M.W=300-350 | Page 6 of 9 | Heterocyclic Building Blocks-piperidine

Eddy, Nicholas A.’s team published research in Organic Letters in 14 | CAS: 219543-09-6

Organic Letters published new progress about 219543-09-6. 219543-09-6 belongs to piperidines, auxiliary class Piperidine,Fluoride,Salt,Amine,Amide, name is 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, and the molecular formula is C11H21BF4N2O2, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate.

Eddy, Nicholas A. published the artcileAccess to Dienophilic Ene-Triketone Synthons by Oxidation of Diketones with an Oxoammonium Salt, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Organic Letters (2012), 14(2), 498-501, database is CAplus and MEDLINE.

The oxidation of 1,3-cycloalkanediones with 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (Bobbitt’s salt) to generate 5-ene-1,2,4-triones in moderate-to-good (40-80%) yields was reported. This inexpensive oxidant facilitated an unprecedented cascade of oxidation and elimination to yield novel ene-triketones. The reactivity of these products was explored in the Diels-Alder reaction and provided moderate-to-good yields of cycloaddition products. The products described in this study represent unique, densely functionalized, and versatile building blocks for the synthesis of more complex mols.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Patel, Gautam’s team published research in Journal of Medicinal Chemistry in 56 | CAS: 859833-21-9

Journal of Medicinal Chemistry published new progress about 859833-21-9. 859833-21-9 belongs to piperidines, auxiliary class Piperidine,Boronic acid and ester,Benzene,Boronic Acids,Boronate Esters, name is 1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine, and the molecular formula is C18H28BNO2, Name: 1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine.

Patel, Gautam published the artcileKinase Scaffold Repurposing for Neglected Disease Drug Discovery: Discovery of an Efficacious, Lapatanib-Derived Lead Compound for Trypanosomiasis, Name: 1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine, the publication is Journal of Medicinal Chemistry (2013), 56(10), 3820-3832, database is CAplus and MEDLINE.

Lapatinib analogs such as I (X = O, CH₂) were prepared as trypanocidal agents for use as lead compounds in the development of treatments for human African trypanosomiasis which do not require i.v. administration. Lapatinib was previously shown to kill T. brucei with low micromolar EC₅₀ values; analogs replacing the methylfurylquinazoline moiety with a heteroarylsulfonylphenylquinazolinyl moiety were prepared and tested against both T. brucei and human hepatocarcinoma cells. 4-Anilinoquinazolines, particularly I (X = O) (NEU617), were found to be highly potent and orally bioavailable inhibitors of trypanosome replication. I (X = O) blocks duplication of the kinetoplast and arrests cytokinesis in T. brucei, which may make it useful as a chem. tool for studying regulation of the trypanosome cell cycle.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Ma, Winson M. J.’s team published research in Organic Letters in 15 | CAS: 859833-21-9

Organic Letters published new progress about 859833-21-9. 859833-21-9 belongs to piperidines, auxiliary class Piperidine,Boronic acid and ester,Benzene,Boronic Acids,Boronate Esters, name is 1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine, and the molecular formula is C18H28BNO2, Application of 1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine.

Ma, Winson M. J. published the artcileSynthesis of Amines with Pendant Boronic Esters by Borrowing Hydrogen Catalysis, Application of 1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine, the publication is Organic Letters (2013), 15(18), 4850-4853, database is CAplus and MEDLINE.

Amine alkylation reactions of alcs. were performed in the presence of boronic ester groups to provide products which are known for their use as mol. sensors. E.g., reaction of (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol with morpholine in the presence of 2.5 mol% [Ru(p-cymene)Cl₂]₂ and 5 mol% DPEphos ligand in xylene/Na₂CO₃ at 155° to give (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)morpholine in 84% yield. The boronic ester moiety could be present in either the alc. or amine starting material and was not compromised in the presence of a Ru catalyst.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Qin, Tian’s team published research in Journal of the American Chemical Society in 133 | CAS: 219543-09-6

Journal of the American Chemical Society published new progress about 219543-09-6. 219543-09-6 belongs to piperidines, auxiliary class Piperidine,Fluoride,Salt,Amine,Amide, name is 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, and the molecular formula is C11H21BF4N2O2, COA of Formula: C11H21BF4N2O2.

Qin, Tian published the artcileVinylogous Addition of Siloxyfurans to Benzopyryliums: A Concise Approach to the Tetrahydroxanthone Natural Products, COA of Formula: C11H21BF4N2O2, the publication is Journal of the American Chemical Society (2011), 133(6), 1714-1717, database is CAplus and MEDLINE.

A concise approach to the tetrahydroxanthone natural products employing vinylogous addition of siloxyfurans to benzopyryliums and a late-stage Dieckmann cyclization was developed. With this methodol., chiral, racemic forms of the natural products blennolide B (I) and blennolide C (II) were synthesized in a maximum of four steps from a 5-hydroxychromone substrate. The regio- and diastereoselectivity of the vinylogous additions was probed using computational studies, which suggested the involvement of Diels-Alder-like transition states.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Ruess, Raffael’s team published research in Journal of Physical Chemistry C in 123 | CAS: 219543-09-6

Journal of Physical Chemistry C published new progress about 219543-09-6. 219543-09-6 belongs to piperidines, auxiliary class Piperidine,Fluoride,Salt,Amine,Amide, name is 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, and the molecular formula is C11H21BF4N2O2, Recommanded Product: 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate.

Ruess, Raffael published the artcileEfficient Electron Collection by Electrodeposited ZnO in Dye-Sensitized Solar Cells with TEMPO⁺/⁰ as the Redox Mediator, Recommanded Product: 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Journal of Physical Chemistry C (2019), 123(36), 22074-22082, database is CAplus.

The power conversion efficiency in established dye-sensitized solar cells (DSSCs) suffers from high overpotentials needed because of slow electron transfer kinetics. If redox couples are used that have a low reorganization energy, fast dye regeneration can be achieved, but fast recombination reactions can barely be suppressed. If they become competitive to electron transport to the back electrode, solar cell efficiencies drastically drop. In this work, it is shown that electron transport is facilitated by substituting the commonly used photoanode material, nanoparticulate TiO₂, by electrodeposited ZnO, which, albeit more complex surface reactions, provides electron transport by orders of magnitude faster than nanoparticulate TiO₂. With TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) as the redox mediator, the dye is efficiently regenerated with overpotentials well below 0.2 V. We demonstrate that the external quantum efficiency with TiO₂-based photoanodes is significantly limited by recombination, while it is maintained at high values for electrodeposited ZnO. It is thereby shown that redox couples with fast kinetics can be employed in DSSCs without drawbacks in quantum efficiency if sufficient fast electron transport in the porous semiconductor network is provided.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Neel, Andrew J.’s team published research in Journal of the American Chemical Society in 135 | CAS: 219543-09-6

Neel, Andrew J. published the artcileAsymmetric Cross-Dehydrogenative Coupling Enabled by the Design and Application of Chiral Triazole-Containing Phosphoric Acids, Formula: C11H21BF4N2O2, the publication is Journal of the American Chemical Society (2013), 135(38), 14044-14047, database is CAplus and MEDLINE.

Nonracemic triazolylbinaphthylphosphoric acids I [R = PhCH₂, Ph₂CH, bis(1-naphthyl)methyl, 1-naphthyl, 9-anthracenyl, 1-pyrenyl, 2,4,6-Me₃C₆H₂, 2,4,6-i-Pr₃C₆H₂, 2,4,6-(c-C₆H₁₁)₃C₆H₂, 4-t-BuC₆H₄, 3,5-t-Bu₂C₆H₃, 1-adamantyl] were prepared using azide-alkyne cycloadditions of a protected diethynylbinaphthol with azides RN₃ [R = PhCH₂, Ph₂CH, bis(1-naphthyl)methyl, 1-naphthyl, 9-anthracenyl, 1-pyrenyl, 2,4,6-Me₃C₆H₂, 2,4,6-i-Pr₃C₆H₂, 2,4,6-(c-C₆H₁₁)₃C₆H₂, 4-t-BuC₆H₄, 3,5-t-Bu₂C₆H₃, 1-adamantyl]; in the presence of I, an acetamidopiperidineoxoammonium salt, and trisodium phosphate in p-xylene, tetrahydroisoquinolinylbenzamides II [R¹ = PhCH₂, 4-MeC₆H₄CH₂, 4-MeOC₆H₄CH₂, 4-O₂NC₆H₄CH₂, 2-MeOC₆H₄CH₂, Ph, 3-MeC₆H₄, 2-MeC₆H₄, 1-naphthyl, 2-ClC₆H₄, 2-HOC₆H₄, t-Bu, cyclohexyl, (R)-MeO₂CCH(i-Pr), (S)-MeO₂CCH(i-Pr); R² = H, Me, Br, F₃C] underwent enantioselective cross-dehydrogenative coupling reactions to give tetrahydroisoquinolinoquinazolinones III [R¹ = PhCH₂, 4-MeC₆H₄CH₂, 4-MeOC₆H₄CH₂, 4-O₂NC₆H₄CH₂, 2-MeOC₆H₄CH₂, Ph, 3-MeC₆H₄, 2-MeC₆H₄, 1-naphthyl, 2-ClC₆H₄, 2-HOC₆H₄, t-Bu, cyclohexyl, (R)-MeO₂CCH(i-Pr), (S)-MeO₂CCH(i-Pr); R² = H, Me, Br, F₃C] in 38-93% yields and in 73-93% ee or in 3:1-7:1 dr. I were designed to use attractive hydrogen-bonding interactions with substrates rather than catalyst steric bulk to improve the stereoselectivity of the coupling reaction. The azides used in the preparation of I are potentially explosive and should be handled and reacted using appropriate precautions.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Kozikowski, Alan P.’s team published research in ChemMedChem in 6 | CAS: 170364-89-3

ChemMedChem published new progress about 170364-89-3. 170364-89-3 belongs to piperidines, auxiliary class Indole,Piperidine,Amide, name is tert-Butyl 4-(1H-indol-1-yl)piperidine-1-carboxylate, and the molecular formula is C18H24N2O2, HPLC of Formula: 170364-89-3.

Kozikowski, Alan P. published the artcileIdentification of a Glycogen Synthase Kinase-3β Inhibitor that Attenuates Hyperactivity in CLOCK Mutant Mice, HPLC of Formula: 170364-89-3, the publication is ChemMedChem (2011), 6(9), 1593-1602, database is CAplus and MEDLINE.

Bipolar disorder is characterized by a cycle of mania and depression, which affects approx. 5 million people in the United States. Current treatment regimes include the so-called “mood-stabilizing drugs”, such as lithium and valproate that are relatively dated drugs with various known side effects. Glycogen synthase kinase-3β (GSK-3β) plays a central role in regulating circadian rhythms, and lithium is known to be a direct inhibitor of GSK-3β. We designed a series of second generation benzofuran-3-yl-(indol-3-yl)maleimides containing a piperidine ring that possess IC₅₀ values in the range of 4 to 680 nM against human GSK-3β. Compound 3a (I) exhibits reasonable kinase selectivity and promising preliminary absorption, distribution, metabolism, and excretion (ADME) data. The administration of this compound at doses of 10 to 25 mg kg^-1 resulted in the attenuation of hyperactivity in amphetamine/chlordiazepoxide-induced manic-like mice together with enhancement of prepulse inhibition, similar to the effects found for valproate (400 mg kg^-1) and the antipsychotic haloperidol (1 mg kg^-1). We also tested this compound in mice carrying a mutation in the central transcriptional activator of mol. rhythms, the CLOCK gene, and found that the same compound attenuates locomotor hyperactivity in response to novelty. This study further demonstrates the use of inhibitors of GSK-3β in the treatment of manic episodes of bipolar/mood disorders, thus further validating GSK-3β as a relevant therapeutic target in the identification of new therapies for bipolar patients.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Faul, Margaret M.’s team published research in Tetrahedron in 59 | CAS: 170364-89-3

Tetrahedron published new progress about 170364-89-3. 170364-89-3 belongs to piperidines, auxiliary class Indole,Piperidine,Amide, name is tert-Butyl 4-(1H-indol-1-yl)piperidine-1-carboxylate, and the molecular formula is C18H24N2O2, HPLC of Formula: 170364-89-3.

Faul, Margaret M. published the artcileStrategies for the synthesis of N-(azacycloalkyl)bisindolylmaleimides: selective inhibitors of PKCβ, HPLC of Formula: 170364-89-3, the publication is Tetrahedron (2003), 59(36), 7215-7229, database is CAplus.

N-(Azacycloalkyl)bisindolylmaleimides such as I have been identified to be selective inhibitors of PKCβ. This manuscript will describe the synthetic approaches employed to prepare this class of compounds that resulted in development of efficient methods for preparation of N-(azacycloalkyl)indoles, indole-3-acetamides, and indole-3-glyoxylate esters.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Zakrzewski, Jerzy’s team published research in Synthesis in | CAS: 219543-09-6

Synthesis published new progress about 219543-09-6. 219543-09-6 belongs to piperidines, auxiliary class Piperidine,Fluoride,Salt,Amine,Amide, name is 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, and the molecular formula is C16H24BF4Ir, Related Products of piperidines.

Zakrzewski, Jerzy published the artcileOxidation of unsaturated primary alcohols and ω-haloalkanols with 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate, Related Products of piperidines, the publication is Synthesis (2007), 2491-2494, database is CAplus.

Unsaturated primary alcs. and ω-haloalkanols, all applied in pheromone synthesis, are oxidized to the corresponding aldehydes using 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (I). Three methods are compared with one another; oxidations with I and silica gel, oxidations with I in the presence of pyridine, and pyridinium chlorochromate (PCC).

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Faul, Margaret M.’s team published research in Bioorganic & Medicinal Chemistry Letters in 13 | CAS: 170364-89-3

Bioorganic & Medicinal Chemistry Letters published new progress about 170364-89-3. 170364-89-3 belongs to piperidines, auxiliary class Indole,Piperidine,Amide, name is tert-Butyl 4-(1H-indol-1-yl)piperidine-1-carboxylate, and the molecular formula is C18H24N2O2, Product Details of C18H24N2O2.

Faul, Margaret M. published the artcileAcyclic N-(azacycloalkyl)bisindolylmaleimides: isozyme selective inhibitors of PKCβ, Product Details of C18H24N2O2, the publication is Bioorganic & Medicinal Chemistry Letters (2003), 13(11), 1857-1859, database is CAplus and MEDLINE.

The synthesis and structure-activity relationship (SAR) trends of a new class of N-(azacycloalkyl)bisindolylmaleimides, e.g. I (R¹ = CH₂-pyridyl, R² = Me, n = 2), acyclic derivatives of staurosporine, is described. I exhibits an IC₅₀ of 40-50 nM against the human PKCβ₁ and PKCβ₂ isoenzymes and selectively inhibits the PKCβ isoenzymes in comparison to other PKC isoenzymes (α, γ, δ, ε, λ, and η). The series is also kinase selective for PKC in comparison to other ATP-dependent kinases. A comparison of the protein kinase C (PKC) isoenzyme and kinase activity of the series is made to the kinase inhibitor staurosporine.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem