piperidines and isopelletierine

Pelletierine, a proposed building block of

Topics: Alkaloids; Lycopodium; Piperidines; Stereoisomerism

Punica granatum (family: Lythraceae) is mainly found in Iran, which is considered to be its primary centre of origin. Studies on pomegranate peel have revealed antioxidant, anti-inflammatory, anti- angiogenesis activities, with prevention of premature aging and reducing inflammation. In addition to this it is also useful in treating various diseases like diabetes, maintaining blood pressure and treatment of neoplasms such as prostate and breast cancer.. In this study we identified anti-cancer targets of active compounds like corilagin (tannins), quercetin (flavonoids) and pseudopelletierine (alkaloids) present in pomegranate peel by employing dual reverse screening and binding analysis.. The potent targets of the pomegranate peel were annotated by the PharmMapper and ReverseScreen 3D, then compared with targets identified from different Bioassay databases (NPACT and HIT's). Docking was then further employed using AutoDock pyrx and validated through discovery studio for studying molecular interactions.. A number of potent anti-cancerous targets were attained from the PharmMapper server according to their fit score and from ReverseScreen 3D server according to decreasing 3D scores.. The identified targets now need to be further validated through in vitro and in vivo studies.

Topics: Alkaloids; Antineoplastic Agents; Computer Simulation; Drug Discovery; Flavonoids; Fruit; Glucosides; Humans; Hydrolyzable Tannins; Lythraceae; Molecular Docking Simulation; Molecular Targeted Therapy; Neoplasms; Piperidines; Quercetin; Tannins

Tropane, tropinone, pseudopelletierine and cocaine were oxidized in situ in a nuclear magnetic resonance (NMR) tube providing mixtures of exo/endo N-oxides. Observed (13)C chemical shifts were correlated with values calculated by gauge-including atomic orbitals density functional theory (DFT) OPBE/6-31G* method using DFT B3LYP/6-31G* optimized geometries. The same method of (13)C chemical shift calculation was applied on series of methyl-substituted 1-methylpiperidines and their epimeric N-oxides described in literature. The results show that using this undemanding calculation method enables assignment of configuration of N-O group in N-epimeric saturated heterocyclic N-oxides. The approach enables assigning of the configuration with high degree of certainty even if NMR data of only one isomer are available. An improved method of in situ oxidation of starting amines in an NMR tube is also described.

Topics: Carbon Isotopes; Cocaine; Cyclic N-Oxides; Models, Chemical; Molecular Conformation; Nitrogen; Nuclear Magnetic Resonance, Biomolecular; Oxidation-Reduction; Oxygen; Piperidines; Predictive Value of Tests; Stereoisomerism; Tropanes

The total syntheses of the Lythracea alkaloids (+)-vertine and (+)-lythrine are described. Enantioenriched pelletierine is used as a chiral building block and engaged into a two step pelletierine condensation leading to two quinolizidin-2-one diastereomers in a 8 : 1 ratio. The major product is used in the synthesis of (+)-vertine via aryl-aryl coupling and ring closing metathesis to provide a Z-alkene α to the lactone carbonyl function. The same procedure was used for (+)-lythrine after base induced epimerization of the main quinolizidin-2-one diastereomer. Alternative classical ring closure strategies like macrolactonisation or aryl-aryl coupling failed.

Topics: Alkaloids; Lythraceae; Models, Molecular; Molecular Structure; Piperidines

A general method for the preparation of enantiopure 2-alkene- or 2-alkyne-containing chain substituted piperidines was established by using nonracemic Betti base as a chiral auxiliary. The key step is that the auxiliary residue was removed by a novel base-catalyzed N-debenzylation via a formation of o-quinone methide mechanism in stead of the traditional hydrogenolysis, by which the alkene or alkyne groups survived. By this method, ten 2-alkene- or 2-alkyne-containing chain substituted piperidines were prepared on the gram scale within a few hours. To demonstrate the efficiency of the method and the versatility of the product, total syntheses of natural alkaloids (+)-pelletierine, (-)-lasubine II, and (+)-cermizine C were achieved by using (S)-2-allyl-N-Boc-piperidine as a versatile building block.

Topics: Alkaloids; Alkenes; Alkynes; Heterocyclic Compounds, 2-Ring; Molecular Structure; Piperidines; Quinolizidines; Quinolizines; Stereoisomerism

The catalytic dynamic resolution (CDR) of rac-2-lithio-N-Boc-piperidine using chiral ligand 8 or its diastereomer 9 in the presence of TMEDA has led to the highly enantioselective syntheses of both enantiomers of 2-substituted piperidines using a wide range of electrophiles. The CDR has been applied to the synthesis of (R)- and (S)-pipecolic acid derivatives, (+)-beta-conhydrine, (S)-(+)-pelletierine, and (S)-(-)-ropivacaine and the formal synthesis of (-)-lasubine II and (+)-cermizine C.

Topics: Alkaloids; Amides; Catalysis; Heterocyclic Compounds, 2-Ring; Lithium; Molecular Conformation; Organometallic Compounds; Pipecolic Acids; Piperidines; Quinolizines; Ropivacaine; Stereoisomerism; Thermodynamics

An improved protocol for the construction of enantioenriched pyrrolidine, indoline, and piperidine rings using an organocatalyzed, intramolecular heteroatom Michael addition is described. Application to the enantioselective synthesis of homoproline, homopipecolic acid, and pelletierine has been accomplished.

Topics: Catalysis; Molecular Structure; Pipecolic Acids; Piperidines; Proline

The stereochemistry of the decarboxylation of meso-alpha,epsilon-diaminopimelate catalyzed by meso-alpha,epsilon-diaminopimelate decarboxylase (EC 4.1.1.20) of Bacillus sphaericus was determined by stereochemical analyses of [6-2H]-L-lysine produced by the reaction in D2O. The product [6-2H]-L-lysine was converted to levorotatory methyl 5-phthalimido[5-2H]valerate by the reactions not affecting the absolute configuration of the asymmetric carbon atom. By contrast, methyl 5-phthalimido[5-2H]valerate derived from [2,6-2H2]-L-lysine, which was produced from [2,6-2H2]diaminopimelate by decarboxylation in H2O, was dextrorotatory. The authentic methyl (R)-5-phthalimido[5-2H]valerate prepared from L-glutamate with glutamate decarboxylase was levorotatory. These results indicate that the meso-alpha,epsilon-diaminopimelate decarboxylase reaction proceeds in an inversion mode. The deuterium label in [6-2H]-L-lysine was fully conserved during the conversion into pelletierine through [1-2H]cadaverine by the stereospecific diamine oxidase reaction. Thus, the enzymatic decarboxylation of meso-alpha,epsilon-diaminopimelate occurs with inversion of configuration in contrast to the other amino acid decarboxylase reported so far.

Topics: Bacillus; Bacterial Proteins; Cadaverine; Carboxy-Lyases; Deuterium; Kinetics; Lysine; Piperidines; Pyridoxal Phosphate; Radioisotope Dilution Technique

Topics: Alkaloids; Animals; Calcium; Calcium, Dietary; Culture Media; Fasciola hepatica; Hydrogen-Ion Concentration; Ketones; Pharmacology; Piperidines; Research

Topics: Alkaloids; Piperidines; Withania

Topics: Anthelmintics; Piperidines

Topics: Autonomic Agents; Ganglia, Autonomic; Lobeline; Nicotine; Phenethylamines; Piperidines; Procaine

Topics: Piperidines

Topics: Piperidines