Day: December 6, 2022

Kennedy, Nicole M. published the artcileOptimization of a Series of Mu Opioid Receptor (MOR) Agonists with High G Protein Signaling Bias, Category: piperidines, the publication is Journal of Medicinal Chemistry (2018), 61(19), 8895-8907, database is CAplus and MEDLINE.

While mu opioid receptor (MOR) agonists are especially effective as broad-spectrum pain relievers, it has been exceptionally difficult to achieve a clear separation of analgesia from many problematic side effects. Recently, MOR agonists that induce minimal βarrestin-mediated signaling were extensively investigated because MOR agonist-treated βarrestin2 knockout mice were found to display enhanced antinociceptive effects with significantly less respiratory depression and tachyphylaxis. Substantial data now exists to support the premise that G protein signaling biased MOR agonists can be effective analgesic agents. It was recently shown that, within a chem. series, the degree of bias correlates linearly with the magnitude of the respiratory safety index. Herein, the synthesis and optimization of (piperidinyl)benzimidazolone MOR agonists I (R¹ = H, 4-Cl, 5-Me, 5-CN, 5,6-Cl₂, etc.; R² = H, Me; R³ = Ph, 2-ClC₆H₄, 2-F-4-BrC₆H₃, etc.) and analogs that display a wide range of bias (G/βarr2) is described. The structural features affecting potency and maximizing bias were identified and many compounds were shown to have desirable properties, such as long half-lives and high brain penetration.

Journal of Medicinal 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, Category: piperidines.

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

Belgsir, E. M. published the artcileTEMPO-modified graphite felt electrodes: attempted enantioselective oxidation of rac-1-phenylethanol in the presence of (-)-sparteine, Application In Synthesis of 219543-09-6, the publication is Chemical Communications (Cambridge) (1999), 435-436, database is CAplus.

At a TEMPO-modified graphite felt electrode (TMGFE) rac-1-phenylethanol 2 is not enantioselectively oxidized in the presence of (-)-sparteine 1, but instead 1 is dehydrogenated to its iminium salt; 2 is oxidized in solution by the oxoammonium salt 6 in the absence of 1, but not on the TMGFE in the range 0-1.0 V vs. Ag/AgNO₃.

Chemical Communications (Cambridge) 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 In Synthesis of 219543-09-6.

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

Izzo, Flavia published the artcileA New, Practical One-Pot Synthesis of Unprotected Sulfonimidamides by Transfer of Electrophilic NH to Sulfinamides, Application of 1-(Phenylsulfinyl)piperidine, the publication is Chemistry – A European Journal (2017), 23(60), 15189-15193, database is CAplus and MEDLINE.

Unprotected tertiary sulfonimidamides RS(O)(=NH)X (R = Ph, (CH₃)₂CH, cyclohexyl, 2-pyridyl, etc.; X = 1-piperidinyl, N(CH₃)₂, (CH₃)N(CH₂)₂OCH₃, etc.) have been prepared in good to excellent yields in a one-pot transformation from tertiary sulfinamides RS(O)X through NH transfer. The reaction is mediated by com. available (diacetoxyiodo)benzene and ammonium carbamate in methanol under convenient conditions. A wide range of functional groups is tolerated and initial results indicate that the NH transfer is stereospecific. A small mol. X-ray anal. of 1-(S-phenylsulfonimidoyl)piperidine and its behavior in selected in vitro assays in comparison to the matched 1-benzenesulfonyl-piperidine are also reported. This new reaction provides a safe, short and efficient approach to sulfonimidamides, which have been the subject of recent, growing interest in the life sciences.

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, Application of 1-(Phenylsulfinyl)piperidine.

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

Galvez, Alberto Osuna published the artcileChemoselective Acylation of Primary Amines and Amides with Potassium Acyltrifluoroborates under Acidic Conditions, SDS of cas: 39546-32-2, the publication is Journal of the American Chemical Society (2017), 139(5), 1826-1829, database is CAplus and MEDLINE.

Amides, imides, acylguanidines, an acylcarbamate, an acylsulfonamide, and acylureas were prepared chemoselectively by reaction of aroyltrifluoroborates with primary amines using dichlorodimethylhydantoin or with primary amides, tert-Bu carbamate, guanidines, ureas, or methanesulfonamide using trichlorocyanuric acid (TCA) in buffered aqueous THF at pH 3; chemoselective acylation of primary amines and amides occurred in the presence of alcs., carboxylic acids, and even secondary amines. Streptomycin, gentamicin C₁, and polymyxin B were chemoselectively acylated using the method, showing its potential utility in later-stage functionalization reactions.

Journal of the American Chemical Society 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, SDS of cas: 39546-32-2.

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

Goto, Kenta published the artcileThe Total Synthesis of Starfish Ganglioside GP3 Bearing a Unique Sialyl Glycan Architecture, COA of Formula: C11H15NOS, the publication is Chemistry – A European Journal (2016), 22(24), 8323-8331, database is CAplus and MEDLINE.

The total synthesis of ganglioside GP3, which is found in the starfish Asterina pectinifera, has been accomplished through stereoselective and effective glycosylation reactions. The sialic acid embedded octasaccharide moiety of the target compound was constructed by [4+4] convergent coupling. A tetrasaccharyl donor and acceptor that contained internal sialic acid residues were synthesized with an orthogonally protected N-Troc sialic acid donor as the key common synthetic unit, and they underwent highly stereoselective glycosidation. The resulting sialosides were subsequently transformed into reactive glycosyl acceptors. [4+4] coupling furnished the octasaccharide framework in 91 % yield as a single stereoisomer. Final conjugation of the octasaccharyl donor and glucosyl ceramide acceptor produced the protected target compound in high yield, which underwent global deprotection to successfully deliver ganglioside GP3.

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, COA of Formula: C11H15NOS.

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

Gaonkar, Supreet published the artcileExploring the potential of newly synthesized 4-methyl-6-morpholino-pyrimidine derivatives as antiproliferative agents, Recommanded Product: Piperidine-4-carboxamide, the publication is New Journal of Chemistry (2018), 42(4), 2790-2803, database is CAplus.

In view of exploring the potential of pyrimidine derivatives as anticancer agents, a series of 4-methyl-6-morpholinopyrimidine derivatives was synthesized and characterised by NMR (¹H & ¹³C), SC-XRD and mass spectral anal. The in vitro anticancer activity of these compounds was investigated using different human cancer cell lines, namely HeLa (cervix), NCI-H460 (lung), MCF-7 (breast), HepG2 (liver) and IMR-32 (brain). Compounds 4c and 5h exhibited potent anticancer activity in a dose-dependent manner as compared to other derivatives, with IC₅₀ values of 5.88 ± 1.22 and 6.11 ± 2.12 μM on HeLa and NCI-H460, cells resp. The inhibitory effect of 4c and 5h on cancer cell proliferation was shown to be a consequence of reactive oxygen species (ROS) generation and subsequent induction of cellular apoptosis, as evidenced by an increase in hypodiploid (subG1) population, early apoptotic cell population, caspase-3/7 activity, loss of mitochondrial membrane potential and degradation of nuclear DNA. Furthermore, mol. docking studies revealed that 4c and 5h compounds bind to the ATP binding pocket of the mammalian target of rapamycin (mTOR). Based on our results, we conclude that 4-methyl-6-morpholinopyrimidine derivatives prevent cancer cell proliferation by inducing apoptosis and thus have potential to be further explored for anticancer properties.

New Journal of 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, Recommanded Product: Piperidine-4-carboxamide.

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

Vilar, Santiago published the artcileProbabilistic Neural Network Model for the In Silico Evaluation of Anti-HIV Activity and Mechanism of Action, COA of Formula: C7H15NO, the publication is Journal of Medicinal Chemistry (2006), 49(3), 1118-1124, database is CAplus and MEDLINE.

A theor. model has been developed that discriminates between active and nonactive drugs against HIV-1 with four different mechanisms of action for the active drugs. The model was built up using a probabilistic neural network (PNN) algorithm and a database of 2720 compounds The model showed an overall accuracy of 97.34% in the training series, 85.12% in the selection series, and 84.78% in an external prediction series. The model not only correctly classified a very heterogeneous series of organic compounds but also discriminated between very similar active/nonactive chems. that belong to the same family of compounds More specifically, the model recognized 96.02% of nonactive compounds, 94.24% of active compounds that inhibited reverse transcriptase, 97.24% of protease inhibitors, 97.14% of virus uncoating inhibitors, and 90.32% of integrase inhibitors. The results indicate that this approach may represent a powerful tool for modeling large databases in QSAR with applications in medicinal chem.

Journal of Medicinal Chemistry 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 C16H14O6, COA of Formula: C7H15NO.

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

Lackner, Aaron D. published the artcileSingle-Operation Deracemization of 3H-Indolines and Tetrahydroquinolines Enabled by Phase Separation, Application In Synthesis of 219543-09-6, the publication is Journal of the American Chemical Society (2013), 135(38), 14090-14093, database is CAplus and MEDLINE.

The single-operation deracemization of 3H indolines and tetrahydroquinolines is described. An asym. redox approach was employed, in which a phosphoric acid catalyst, oxidant, and reductant are present in the reaction mixture The simultaneous presence of both oxidant and reductant was enabled by phase separation and resulted in the isolation of highly enantioenriched starting materials in high yields.

Journal of the American Chemical Society 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 In Synthesis of 219543-09-6.

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

Dileep, K. V. published the artcilePiperidine-4-carboxamide as a new scaffold for designing secretory glutaminyl cyclase inhibitors, Application In Synthesis of 39546-32-2, the publication is International Journal of Biological Macromolecules (2021), 415-423, database is CAplus and MEDLINE.

Alzheimer’s disease (AD), a common chronic neurodegenerative disease, has become a major public health concern. Despite years of research, therapeutics for AD are limited. Overexpression of secretory glutaminyl cyclase (sQC) in AD brain leads to the formation of a highly neurotoxic pyroglutamate variant of amyloid beta, pGlu-Aβ, which acts as a potential seed for the aggregation of full length Aβ. Preventing the formation of pGlu-Aβ through inhibition of sQC has become an attractive disease-modifying therapy in AD. In this current study, through a pharmacophore assisted high throughput virtual screening, we report a novel sQC inhibitor (Cpd-41) with a piperidine-4-carboxamide moiety (IC₅₀ = 34μM). Systematic mol. docking, MD simulations and X-ray crystallog. anal. provided atomistic details of the binding of Cpd-41 in the active site of sQC. The unique mode of binding and moderate toxicity of Cpd-41 make this mol. an attractive candidate for designing high affinity sQC inhibitors.

International Journal of Biological Macromolecules 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 In Synthesis of 39546-32-2.

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

Wan, Wen-jing published the artcileImprovement of 2,2,6,6-tetramethyl-4-piperidinamine synthesis via catalytic amination, Product Details of C9H17NO, the publication is Gaoxiao Huaxue Gongcheng Xuebao (2020), 34(2), 457-462, database is CAplus.

2,2,6,6-Tetramethylpiperidinamine as light stabilizer of hindered amines was synthesized via catalytic amination of 2,2,6,6-tetramethylpiperidone. Imine formation was promoted by adjusting reaction system pH, which facilitated the catalytic amination under mild condition. The selectivity of the product was increased. When studied under pH∼12.5, reaction temperature 60°C and pressure 2 MPa, the selectivity of TEMP was up to 95.2%. The result shows that pH=12.5 is the most favorable condition for the formation of TEMP.

Gaoxiao Huaxue Gongcheng Xuebao 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 C20H18BrN3, Product Details of C9H17NO.

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