Category: piperidines

Combined Cardioprotective and Adipocyte Browning Effects Promoted by the Eutomer of Dual sEH/PPAR纬 Modulator was written by Hartmann, Markus;Bibli, Sofia-Iris;Tews, Daniel;Ni, Xiaomin;Kircher, Theresa;Kramer, Jan S.;Kilu, Whitney;Heering, Jan;Hernandez-Olmos, Victor;Weizel, Lilia;Scriba, Gerhard K. E.;Krait, Sulaiman;Knapp, Stefan;Chaikuad, Apirat;Merk, Daniel;Fleming, Ingrid;Fischer-Posovszky, Pamela;Proschak, Ewgenij. And the article was included in Journal of Medicinal Chemistry in 2021.Category: piperidines The following contents are mentioned in the article:

The metabolic syndrome (MetS) is a constellation of cardiovascular and metabolic symptoms involving insulin resistance, steatohepatitis, obesity, hypertension, and heart disease, and patients suffering from MetS often require polypharmaceutical treatment. PPAR纬 agonists are highly effective oral antidiabetics with great potential in MetS, which promote adipocyte browning and insulin sensitization. However, the application of PPAR纬 agonists in clinics is restricted by potential cardiovascular adverse events. We have previously demonstrated that the racemic dual sEH/PPAR纬 modulator RB394 (3) simultaneously improves all risk factors of MetS in vivo. In this study, we identify and characterize (R)-3 (I), the eutomer of 3. We provide structural rationale for mol. recognition of the eutomer. Furthermore, we could show that the dual sEH/PPAR纬 modulator is able to promote adipocyte browning and simultaneously exhibits cardioprotective activity which underlines its exciting potential in treatment of MetS. This study involved multiple reactions and reactants, such as 1-(1-Propionylpiperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea (cas: 1222780-33-7Category: piperidines).

1-(1-Propionylpiperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea (cas: 1222780-33-7) 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 prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N鈥揌 bond in an axial position, and the other in an equatorial position.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Neonicotine and isomeric pyridylpiperidines was written by Smith, C. R.. And the article was included in Journal of the American Chemical Society in 1931.Category: piperidines The following contents are mentioned in the article:

cf. C. A. 18, 2006. Details are given for the isolation of neonicotine (尾-pyridyl-伪-piperidine) (I) from the reaction product of C₅H₅N, Na and O; I b₇₇₅ 280-1掳 and yields a picrate, m. 213掳 (con.); this is probably not identical with nicotimine, isolated by Pictet and Rotschky (Ber. 34, 696(1901)) from the nicotine alkaloids. Reduction of I gives 伪,尾-dipiperidyl, b. 269-70掳. Reduction of 伪,尾-dipyridyl gives isoneonicotine (伪-pyridyl-尾-piperidine), b₇₆₀ 282掳, whose picrate m. 217-8掳 (corrected). 伪,伪-Pyridylpiperidyl, b₇₅₅ 265-6掳, whose picrate m. 187掳; the NO derivative is an oil. Isonicotine (纬,纬-pyridylpiperidine) b₇₆₀ 292掳; the picrate m. 215-8掳 (decomposition); the NO derivative m. 112掳. Nicotidine (尾,尾-pyridylpiperidine) b. 284-5掳; picrate m. about 206掳. 尾-Pyridyl-纬-piperidine yields a picrate, m. 240掳. The ease of reduction by Sn and HCl of the dipyridyls is in the order 纬,纬-, 尾,纬, 伪,伪- and 尾,尾, the first being the most easily reduced. This study involved multiple reactions and reactants, such as 3-(Piperidin-3-yl)pyridine (cas: 31251-28-2Category: piperidines).

3-(Piperidin-3-yl)pyridine (cas: 31251-28-2) 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. 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.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

C-Terminal Residue Optimization and Fragment Merging: Discovery of a Potent Peptide-Hybrid Inhibitor of Dengue Protease was written by Behnam, Mira A. M.;Nitsche, Christoph;Vechi, Sergio M.;Klein, Christian D.. And the article was included in ACS Medicinal Chemistry Letters in 2014.Electric Literature of C21H21NO4 The following contents are mentioned in the article:

Dengue virus protease is a promising target for the development of antiviral drugs. We describe here a two-step rational optimization that led to the discovery of the potent inhibitor 35 with nanomolar binding affinity at dengue protease serotype 2 (IC₅₀ = 0.6 渭M, K_i = 0.4 渭M). First, a large number of natural and non-natural amino acids were screened at the C-terminal position of the previously reported, canonical peptide sequence (Cap-Arg-Lys-Nle-NH₂). Compared to the reference compound 1 (Bz-Arg-Lys-Nle-NH₂, IC₅₀ = 13.3 渭M), a 4-fold higher inhibitory potential was observed with the incorporation of a C-terminal phenylglycine (compound 9, IC₅₀ = 3.3 渭M). Second, we applied fragment merging of 9 with the previously reported thiazolidinedione peptide hybrid 33 (IC₅₀ = 2.5 渭M). This approach led to the fusion of two inhibitor-fragments with micromolar affinity into a 20-fold more potent, competitive inhibitor of dengue protease. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Electric Literature of C21H21NO4).

(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) 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. 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.Electric Literature of C21H21NO4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

C-Terminal Residue Optimization and Fragment Merging: Discovery of a Potent Peptide-Hybrid Inhibitor of Dengue Protease was written by Behnam, Mira A. M.;Nitsche, Christoph;Vechi, Sergio M.;Klein, Christian D.. And the article was included in ACS Medicinal Chemistry Letters in 2014.Related Products of 86069-86-5 The following contents are mentioned in the article:

Dengue virus protease is a promising target for the development of antiviral drugs. We describe here a two-step rational optimization that led to the discovery of the potent inhibitor 35 with nanomolar binding affinity at dengue protease serotype 2 (IC₅₀ = 0.6 渭M, K_i = 0.4 渭M). First, a large number of natural and non-natural amino acids were screened at the C-terminal position of the previously reported, canonical peptide sequence (Cap-Arg-Lys-Nle-NH₂). Compared to the reference compound 1 (Bz-Arg-Lys-Nle-NH₂, IC₅₀ = 13.3 渭M), a 4-fold higher inhibitory potential was observed with the incorporation of a C-terminal phenylglycine (compound 9, IC₅₀ = 3.3 渭M). Second, we applied fragment merging of 9 with the previously reported thiazolidinedione peptide hybrid 33 (IC₅₀ = 2.5 渭M). This approach led to the fusion of two inhibitor-fragments with micromolar affinity into a 20-fold more potent, competitive inhibitor of dengue protease. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Related Products of 86069-86-5).

(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) 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 prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N鈥揌 bond in an axial position, and the other in an equatorial position.Related Products of 86069-86-5

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Conformational Properties of Secondary Amino Acids: Replacement of Pipecolic Acid by N-Methyl-L-alanine in Efrapeptin C was written by Dutt Konar, Anita;Vass, Elemer;Hollosi, Miklos;Majer, Zsuzsanna;Grueber, Gerhard;Frese, Katrin;Sewald, Norbert. And the article was included in Chemistry & Biodiversity in 2013.Safety of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid The following contents are mentioned in the article:

The efrapeptins, a family of naturally occurring peptides with inhibitory activities against ATPases, contain several 伪,伪-disubstituted 伪-amino acids such as 伪-aminoisobutyric acid (Aib) or isovaline (Iva) besides pipecolic acid (Pip), 尾-Ala, Leu, Gly, and a C-terminal heterocyclic residue. Secondary 伪-amino acids such as proline are known to stabilize discrete conformations in peptides. A similar influence is ascribed to N-alkyl 伪-amino acids. We synthesized two efrapeptin C analogs with replacement of Pip by N-methyl-L-alanine (MeAla) using a combination of solid- and solution-phase techniques in a fragment-condensation strategy to compare the conformational bias of both secondary amino acids. The solution conformation was investigated by vibrational CD (VCD) to probe whether the analogs adopt a 3₁₀-helical conformation. The MeAla-containing analogs [MeAla^1,3]efrapeptin C and [MeAla^1,3,11]efrapeptin C inhibit ATP hydrolysis by the A₃B₃ complex of A₁A₀-ATP synthase from Methanosarcina mazei Goe1. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Safety of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid).

(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Safety of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Conformational Properties of Secondary Amino Acids: Replacement of Pipecolic Acid by N-Methyl-L-alanine in Efrapeptin C was written by Dutt Konar, Anita;Vass, Elemer;Hollosi, Miklos;Majer, Zsuzsanna;Grueber, Gerhard;Frese, Katrin;Sewald, Norbert. And the article was included in Chemistry & Biodiversity in 2013.Quality Control of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid The following contents are mentioned in the article:

The efrapeptins, a family of naturally occurring peptides with inhibitory activities against ATPases, contain several 伪,伪-disubstituted 伪-amino acids such as 伪-aminoisobutyric acid (Aib) or isovaline (Iva) besides pipecolic acid (Pip), 尾-Ala, Leu, Gly, and a C-terminal heterocyclic residue. Secondary 伪-amino acids such as proline are known to stabilize discrete conformations in peptides. A similar influence is ascribed to N-alkyl 伪-amino acids. We synthesized two efrapeptin C analogs with replacement of Pip by N-methyl-L-alanine (MeAla) using a combination of solid- and solution-phase techniques in a fragment-condensation strategy to compare the conformational bias of both secondary amino acids. The solution conformation was investigated by vibrational CD (VCD) to probe whether the analogs adopt a 3₁₀-helical conformation. The MeAla-containing analogs [MeAla^1,3]efrapeptin C and [MeAla^1,3,11]efrapeptin C inhibit ATP hydrolysis by the A₃B₃ complex of A₁A₀-ATP synthase from Methanosarcina mazei Goe1. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Quality Control of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid).

(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) 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鈥揌 bond in an axial position, and the other in an equatorial position.Quality Control of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Three-Dimensional Quantitative Structure-Activity Relationship Analyses of 尾-Lactam Antibiotics and Tripeptides as Substrates of the Mammalian H⁺/Peptide Cotransporter PEPT1 was written by Biegel, Annegret;Gebauer, Sabine;Hartrodt, Bianka;Brandsch, Matthias;Neubert, Klaus;Thondorf, Iris. And the article was included in Journal of Medicinal Chemistry in 2005.Related Products of 86069-86-5 The following contents are mentioned in the article:

The utilization of the membrane transport protein PEPT1 as a drug delivery system is a promising strategy to enhance the oral bioavailability of drugs. Since very little is known about the substrate binding site of PEPT1, computational methods are a meaningful tool to gain a more detailed insight into the structural requirements for substrates. Three-dimensional quant. structure-activity relationship (3D-QSAR) studies using the comparative mol. similarity indexes anal. (Co-MSIA) method were performed on a training set of 98 compounds Affinity constants of 尾-lactam antibiotics and tripeptides were determined at Caco-2 cells. A statistically reliable model of high predictive power was obtained (q² = 0.828, r² = 0.937). The results derived from Co-MSIA were graphically interpreted using different field contribution maps. The authors identified those regions which are crucial for the interaction between peptidomimetics and PEPT1. The new 3D-QSAR model was used to design a new druglike compound mimicking a dipeptide. The predicted K_i value was confirmed exptl. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Related Products of 86069-86-5).

(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. Piperidine prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N鈥揌 bond in an axial position, and the other in an equatorial position.Related Products of 86069-86-5

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Three-Dimensional Quantitative Structure-Activity Relationship Analyses of 尾-Lactam Antibiotics and Tripeptides as Substrates of the Mammalian H⁺/Peptide Cotransporter PEPT1 was written by Biegel, Annegret;Gebauer, Sabine;Hartrodt, Bianka;Brandsch, Matthias;Neubert, Klaus;Thondorf, Iris. And the article was included in Journal of Medicinal Chemistry in 2005.Category: piperidines The following contents are mentioned in the article:

The utilization of the membrane transport protein PEPT1 as a drug delivery system is a promising strategy to enhance the oral bioavailability of drugs. Since very little is known about the substrate binding site of PEPT1, computational methods are a meaningful tool to gain a more detailed insight into the structural requirements for substrates. Three-dimensional quant. structure-activity relationship (3D-QSAR) studies using the comparative mol. similarity indexes anal. (Co-MSIA) method were performed on a training set of 98 compounds Affinity constants of 尾-lactam antibiotics and tripeptides were determined at Caco-2 cells. A statistically reliable model of high predictive power was obtained (q² = 0.828, r² = 0.937). The results derived from Co-MSIA were graphically interpreted using different field contribution maps. The authors identified those regions which are crucial for the interaction between peptidomimetics and PEPT1. The new 3D-QSAR model was used to design a new druglike compound mimicking a dipeptide. The predicted K_i value was confirmed exptl. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Category: piperidines).

(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. 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.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

A Supervised Molecular Dynamics Approach to Unbiased Ligand-Protein Unbinding was written by Deganutti, Giuseppe;Moro, Stefano;Reynolds, Christopher A.. And the article was included in Journal of Chemical Information and Modeling in 2020.Application of 1222780-33-7 The following contents are mentioned in the article:

The recent paradigm shift toward the use of the kinetics parameters in place of thermodn. constants is leading the computational chem. community to develop methods for studying the mechanisms of drug binding and unbinding. From this standpoint, mol. dynamics (MD) plays an important role in delivering insight at the mol. scale. However, a known limitation of MD is that the time scales are usually far from those involved in ligand-receptor unbinding events. Here, we show that the algorithm behind supervised MD (SuMD) can simulate the dissociation mechanism of druglike small mols. while avoiding the input of any energy bias to facilitate the transition. SuMD was tested on seven different intermol. complexes, covering four G protein-coupled receptors: the A_2A and A₁ adenosine receptors, the orexin 2 and the muscarinic 2 receptors, and the soluble globular enzyme epoxide hydrolase. SuMD well-described the multi-step nature of ligand-receptor dissociation, rationalized previous exptl. data and produced valuable working hypotheses for structure-kinetics relationships. This study involved multiple reactions and reactants, such as 1-(1-Propionylpiperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea (cas: 1222780-33-7Application of 1222780-33-7).

1-(1-Propionylpiperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea (cas: 1222780-33-7) 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. 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.Application of 1222780-33-7

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Probing the orientation of inhibitor and epoxy-eicosatrienoic acid binding in the active site of soluble epoxide hydrolase was written by Lee, Kin Sing Stephen;Henriksen, Niel M.;Ng, Connie J.;Yang, Jun;Jia, Weitao;Morisseau, Christophe;Andaya, Armann;Gilson, Michael K.;Hammock, Bruce D.. And the article was included in Archives of Biochemistry and Biophysics in 2017.Product Details of 1222780-33-7 The following contents are mentioned in the article:

Soluble epoxide hydrolase (sEH) is an important therapeutic target of many diseases, such as chronic obstructive pulmonary disease (COPD) and diabetic neuropathic pain. It acts by hydrolyzing and thus regulating specific bioactive long chain polyunsaturated fatty acid epoxides (lcPUFA), like epoxyeicosatrienoic acids (EETs). To better predict which epoxides could be hydrolyzed by sEH, one needs to dissect the important factors and structural requirements that govern the binding of the substrates to sEH. This knowledge allows further exploration of the physiol. role played by sEH. Unfortunately, a crystal structure of sEH with a substrate bound has not yet been reported. In this report, new photoaffinity mimics of a sEH inhibitor and EET regioisomers were prepared and used in combination with peptide sequencing and computational modeling, to identify the binding orientation of different regioisomers and enantiomers of EETs into the catalytic cavity of sEH. Results indicate that the stereochem. of the epoxide plays a crucial role in dictating the binding orientation of the substrate. This study involved multiple reactions and reactants, such as 1-(1-Propionylpiperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea (cas: 1222780-33-7Product Details of 1222780-33-7).

1-(1-Propionylpiperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea (cas: 1222780-33-7) 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.Product Details of 1222780-33-7

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem