Month: November 2022

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

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

Movement to the Clinic of Soluble Epoxide Hydrolase Inhibitor EC5026 as an Analgesic for Neuropathic Pain and for Use as a Nonaddictive Opioid Alternative was written by Hammock, Bruce D.;McReynolds, Cindy B.;Wagner, Karen;Buckpitt, Alan;Cortes-Puch, Irene;Croston, Glenn;Lee, Kin Sing Stephen;Yang, Jun;Schmidt, William K.;Hwang, Sung Hee. And the article was included in Journal of Medicinal Chemistry in 2021.Synthetic Route of C16H20F3N3O3 The following contents are mentioned in the article:

This report describes the development of an orally active analgesic that resolves inflammation and neuropathic pain without the addictive potential of opioids. EC5026 (I) acts on the cytochrome P 450 branch of the arachidonate cascade to stabilize epoxides of polyunsaturated fatty acids (EpFA), which are natural mediators that reduce pain, resolve inflammation, and maintain normal blood pressure. EC5026 is a slow-tight binding transition-state mimic that inhibits the soluble epoxide hydrolase (sEH) at picomolar concentrations The sEH rapidly degrades EpFA; thus, inhibiting sEH increases EpFA in vivo and confers beneficial effects. This mechanism addresses disease states by shifting endoplasmic reticulum stress from promoting cellular senescence and inflammation toward cell survival and homeostasis. We describe the synthesis and optimization of EC5026 and its development through human Phase 1a trials with no drug-related adverse events. Addnl., we outline fundamental work leading to discovery of the analgesic and inflammation-resolving CYP450 branch of the arachidonate cascade. This study involved multiple reactions and reactants, such as 1-(1-Propionylpiperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea (cas: 1222780-33-7Synthetic Route of C16H20F3N3O3).

1-(1-Propionylpiperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea (cas: 1222780-33-7) 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.Synthetic Route of C16H20F3N3O3

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Oral treatment of rodents with soluble epoxide hydrolase inhibitor 1-(1-propanoylpiperidin-4-yl)-3-[4-(trifluoromethoxy)phenyl]urea (TPPU): Resulting drug levels and modulation of oxylipin pattern was written by Ostermann, Annika I.;Herbers, Jan;Willenberg, Ina;Chen, Rongjun;Hwang, Sung Hee;Greite, Robert;Morisseau, Christophe;Gueler, Faikah;Hammock, Bruce D.;Schebb, Nils Helge. And the article was included in Prostaglandins and Other Lipid Mediators in 2015.Formula: C16H20F3N3O3 The following contents are mentioned in the article:

Epoxides from polyunsaturated fatty acids (PUFAs) are potent lipid mediators. In vivo stabilization of these epoxides by blockade of the soluble epoxide hydrolase (sEH) leads to anti-inflammatory, analgesic and normotensive effects. Therefore, sEH inhibitors (sEHi) are a promising new class of drugs. Herein, we characterized pharmacokinetic (PK) and pharmacodynamic properties of a com. available potent sEHi 1-(1-propanoylpiperidin-4-yl)-3-[4-(trifluoromethoxy)phenyl]urea (TPPU). Cell culture studies suggest its high absorption and metabolic stability. Following administration in drinking water to rats (0.2, 1, and 5 mg TPPU/L with 0.2% PEG400), TPPU’s blood concentration increased dose dependently within the treatment period to reach an almost steady state after 8 days. TPPU was found in all the tissues tested. The linoleic epoxide/diol ratios in most tissues were dose dependently increased, indicating significant sEH inhibition. Overall, administration of TPPU with the drinking water led to systemic distribution as well as high drug levels and thus makes chronic sEH inhibition studies possible. This study involved multiple reactions and reactants, such as 1-(1-Propionylpiperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea (cas: 1222780-33-7Formula: C16H20F3N3O3).

1-(1-Propionylpiperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea (cas: 1222780-33-7) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. Piperidine derivatives bearing a masked aldehyde function in the 蔚-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Formula: C16H20F3N3O3

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

A HaloTag-Based Small Molecule Microarray Screening Methodology with Increased Sensitivity and Multiplex Capabilities was written by Noblin, Devin J.;Page, Charlotte M.;Tae, Hyun Seop;Gareiss, Peter C.;Schneekloth, John S.;Crews, Craig M.. And the article was included in ACS Chemical Biology in 2012.Recommanded Product: (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid The following contents are mentioned in the article:

Small Mol. Microarrays (SMMs) represent a general platform for screening small mol.-protein interactions independent of functional inhibition of target proteins. In an effort to increase the scope and utility of SMMs, the authors have modified the SMM screening methodol. to increase assay sensitivity and facilitate multiplex screening. Fusing target proteins to the HaloTag protein allows the authors to covalently prelabel fusion proteins with fluorophores, leading to increased assay sensitivity and an ability to conduct multiplex screens. The authors use the interaction between FKBP12 and two ligands, rapamycin and ARIAD’s bump ligand, to show that the HaloTag-based SMM screening methodol. significantly increases assay sensitivity. Addnl., using wild type FKBP12 and the FKBP12 F36V mutant, prelabeling various protein isoforms with different fluorophores allows the authors to conduct multiplex screens and identify ligands to a specific isoform. Finally, the authors show this multiplex screening technique is capable of identifying ligands selective for a specific PTP1B isoform using a 20,000-compound screening deck. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Recommanded Product: (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 has a role as a reagent, a protic solvent, a base, a catalyst, a plant metabolite, a human metabolite and a non-polar solvent. 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.Recommanded Product: (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

A HaloTag-Based Small Molecule Microarray Screening Methodology with Increased Sensitivity and Multiplex Capabilities was written by Noblin, Devin J.;Page, Charlotte M.;Tae, Hyun Seop;Gareiss, Peter C.;Schneekloth, John S.;Crews, Craig M.. And the article was included in ACS Chemical Biology in 2012.Recommanded Product: (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid The following contents are mentioned in the article:

Small Mol. Microarrays (SMMs) represent a general platform for screening small mol.-protein interactions independent of functional inhibition of target proteins. In an effort to increase the scope and utility of SMMs, the authors have modified the SMM screening methodol. to increase assay sensitivity and facilitate multiplex screening. Fusing target proteins to the HaloTag protein allows the authors to covalently prelabel fusion proteins with fluorophores, leading to increased assay sensitivity and an ability to conduct multiplex screens. The authors use the interaction between FKBP12 and two ligands, rapamycin and ARIAD’s bump ligand, to show that the HaloTag-based SMM screening methodol. significantly increases assay sensitivity. Addnl., using wild type FKBP12 and the FKBP12 F36V mutant, prelabeling various protein isoforms with different fluorophores allows the authors to conduct multiplex screens and identify ligands to a specific isoform. Finally, the authors show this multiplex screening technique is capable of identifying ligands selective for a specific PTP1B isoform using a 20,000-compound screening deck. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Recommanded Product: (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 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 bearing a masked aldehyde function in the 蔚-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Recommanded Product: (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Sediment-Water Distribution and Benthic Boundary Layer Fluxes of Pharmaceuticals and Personal Care Products near Wastewater Discharge into a Tidal River Shoal was written by Foster, Gregory D.;Leahigh, Arion. And the article was included in ACS ES&T Water in 2021.Formula: C32H39NO4 The following contents are mentioned in the article:

Pharmaceuticals and personal care products (PPCPs) were measured in porewater, sediment, and surface water at three sites near wastewater treatment plant (WTP) discharge along a 2 km downstream transect in a tributary shoal embayment (Alexandria, VA) of the tidal Potomac River. A benthic diffusion layer model evaluated water-only, dissolved organic carbon (DOC)-associated, and bioturbation mass transport pathways. Fluxes of 17 PPCPs nearest the WTP were all in the direction of surface water to sediment porewater (neg.) with magnitudes of -0.0016 to -7.4 ng m-2 s-1. At the next downstream site, fluxes of seven PPCPs were bidirectional (neg. and pos.) and ranged from -4.8 x 10-4 to 0.0051 ng m-2 s-1. The furthest site downstream yielded fluxes of six PPCPs that were predominantly sediment to water (pos.), ranging in magnitude from -0.0020 to 7.0 x 10-4 ng m-2 s-1. The bioturbation and water-only mass transport coefficients contributed most to fluxes for PPCPs. The DOC-associated mass transport term was negligible. The fluxes indicated sediments will continue serve as a source of PPCPs 2 km downstream from WTP discharge. This study involved multiple reactions and reactants, such as 2-(4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butyl)phenyl)-2-methylpropanoic acid (cas: 83799-24-0Formula: C32H39NO4).

2-(4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butyl)phenyl)-2-methylpropanoic acid (cas: 83799-24-0) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Formula: C32H39NO4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Mosquito saliva enhances virus infection through sialokinin-dependent vascular leakage was written by Lefteri, Daniella A.;Bryden, Steven R.;Pingen, Marieke;Terry, Sandra;McCafferty, Ailish;Beswick, Emily F.;Georgiev, Georgi;Van der Laan, Marleen;Mastrullo, Valeria;Campagnolo, Paola;Waterhouse, Robert M.;Varjak, Margus;Merits, Andres;Fragkoudis, Rennos;Griffin, Stephen;Shams, Kave;Pondeville, Emilie;McKimmie, Clive S.. And the article was included in Proceedings of the National Academy of Sciences of the United States of America in 2022.Product Details of 83799-24-0 The following contents are mentioned in the article:

Viruses transmitted by Aedes mosquitoes are an increasingly important global cause of disease. Defining common determinants of host susceptibility to this large group of heterogenous pathogens is key for informing the rational design of panviral medicines. Infection of the vertebrate host with these viruses is enhanced by mosquito saliva, a complex mixture of salivary-gland-derived factors and microbiota. We show that the enhancement of infection by saliva was dependent on vascular function and was independent of most antisaliva immune responses, including salivary microbiota. Instead, the Aedes gene product sialokinin mediated the enhancement of virus infection through a rapid reduction in endothelial barrier integrity. Sialokinin is unique within the insect world as having a vertebrate-like tachykinin sequence and is absent from Anopheles mosquitoes, which are incompetent for most arthropod-borne viruses, whose saliva was not proviral and did not induce similar vascular permeability. Therapeutic strategies targeting sialokinin have the potential to limit disease severity following infection with Aedes-mosquito-borne viruses. This study involved multiple reactions and reactants, such as 2-(4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butyl)phenyl)-2-methylpropanoic acid (cas: 83799-24-0Product Details of 83799-24-0).

2-(4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butyl)phenyl)-2-methylpropanoic acid (cas: 83799-24-0) 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. 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 83799-24-0

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Targeting spinal microglia with fexofenadine-loaded nanoparticles prolongs pain relief in a rat model of neuropathic pain was written by Tran, Quangdon;Pham, Thuy Linh;Shin, Hyo Jung;Shin, Juhee;Shin, Nara;Kwon, Hyeok Hee;Park, Hyewon;Kim, Song I.;Choi, Seoung Gyu;Wu, Junhua;Ngo, Van T. H.;Park, Jin Bong;Kim, Dong Woon. And the article was included in Nanomedicine (New York, NY, United States) in 2022.Synthetic Route of C32H39NO4 The following contents are mentioned in the article:

Targeting microglial activation is emerging as a clin. promising drug target for neuropathic pain treatment. Fexofenadine, a histamine receptor 1 antagonist, is a clin. drug for the management of allergic reactions as well as pain and inflammation. However, the effect of fexofenadine on microglial activation and pain behaviors remains elucidated. Here, we investigated nanomedicinal approach that targets more preferentially microglia and long-term analgesics. Fexofenadine significantly abolished histamine-induced microglial activation. The fexofenadine-encapsulated poly(lactic-co-glycolic acid) nanoparticles (Fexo NPs) injection reduced the pain sensitivity of spinal nerve ligation rats in a dose-dependent manner. This alleviation was sustained for 4 days, whereas the effective period by direct fexofenadine injection was 3 h. Moreover, Fexo NPs inhibited microglial activation, inflammatory signaling, cytokine release, and a macrophage phenotype shift towards the alternative activated state in the spinal cord. These results show that Fexo NPs exhibit drug repositioning promise as a long-term treatment modality for neuropathic pain. This study involved multiple reactions and reactants, such as 2-(4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butyl)phenyl)-2-methylpropanoic acid (cas: 83799-24-0Synthetic Route of C32H39NO4).

2-(4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butyl)phenyl)-2-methylpropanoic acid (cas: 83799-24-0) 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. 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.Synthetic Route of C32H39NO4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Effects of Osthole on Inflammatory Gene Expression and Cytokine Secretion in Histamine-Induced Inflammation in the Caco-2 Cell Line was written by Kordulewska, Natalia K.;Topa, Justyna;Rozmus, Dominika;Jarmolowska, Beata. And the article was included in International Journal of Molecular Sciences in 2021.Product Details of 83799-24-0 The following contents are mentioned in the article:

Hyperactivity of the immune system in the gastrointestinal tract leads to the development of chronic, inflammation-associated disorders. Such diseases, including inflammatory bowel disease, are not completely curable, but the specific line of treatment may reduce its symptoms. However, the response to treatment varies among patients, creating a necessity to uncover the pathophysiol. basis of immune-mediated diseases and apply novel therapeutic strategies. The present study describes the anti-inflammatory properties of osthole during histamine-induced inflammation in the intestinal Caco-2 cell line. Osthole reduced the secretion of cytokines (CKs) and the expression level of inflammation-associated genes, which were increased after a histamine treatment. We have shown that the secretion of pro-inflammatory CKs (IL-1尾, IL-6, IL-8, and TNF-伪) during inflammation may be mediated by NF魏B, and, after osthole treatment, this signaling pathway was disrupted. Our results suggest a possible role for osthole in the protection against inflammation in the gastrointestinal tract; thus, osthole may be considered as an anti-inflammatory modulator. This study involved multiple reactions and reactants, such as 2-(4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butyl)phenyl)-2-methylpropanoic acid (cas: 83799-24-0Product Details of 83799-24-0).

2-(4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butyl)phenyl)-2-methylpropanoic acid (cas: 83799-24-0) 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 83799-24-0

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem