Heterocyclic Building Blocks-piperidine

Wang, Liming published the artcileReagent Controlled Stereoselective Synthesis of α-Glucans, Recommanded Product: 1-(Phenylsulfinyl)piperidine, the publication is Journal of the American Chemical Society (2018), 140(13), 4632-4638, database is CAplus and MEDLINE.

The development of a general glycosylation method that allows for the stereoselective construction of glycosidic linkages is a tremendous challenge. Because of the differences in steric and electronic properties of the building blocks used, the outcome of a glycosylation reaction can vary greatly when switching form one glycosyl donor-acceptor pair to another. We here report a strategy to install cis-glucosidic linkages in a fully stereoselective fashion that is under direct control of the reagents used to activate a single type of donor building block. The activating reagents are tuned to the intrinsic reactivity of the acceptor alc. to match the reactivity of the glycosylation agent with the reactivity of the incoming nucleophile. A protecting group strategy is introduced that is based on the sole use of benzyl-ether type protecting groups to circumvent changes in reactivity as a result of the protecting groups. For the stereoselective construction of the α-glucosyl linkages to a secondary alc., a per-benzylated glusosyl imidate donor is activated with a combination of trimethylsilyltriflate and DMF, while activation of the same imidate donor with trimethylsilyl iodide in the presence of triphenylphosphine oxide allows for the stereoselective cis-glucosylation of primary alcs. The effectiveness of the strategy is illustrated in the modular synthesis of a Mycobacterium tuberculosis nonasaccharide, composed of an α-(1-4)-oligoglucose backbone bearing different α-glucosyl branches.

Journal of the American Chemical Society published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C18H22BNO7, Recommanded Product: 1-(Phenylsulfinyl)piperidine.

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

Abood, L. G. published the artcileA new class of psychotogenic substances, Computed Properties of 13444-24-1, the publication is Mol. Mental Health, Papers Sci. Congrs. Brain Research Foundation; New York and Chicago (1959), 69-76, database is CAplus.

Piperidyl benzilate derivatives of formula CH₂(CH₂)₂NACH₂CHOCOCBRC₆H₅ were tested on humans for psychotogenic effects. With A, B, and R, resp., Et, OH, cyclohexyl; Et, OH, cyclopentyl; Me, OH, Ph; Me, OH, 2-thienyl; Et, OH, Ph; Et, OH, Pr; Et, H, Ph; 2Me, OH, Ph; and Et and Me, OH, Ph. With R as some cycloalkyl group the psychotogenic potency is greater than with phenyl substitution. If R is a thienyl group, the duration of the response is considerably less, although the psychotogenic effectiveness is about the same. The 4-piperidine linked isomers are less active than the 3 isomers. If A is Me, the maximum potency is obtained; with higher aliphatic chains the potency decreases. Replacement of H in the benzilic acid moiety by OH leads to a disappearance of potency. The same effect occurs if the piperidine N is made quaternary. No correlation between psychotogenic and anticholinergic potency was found.

Mol. Mental Health, Papers Sci. Congrs. Brain Research Foundation; New York and Chicago published new progress about 13444-24-1. 13444-24-1 belongs to piperidines, auxiliary class Piperidine,Alcohol, name is 1-Ethylpiperidin-3-ol, and the molecular formula is C7H15NO, Computed Properties of 13444-24-1.

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

Abood, L. G. published the artcileStructure-activity relationships of 3-piperidyl benzilates with psychotogenic properties, Related Products of piperidines, the publication is Archives Internationales de Pharmacodynamie et de Therapie (1959), 186-200, database is CAplus.

Correlation of pharmacol. and psychotogenic properties of compounds of structure CH₂.CH₂.CH₂NA.CH₂.CHOCOC(Ph)(B)(R) was attempted. In addition to auditory and visual hallucinations, mood changes, disorientation, hypochondriacal and paranoid delusions, and partial loss of contact were observed on administration of such compounds The most effective compound was N-methyl-3-piperidyl phenylcyclohexyl glycolate (I). Other materials studied included (given in order are A, B, and R): Me, OH, cyclohexyl (II); Et, OH, II; Et, OH, cyclopentyl; Me, OH, Ph; Me, OH, 2-thienyl; Et, OH, Ph; CH₂CH₂NMe₂, OH, Ph; 1,2,2,6,6-pentamethyl (3-piperidyl isomer), OH, Ph; Me, OH, Ph; Et, OH, Pr; H, OH, Ph; Et, H, Ph; (CH₃)₂, OH, Ph; and (C₂H₅)CH₃, OH, Ph. These compounds were potent anticholinergic agents, the best being the 2-thienyl compound Most compounds were antihistamines. Physostigmine counteracted anticholinergic effects but potentiated muscular ones. These compounds effectively blocked mydriasis, tachycardia, and hyperemia. Substitution of H for OH abolishes psychotogenic properties as does quaternization of the piperidyl ring. Replacement of Ph with II in compounds containing N-Me or N-Et enhances psychotogenic effects. Substitution of 2-thienyl for Ph diminishes reaction duration but increases anticholinergic and antihistaminic potencies. The psychotogenic properties do not correlate with toxicity, antispasmodic potency, of mydriasis.

Archives Internationales de Pharmacodynamie et de Therapie published new progress about 13444-24-1. 13444-24-1 belongs to piperidines, auxiliary class Piperidine,Alcohol, name is 1-Ethylpiperidin-3-ol, and the molecular formula is C7H15NO, Related Products of piperidines.

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

Furukawa, Mitsuru published the artcileNovel one-step preparation of sulfinic acid derivatives from sulfinic acid, Recommanded Product: 1-(Phenylsulfinyl)piperidine, the publication is Chemical & Pharmaceutical Bulletin (1980), 28(1), 134-41, database is CAplus.

Convenient one-step syntheses of sulfinamides and sulfinate esters from sulfinic acids were achieved by using coupling reagents, such as 2-chloro-1-methylpyridinium iodide, γ-saccharine chloride, N,N‘-dicyclohexylcarbodiimide, and EtO₂CN:NCO₂Et-PPh₃. Ammonolysis of sulfinate esters also gave sulfinamides.

Chemical & Pharmaceutical Bulletin published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C11H15NOS, Recommanded Product: 1-(Phenylsulfinyl)piperidine.

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

Blazenovic, Ivana published the artcileEffects of Gut Bacteria Depletion and High-Na⁺ and Low-K⁺ Intake on Circulating Levels of Biogenic Amines, Name: Piperidine-4-carboxamide, the publication is Molecular Nutrition & Food Research (2019), 63(4), n/a, database is CAplus and MEDLINE.

Scope : High-sodium and low-potassium (HNaLK) content in Western diets increases the risk of hypertension and cardiovascular disease (CVD). It is investigated if the dietary minerals interact with gut bacteria to modulate circulating levels of biogenic amines, which are implicated in various pathologies, including hypertension and CVD. Methods and results : Using a metabolomic approach to target biogenic amines, the effects of gut bacteria depletion and HNaLK intake on circulating levels of biogenic amines in rats are examined Forty-five metabolites whose plasma levels are significantly altered by gut bacteria depletion (p < 0.05) are found, indicating their regulation by gut bacteria. Many of them are not previously linked to gut bacteria; therefore, these data provide novel insights into physiol. or pathol. roles of gut bacteria. A number of plasma metabolites that are altered both by gut bacteria and HNaLK intake are also found, suggesting possible interactions of the diet and gut bacteria in the modulation of these metabolites. The diet effects are observed with significant changes in the gut bacterial taxa Porphyromonadaceae and Prevotellaceae (p < 0.05). Conclusion : The dietary minerals may regulate abundances of certain gut bacteria to alter circulating levels of biogenic amines, which may be linked to host physiol. or pathol.

Molecular Nutrition & Food Research published new progress about 39546-32-2. 39546-32-2 belongs to piperidines, auxiliary class Piperidine,Amine,Amide, name is Piperidine-4-carboxamide, and the molecular formula is C6H12N2O, Name: Piperidine-4-carboxamide.

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

Kelly, Richard P. published the artcileβ-Elimination of 9-(dimethylaminomethyl)fluorene; buffer catalysis and pH dependence indicating a zwitterion intermediate, Product Details of C19H21N, the publication is Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) (1979), 681-9, database is CAplus.

In aqueous NaOH and tertiary amine buffers at 25°, 9-(dimethylaminomethyl)fluorene eliminates Me₂NH to form dibenzofulvene. At 0.02-0.2M HO^–, the reaction is 1st order in HO^– with a rate constant expected of ionization to a fluorenyl anion. At >0.2M the order in HO^– falls, consistent with a change in rate-determining step to loss of the leaving group. At <0.02M the order also falls and in buffer solutions the reaction shows general acid catalysis, as expected of rate-determining attack of HO^– and buffer base on protonated substrate. A stepwise mechanism is proposed with formation of a zwitterion intermediate preceded resp. at high pH by a fluoren-9-yl anion and at low pH by a dimethylammonium cation.

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) published new progress about 35661-58-6. 35661-58-6 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-((9H-Fluoren-9-yl)methyl)piperidine, and the molecular formula is C19H21N, Product Details of C19H21N.

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

Kobayashi, Hirokazu published the artcileMolecular Orientation and Dynamics of a Derivative of 2,2,6,6-Tetramethyl-1-Piperidinyloxyl Radical with a Large Substituent Group Dispersed in 1D-Nanochannels of 2,4,6-Tris(4-Chlorophenoxy)-1,3,5-Triazine Crystal, Product Details of C9H17NO, the publication is Applied Magnetic Resonance (2020), 51(8), 711-724, database is CAplus.

