Category: piperidines

Development of an L-band resonator optimized for fast scan EPR imaging of the mouse head was written by Samouilov, Alexandre;Komarov, Denis;Petryakov, Sergey;Iosilevich, Arkadiy;Zweier, Jay L.. And the article was included in Magnetic Resonance in Medicine in 2021.Recommanded Product: 4-Oxo-tempo This article mentions the following:

To develop a novel resonator for high-quality fast scan ESR (EPR) and EPR/NMR co-imaging of the head and brain of mice at 1.25 GHz. Resonator dimensions were scaled to fit the mouse head with maximum filling factor. A single-loop 6-gap resonator of 20 mm diameter and 20 mm length was constructed. High resonator stability was achieved utilizing a fixed position double coupling loop. Sym. mutually inverted connections rendered it insensitive to field modulation and fast scan. Coupling adjustment was provided by a parallel-connected variable capacitor located at the feeding line at λ/4 distance. To minimize radiation loss, the shield around the resonator was supplemented with a planar conductive disk that focuses return magnetic flux. Coupling of the resonator loaded with the mouse head was efficient and easy. This resonator enabled high-quality in vivo 3D EPR imaging of the mouse head following i.v. infusion of nitroxide probes. With this resonator and rapid scan EPR system, 4 ms scans were acquired in forward and reverse directions so that images with 2-scan 3,136 projections were acquired in 25 s. Head images were achieved with resolutions of 0.4 mm, enabling visualization of probe localization and uptake across the blood-brain barrier. This resonator design provides good sensitivity, high stability, and B₁ field homogeneity for in vivo fast scan EPR of the mouse head and brain, enabling faster measurements and higher resolution imaging of probe uptake, localization, and metabolism than previously possible. In the experiment, the researchers used many compounds, for example, 4-Oxo-tempo (cas: 2896-70-0Recommanded Product: 4-Oxo-tempo).

4-Oxo-tempo (cas: 2896-70-0) 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. Several piperidine alkaloids isolated from natural herbs, were found to exhibit antiproliferation and antimetastatic effects on various types of cancers both in vitro and in vivo for example Piperine, Evodiamine, Matrine, Berberine and Tetrandine.Recommanded Product: 4-Oxo-tempo

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of Sulfonamides Incorporating Piperidinyl-Hydrazidoureido and Piperidinyl-Hydrazidothioureido Moieties and Their Carbonic Anhydrase I, II, IX and XII Inhibitory Activity was written by Moi, Davide;Deplano, Alessandro;Angeli, Andrea;Balboni, Gianfranco;Supuran, Claudiu T.;Onnis, Valentina. And the article was included in Molecules in 2022.Recommanded Product: 1126-09-6 This article mentions the following:

Here, we report a small library of hydrazinocarbonyl-ureido and -thioureido benzenesulfonamide derivatives, I [R = Ph, C₆H₁₁, PhCH₂, etc., X = O, S], that were designed and synthesized as potent and selective human carbonic anhydrase inhibitors (hCAIs). The synthesized compounds were ev=aluated against isoforms hCA I, II, IX and XII using acetazolamide (AAZ) as standard inhibitor. Several urea and thiourea derivatives showed inhibitory activity at low nanomolar levels with selectivity against the cytosolic hCA II isoform, as well as the transmembrane, tumor-associated enzymes hCA IX and XII. The thiourea derivatives showed enhanced potency as compared to urea analogs. Addnl., eight compounds, I [R = 3-FC₆H₄, 2,6-Me₂C₆H₃, 2-MeOC₆H₄, 4-MeOC₆H₄, X = O, S], were selected for docking anal. on isoform I, II, IX, XII to illustrate the potential interaction with the enzyme to better understand the activity against the different isoforms. In the experiment, the researchers used many compounds, for example, Ethyl piperidine-4-carboxylate (cas: 1126-09-6Recommanded Product: 1126-09-6).

Ethyl piperidine-4-carboxylate (cas: 1126-09-6) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Piperidine prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N–H bond in an axial position, and the other in an equatorial position.Recommanded Product: 1126-09-6

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Two-Way Regulation of MmpL3 Expression Identifies and Validates Inhibitors of MmpL3 Function in Mycobacterium tuberculosis was written by Grover, Shipra;Engelhart, Curtis A.;Perez-Herran, Esther;Li, Wei;Abrahams, Katherine A.;Papavinasasundaram, Kadamba;Bean, James M.;Sassetti, Christopher M.;Mendoza-Losana, Alfonso;Besra, Gurdyal S.;Jackson, Mary;Schnappinger, Dirk. And the article was included in ACS Infectious Diseases in 2021.Name: 10-(2-(1-Methylpiperidin-2-yl)ethyl)-2-(methylthio)-10H-phenothiazine This article mentions the following:

MmpL3, an essential mycolate transporter in the inner membrane of Mycobacterium tuberculosis (Mtb), has been identified as a target of multiple, chem. diverse antitubercular drugs. However, several of these mols. seem to have secondary targets and inhibit bacterial growth by more than one mechanism. Here, we describe a cell-based assay that utilizes two-way regulation of MmpL3 expression to readily identify MmpL3-specific inhibitors. We successfully used this assay to identify a novel guanidine-based MmpL3 inhibitor from a library of 220 compounds that inhibit growth of Mtb by largely unknown mechanisms. We furthermore identified inhibitors of cytochrome bc₁-aa₃ oxidase as one class of off-target hits in whole-cell screens for MmpL3 inhibitors and report a novel sulfanylacetamide as a potential QcrB inhibitor. In the experiment, the researchers used many compounds, for example, 10-(2-(1-Methylpiperidin-2-yl)ethyl)-2-(methylthio)-10H-phenothiazine (cas: 50-52-2Name: 10-(2-(1-Methylpiperidin-2-yl)ethyl)-2-(methylthio)-10H-phenothiazine).

10-(2-(1-Methylpiperidin-2-yl)ethyl)-2-(methylthio)-10H-phenothiazine (cas: 50-52-2) 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 prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N–H bond in an axial position, and the other in an equatorial position.Name: 10-(2-(1-Methylpiperidin-2-yl)ethyl)-2-(methylthio)-10H-phenothiazine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Design and Synthesis of Potent Quinazolines as Selective β-Glucocerebrosidase Modulators was written by Zheng, Jianbin;Chen, Long;Schwake, Michael;Silverman, Richard B.;Krainc, Dimitri. And the article was included in Journal of Medicinal Chemistry in 2016.Quality Control of 4-Amino-1-methylpiperidine This article mentions the following:

Gaucher’s disease is a common genetic disease caused by mutations in the β-glucocerebrosidase (GBA1) gene that have been also linked to increased risk of Parkinson’s disease and Lewy body dementia. Stabilization of misfolded mutant β-glucocerebrosidase (GCase) represents an important therapeutic strategy in synucleinopathies. Here we report a novel class of GCase quinazoline inhibitors, obtained in a high throughput screening, with moderate potency against wild-type GCase. Rational design and a SAR study of this class of compounds led to a new series of quinazoline derivatives with single-digit nanomolar potency. These compounds were shown to selectively stabilize GCase when compared to other lysosomal enzymes and to increase N370S mutant GCase protein concentration and activity in cell assays. To the best of our knowledge, these mols. are the most potent noniminosugar GCase modulators to date that may prove useful for future mechanistic studies and therapeutic approaches in Gaucher’s and Parkinson’s diseases. In the experiment, the researchers used many compounds, for example, 4-Amino-1-methylpiperidine (cas: 41838-46-4Quality Control of 4-Amino-1-methylpiperidine).

4-Amino-1-methylpiperidine (cas: 41838-46-4) 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. Several piperidine alkaloids isolated from natural herbs, were found to exhibit antiproliferation and antimetastatic effects on various types of cancers both in vitro and in vivo for example Piperine, Evodiamine, Matrine, Berberine and Tetrandine.Quality Control of 4-Amino-1-methylpiperidine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Marine colloids promote the adaptation of diatoms to nitrate contamination by directional electron transfer was written by Kang, Weilu;Yu, Fubo;Wang, Shuting;Hu, Xiangang. And the article was included in Environmental Science & Technology in 2022.Electric Literature of C9H16NO2 This article mentions the following:

Nitrate contamination from human activities (e.g., domestic pollution, livestock breeding, and fertilizer application) threatens marine ecosystems and net primary productivity. As the main component of primary productivity, diatoms can adapt to high nitrate environments, but the mechanism is unclear. We found that electron transfer from marine colloids to diatoms enhances nitrogen uptake and assimilation under visible-light irradiation, providing a new pathway for nitrogen adaptation. Under irradiation, marine colloids exhibit semiconductor properties (e.g., the separation of electron-hole pairs) and can trigger the generation of free electrons and singlet oxygen. They also exhibit electron acceptor and donor properties, with the former being stronger than the latter, reacting with polysaccharides in extracellular polymeric substances (EPSs) under high nitrogen stress, enhancing the elasticity and permeability of cells, and promoting nitrogen assimilation and electron transfer to marine diatom EPSs. Electron transfer promotes extracellular-to-intracellular nitrate transport by upregulating membrane nitrate transporters and nitrate reductase. The upregulation of anion transport genes and unsaturated fatty acids contributes to nitrogen assimilation. We estimate that colloids may increase the nitrate uptake efficiency of marine diatoms by 10.5-82.2%. These findings reveal a mechanism by which diatoms adapt to nitrate contamination and indicate a low-cost strategy to control marine pollution. In the experiment, the researchers used many compounds, for example, 4-Oxo-tempo (cas: 2896-70-0Electric Literature of C9H16NO2).

4-Oxo-tempo (cas: 2896-70-0) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. Piperidine prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N–H bond in an axial position, and the other in an equatorial position.Electric Literature of C9H16NO2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of a 1,3,5-benzotriazepine-2,4-dione based library was written by Chuckowree, Irina;Ali Syed, Murtaza;Getti, Giulia;Parbhu Patel, Asha;Garner, Hannah;Tizzard, Graham J.;Coles, Simon J.;Spencer, John. And the article was included in Tetrahedron Letters in 2012.Related Products of 144222-22-0 This article mentions the following:

A library of benzotriazepines has been synthesized employing microwave-mediated synthesis, supported resins and parallel synthesis methodol. In the experiment, the researchers used many compounds, for example, 1-Boc-4-(Aminomethyl)piperidine (cas: 144222-22-0Related Products of 144222-22-0).

1-Boc-4-(Aminomethyl)piperidine (cas: 144222-22-0) 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. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Related Products of 144222-22-0

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Chiral, piperidine-based analogs of AF64A and acetylcholine was written by Huh, Nam;Thompson, Charles M.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 1992.Formula: C13H17NO3 This article mentions the following:

Chiral analogs (I, II) of acetylcholine and AF64A were prepared from l-glutamic acid via the central intermediate, (S)-3-acetoxypiperidine. In the experiment, the researchers used many compounds, for example, (S)-1-Cbz-3-hydroxypiperidine (cas: 94944-69-1Formula: C13H17NO3).

(S)-1-Cbz-3-hydroxypiperidine (cas: 94944-69-1) belongs to piperidine derivatives.Piperidine is a key saturated heterocyclic scaffold found in several of the top-selling small molecule pharmaceuticals and natural alkaloids, with a diverse range of biological activities. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Formula: C13H17NO3

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Anticonvulsant effects of GABA uptake inhibitors: their profile of action in the rat kindling model of epilepsy was written by Sato, Hitoshi;Morimoto, Kiyoshi;Suwaki, Hiroshi. And the article was included in Tenkan Kenkyu in 1996.Computed Properties of C22H26ClNO2 This article mentions the following:

GABA uptake inhibitors are newly developed antiepileptic drugs. In this study, we analyzed the antiepileptic profile of GABA uptake inhibitors, Tiagabine, SKF-89976A and NNC-711, in the rat kindling model, which is a chronic exptl. model of human complex partial seizures with secondary generalization. We examined the dose-dependent anticonvulsant effects of the GABA uptake inhibitors in amygdala (AM)- and hippocampal (HIPP)-kindled seizures, and compared their anticonvulsant and behavioral side effects with those of Valproate (VPA) and Carbamazepine (CBZ). In AM- and HIPP-kindled rats, i.p. administration of the GABA uptake inhibitors (2.50-20 mg/kg) significantly reduced the seizure stage and after-discharge (AD) duration in dose-dependent manners, compared with vehicle treatment. The anticonvulsant potencies of the 3 GABA uptake inhibitors were in the order: NNC-711 > Tiagabine >> SKF89976A, which was related to the in vitro GABA uptake efficacy, and they were similar between AM- and HIPP-kindled seizures. High doses of GABA uptake inhibitors (20-40 mg/kg) caused sedation, motor impairment and EEG paroxyms with myoclonus. When the correlation between the anticonvulsant and behavioral side effects was examined, GABA uptake inhibitors showed more potent anticonvulsant and less side effects, compared with VPA and CBZ. These results indicate the clin. usefulness of GABA uptake inhibitors in temporal lobe epilepsy. In the experiment, the researchers used many compounds, for example, SKF-89976A Hydrochloride (cas: 85375-15-1Computed Properties of C22H26ClNO2).

SKF-89976A Hydrochloride (cas: 85375-15-1) belongs to piperidine derivatives.Piperidine is a key saturated heterocyclic scaffold found in several of the top-selling small molecule pharmaceuticals and natural alkaloids, with a diverse range of 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.Computed Properties of C22H26ClNO2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Glasdegib in the treatment of acute myeloid leukemia was written by Wolska-Washer, Anna;Robak, Tadeusz. And the article was included in Future Oncology in 2019.Application of 1095173-27-5 This article mentions the following:

Pharmacol. inhibition of the Hedgehog pathway significantly enhanced the sensitivity of leukemic cells to cytotoxic drugs. Glasdegib (PF-04449913; DAURISMO is a potent and selective oral inhibitor of the Hedgehog signaling pathway with clin. activity in patients with acute myeloid leukemia (AML) and myelodysplastic syndrome (MDS), particularly in combination with chemotherapy. The results of Phase Ib/II studies evaluating safety and efficacy of glasdegib combined with chemotherapy in previously untreated patients with AML or high-risk myelodysplastic syndrome have recently been published. In the BRIGHT AML 1003 study, glasdegib in combination with low-dose cytarabine (LDAC) was well tolerated and demonstrated a significant 54% reduction in mortality compared with LDAC for AML patients. In 2018, the US FDA approved glasdegib in combination with LDAC for the treatment of newly diagnosed patients with AML who are 75 years old or older or who have co-morbidities that preclude use of intensive induction chemotherapy. In the experiment, the researchers used many compounds, for example, 1-((2R,4R)-2-(1H-Benzo[d]imidazol-2-yl)-1-methylpiperidin-4-yl)-3-(4-cyanophenyl)urea (cas: 1095173-27-5Application of 1095173-27-5).

1-((2R,4R)-2-(1H-Benzo[d]imidazol-2-yl)-1-methylpiperidin-4-yl)-3-(4-cyanophenyl)urea (cas: 1095173-27-5) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Piperidine prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N–H bond in an axial position, and the other in an equatorial position.Application of 1095173-27-5

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

The formation of all-cis-(multi)fluorinated piperidines by a dearomatization-hydrogenation process was written by Nairoukh, Zackaria;Wollenburg, Marco;Schlepphorst, Christoph;Bergander, Klaus;Glorius, Frank. And the article was included in Nature Chemistry in 2019.Formula: C5H11ClFN This article mentions the following:

Piperidines and fluorine substituents are both independently indispensable components in pharmaceuticals, agrochems. and materials. Logically, the incorporation of fluorine atoms into piperidine scaffolds is therefore an area of tremendous potential. However, synthetic approaches towards the formation of these architectures are often impractical. The diastereoselective synthesis of substituted monofluorinated piperidines often requires substrates with pre-defined stereochem. That of multifluorinated piperidines is even more challenging, and often needs to be carried out in multistep syntheses. In this report, we describe a straightforward process for the one-pot rhodium-catalyzed dearomatization-hydrogenation of fluoropyridine precursors. This strategy enables the formation of a plethora of substituted all-cis-(multi)fluorinated piperidines in a highly diastereoselective fashion through pyridine dearomatization followed by complete saturation of the resulting intermediates by hydrogenation. Fluorinated piperidines with defined axial/equatorial orientation of fluorine substituents were successfully applied in the preparation of com. drug analogs. Addnl., fluorinated PipPhos as well as fluorinated ionic liquids were obtained by this dearomatization-hydrogenation process. In the experiment, the researchers used many compounds, for example, 3-Fluoropiperidine hydrochloride (cas: 737000-77-0Formula: C5H11ClFN).

3-Fluoropiperidine hydrochloride (cas: 737000-77-0) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Piperidine prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N–H bond in an axial position, and the other in an equatorial position.Formula: C5H11ClFN

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem