Tag: M.W=200-250

Sargent, Brendon T. published the artcileCobalt-Catalyzed Aminocarbonylation of Alkyl Tosylates: Stereospecific Synthesis of Amides, Name: tert-Butyl piperidin-4-ylcarbamate, the main research area is amide stereospecific synthesis cobalt catalyzed aminocarbonylation unactivated alkyl tosylate; alkyl tosylates; aminocarbonylation; cobalt; homogenous catalysis; synthetic methods.

Metal-catalyzed aminocarbonylation is a standard approach for installing amide functionality in chem. synthesis. Despite broad application of this transformation using aryl or vinyl electrophiles, there are few examples involving unactivated aliphatic substrates. Furthermore, there are no stereocontrolled aminocarbonylations of alkyl electrophiles known. Herein, we report a stereospecific aminocarbonylation of unactivated alkyl tosylates for the synthesis of enantioenriched amides. This cobalt-catalyzed transformation uses a remarkably broad range of amines and proceeds with excellent stereospecificity and chemoselectivity.

Angewandte Chemie, International Edition published new progress about Acylation. 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Name: tert-Butyl piperidin-4-ylcarbamate.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Onodera, Toshiharu published the artcilePEGylated AdipoRon derivatives improve glucose and lipid metabolism under insulinopenic and high-fat diet conditions, HPLC of Formula: 73874-95-0, the main research area is adiponectin glucose lipid metabolism insulinopenic high fat diet; INS-1 beta cells; adiponectin; ceramides; diabetes; drug optimization; drug therapy/hypolipidemic drugs; high-fat diet; insulin resistance; lipid metabolism; sphingosine-1-phosphate.

The pleiotropic actions of adiponectin in improving cell survival and metabolism have motivated the development of small-mol. therapeutic agents for treating diabetes and lipotoxicity. AdipoRon is a synthetic agonist of the adiponectin receptors, yet is limited by its poor solubility and bioavailability. In this work, we expand on the protective effects of AdipoRon in pancreatic β-cells and examine how structural modifications could affect the activity, pharmacokinetics, and bioavailability of this small mol. We describe a series of AdipoRon analogs containing amphiphilic ethylene glycol (PEG) chains. Among these, AdipoRonPEG5 induced pleiotropic effects in mice under insulinopenic and high-fat diet (HFD) conditions. While both AdipoRon and AdipoRonPEG5 substantially attenuate palmitate-induced lipotoxicity in INS-1 cells, only AdipoRonPEG5 treatment is accompanied by a significant reduction in cytotoxic ceramides. In vivo, AdipoRonPEG5 can substantially reduce pancreatic, hepatic, and serum ceramide species, with a concomitant increase in the corresponding sphingoid bases and improves insulin sensitivity of mice under HFD feeding conditions. Furthermore, hyperglycemia in streptozotocin (STZ)-induced insulinopenic adiponectin-null mice is also attenuated upon AdipoRonPEG5 treatment. Our results suggest that AdipoRonPEG5 is more effective in reducing ceramides and dihydroceramides in the liver of HFD-fed mice than AdipoRon, consistent with its potent activity in activating ceramidase in vitro in INS-1 cells. Addnl., these results indicate that the beneficial effects of AdipoRonPEG5 can be partially attributed to improved pharmacokinetics as compared with AdipoRon, thus suggesting that further derivatization may improve affinity and tissue-specific targeting.

Journal of Lipid Research published new progress about Adipocyte. 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, HPLC of Formula: 73874-95-0.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Kathiravan, Subban published the artcileElectrooxidative Amination of sp2 C-H Bonds: Coupling of Amines with Aryl Amides via Copper Catalysis, Application In Synthesis of 73874-95-0, the main research area is electrooxidative amination amine aryl amide; copper catalyzed cross coupling amine aryl amide.

Metal-catalyzed cross-coupling reactions are among the most important transformations in organic synthesis. However, the use of C-H activation for sp2 C-N bond formation remains one of the major challenges in the field of cross-coupling chem. Described herein is the first example of the synergistic combination of copper catalysis and electrocatalysis for aryl C-H amination under mild reaction conditions in an atom-and step-economical manner with the liberation of H2 as the sole and benign byproduct.

Organic Letters published new progress about Amination. 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Application In Synthesis of 73874-95-0.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Zhou, Xueying published the artcileCu-catalyzed vinylamination of S-alkylisothiouronium salts with maleimides and alkylamines, HPLC of Formula: 73874-95-0, the main research area is aminoalkylthiolated maleimide preparation; alkylisothiouronium salt maleimide alkylamine vinylamination copper catalyst.

A copper-catalyzed vinylamination of S-alkylisothiouronium salts with maleimide and organic amines with the assistance of FeCl3, enabling the preparation of structurally diverse aminoalkylthiolated maleimides and applying them to late-stage modification of pharmaceuticals is reported. Importantly, this strategy makes it possible to introduce the SCD3 functional group into the maleimide skeleton by using the prepared S-trideuteromethyl isothiouronium iodide. Preliminary mechanistic investigation shows that FeCl3 is essential to the current multi-component reaction by triggering S-alkylisothiouronium salts.

Applied Organometallic Chemistry published new progress about Amination. 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, HPLC of Formula: 73874-95-0.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Chen, Kai published the artcileCatalytic Amination of Phenols with Amines, Quality Control of 73874-95-0, the main research area is aryl amine preparation; phenol amine amination rhodium catalyst.

Herein, a rhodium-catalyzed amination of phenols, which provided concise access to diverse anilines, with water as the sole byproduct was described. The arenophilic rhodium catalyst facilitated the inherently difficult keto-enol tautomerization of phenols by means of π-coordination, allowing for the subsequent dehydrative condensation with amines. The generality of this redox-neutral catalysis by carrying out reactions of a large array of phenols with various electronic properties and a wide variety of primary and secondary amines was demonstrated. Several examples of late-stage functionalization of structurally complex bioactive mols., including pharmaceuticals, further illustrated the potential broad utility of the method.

Journal of the American Chemical Society published new progress about Amination. 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Quality Control of 73874-95-0.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Andrews, Jonathan A. published the artcileSulfinates from Amines: A Radical Approach to Alkyl Sulfonyl Derivatives via Donor-Acceptor Activation of Pyridinium Salts, Application of tert-Butyl piperidin-4-ylcarbamate, the main research area is alkyl sulfinate preparation photochem; Katritzky pyridinium salt preparation carbon electrophile alkylation; primary amine triphenylpyrylium tetrafluoroborate amination.

Synthetically versatile alkyl sulfinates RSO2R1 (R = cyclobutyl, Bn, pyridin-2-ylmethyl, etc.; R1 = F, 2-(tert-butoxy)-2-oxoethyl, Ph, Bn, etc.) can be prepared from readily available amines RNH2, using Katritzky pyridinium salt intermediates I. In a catalyst-free procedure, primary, secondary, and benzylic alkyl radicals are generated by photoinduced or thermally induced single-electron transfer (SET) from an electron donor-acceptor (EDA) complex, and trapped by SO2 to generate sulfonyl radicals. Hydrogen atom transfer (HAT) from Hantzsch ester gives alkyl sulfinate products, which are used to prepare a selection of medicinal chem. relevant sulfonyl-containing motifs.

Organic Letters published new progress about Amination. 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Application of tert-Butyl piperidin-4-ylcarbamate.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Zhang, Wenliang published the artcileAmine hydrochloride salts as bifunctional reagents for the radical aminochlorination of maleimides, Quality Control of 73874-95-0, the main research area is pyrrole dione phenyl chloro amino preparation green chem; maleimide amine radical oxidative aminochlorination copper catalyst.

Herein, a new utilization of amine hydrochloride as a bifunctional reagent was disclosed and demonstrated via the copper-catalyzed aminochlorination of maleimides I (R = Me, Ph, cyclohexyl, thiophen-2-ylmethyl, etc.). The prominent features of this transformation were found to include the simple and efficient catalyst system, broad substrate scope, readily scalable reaction, and late-stage modification of small-mol. drugs such as maprotiline hydrochloride, fluoxetine hydrochloride, nortropine hydrochloride, etc.

Organic Chemistry Frontiers published new progress about Amination. 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Quality Control of 73874-95-0.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Ye, Wenjun published the artcileDesign, synthesis and biological evaluation of novel triazoloquinazolinone and imidazoquinazolinone derivatives as allosteric inhibitors of SHP2 phosphatase, Product Details of C10H20N2O2, the main research area is melanoma SHP2 phosphatase triazoloquinazolinone imidazoquinazolinone; SHP2; allosteric inhibitors; antitumor activity; synthesis.

A series of novel triazoloquinolinone and imidazoquinazolinone derivatives were designed and synthesized, and their biol. activities against SHP2 protein and melanoma A357 cell line were evaluated in vitro. The results show that some target compounds have moderate to excellent inhibitory activity on SHP2 protein and melanoma A357 cell line. Structure-activity relationships (SARs) showed that both imidazoquinazolinone and triazoloquinazolinone derivatives have good SHP2 protein kinase and melanoma cell line A357 inhibitory activity. The results of mol. docking also showed that the cores of imidazoquinazolinone and triazoloquinazolinone have a certain affinity for SHP2 protein at the same time. Compared with SHP244, the target compounds have quite good liver microsomal stability and has more drug potential. The most promising compound has a strong inhibitory effect on the melanoma cell line A357 at 100 μM (76.15% inhibition).

Journal of Enzyme Inhibition and Medicinal Chemistry published new progress about Melanoma. 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Product Details of C10H20N2O2.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Wong, Siu Wai published the artcileDevelopment of [18F]MIPS15692, a radiotracer with in vitro proof-of-concept for the imaging of MER tyrosine kinase (MERTK) in neuroinflammatory disease, HPLC of Formula: 73874-95-0, the main research area is neuroinflammatory disease MER tyrosine kinase 18F MIPS15692 radiotracer; Autoradiography; CNS radiotracer; MER tyrosine Kinase; Multiple sclerosis; Positron emission tomography; X-ray crystallography.

MER tyrosine kinase (MERTK) upregulation is associated with M2 polarization of microglia, which plays a vital role in neuroregeneration following damage induced by neuroinflammatory diseases such as multiple sclerosis (MS). Therefore, a radiotracer specific for MERTK could be of great utility in the clin. management of MS, for the detection and differentiation of neuroregenerative and neurodegenerative processes. This study aimed to develop an [18F] ligand with high affinity and selectivity for MERTK as a potential positron emission tomog. (PET) radiotracer. MIPS15691 and MIPS15692 were synthesized and kinase assays were utilized to determine potency and selectivity for MERTK. Both compounds were shown to be potent against MERTK, with resp. IC50 values of 4.6 nM and 4.0 nM, and were also MERTK-selective. Plasma and brain pharmacokinetics were measured in mice and led to selection of MIPS15692 over MIPS15691. X-ray crystallog. was used to visualize how MIPS15692 is recognized by the enzyme. [18F]MIPS15692 was synthesized using an automated iPHASE FlexLab module, with a molar activity (Am) of 49 ± 26 GBq/μmol. The radiochem. purity of [18F]MIPS15692 was >99% and the decay-corrected radiochem. yields (RCYs) were determined as 2.45 ± 0.85%. Brain MERTK protein d. was measured by a saturation binding assay in the brain slices of a cuprizone mouse model of MS. High levels of specific binding of [18F]MIPS15692 to MERTK were found, especially in the corpus callosum/hippocampus (CC/HC). The in vivo PET imaging study of [18F]MIPS15692 suggested that its neuroPK is sub-optimal for clin. use. Current efforts are underway to optimize the neuroPK of our next generation PET radiotracers for maximal in vivo utility.

European Journal of Medicinal Chemistry published new progress about Blood plasma. 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, HPLC of Formula: 73874-95-0.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Pasqualetto, Gaia published the artcileLigand-based rational design, synthesis and evaluation of novel potential chemical chaperones for opsin, Recommanded Product: tert-Butyl piperidin-4-ylcarbamate, the main research area is rhodopsin binding site chromophore preparation chem chaperone opsin; cyclohexene preparation rhodopsin binding site chromophore chem chaperone opsin; Molecular modelling; Rhodopsin; Severe inherited blinding diseases; Small-molecule agents; Synthetic organic chemistry.

Inherited blinding diseases retinitis pigmentosa (RP) and a subset of Leber’s congenital amaurosis (LCA) are caused by the misfolding and mistrafficking of rhodopsin mols., which aggregate and accumulate in the endoplasmic reticulum (ER), leading to photoreceptor cell death. One potential therapeutic strategy to prevent the loss of photoreceptors in these conditions is to identify opsin-binding compounds that act as chem. chaperones for opsin, aiding its proper folding and trafficking to the outer cell membrane. Aiming to identify novel compounds with such effect, a rational ligand-based approach was applied to the structure of the visual pigment chromophore, 11-cis-retinal, and its locked analog 11-cis-6mr-retinal. Following mol. docking studies on the main chromophore binding site of rhodopsin, 49 novel compounds, e.g., I, were synthesized according to optimized one-to seven-step synthetic routes. These agents were evaluated for their ability to compete for the chromophore binding site of opsin, and their capacity to increase the trafficking of the P23H opsin mutant from the ER to the cell membrane. Different new mols. displayed an effect in at least one assay, acting either as chem. chaperones or as stabilizers of the 9-cis-retinal-rhodopsin complex. These compounds could provide the basis to develop novel therapeutics for RP and LCA.

European Journal of Medicinal Chemistry published new progress about Cytotoxicity. 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Recommanded Product: tert-Butyl piperidin-4-ylcarbamate.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem