Day: December 6, 2022

Crich, David published the artcileOn the nitrile effect in L-rhamnopyranosylation, Safety of 1-(Phenylsulfinyl)piperidine, the publication is Carbohydrate Research (2006), 341(10), 1467-1475, database is CAplus and MEDLINE.

It is shown that the use of 5% acetonitrile or propionitrile in dichloromethane functions to increase the β-selectivity of a number of L-rhamnopyranosylation reactions conducted by the thioglycoside method with activation by the 1-benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride couple. The use of more significant quantities of acetonitrile or propionitrile results in the formation of complex reaction mixtures containing little coupled product, but from which Ritter-type products can be isolated.

Carbohydrate Research 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, Safety of 1-(Phenylsulfinyl)piperidine.

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

Koltun, Dmitry O. published the artcileNovel, potent, selective, and metabolically stable stearoyl-CoA desaturase (SCD) inhibitors, Recommanded Product: 4-(2-Chlorophenoxy)-N-(3-(methylcarbamoyl)phenyl)piperidine-1-carboxamide, the publication is Bioorganic & Medicinal Chemistry Letters (2009), 19(7), 2048-2052, database is CAplus and MEDLINE.

We identified a series of structurally novel SCD (Δ9 desaturase) inhibitors via high-throughput screening and follow-up SAR studies. Modification of the central bicyclic scaffold has proven key to our potency optimization effort. The most potent analog (8g) had IC₅₀ value of 50 pM in a HEPG2 SCD assay and has been shown to be metabolically stable and selective against Δ5 and Δ6 desaturases.

Bioorganic & Medicinal Chemistry Letters published new progress about 1032229-33-6. 1032229-33-6 belongs to piperidines, auxiliary class Metabolic Enzyme,SCD, name is 4-(2-Chlorophenoxy)-N-(3-(methylcarbamoyl)phenyl)piperidine-1-carboxamide, and the molecular formula is C20H22ClN3O3, Recommanded Product: 4-(2-Chlorophenoxy)-N-(3-(methylcarbamoyl)phenyl)piperidine-1-carboxamide.

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

Yonekuta, Yasunori published the artcileStructural implication of oxoammonium cations for reversible organic one-electron redox reaction to nitroxide radicals, Related Products of piperidines, the publication is Chemistry Letters (2007), 36(7), 866-867, database is CAplus.

Structures and electrochem. behaviors of nitroxide radicals reveal that their rapid and reversible redox reactions are based not only on their chem. stability but also on the increased sp² character of nitrogens which is intermediate between the purely sp² and sp³ nitrogens in oxoammonium cations and amines, resp.

Chemistry 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 C2H4ClNO, Related Products of piperidines.

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

Kelly, Christopher B. published the artcileOxidative cleavage of allyl ethers by an oxoammonium salt, Recommanded Product: 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Organic & Biomolecular Chemistry (2015), 13(14), 4255-4259, database is CAplus and MEDLINE.

A method to oxidatively cleave allyl ethers to their corresponding aldehydes mediated by an oxoammonium salt is described. Using a biphasic solvent system and mild heating, the cleavage proceeds readily, furnishing a variety of α,β-unsaturated aldehydes and ketones. E.g, oxidative cleavage of allyl ether (I) in presence of oxoammonium salt (II) gave 79% α,β-unsaturated aldehyde (III).

Organic & Biomolecular Chemistry 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.

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

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