Month: December 2022

Litjens, Remy E. J. N. published the artcileSulfonium triflate mediated glycosidations of aryl 2-azido-2-deoxy-1-thio-D-mannosides, Category: piperidines, the publication is European Journal of Organic Chemistry (2005), 918-924, database is CAplus.

The effectiveness in terms of yield and stereoselectivity of (phenylsulfinyl)piperidine (BSP)/ trifluoromethanesulfonic anhydride (Tf₂O) and di-Ph sulfoxide (DPS)/ Tf₂O-mediated glycosidations of 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-thiomannosides is described. Application of the BSP/Tf₂O activator led to productive condensations using p-methoxyphenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-thiomannoside as a donor, while the more powerful DPS/Tf₂O combination gave similar results using both p-methoxyphenyl and Ph 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-thiomannosides.

European Journal of Organic Chemistry 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, Category: piperidines.

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

Khanjani, Pegah published the artcileAssessing the reactivity of cellulose by oxidation with 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxo-piperidinium cation under mild conditions, Formula: C11H21BF4N2O2, the publication is Carbohydrate Polymers (2017), 293-298, database is CAplus and MEDLINE.

The accessibility and reactivity of cellulose are key parameters in its conversion into various products. Several indirect measures, such as water retention value (WRV), fiber saturation point (FSP) and sp. surface area (SSA), are often used to characterize cellulosic samples for their reactivity. In this paper, we report on using oxidation with 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxo-piperidinium cation (4-AcNH-TEMPO⁺) as a probe reaction for the reactivity of cellulose in mild conditions (pH 9, room temperature). 4-AcNH-TEMPO⁺ is able to selectively convert hydroxymethyl groups into carboxylate groups. The time dependence of the conversion was monitored by iodometric quantification of the residual 4-AcNH-TEMPO⁺. Soluble substrates, such as 1-propanol and maltose, were quant. oxidized in ca. 1 min while 3-16% of cellulose was oxidized in ca. 15 min depending on its origin. Extrapolation of the slow residual oxidation to zero time allowed quantification of the easily reactive or accessible cellulose. The 4-AcNH-TEMPO⁺ reactivity was correlated with several pulp characteristics, including WRV, FSP, SSA, chem. composition, crystallinity, the pulping process and the drying history.

Carbohydrate Polymers 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, Formula: C11H21BF4N2O2.

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

Naruto, Shunsuke published the artcileSynthesis and spasmolytic activity of aminoalkyl 2-substituted 2-(1,2-benzisoxazol-3-yl)acetates, Recommanded Product: 1-Ethylpiperidin-3-ol, the publication is Chemical & Pharmaceutical Bulletin (1987), 35(5), 2095-100, database is CAplus and MEDLINE.

Several aminoalkyl esters (I, II, and III, R = aminoalkyl or alkylpiperidino of 2-(1,2-benzisoxazol-3-yl)-2-cyclohexylacetic acid, 1-(1,2-benzisoxazol-3-yl)-1-cyclopentanecarboxylic acid, and 1-(1,3-benzisoxazol-3-yl)-1-cyclohexanecarboxylic acid and their quaternary ammonium salts were prepared Me 1,2-benzisoxazole-3-acetate was treated with NaH and then cyclohexyl iodide or Br(CH₂)₄Br or Br(CH₂)₅Br to give esters which were hydrolyzed and esterified to give I–III, resp. The anticholinergic (anti-Ach) and musculotropic (anti-KCl) activities of these compounds were examined 3-(N,N-Diethylamino)propyl 2-(1,2-benziosoxazol-3-yl)-2-cyclohexylacetate [I, R = (CH₂)₃NEt₂] showed potent anti-Ach and anti-KCl activities.

Chemical & Pharmaceutical Bulletin 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, Recommanded Product: 1-Ethylpiperidin-3-ol.

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

Hashimoto, Tadashi published the artcileSyntheses and biological activities of substance P analogs containing L– and D-homoglutamine and L– and D-pyrohomoglutamic acid at positions 5 and 6, HPLC of Formula: 72002-30-3, the publication is Bulletin of the Chemical Society of Japan (1987), 60(3), 1207-9, database is CAplus.

Six title substance P (SP) analogs were prepared by the solid-phase method on a benzylhydrylamine resin. The smooth muscle contractile activities of these analogs were compared with the activity of SP on isolated guinea pig ileum and trachea. The potency of [D-Hgn⁵,Hgn⁶]-SP (Hgn = homoglutamine residue) was as high as that of SP in the guinea pig ileum assay. The replacements of both Gln residues at positions 5 and 6 with the Hgn-D-Hgn sequence brought a drastic decrease in activity. The D-pyroHgu-Hgn-Phe-Phe-Gly-Leu-Met-NH₂ (pyroHgu = pyrohomoglutamic acid) analog possessed the highest potency among the 6 analogs.

Bulletin of the Chemical Society of Japan published new progress about 72002-30-3. 72002-30-3 belongs to piperidines, auxiliary class Piperidine,Chiral,Carboxylic acid,Amide, name is (R)-6-Oxopiperidine-2-carboxylic acid, and the molecular formula is C6H9NO3, HPLC of Formula: 72002-30-3.

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

Wu, Yu-Fa published the artcileTotal Synthesis of the Echinodermatous Ganglioside LLG-3 Possessing the Biological Function of Promoting the Neurite Outgrowth, Synthetic Route of 219543-09-6, the publication is Organic Letters (2020), 22(19), 7491-7495, database is CAplus and MEDLINE.

A total synthesis of echinodermatous ganglioside LLG-3 with neuritogenic activity was accomplished by a convergent strategy. The synthesis of 2-hydroxyethyl 8-O-Me-α-sialoside 2 was started from the Ph 7,8-di-O-Pico-thiosialoside 5, which can be chemoselectively removed the picoloyl group, and then the Me group in 8-O-MeNeu5Ac moiety was chemoselectively prepared using TMSCHN₂/FeCl₃. For preparation of the terminal disialic unit, oxidative amidation was initially utilized by our group to efficiently construct the α(2,11) linkage of 8-O-Me-Neu5Acα(2,11)Neu5Gc. Herein, we also demonstrate that the synthesized ganglioside LLG-3 exhibited the neuritogenic activity toward the primary cortical neurons and that biol. activity is superior to that of ganglioside DSG-A.

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 C13H15NO6S, Synthetic Route of 219543-09-6.

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

Kumar, Chidambaram Ramesh published the artcileThe first total synthesis of cytopiloyne, an anti-diabetic, polyacetylenic glucoside, Name: 1-(Phenylsulfinyl)piperidine, the publication is Chemistry – A European Journal (2011), 17(31), 8696-8703, S8696/1-S8696/29, database is CAplus and MEDLINE.

The first total synthesis of cytopiloyne 1, a novel bioactive polyacetylenic glucoside isolated from the extract of Bidens pilosa, is described. The structure of cytopiloyne was determined to be 2-β-D-glucopyranosyloxy-1-hydroxytrideca-5,7,9,11-tetra-yne by using various spectroscopic methods, but the chirality of the poly-yne moiety was unknown. Herein, the convergent synthesis of two diastereomers of cytopiloyne by starting from com. available 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-diozolane is described. The synthetic sequence involved two key steps: stereoselective glycosylation of the glucosyl trichloroacetimidate with 1-[(4-methoxybenzyl)oxy]hex-5-yn-2-ol to give the desired β-glycoside and the construction of the glucosyl tetra-yne skeleton by using a palladium/silver-catalyzed cross-coupling reaction to form the alkyne-alkyne bond, the first such use of this reaction. Comparison between the observed and published characterization data showed the 2R isomer to be the natural product cytopiloyne.

Chemistry – A European Journal 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, Name: 1-(Phenylsulfinyl)piperidine.

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

Nguyen, Son Hong published the artcileDirect O-glycosylation of resin bound thioglycosides, Product Details of C11H15NOS, the publication is Organic & Biomolecular Chemistry (2012), 10(12), 2373-2376, database is CAplus and MEDLINE.

The application to solid-phase glycoconjugate synthesis is described. The process allows for direct conjugation of resin bound glycans to complex aglycons during cleavage. Large excesses of either coupling partner are not required, and even very hindered alcs. serve as acceptors in the reaction.

Organic & Biomolecular Chemistry 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, Product Details of C11H15NOS.

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

Pulici, Maurizio published the artcileOptimization of Diarylthiazole B-Raf Inhibitors: Identification of a Compound Endowed with High Oral Antitumor Activity, Mitigated hERG Inhibition, and Low Paradoxical Effect, Safety of Piperidine-4-carboxamide, the publication is ChemMedChem (2015), 10(2), 276-295, database is CAplus and MEDLINE.

Aberrant activation of the mitogen-activated protein kinase (MAPK)-mediated pathway components, RAF-MEK-ERK, is frequently observed in human cancers and clearly contributes to oncogenesis. As part of a project aimed at finding inhibitors of B-Raf, a key player in the MAPK cascade, the authors originally identified a thiazole derivative endowed with high potency and selectivity, optimal in vitro ADME properties, and good pharmacokinetic profiles in rodents, but that suffers from elevated hERG inhibitory activity. An optimization program was thus undertaken, focused mainly on the elaboration of the R¹ and R² groups of the scaffold. This effort ultimately led to I, which maintains favorable in vitro and in vivo properties, but lacks hERG liability. Besides exhibiting potent antiproliferative activity against only cell lines bearing B-Raf V600E or V600D mutations, compound I also intriguingly shows a weaker “paradoxical” activation of MEK in nonmutant B-Raf cells than other known B-Raf inhibitors. It also demonstrates very good efficacy in vivo against the A375 xenograft melanoma model (tumor volume inhibition >90% at 10 mg kg^-1); it is therefore a suitable candidate for preclin. development.

ChemMedChem 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, Safety of Piperidine-4-carboxamide.

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