Category: piperidines

Designing a small fluorescent inhibitor to investigate soluble epoxide hydrolase engagement in living cells was written by Brunst, Steffen;Schoenfeld, Julia;Breunig, Peter;Burgers, Luisa D.;DeMeglio, Murphy;Ehrler, Johanna H. M.;Lillich, Felix F.;Weizel, Lilia;Hefendehl, Jasmin K.;Fuerst, Robert;Proschak, Ewgenij;Hiesinger, Kerstin. And the article was included in ACS Medicinal Chemistry Letters in 2022.Formula: C16H20F3N3O3 The following contents are mentioned in the article:

Soluble epoxide hydrolase (sEH) is a promising target for a number of inflammation-related diseases. In addition, inhibition of sEH has been shown to reduce neuroinflammation, which plays a critical role in the development of central nervous system (CNS) diseases such as Alzheimer’s disease. In this study, we present the rational design of a small fluorescent sEH inhibitor. Starting from the clin. candidate GSK2256294A, we replaced the triazine moiety with the 4-chloro-7-nitrobenzo-2-oxa-1,3-diazole (NBD-Cl) fluorophore. The resulting fluorescent sEH inhibitor displayed excellent potency in an in vitro enzyme activity assay (IC₅₀ < 2 nM). The developed inhibitor is applicable in a NanoBRET-based assay system suitable for studying sEH target engagement in living cells. Furthermore, the inhibitor can be used to visualize sEH in sEH-transfected HEK293 cells and in primary mouse astrocytes by fluorescence microscopy. 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 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. 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.Formula: C16H20F3N3O3

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Introduction of Pro and its analogues in the conserved P₁‘ position of trypsin inhibitor SFTI-1 retains its inhibitory activity was written by Legowska, Anna;Debowski, Dawid;Lukajtis, Rafal;Sztabkowska, Emilia;Mizeria, Aneta;Brzozowski, Krzysztof;Wysocka, Magdalena;Lesner, Adam;Rolka, Krzysztof. And the article was included in Protein & Peptide Letters in 2011.SDS of cas: 86069-86-5 The following contents are mentioned in the article:

A number of monocyclic SFTI-1 analogs modified in the conserved inhibitor P₁‘ position by Pro, its L-hydroxyproline (Hyp) derivative as well as mimetics with different ring size were synthesized by the solid-phase method. Replacement of Ser6 by Pro, Hyp, and a four-member ring, L-azetidine-2-carboxylic acid (Aze), retained trypsin or chymotrypsin inhibitory activity. The determined association equilibrium constants of these analogs with a cognate enzyme were about two orders of magnitude lower than those obtained for ones with conserved Ser6. In all analogs, with the exception of one, [Phe⁵,Aze⁶]SFTI-1, the P₁-P₁‘ reactive site remained intact. The results provide first evidence that the conserved Ser in the P₁‘ position of Bowman-Birk inhibitors can be successfully replaced by an amino acid with a secondary amine group. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5SDS of cas: 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 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.SDS of cas: 86069-86-5

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Introduction of Pro and its analogues in the conserved P₁‘ position of trypsin inhibitor SFTI-1 retains its inhibitory activity was written by Legowska, Anna;Debowski, Dawid;Lukajtis, Rafal;Sztabkowska, Emilia;Mizeria, Aneta;Brzozowski, Krzysztof;Wysocka, Magdalena;Lesner, Adam;Rolka, Krzysztof. And the article was included in Protein & Peptide Letters in 2011.Recommanded Product: 86069-86-5 The following contents are mentioned in the article:

A number of monocyclic SFTI-1 analogs modified in the conserved inhibitor P₁‘ position by Pro, its L-hydroxyproline (Hyp) derivative as well as mimetics with different ring size were synthesized by the solid-phase method. Replacement of Ser6 by Pro, Hyp, and a four-member ring, L-azetidine-2-carboxylic acid (Aze), retained trypsin or chymotrypsin inhibitory activity. The determined association equilibrium constants of these analogs with a cognate enzyme were about two orders of magnitude lower than those obtained for ones with conserved Ser6. In all analogs, with the exception of one, [Phe⁵,Aze⁶]SFTI-1, the P₁-P₁‘ reactive site remained intact. The results provide first evidence that the conserved Ser in the P₁‘ position of Bowman-Birk inhibitors can be successfully replaced by an amino acid with a secondary amine group. 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: 86069-86-5).

(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) 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. 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.Recommanded Product: 86069-86-5

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Potent bactericidal antimycobacterials targeting the chaperone ClpC1 based on the depsipeptide natural products Ecumicin and Ohmyungsamycin A was written by Hawkins, Paige M. E.;Hoi, David M.;Cheung, Chen-Yi;Wang, Trixie;Quan, Diana;Sasi, Vishnu Mini;Liu, Dennis Y.;Linington, Roger G.;Jackson, Colin J.;Oehlers, Stefan H.;Cook, Gregory M.;Britton, Warwick J.;Clausen, Tim;Payne, Richard J.. And the article was included in Journal of Medicinal Chemistry in 2022.Application of 86069-86-5 The following contents are mentioned in the article:

Ohmyungsamycin A and ecumicin are structurally related cyclic depsipeptide natural products that possess activity against Mycobacterium tuberculosis (Mtb), the causative agent of tuberculosis (TB). Herein, we describe the design and synthesis of a library of analogs of these two natural products using an efficient solid-phase synthesis and late-stage macrolactamization strategy. Lead analogs possessed potent activity against Mtb in vitro (min. inhibitory concentration 125-500 nM) and were shown to inhibit protein degradation by the mycobacterial ClpC1-ClpP1P2 protease with an associated enhancement of ClpC1 ATPase activity. The most promising analog from the series exhibited rapid bactericidal killing activity against Mtb, capable of sterilizing cultures after 7 days, and retained bactericidal activity against hypoxic non-replicating Mtb. This natural product analog was also active in an in vivo zebrafish model of infection. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Application 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. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising α-glucosidase inhibitors. The former are analogs of DNJ with an improved α-glucosidase inhibitory profile than that of DNJ. Boisson et al.Application of 86069-86-5

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Potent bactericidal antimycobacterials targeting the chaperone ClpC1 based on the depsipeptide natural products Ecumicin and Ohmyungsamycin A was written by Hawkins, Paige M. E.;Hoi, David M.;Cheung, Chen-Yi;Wang, Trixie;Quan, Diana;Sasi, Vishnu Mini;Liu, Dennis Y.;Linington, Roger G.;Jackson, Colin J.;Oehlers, Stefan H.;Cook, Gregory M.;Britton, Warwick J.;Clausen, Tim;Payne, Richard J.. And the article was included in Journal of Medicinal Chemistry in 2022.Application In Synthesis of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid The following contents are mentioned in the article:

Ohmyungsamycin A and ecumicin are structurally related cyclic depsipeptide natural products that possess activity against Mycobacterium tuberculosis (Mtb), the causative agent of tuberculosis (TB). Herein, we describe the design and synthesis of a library of analogs of these two natural products using an efficient solid-phase synthesis and late-stage macrolactamization strategy. Lead analogs possessed potent activity against Mtb in vitro (min. inhibitory concentration 125-500 nM) and were shown to inhibit protein degradation by the mycobacterial ClpC1-ClpP1P2 protease with an associated enhancement of ClpC1 ATPase activity. The most promising analog from the series exhibited rapid bactericidal killing activity against Mtb, capable of sterilizing cultures after 7 days, and retained bactericidal activity against hypoxic non-replicating Mtb. This natural product analog was also active in an in vivo zebrafish model of infection. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Application In Synthesis 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. 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 In Synthesis of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Pharmacological inhibition of soluble epoxide hydrolase or genetic deletion reduces diclofenac-induced gastric ulcers was written by Goswami, Sumanta Kumar;Rand, Amelia Ann;Wan, Debin;Yang, Jun;Inceoglu, Bora;Thomas, Melany;Morisseau, Christophe;Yang, Guang-Yu;Hammock, Bruce D.. And the article was included in Life Sciences in 2017.Category: piperidines The following contents are mentioned in the article:

This research was conducted to evaluate the hypothesis that gastric ulcers caused by the NSAID diclofenac sodium (DCF) can be prevented by the soluble epoxide hydrolase inhibitor TPPU. Mice were administered a single dose of 10, 30 or 100 mg/kg of DCF. Once an ulcerative dose of DCF was chosen, mice were pretreated with TPPU for 7 days at 0.1 mg/kg to evaluate anti-ulcer effects of the sEH inhibitor on anatomy, histopathol., pH, inflammatory markers and epithelial apoptosis of stomachs. Diclofenac caused ulceration of the stomach at a dose of 100 mg/kg and a time post dose of 6 h. Ulcers generated under these conditions were associated with a significant increase in the levels of TNF-α and IL-6 in serum and increased apoptosis compared to control mice. Pretreatment with TPPU resulted in a decrease of ulceration in mice treated with DCF with a significant decrease in the level of apoptosis, TNF-α and IL-6 in the serum in comparison to diclofenac-treated mice. TPPU did not affect the pH of the stomach, whereas omeprazole elevated the pH of the stomach as expected. A similar anti-ulcer effect was observed in sEH gene knockout mice treated with DCF. The sEH inhibitor TPPU decreases the NSAID-induced stomach ulcers. 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 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.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Microparticle Matrix Encoding of Beads was written by Meldal, Morten;Christensen, Soeren Flygering. And the article was included in Angewandte Chemie, International Edition in 2010.Name: (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid The following contents are mentioned in the article:

The authors present a versatile, simple encoding principle that may solve many problems in solid-phase screening and decoding: optical microparticle matrix encoding (MPM encoding) with fluorescent microparticles. The utility of this technique has been demonstrated in the identification of avidin ligands from a focused library, in which compounds could not be distinguished with mass spectrometric methods. The library design was based upon previously reported L– and D-amino acid libraries for avidin and streptavidin, thus indicating selectivity for aromatic residues. Uniform 10 μm Tentagel microparticles labeled with a chem. stable fluorophore ATOTA [tris(dialkylamino)trioxatriangulenium ion] were randomly distributed in a bis(acrylamido)polyethylene glycol (PEG) macromonomer (64,000 cm^-3) by ultrasound and homogenization. Inverse suspension polymerization of the microparticle-containing macromonomer in the presence of bis(tert-butyldiphenylmethylsilyl)PEG1500 stabilizer provided 500,000 uniform, amino-functionalized, uniquely encoded beads (72 mL; ca 6.5 g dry weight), which contained an average of 8 microparticles per bead, with a bead size of (550±100) μm. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Name: (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 key saturated heterocyclic scaffold found in several of the top-selling small molecule pharmaceuticals and natural alkaloids, with a diverse range of biological activities. 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.Name: (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Microparticle Matrix Encoding of Beads was written by Meldal, Morten;Christensen, Soeren Flygering. And the article was included in Angewandte Chemie, International Edition in 2010.SDS of cas: 86069-86-5 The following contents are mentioned in the article:

The authors present a versatile, simple encoding principle that may solve many problems in solid-phase screening and decoding: optical microparticle matrix encoding (MPM encoding) with fluorescent microparticles. The utility of this technique has been demonstrated in the identification of avidin ligands from a focused library, in which compounds could not be distinguished with mass spectrometric methods. The library design was based upon previously reported L– and D-amino acid libraries for avidin and streptavidin, thus indicating selectivity for aromatic residues. Uniform 10 μm Tentagel microparticles labeled with a chem. stable fluorophore ATOTA [tris(dialkylamino)trioxatriangulenium ion] were randomly distributed in a bis(acrylamido)polyethylene glycol (PEG) macromonomer (64,000 cm^-3) by ultrasound and homogenization. Inverse suspension polymerization of the microparticle-containing macromonomer in the presence of bis(tert-butyldiphenylmethylsilyl)PEG1500 stabilizer provided 500,000 uniform, amino-functionalized, uniquely encoded beads (72 mL; ca 6.5 g dry weight), which contained an average of 8 microparticles per bead, with a bead size of (550±100) μm. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5SDS of cas: 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. 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.SDS of cas: 86069-86-5

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Barrel-shaped ClpP Proteases Display Attenuated Cleavage Specificities was written by Gersch, Malte;Stahl, Matthias;Poreba, Marcin;Dahmen, Maria;Dziedzic, Anna;Drag, Marcin;Sieber, Stephan A.. And the article was included in ACS Chemical Biology in 2016.Quality Control of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid The following contents are mentioned in the article:

ClpP is a self-compartmentalizing protease with crucial roles in bacterial and mitochondrial protein quality control. Although the ClpP homocomplex is composed of 14 equiv active sites, it degrades a multitude of substrates to small peptides, demonstrating its capability to carry out diverse cleavage reactions. Here, we show that ClpP proteases from E. coli, S. aureus, and human mitochondria exhibit preferences for certain amino acids in the P1, P2, and P3 positions using a tailored fluorogenic substrate library. However, this high specificity is not retained during proteolysis of endogenous substrates as shown by mass spectrometric anal. of peptides produced in ClpXP-mediated degradation reactions. Our data suggest a mechanism that implicates the barrel-shaped architecture of ClpP not only in shielding the active sites to prevent uncontrolled proteolysis but also in providing high local substrate concentrations to enable efficient proteolytic processing. Furthermore, we introduce customized fluorogenic substrates with unnatural amino acids that greatly surpass the sensitivity of previously used tools. We used these to profile the activity of cancer-patient- and Perrault-syndrome-derived ClpP mutant proteins. 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. 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 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.Quality Control of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Barrel-shaped ClpP Proteases Display Attenuated Cleavage Specificities was written by Gersch, Malte;Stahl, Matthias;Poreba, Marcin;Dahmen, Maria;Dziedzic, Anna;Drag, Marcin;Sieber, Stephan A.. And the article was included in ACS Chemical Biology in 2016.SDS of cas: 86069-86-5 The following contents are mentioned in the article:

ClpP is a self-compartmentalizing protease with crucial roles in bacterial and mitochondrial protein quality control. Although the ClpP homocomplex is composed of 14 equiv active sites, it degrades a multitude of substrates to small peptides, demonstrating its capability to carry out diverse cleavage reactions. Here, we show that ClpP proteases from E. coli, S. aureus, and human mitochondria exhibit preferences for certain amino acids in the P1, P2, and P3 positions using a tailored fluorogenic substrate library. However, this high specificity is not retained during proteolysis of endogenous substrates as shown by mass spectrometric anal. of peptides produced in ClpXP-mediated degradation reactions. Our data suggest a mechanism that implicates the barrel-shaped architecture of ClpP not only in shielding the active sites to prevent uncontrolled proteolysis but also in providing high local substrate concentrations to enable efficient proteolytic processing. Furthermore, we introduce customized fluorogenic substrates with unnatural amino acids that greatly surpass the sensitivity of previously used tools. We used these to profile the activity of cancer-patient- and Perrault-syndrome-derived ClpP mutant proteins. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5SDS of cas: 86069-86-5).

(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. 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.SDS of cas: 86069-86-5

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem