Category: piperidines

Straightforward and scalable synthesis of orthogonally protected 3,7-diazabicyclo[4.1.0]heptane was written by Schramm, Heiko;Pavlova, Maria;Hoenke, Christoph;Christoffers, Jens. And the article was included in Synthesis in 2009.Name: N-Cbz-7-oxa-3-azabicyclo[4.1.0]heptane This article mentions the following:

Orthogonally N-protected (Boc and Cbz) 3,4-aziridinopiperidine is a versatile building block for the synthesis of 4-substituted 3-aminopiperidines, which are compounds with a high potential for biol. activity. A multigram synthesis over five steps, starting with extraordinarily simple materials (pyridine and benzyl chloride), was developed. In the experiment, the researchers used many compounds, for example, N-Cbz-7-oxa-3-azabicyclo[4.1.0]heptane (cas: 66207-08-7Name: N-Cbz-7-oxa-3-azabicyclo[4.1.0]heptane).

N-Cbz-7-oxa-3-azabicyclo[4.1.0]heptane (cas: 66207-08-7) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. Fluorinated piperidines are also the subject of continued interest in medicinal chemistry, for example in the synthesis of selective dipeptidyl peptidase II (DPP II) inhibitors. Piperidine derivatives are also used in solid-phase peptide synthesis (SPPS) and many degradation reactions.Name: N-Cbz-7-oxa-3-azabicyclo[4.1.0]heptane

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

The chemistry and pharmacology of some 4-aminopiperidines and their derivatives was written by Harper, Norman J.;Chignell, Colin F.. And the article was included in Journal of Medicinal Chemistry in 1964.Category: piperidines This article mentions the following:

A number of 4-aminopiperidines and their derivatives (I) have been synthesized and assessed pharmacol. for central nervous system activity. These compounds were prepared from the corresponding piperidones, which were converted to their oximes and then reduced to the amino compounds In the experiment, the researchers used many compounds, for example, 1-Benzylpiperidin-4-one oxime (cas: 949-69-9Category: piperidines).

1-Benzylpiperidin-4-one oxime (cas: 949-69-9) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst. Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Non-oxime pyrazole based inhibitors of B-Raf kinase was written by Newhouse, Bradley J.;Hansen, Joshua D.;Grina, Jonas;Welch, Mike;Topalov, George;Littman, Nicole;Callejo, Michele;Martinson, Matthew;Galbraith, Sarah;Laird, Ellen R.;Brandhuber, Barbara J.;Vigers, Guy;Morales, Tony;Woessner, Rich;Randolph, Nikole;Lyssikatos, Joseph;Olivero, Alan. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Recommanded Product: N-Cbz-7-oxa-3-azabicyclo[4.1.0]heptane This article mentions the following:

The synthesis and biol. evaluation of non-oxime pyrazole based B-Raf inhibitors is reported. Several oxime replacements have been prepared and have shown excellent enzyme activity. Further optimization of fused pyrazole 2a led to compound 38 (I), a selective and potent B-Raf inhibitor. In the experiment, the researchers used many compounds, for example, N-Cbz-7-oxa-3-azabicyclo[4.1.0]heptane (cas: 66207-08-7Recommanded Product: N-Cbz-7-oxa-3-azabicyclo[4.1.0]heptane).

N-Cbz-7-oxa-3-azabicyclo[4.1.0]heptane (cas: 66207-08-7) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising 伪-glucosidase inhibitors. The former are analogs of DNJ with an improved 伪-glucosidase inhibitory profile than that of DNJ. Boisson et al.Recommanded Product: N-Cbz-7-oxa-3-azabicyclo[4.1.0]heptane

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Antidepressant-like actions of the polyamine site NMDA antagonist, eliprodil (SL-82.0715) was written by Layer, Richard T.;Popik, Piotr;Olds, Tia;Skolnick, Phil. And the article was included in Pharmacology, Biochemistry and Behavior in 1995.Category: piperidines This article mentions the following:

Functional N-methyl-D-aspartate (NMDA) antagonists including competitive antagonists, glycine partial agonists, and use-dependent channel blockers exhibit antidepressant-like actions in preclin. models. The present study examined the effects of eliprodil (SL-82.0715), an NMDA antagonist acting at polyamine sites, in behavioral and neurochem. tests predictive of antidepressant activity. In mice, eliprodil produced a dose-dependent reduction in immobility in the forced swim test, but was inactive in the tail suspension test. Chronic treatment with eliprodil produced both a significant down-regulation of 尾-adrenoreceptors and a reduction in the potency of glycine to inhibit [³H]5,7-dichlorokynurenic acid binding to strychnine-insensitive glycine receptors in neocortical membranes. In toto, these data indicate that like other NMDA antagonists, eliprodil possess antidepressant-like actions in preclin. tests predictive of clin. efficacy. In the experiment, the researchers used many compounds, for example, 1-(4-Chlorophenyl)-2-(4-(4-fluorobenzyl)piperidin-1-yl)ethan-1-ol (cas: 119431-25-3Category: piperidines).

1-(4-Chlorophenyl)-2-(4-(4-fluorobenzyl)piperidin-1-yl)ethan-1-ol (cas: 119431-25-3) belongs to piperidine derivatives. Piperidine has a role as a reagent, a protic solvent, a base, a catalyst, a plant metabolite, a human metabolite and a non-polar solvent. Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst. Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Transition metal-free methylation of amines with formaldehyde as the reductant and methyl source was written by Man, Nikki Y. T.;Li, Wanfang;Stewart, Scott G.;Wu, Xiao-Feng. And the article was included in Chimia in 2015.Application of 79-55-0 This article mentions the following:

A simple transition metal-free procedure using formaldehyde for the N,N-dimethylation and N-methylation of primary and secondary anilines is reported. The reaction showed limitations on sterically hindered and electron-withdrawing anilines, but is successful on amines with electron-donating substituents. Formaldehyde acts as both the reducing agent and the carbon source in the reaction. In the experiment, the researchers used many compounds, for example, 1,2,2,6,6-Pentamethylpiperidine (cas: 79-55-0Application of 79-55-0).

1,2,2,6,6-Pentamethylpiperidine (cas: 79-55-0) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Piperidine derivatives bearing a masked aldehyde function in the 蔚-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Application of 79-55-0

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Double-Network Hydrogels Including Enzymatically Crosslinked Poly-(2-alkyl-2-oxazoline)s for 3D Bioprinting of Cartilage-Engineering Constructs was written by Trachsel, Lucca;Johnbosco, Castro;Lang, Thamar;Benetti, Edmondo M.;Zenobi-Wong, Marcy. And the article was included in Biomacromolecules in 2019.Formula: C8H15NO2 This article mentions the following:

Double-network (DN) hydrogels are fabricated from poly(2-ethyl-2-oxazoline) (PEOXA)-peptide conjugates, which can be enzymically crosslinked in the presence of Sortase A (SA), and phys. networks of alginate (Alg), yielding matrixes with improved mech. properties with respect to the corresponding PEOXA and Alg single networks and excellent cell viability of encapsulated human auricular chondrocytes (hACs). The addition of a low content of cellulose nanofibrils (CNFs) within DN hydrogel formulations provides the rheol. properties needed for extrusion-based three-dimensional (3D) printing, generating constructs with a good shape fidelity. In the presence of hACs, PEOXA-Alg-CNF prehydrogel mixtures can be bioprinted, finally generating 3D-structured DN hydrogel supports showing a cell viability of more than 90%. Expanding the application of poly(2-alkyl-2-oxazoline)-based formulations in the design of tissue-engineering constructs, this study further demonstrates how SA-mediated enzymic crosslinking represents a suitable and fully orthogonal method to generate biocompatible hydrogels with fast kinetics. In the experiment, the researchers used many compounds, for example, Ethyl piperidine-4-carboxylate (cas: 1126-09-6Formula: C8H15NO2).

Ethyl piperidine-4-carboxylate (cas: 1126-09-6) belongs to piperidine derivatives. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. Piperidine derivatives bearing a masked aldehyde function in the 蔚-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Formula: C8H15NO2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Decarboxylative and Deaminative Alkylation of Difluoroenoxysilanes via Photoredox Catalysis: A General Method for Site-Selective Synthesis of Difluoroalkylated Alkanes was written by Song, Heng;Cheng, Ran;Min, Qiao-Qiao;Zhang, Xingang. And the article was included in Organic Letters in 2020.Synthetic Route of C19H22N2O6 This article mentions the following:

A general method for site-selective difluoroalkylation of alkyl carboxylic redox esters with difluoroenoxysilanes through photoredox-catalyzed decarboxylative reaction has been developed. The reaction can also be extended to aliphatic amine derived pyridinium salts. This method has the advantages of high efficiency, mild reaction conditions, and broad substrate scope, including primary, secondary, and sterically hindered tertiaryl alkyl substrates, providing a general and practical route for applications in organic synthesis and pharmaceutical studies. In the experiment, the researchers used many compounds, for example, 1-(tert-Butyl) 4-(1,3-dioxoisoindolin-2-yl) piperidine-1,4-dicarboxylate (cas: 1872262-73-1Synthetic Route of C19H22N2O6).

1-(tert-Butyl) 4-(1,3-dioxoisoindolin-2-yl) piperidine-1,4-dicarboxylate (cas: 1872262-73-1) belongs to piperidine derivatives. The piperidine ring can be found not only in more than half of the currently known structures of alkaloids, but also in many natural or synthetic compounds with interesting biological activities. Piperidine derivatives are being utilized in different ways as anticancer, antiviral, antimalarial, antimicrobial, antifungal, antihypertension, analgesic, anti-inflammatory, anti-Alzheimer, antipsychotic and/or anticoagulant agents.Synthetic Route of C19H22N2O6

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

General procedure for the synthesis of spirocyclic 3-hydroxy- and 3-oxotetrahydrofurans containing carbo- and heterocyclic fragments was written by Moskalenko, A. I.;Belopukhov, S. L.;Ivlev, A. A.;Boev, V. I.. And the article was included in Russian Journal of Organic Chemistry in 2011.Product Details of 203662-51-5 This article mentions the following:

Reactions of cyclopentanone, cyclohexanone, N-substituted pyrrolidin-3-one and piperidin-4-one, and tetrahydropyran-4-one with allyl bromide in the presence of zinc and ammonium chloride gave the corresponding geminal hydroxy allyl derivatives Treatment of the latter with sodium periodate in the presence of sodium metabisulfite resulted in their oxidative cyclization with formation of oxa spirocyclic alcs. containing carbo- and heterocyclic fragments. Swern oxidation of the spiro alcs. afforded the corresponding ketones which were characterized as 2,4-dinitrophenylhydrazones. In the experiment, the researchers used many compounds, for example, 4-Allyl-1-Boc-4-hydroxypiperidine (cas: 203662-51-5Product Details of 203662-51-5).

4-Allyl-1-Boc-4-hydroxypiperidine (cas: 203662-51-5) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Fluorinated piperidines are also the subject of continued interest in medicinal chemistry, for example in the synthesis of selective dipeptidyl peptidase II (DPP II) inhibitors. Piperidine derivatives are also used in solid-phase peptide synthesis (SPPS) and many degradation reactions.Product Details of 203662-51-5

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Exploring Ugi-Azide Four-Component Reaction Products for Broad-Spectrum Influenza Antivirals with a High Genetic Barrier to Drug Resistance was written by Zhang, Jiantao;Hu, Yanmei;Foley, Christopher;Wang, Yuanxiang;Musharrafieh, Rami;Xu, Shuting;Zhang, Yongtao;Ma, Chunlong;Hulme, Christopher;Wang, Jun. And the article was included in Scientific Reports in 2018.Product Details of 17403-09-7 This article mentions the following:

Influenza viruses are respiratory pathogens that are responsible for seasonal influenza and sporadic influenza pandemic. The therapeutic efficacy of current influenza vaccines and small mol. antiviral drugs is limited due to the emergence of multidrug-resistant influenza viruses. In response to the urgent need for the next generation of influenza antivirals, we utilized a fast-track drug discovery platform by exploring multi-component reaction products for antiviral drug candidates. Specifically, mol. docking was applied to screen a small mol. library derived from the Ugi-azide four-component reaction methodol. for inhibitors that target the influenza polymerase PA_C-PB1_N interactions. One hit compound 5 was confirmed to inhibit PA_C-PB1_N interactions in an ELISA assay and had potent antiviral activity in an antiviral plaque assay. Subsequent structure-activity relationship studies led to the discovery of compound 12a, which had broad-spectrum antiviral activity and a higher in vitro genetic barrier to drug resistance than oseltamivir. Overall, the discovery of compound 12a as a broad-spectrum influenza antiviral with a high in vitro genetic barrier to drug resistance is significant, as it offers a second line of defense to combat the next influenza epidemics and pandemics if vaccines and oseltamivir fail to confine the disease outbreak. In the experiment, the researchers used many compounds, for example, 3-(Piperidin-4-yl)-1H-indole (cas: 17403-09-7Product Details of 17403-09-7).

3-(Piperidin-4-yl)-1H-indole (cas: 17403-09-7) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising 伪-glucosidase inhibitors. The former are analogs of DNJ with an improved 伪-glucosidase inhibitory profile than that of DNJ. Boisson et al.Product Details of 17403-09-7

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Electrocatalytic Alcohol Oxidation with TEMPO and Bicyclic Nitroxyl Derivatives: Driving Force Trumps Steric Effects was written by Rafiee, Mohammad;Miles, Kelsey C.;Stahl, Shannon S.. And the article was included in Journal of the American Chemical Society in 2015.Application In Synthesis of 4-Acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl This article mentions the following:

Bicyclic nitroxyl derivatives, such as 2-azaadamantane N-oxyl (AZADO) and 9-azabicyclo[3.3.1]nonane N-oxyl (ABNO), have emerged as highly effective alternatives to TEMPO-based catalysts for selective oxidation reactions (TEMPO = 2,2,6,6-tetramethyl-1-piperidine N-oxyl). Their efficacy is widely attributed to their smaller steric profile; however, electrocatalysis studies described herein show that the catalytic activity of nitroxyls is more strongly affected by the nitroxyl/ oxoammonium redox potential than by steric effects. The inexpensive, high-potential TEMPO derivative, 4-acetamido-TEMPO (ACT), exhibits higher electrocatalytic activity than AZADO and ABNO for the oxidation of primary and secondary alcs. Mechanistic studies provide insights into the origin of these unexpected reactivity trends. The superior activity of ACT is especially noteworthy at high pH, where bicyclic nitroxyls are inhibited by formation of an oxoammonium hydroxide adduct. In the experiment, the researchers used many compounds, for example, 4-Acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl (cas: 14691-89-5Application In Synthesis of 4-Acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl).

4-Acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl (cas: 14691-89-5) belongs to piperidine derivatives. Piperidine has a role as a reagent, a protic solvent, a base, a catalyst, a plant metabolite, a human metabolite and a non-polar solvent. Piperidine derivatives are being utilized in different ways as anticancer, antiviral, antimalarial, antimicrobial, antifungal, antihypertension, analgesic, anti-inflammatory, anti-Alzheimer, antipsychotic and/or anticoagulant agents.Application In Synthesis of 4-Acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem