. This observation is unambiguously evidenced very small radiative rate constants these emitting conformers,...
(−)‐Cytisine and its derivatives, characterised by high affinity to neuronal nicotinic acetylcholine receptors with specificity for the α4β2 subtype, have been shown be important probes in central nervous system (CNS) research. Electron impact mass spectral (EI‐MS) fragmentations of halogenated derivatives N ‐acetylcytisine ‐propionylcytisine investigated. Detailed fragmentation pathways identified all significant ions including a few characteristic fragment ions. The principal routes iodine...
A practical method for the conversion of tetrahydrothebaine to dihydromorphine in 92% yield is described. The procedure should allow more efficient production opium products and may be easily modified large-scale synthesis. codeine (8S)-8-bromomorphide, a potentially valuable intermediate 6-demethoxyoripavine derivatives, also absolute configuration (8S)-8-bromomorphide was determined by single-crystal X-ray diffraction study hydrobromide salt.