The mol. orientation and dynamics were examined for 4-acetamido-2,2,6,6-tetramethyl-1-piperidinyloxyl (4-acetamido-TEMPO) radicals, which have a larger substituent group than many other TEMPO radicals, dispersed in the one-dimensional (1D) nanochannel of 2,4,6-tris(4-chlorophenoxy)-1,3,5-triazine (CLPOT) with 4-substituted-2,2,6,6-tetramethylpiperidine (R-TEMP; R=OH or H). When TEMPOH (R=OH) was used as a spacer for dispersion in the CLPOT nanochannels, the mol. orientation of 4-acetamido-TEMPO in the CLPOT nanochannels was similar to that of other previously reported 4-substituted-TEMPO (4-X-TEMPO; X=OH, =O or OCH₃) radicals. However, the activation energy for the rotational diffusion of 4-acetamido-TEMPO in the CLPOT nanochannels, estimated to be 11 kJ mol^-1, was larger than that of other 4-X-TEMPO mols. (6-8 kJ mol^-1). These results indicate that the mol. dynamics of 4-X-TEMPO in the CLPOT nanochannels can be controlled by the selection of a larger substituent X at the 4-position in 4-X-TEMPO (in this study, X=NHCOCH₃), and also suggest an important concept for the design of new organic magnets.

Applied Magnetic Resonance published new progress about 826-36-8. 826-36-8 belongs to piperidines, auxiliary class Natural product, name is 2,2,6,6-Tetramethylpiperidin-4-one, and the molecular formula is C9H17NO, Product Details of C9H17NO.

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

Asif, Kanwal published the artcileSolid phase syntheses of peptoid like arylureido compounds and sequencing of isobars without molecular encoding, Computed Properties of 39546-32-2, the publication is Organic & Biomolecular Chemistry (2019), 17(17), 4204-4207, database is CAplus and MEDLINE.

Arylureido-backbone containing peptoid-like trimers were prepared using the one-bead-one-compound approach. Isobaric mols. were synthesized from isocyanate precursors that contain alkyl halide handles at the ortho and para-positions in the Ph ring. After chain extension with a primary amine, the piperazine-capped mols. were sequenced using tandem mass spectrometry and successfully identified based on their fragmentation pattern without a need for internal mol. encoding.

Organic & Biomolecular Chemistry published new progress about 39546-32-2. 39546-32-2 belongs to piperidines, auxiliary class Piperidine,Amine,Amide, name is Piperidine-4-carboxamide, and the molecular formula is C6H12N2O, Computed Properties of 39546-32-2.

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

Bindschadler, Pascal published the artcileSynthesis of a potential 10E4 tetrasaccharide antigen involved in scrapie pathogenesis, COA of Formula: C11H15NOS, the publication is Helvetica Chimica Acta (2006), 89(11), 2591-2610, database is CAplus.

To test the hypothesis that tetrasaccharide 3 is involved in scrapie pathogenesis, tetrasaccharide derivative 32 functionalized with an amine linker at the reducing end was synthesized. A (2+2) glycosylation approach was chosen to furnish the target compound in fully protected form. To investigate its biol. role, tetrasaccharide 32 was further functionalized to the corresponding thiol 33 using Traut’s reagent. During the course of the synthesis, the N,N-diacetyl protecting group proved surprisingly labile to radical and acidic conditions.

Helvetica Chimica Acta published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C11H15NOS, COA of Formula: C11H15NOS.

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

Rohland, Philip published the artcileStructural alterations on the TEMPO scaffold and their impact on the performance as active materials for redox flow batteries, SDS of cas: 826-36-8, the publication is Materials Advances (2022), 3(10), 4278-4288, database is CAplus.

Trimethylammonium-2,2,6,6-tetramethylpiperidine-1-oxyl chloride (TMA-TEMPO) has been intensively studied for its usage in aqueous organic redox flow batteries. Straightforward synthesis, reliable electrochem., fast kinetics and high cycling stability are the advantages of this active material. Nevertheless, it has been shown that elevated temperatures and high states of charge accelerate the decomposition of this material. Hence, a comparative study was performed with five new and one known TEMPO derivatives, to elucidate the structure-stability relationship of the TEMPO scaffold and to investigate the influence on the battery performance. The results show that the introduction of linkers between the solubility-promoting group and the piperidyl core or enhanced shielding of the radical has a great impact on the stability during cycling.

Materials Advances published new progress about 826-36-8. 826-36-8 belongs to piperidines, auxiliary class Natural product, name is 2,2,6,6-Tetramethylpiperidin-4-one, and the molecular formula is C9H17NO, SDS of cas: 826-36-8.

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