Day: November 21, 2022

Del Bubba, Massimo published the artcileEnantiomeric resolution of chiral aromatic sulfoxides on non-commercial cellulose tribenzoate plates, Quality Control of 4972-31-0, the publication is Journal of Planar Chromatography–Modern TLC (2012), 25(3), 214-219, database is CAplus.

This paper reports a number of original thin-layer chromatog. enantioseparations of chiral sulfoxides that are important for their use as drugs and drug metabolites, pesticides, or chiral auxiliaries, obtained by elution with alcs. or aqueous-alc. mixtures at different ratios on cellulose tribenzoate. Detection was performed by exposing the plates to iodine vapor, followed by densitometry at 410 nm. Under these exptl. conditions, ten of the eighteen chiral aromatic sulfoxides studied were baseline or partially resolved, thus providing useful chromatog. information for this important class of racemic compounds Data obtained with cellulose tribenzoate were compared to those achieved with microcrystalline cellulose triacetate for the same group of chiral sulfoxides, evidencing an interesting complementary behavior of the two stationary phases.

Journal of Planar Chromatography–Modern TLC 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, Quality Control of 4972-31-0.

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

Demeter, Fruzsina published the artcileAn Efficient Synthesis of the Pentasaccharide Repeating Unit of Pseudomonas aeruginosa Psl Exopolysaccharide, Safety of 1-(Phenylsulfinyl)piperidine, the publication is Synlett (2020), 31(5), 469-474, database is CAplus.

Pseudomonas aeruginosais a biofilm-forming Gram-neg. bacterium and a leading cause of life-threatening nosocomial infections. The polysaccharide synthesis locus (Psl) exopolysaccharide of P. aeruginosais a key constituent of the defending bacterial biofilm layer and is a promising therapeutic target for resistant species. The Psl exopolysaccharide is built up from repeating pentasaccharide units which contain one α- and two β-mannosidic linkages, and one L-rhamnose and one D-glucose moieties. The preparation of this pentasaccharide was first described by Boons et al. in a 34-step synthesis. Based on their work, we have developed a new and effective pathway for the synthesis of the repeating pentasaccharide unit of the Psl exopolysaccharide. We have succeeded in simplifying the synthesis of the L-rhamnose and the α-selective D-mannose building blocks. Furthermore, taking advantage of a chemoselective pre-activation-based β-mannosylation, we directly prepare a thioglycoside disaccharide donor and use it in the next coupling reaction without further transformation. The pentasaccharide, in the form of a p-methoxyphenyl glycoside, is prepared in 26 steps, which is suitable for biol. testing.

Synlett 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

Murugesan, Kathiravan published the artcileA General Catalyst Based on Cobalt Core-Shell Nanoparticles for the Hydrogenation of N-Heteroarenes Including Pyridines, Application of Piperidine-4-carboxamide, the publication is Angewandte Chemie, International Edition (2020), 59(40), 17408-17412, database is CAplus and MEDLINE.

Herein, we report the synthesis of specific silica-supported Co/Co₃O₄ core-shell based nanoparticles prepared by template synthesis of cobalt-pyromellitic acid on silica and subsequent pyrolysis. The optimal catalyst material allows for general and selective hydrogenation of pyridines, quinolines, and other heteroarenes including acridine, phenanthroline, naphthyridine, quinoxaline, imidazo[1,2-a]pyridine, and indole under comparably mild reaction conditions. In addition, recycling of these Co nanoparticles and their ability for dehydrogenation catalysis are showcased.

Angewandte Chemie, International Edition 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, Application of Piperidine-4-carboxamide.

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

Najer, Henri published the artcileSpasmolytically active α-phenyl-α-tertiary-aminoacetates, Application of 1-Ethylpiperidin-3-ol, the publication is Bulletin de la Societe Chimique de France (1958), 355-9, database is CAplus.

cf. C.A. 52, 10073a. To assess their spasmolytic activity with respect to acetylcholine and BaCl₂, beta;-tertiary-aminoethyl β-tertiary-aminoethoxyethyl α-phenyl-α-tertiary-aminoacetate dihydrochlorides, RPhCHCO₂R¹.2HCl (R¹ = CH₂CH₂R²) (I) and (R¹ =CH₂CH₂OCH₂CH₂R²) (II) were prepared Treatment of the appropriate alc in Et₂O at 0° with PhCHClCOCl gave α-phenyl-α-chloroacetate HCl salts, PhCHClCO₂R¹.HCl (R¹ = CH₂CH₂R²) (III), and (R¹ = CH₂CH₂OCH₂CH₂R²) (IV). The unstable corresponding bases (V, VI) refluxed several hrs. in C₆H₆ with a suitable secondary amine gave the bases of I and II (VII, VIII). The toxicity (L.D.₅₀ in mg./kg.) was determined by intravenous injection in white mice according to the method of Kaerber and Behrens. The spasmolytic activity on isolated guinea pig intestine against acetylcholine spasm and BaCl₂ spasm was measured in comparison with Ph₂CHCO₂CH₂CH₂NEt₂.HCl (IX) and papaverine hydrochloride (X), resp. Piperidine (76.5 g.) and 50 g. AcOCH₂CH₂OCH₂CH₂Cl in 75 ml. absolute alc. heated 18 hrs. in a sealed tube, the cooled solution evaporated in vacuo, the residue in 30 ml. H₂O made alk. with 40 ml. 40% Na₂CO₃, the oily product extracted 4 times with 100 ml. Et₂O, the dried extracts (Na₂SO₄) evaporated, the residual oil distilled gave 39.5 g. β-piperidinoethoxyethanol, b₃ 105-6°; HCl salt, m. 120° (Me₂CO) (all m.ps. on Maquenne block). Similarly was prepared 70% β-morpholinoethoxyethanol, b₃ 106-8°; HCl salt, m. 157° (iso-PrOH). PhCHClCOCl (245 g.) in 1 l. anhydrous Et₂O at 0° stirred 1 hr. with gradual addition of 151 g. Et₂NCH₂CH₂OH in 800 ml. Et₂O and the mixture kept 1 hr. at 0° and 24 hrs. at room temperature, filtered, and the Et₂O-washed product air-dried gave III (R² = NEt₂) (IIIa). IIIa (357 g.) in 1 l. H₂O adjusted to pH 9 with saturated aqueous Na₂CO₃ and the oily product extracted 4 times with 500 ml. Et₂O gave 236 g. crude V (R² = NEt₂) (Va) suitable for immediate condensation with the appropriate secondary amine. PhCHClCOCl (48 g.) in 200 ml. Et₂O at 0° stirred with gradual addition in 20 min. of 32 g. β-(1,2,5,6-tetrahydro-1-pyridyl)ethanol (cf. C., et al., loc. cit.) in 200 ml. Et₂O and the mixture kept 30 min. at 0° and 24 hrs. at room temperature gave 50 g. oily III (R² = NC₅H₉). Similarly were prepared the analogous hydrochlorides, III and IV (series, R², m.p. (solvent), and % yield given): III, NEt₂, 123° (iso-BuOH), 91; III, NC₄H₈O (= morpholino), 166° (iso-BuOH), 74; 3-(N-ethylpiperidinyl), 166° (iso-PrOH) (hygroscopic), 99; IV, NEt₂, oil (-), -; IV, NC₅H₁₀ (= piperidino), 116° (AcEt), 98; IV, NC₄H₈O, 84° (EtOAc), 80. Va (56.4 g.) in 250 ml. dry C₆H₆ refluxed 8 hrs. with 34.8 g. 1,2,5,6-tetrahydropyridine, the cooled mixture filtered, the precipitated HCl salt washed repeatedly with dry C₆H₆, the filtrate and washings evaporated in vacuo, the residue in 200 ml. H₂O extracted 3 times with 200 ml. Et₂O and the dried extract evaporated gave VII (R = NC₅H₈, R² = NEt₂), converted in dry Et₂O by passage of dry HCl to the corresponding I; di-HBr salt, m. 197-200° (iso-PrOH). Similarly were prepared the analogous bases VII, VIII and the corresponding di-HCl salts [series, R, R², b.p./mm. and % yield of base, m.p. (solvent) of dihydrochlorides, toxicity (L.D.₅₀), and spasmolytic activity in respect to acetylcholine and BaCl₂ given]: I (Ia), NC₅H₁₀, NEt₂, 163-4°/0.2, 68, 214-15° (alc.-Et₂O), 55, 1.30, 0.9; I (Ib) NC₅H₁₀, NC₅H₁₀, 169-70°/0.4 79, 238° (iso-PrOH), 80, 2, 6; I, NC₅H₁₀, C₇H₁₄N (= 1-ethyl-3-piperidyl), 170-2°/0.5, 61, 235° (alc.-Et₂O), 85, 0.2, 0.2; I, NC₅H₁₀, NC₅H₈, 180-2°/0.5, 90, 227-8° (iso-PrOH), 92, 0.8, 3; I, NC₅H₁₀, NC₄H₈O, 180-3°/0.09, 70, 195-200° (alc.-Et₂O), 205, 0.02, 0.1; II, NC₅H₁₀, NEt₂, 186-7°/0.4, 74, paste (-), 57, 0.75, 1.0; II, NC₅H₁₀, NC₅H₁₀, 190-2°/0.2, 45, 214° (iso-PrOH), 77, 0.10, 0.7; II, NC₅H₁₀, NC₄H₈O, 218-20°/1.0, 72, 211-12° (iso-PrOH), 210, 0.02, 0.2; I, 3-methylpiperidino, NEt₂, 164-6°/0.5-0.6, 68, 227° (alc.-Et₂O), 67.5, 0.25, 1.0; I, 3-methylpiperidino, NC₅H₁₀, 180-2°/0.6-0.8, 69, 229° (alc.-Et₂O), 75, 0.40, 1.2; I, 3-methylpiperidino, C₇H₁₄N, 177/0.4, 64, 216° (alc.-Et₂O), 90, 0.07, 1.0; I, 4-methylpiperidino, NEt₂, 192-3°/3.0, 42, 225° (alc.-EtOAc), 80, 0.75, 6; I, 4-methylpiperidino, NC₅H₁₀, 185-7°/1.0, 67, 239° (alc.-Et₂O), 70, 0.45, 1.0; I, 4-methylpiperidino, C₇H₁₄N, 168-9°/0.2, 61, 233° (alc.-Et₂O), 80, 0.15, 0.8; I, NC₅H₈, NEt₂, 167-70°/0.8-0.9, 69, hygroscopic (iso-PrOH-Et₂O), 97, 1.0, 5.0; I, NC₅H₈, NC₅H₁₀, 215-18°/1.5, 49, 236° (iso-PrOH), 92.5, 1.0, 1.0; I, NC₅H₈, NC₅H₈, 189-90°/0.8, 70, 222-4° (iso-PrOH), 107, 0.5, 4.0; II, NC₅H₈, NEt₂, 189-91°/0.3, 42, 161° (Me₂CO), 55, 0.5, 1.0; II, NC₅H₈, NC₅H₁₀, 199-200°/0.5, 76, hygroscopic (-), 82, 0.05, 1.5; II, NC₅H₈, NC₄H₈O, 203-5°/0.2, 57, 198° (iso-PrOH), 285, 0.01, 0.4 I, NC₄H₈, NEt₂, 138-40°/0.05, 60, 135-40° (hygroscopic), 117.5, 1.0, 1.3; I, NC₄H₈, NC₅H₁₀, 168-70°/0.5, 66, 218° (alc.-Et₂O), 87.5, 1.0, 0.5; I, NC₄H₈, C₇H₁₄N, 160-2°/0.5, 70, hygroscopic (iso-PrOH-Et₂O), 82.5, 0.05, 1.0; I, NC₄H₈O, NEt₂, 154-6°/0.05-0.06, 56, 217° (AcEt-alc.), 275, 0.03, 0.9; I, NC₄H₈O, NC₅H₁₀, 174-6°/0.05, 36, 170-5° (hygroscopic), 138, 0.1, 0.1; I, NC₄H₈O, C₇H₁₄N, 170-4°/0.7, 60, 214° (iso-PrOH-Et₂O), 180, less than 0.1, 0.2. In comparison, IX and X had L.D.₅₀ 42 and 30 and spasmolylic activities 1 against acetylcholine and 1 against BaCl₂, resp. The compounds with most favorable spasmoltyic action are I in which R is piperidino or 1,2,5,6-tetrahydropyridyl, and whatever the nature of R the antiacetylcholenic action is greatest when R² is NEt₂ or piperidino. No particular conclusion was made as to the relation between the nature of R² and the musculotropic activity against BaCl₂. Ib had the most favorable activities of all the compounds examined and had a favorable therapeutic coefficient in comparison with IX and X.

Bulletin de la Societe Chimique de France 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, Application of 1-Ethylpiperidin-3-ol.

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

Falsini, Matteo published the artcileNew 8-amino-1,2,4-triazolo[4,3-a]pyrazin -3-one derivatives. Evaluation of different moieties on the 6-aryl ring to obtain potent and selective human A_2A adenosine receptor antagonists, Product Details of C6H12N2O, the publication is Bioorganic & Medicinal Chemistry Letters (2020), 30(11), 127126, database is CAplus and MEDLINE.

In this work, further structural investigations on the 8-amino-2-phenyl-6-aryl-1,2,4-triazolo[4,3-a]pyrazin-3-one series were carried out to achieve potent and selective human A_2A adenosine receptor (AR) antagonists. Different ether and amide moieties were attached at the para-position of the 6-Ph ring, thus leading to compounds 1-9 and 10-18, resp. Most of these moieties contained terminal basic rings (pyrrolidine, morpholine, piperidine and substituted piperazines) which were thought to confer good physicochem. and drug-like properties. Compounds 11-16, bearing the amide linker, possessed high affinity and selectivity for the hA_2A AR (K_i = 3.6-11.8 nM). Also derivatives 1-9, featuring an ether linker, preferentially targeted the hA_2A AR but with lower affinity, compared to those of the relative amide compounds Docking studies, carried out at the hA_2A AR binding site, highlighted some crucial ligand-receptor interactions, particularly those provided by the appended substituent whose nature deeply affected hA_2A AR affinity.

Bioorganic & Medicinal Chemistry Letters 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, Product Details of C6H12N2O.

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

Loman, Jacob. J. published the artcileA combined computational and experimental investigation of the oxidative ring-opening of cyclic ethers by oxoammonium cations, Recommanded Product: 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Organic & Biomolecular Chemistry (2016), 14(16), 3883-3888, database is CAplus and MEDLINE.

The propensity of oxoammonium cations to facilitate the oxidative ring-opening of cyclic ethers to their corresponding distal hydroxy ketones is investigated. The reaction has been evaluated using exptl. and computational methods to gain deeper insight into trends in reactivity.

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

Winterton, Sarah E. published the artcileDiscovery of Cytochrome P450 4F11 Activated Inhibitors of Stearoyl Coenzyme A Desaturase, COA of Formula: C20H22ClN3O3, the publication is Journal of Medicinal Chemistry (2018), 61(12), 5199-5221, database is CAplus and MEDLINE.

Stearoyl-CoA desaturase (SCD) catalyzes the first step in the conversion of saturated fatty acids to unsaturated fatty acids. Unsaturated fatty acids are required for membrane integrity and for cell proliferation. For these reasons, inhibitors of SCD represent potential treatments for cancer. However, systemically active SCD inhibitors result in skin toxicity, which presents an obstacle to their development. We recently described a series of oxalic acid diamides that are converted into active SCD inhibitors within a subset of cancers by CYP4F11-mediated metabolism Herein, we describe the optimization of the oxalic acid diamides and related N-acyl ureas and an anal. of the structure-activity relationships related to metabolic activation and SCD inhibition.

Journal of Medicinal Chemistry 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 C13H19BN2O3, COA of Formula: C20H22ClN3O3.

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

Li, Guang published the artcileFe₃O₄ supported on water caltrop-derived biochar toward peroxymonosulfate activation for urea degradation: the key role of sulfate radical, Recommanded Product: 2,2,6,6-Tetramethylpiperidin-4-one, the publication is Chemical Engineering Journal (Amsterdam, Netherlands) (2022), 433(Part_2), 133595, database is CAplus.

A new type of iron-doped and porous biochar (Fe@BC) derived from water caltrop was systematically investigated to catalyze the organic pollutants degradation by peroxymonosulfate (PMS). The effectiveness of this novel material was tested by treating excessive urea concentrations in swimming pool water. It exhibited good PMS activation capacity, achieving urea removal of 100% within 15 min. The Fe@BC/PMS system exhibited excellent resistance to common anions. Only chloride showed a small inhibitory effect, and the removal efficiency of urea decreased by 10% ([Cl^–]₀ = 10 mM). Quenching experiments and ESR spectroscopy analyses demonstrated that urea degradation was mainly mediated by the radical pathway, which in turn was dominated by surface-bound sulfate radicals (SO₄^·-). Further, reusability experiments confirmed the stability of the material. After three cycles, the degradation efficiency can still reach 86%. Therefore, the conversion of water caltrop-derived biochar into a composite catalytic material provides a novel strategy for value-added utilization of aquatic waste biomass, and it is also a promising alternative for the treatment of urea from swimming pool water.

Chemical Engineering Journal (Amsterdam, Netherlands) 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, Recommanded Product: 2,2,6,6-Tetramethylpiperidin-4-one.

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

Liang, Huazhe published the artcilePolyamidoamine Immobilized TEMPO Mediated Oxidation of Cellulose: Effect of Macromolecular Catalyst Structure on the Reaction Rate, Oxidation Degree and Degradation Degree, Application In Synthesis of 826-36-8, the publication is Fibers and Polymers (2020), 21(6), 1251-1258, database is CAplus.

A series of polyamidoamine (PAMAM) immobilized TEMPO macromol. catalysts were prepared by condensation reduction reactions between carbonyl groups in 4-O-TEMPO and primary amines in PAMAM. The macromol. catalyst and NaBr/NaClO were used as catalytic system for selective oxidation of cellulose in aqueous medium. Effects of various factors, such as TEMPO loading ratios and PAMAM generations, were studied on the catalytic performances. Compared with free TEMPO, the macromol. catalyst with less than 50% TEMPO loading ratio had a higher reaction rate in the initial stage of the reaction. Especially, the reaction rate of G1.0 PAMAM with 30% TEMPO loading ratio was comparable to free TEMPO in the whole reaction process. Its cellulose oxidation degree (or catalytic activity) was also equivalent to the level of free TEMPO. Interestingly, the cellulose depolymerization degree of macromol. catalyst was not affected by the cellulose oxidation degree and was lower than that of free TEMPO. The macromol. catalyst could be recycled efficiently by the combination of supernatant circulation and salting-out extraction, and the recycling performance was excellent.

Fibers and Polymers 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, Application In Synthesis of 826-36-8.

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

Gandioso, Albert published the artcileA Green Light-Triggerable RGD Peptide for Photocontrolled Targeted Drug Delivery: Synthesis and Photolysis Studies, Product Details of C19H21N, the publication is Journal of Organic Chemistry (2016), 81(23), 11556-11564, database is CAplus and MEDLINE.

We describe for the first time the synthesis and photochem. properties of a coumarin-caged cyclic RGD peptide and demonstrate that uncaging can be efficiently performed with biol. compatible green light. This was accomplished by using a new dicyanocoumarin derivative (DEAdcCE) for the protection of the carboxyl function at the side chain of the aspartic acid residue, which was selected on the basis of Fmoc-tBu SPPS compatibility and photolysis efficiency. The shielding effect of a Me group incorporated in the coumarin derivative near the ester bond linking both moieties in combination with the use of acidic additives such as HOBt or Oxyma during the basic Fmoc-removal treatment were found to be very effective for minimizing aspartimide-related side reactions. In addition, a conjugate between the dicyanocoumarin-caged cyclic RGD peptide and ruthenocene, which was selected as a metallodrug model cargo, has been synthesized and characterized. The fact that green-light triggered photoactivation can be efficiently performed both with the caged peptide and with its ruthenocenoyl bioconjugate reveals great potential for DEAdcCE-caged peptide sequences as selective drug carriers in the context of photocontrolled targeted anticancer strategies.

Journal of Organic Chemistry 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