Month: November 2022

Gorski, Bartosz published the artcileCopper-catalysed amination of alkyl iodides enabled by halogen-atom transfer, Synthetic Route of 170364-89-3, the publication is Nature Catalysis (2021), 4(7), 623-630, database is CAplus.

Here, an alternative amination strategy was demonstrated for the synthesis of alkyl amines, e.g., I where alkyl iodides are used as radical precursors instead of electrophiles. Use of α-aminoalkyl radicals enabled the efficient conversion of the iodides into the corresponding alkyl radical by halogen-atom transfer, while copper catalysis assembled the sp³ C-N bonds at room temperature The process provided SN²-like programmability, and application in late-stage functionalization of several densely functionalized pharmaceuticals demonstrated its utility in the preparation of valuable N-alkylated drug analogs.

Nature Catalysis 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, Synthetic Route of 170364-89-3.

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

Bobbitt, James M. published the artcileOxoammonium Salt Oxidations of Alcohols in the Presence of Pyridine Bases, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Journal of Organic Chemistry (2014), 79(3), 1055-1067, database is CAplus and MEDLINE.

Oxidations of alcs. containing a β-oxygen atom with the oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate in the presence of pyridine yielded dimeric esters, while in the presence of 2,6-lutidine the oxidations yielded aldehydes. The changes in oxidation reactivity with the steric hindrance of the pyridine catalyst are explained by formation of betaines between unhindered pyridines and aldehydes which undergo oxidation to acylpyridinium ions followed by substitution reactions with the starting alcs. to yield esters; hindered pyridines do not form betaines with aldehydes and so do not react further. Six alcs. containing β-oxygen substituents were oxidized chemoselectively to aldehydes in the presence of 2,6-lutidine. The relative reactivities of a set of alcs. toward oxoammonium ion-mediated oxidation was determined An overall mechanism for oxoammonium cation oxidations is suggested based on the premise that nucleophilic additions to the oxoammonium ions occur by addition to the oxygen atom of the pos. charged nitrogen-oxygen double bond; possible mechanisms for oxidations of β-alkoxy alcs. to aldehydes and esters are given. Transition state structures and free energies of transition states and products were calculated for two of three potential mechanisms.

Journal of Organic 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, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate.

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

Shannon, Simon K. published the artcile4-(9-Fluorenylmethyloxycarbonyl)phenylhydrazine (FmPH): A New Chromophoric Reagent for Quantitative Monitoring of Solid-Phase Aldehydes, Formula: C19H21N, the publication is Journal of Organic Chemistry (2004), 69(14), 4586-4594, database is CAplus and MEDLINE.

A direct method for quantifying solid-phase aldehydes was developed, using a new reagent, 4-(9-fluorenylmethyloxycarbonyl)phenylhydrazine (FmPH). The FmPH reagent was synthesized in three steps (24% overall yield) from com. available p-hydrazinobenzoic acid. Resin-bound aldehydes reacted quant. with FmPH, in the presence of trimethylorthoformate (TMOF) as a dehydrating agent, to form a highly conjugated, immobilized FmPH-hydrazone. Next, mild treatment of the hydrazone with an excess of piperidine-DMF (1:1) released the piperidine-dibenzofulvene adduct chromophore (ε_301nm = 7800 M^-1 cm^-1) from the support. FmPH quantitation of aldehydes proved to be a straightforward, sensitive, and reproducible technique for monitoring resin-bound aldehydes [albeit insufficiently reactive to allow reliable quantification of ketones]. The FmPH aldehyde assay is applicable to a range of solid supports, as demonstrated specifically for poly(ethylene glycol)-polystyrene (PEG-PS), aminomethylpolystyrene (AMP), and cross-linked ethoxylate acrylate resin (CLEAR).

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 C9H13NO2, Formula: C19H21N.

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

Billin, Andrew N. published the artcileDiscovery of Novel Small Molecules that Activate Satellite Cell Proliferation and Enhance Repair of Damaged Muscle, Name: (1-Methylpiperidin-3-yl)methanamine, the publication is ACS Chemical Biology (2016), 11(2), 518-529, database is CAplus and MEDLINE.

Skeletal muscle progenitor stem cells (referred to as satellite cells) represent the primary pool of stem cells in adult skeletal muscle responsible for the generation of new skeletal muscle in response to injury. Satellite cells derived from aged muscle display a significant reduction in regenerative capacity to form functional muscle. This decrease in functional recovery has been attributed to a decrease in proliferative capacity of satellite cells. Hence, agents that enhance the proliferative abilities of satellite cells may hold promise as therapies for a variety of pathol. settings, including repair of injured muscle and age- or disease-associated muscle wasting. Through phenotypic screening of isolated murine satellite cells, we identified a series of 2,4-diaminopyrimidines (e.g., 2) that increased satellite cell proliferation. Importantly, compound 2 was effective in accelerating repair of damaged skeletal muscle in an in vivo mouse model of skeletal muscle injury. While these compounds were originally prepared as c-Jun N-terminal kinase 1 (JNK-1) inhibitors, structure-activity analyses indicated JNK-1 inhibition does not correlate with satellite cell activity. Screening against a broad panel of kinases did not result in identification of an obvious mol. target, so we conducted cell-based proteomics experiments in an attempt to identify the mol. target(s) responsible for the potentiation of the satellite cell proliferation. These data provide the foundation for future efforts to design improved small mols. as potential therapeutics for muscle repair and regeneration.

ACS Chemical Biology published new progress about 14613-37-7. 14613-37-7 belongs to piperidines, auxiliary class Piperidine,Amine, name is (1-Methylpiperidin-3-yl)methanamine, and the molecular formula is C7H16N2, Name: (1-Methylpiperidin-3-yl)methanamine.

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

Hu, Ziwei published the artcileIdentification of Human Toll-like Receptor 2-Agonistic Activity in Dihydropyridine-Quinolone Carboxamides, Formula: C7H16N2, the publication is ACS Medicinal Chemistry Letters (2019), 10(1), 132-136, database is CAplus and MEDLINE.

Using a multiplexed, reporter gene-based, high-throughput screen, we identified 9-fluoro-7-hydroxy-3-methyl-5-oxo-N-(pyridin-3-ylmethyl)-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxamide as a TLR2 agonist. Preliminary structure-activity relationship studies on the carboxamide moiety led to the identification of analogs that induce chemokines and cytokines in a TLR2-dependent manner. These results represent new leads for the development of vaccine adjuvants.

ACS Medicinal Chemistry Letters published new progress about 14613-37-7. 14613-37-7 belongs to piperidines, auxiliary class Piperidine,Amine, name is (1-Methylpiperidin-3-yl)methanamine, and the molecular formula is C7H16N2, Formula: C7H16N2.

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

Crich, David published the artcileImproved synthesis of 1-benzenesulfinyl piperidine and analogs for the activation of thioglycosides in conjunction with trifluoromethanesulfonic anhydride, Related Products of piperidines, the publication is Journal of Carbohydrate Chemistry (2005), 24(4-6), 415-424, database is CAplus and MEDLINE.

An improved protocol for the large-scale production of 1-benzenesulfinyl piperidine and other sulfinamides is described. It is demonstrated that 1-benzenesulfinyl pyrrolidine and N,N-di-Et benzenesulfinamide function analogously to 1-benzenesulfinyl piperidine in the trifluoromethanesulfonic anhydride-mediated activation of thioglycosides, and that their less crystalline nature enables them to be used at -78°C as opposed to the -60°C required to keep 1-benzenesulfinyl piperidine in solution N,N-Dicyclohexyl benzenesulfinamide does not activate thioglycosides in combination with trifluoromethanesulfonic anhydride, which is attributed to its greater steric bulk.

Journal of Carbohydrate 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, Related Products of piperidines.

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

Crich, David published the artcileDirect Chemical Synthesis of the β-D-Mannans: The β-(1→2) and β-(1→4) Series, Safety of 1-(Phenylsulfinyl)piperidine, the publication is Journal of the American Chemical Society (2004), 126(45), 14930-14934, database is CAplus and MEDLINE.

The direct syntheses of a β-(1→2)-mannooctaose and of a β-(1→4)-mannohexaose are reported by means of 4,6-O-benzylidene-protected β-mannosyl donors. The synthesis of the (1→2)-mannan was achieved by means of the sulfoxide coupling protocol, whereas the (1→4)-mannan was prepared using the analogous thioglycoside/sulfinamide methodol. In the synthesis of the (1→4)-mannan, the glycosylation yields and stereoselectivities remain approx. constant with increasing chain length, whereas those for the (1→2)-mannan consist of two groups with the formation of the tetra- and higher saccharides giving yields and selectivities consistently lower than those of the lower homologs. The decrease in yield after the trisaccharide in the (1→2)-mannan synthesis is attributed to steric interference by the n-3 residue and is consistent with the collapsed, disordered structure predicted by early computational work. The consistently high yields and selectivities seen in the synthesis of the (1→4)-mannan are congruent with the more open, ordered structure originally predicted for this polymer. The lack of order in the structure of the (1→2)-mannan, as compared to the high degree of order in the (1→4)-mannan, is also evident from a comparison of the NMR spectra of the two polymers and even from their phys. nature: the (1→2)-mannan is a gum and the (1→4)-mannan is a high melting solid.

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 C11H15NOS, Safety of 1-(Phenylsulfinyl)piperidine.

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

Hopkins, Brian T. published the artcileDiscovery and Preclinical Characterization of BIIB091, a Reversible, Selective BTK Inhibitor for the Treatment of Multiple Sclerosis, Related Products of piperidines, the publication is Journal of Medicinal Chemistry (2022), 65(2), 1206-1224, database is CAplus and MEDLINE.

Multiple Sclerosis is a chronic autoimmune neurodegenerative disorder of the central nervous system (CNS) that is characterized by inflammation, demyelination, and axonal injury leading to permeant disability. In the early stage of MS, inflammation is the primary driver of the disease progression. There remains an unmet need to develop high efficacy therapies with superior safety profiles to prevent the inflammation processes leading to disability. Herein, we describe the discovery of BIIB091 (I), a structurally distinct orthosteric ATP competitive, reversible inhibitor that binds the BTK protein in a DFG-in confirmation designed to sequester Tyr-551, an important phosphorylation site on BTK, into an inactive conformation with excellent affinity. Preclin. studies demonstrated BIB091 to be a high potency mol. with good drug-like properties and a safety/tolerability profile suitable for clin. development as a highly selective, reversible BTKi for treating autoimmune diseases such as MS.

Journal of Medicinal Chemistry published new progress about 1971920-73-6. 1971920-73-6 belongs to piperidines, auxiliary class Other Aliphatic Heterocyclic,Piperidine,Alkenyl,Amine,Benzene,Ether,Inhibitor,Inhibitor, name is (R)-1-(1-Acryloylpiperidin-3-yl)-4-amino-3-(4-phenoxyphenyl)-1H-imidazo[4,5-c]pyridin-2(3H)-one, and the molecular formula is C26H25N5O3, Related Products of piperidines.

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

Spencer, John published the artcileMicrowave-mediated synthesis of an arylboronate library, Formula: C18H28BNO2, the publication is ACS Combinatorial Science (2011), 13(1), 24-31, database is CAplus and MEDLINE.

A series of arylboronates has been synthesized from the reaction of 2-(2-, (3-, or (4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane resp. with a range of N-, S-, and O-nucleophiles, using microwave-mediated chem. For the synthesis of N- and S-substituted boronates, a supported base, PS-NMM, was employed, and many reactions were complete within 15 min. With O-nucleophiles, a mixture of tetrabutylammonium bromide, potassium carbonate, and sodium hydroxide was employed. The resulting aminomethyl, mercaptomethyl, or alkoxy-/phenoxymethyl-arylboronates were subjected to microwave-mediated Suzuki Miyaura coupling reactions to afford a range of biaryls in moderate to good yields. The x-ray structures of five boronates were determined

ACS Combinatorial Science 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 C6H12Br2, Formula: C18H28BNO2.

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

Wu, Wenjie published the artcileDefect-Engineered Graphene Films as Ozonation Catalysts for the Devastation of Sulfamethoxazole: Insights into the Active Sites and Oxidation Mechanism, Product Details of C9H17NO, the publication is ACS Applied Materials & Interfaces (2021), 13(44), 52706-52716, database is CAplus and MEDLINE.

Graphene-based catalysts have been widely applied for catalytic ozonation. However, as it is difficult to obtain graphene with high structural precision, it is currently unfeasible to comprehend the relationships between the intrinsic structure of the layered carbon catalysts with its catalytic activities. Here, an advanced plasma-assisted etch strategy was used to fine tune the ozonation activity of monolayered graphene films by tailoring the defect types. Raman mapping indicated that the defects of the as-prepared monolayered graphene films were predominantly sp³, vacancy, and boundary-type defects, resp. The roles and contributions of these active defects in manipulating the oxidative potential of monolayered graphene films were revealed by quenching experiments, ESR results, and d. functional theory calculations The catalytic results showed that the monolayered graphene films with boundary-like defects exhibited the best catalytic performance toward the degradation of sulfamethoxazole. This work contributes new insights into the design of high-efficiency carbonaceous catalysts by structuring addnl. defective sites.

ACS Applied Materials & Interfaces 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 C15H20O6, Product Details of C9H17NO.

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