Day: November 28, 2022

Rapid, Structure-Based Exploration of Pipecolic Acid Amides as Novel Selective Antagonists of the FK506-Binding Protein 51 was written by Gaali, Steffen;Feng, Xixi;Haehle, Andreas;Sippel, Claudia;Bracher, Andreas;Hausch, Felix. And the article was included in Journal of Medicinal Chemistry in 2016.Synthetic Route of C21H21NO4 The following contents are mentioned in the article:

The FK506-binding protein 51 (FKBP51) is a key regulator of stress hormone receptors and an established risk factor for stress-related disorders. Drug development for FKBP51 has been impaired by the structurally similar but functionally opposing homolog FKBP52. High selectivity between FKBP51 and FKBP52 can be achieved by ligands that stabilize a recently discovered FKBP51-favoring conformation. However, drug-like parameters for these ligands remained unfavorable. In the present study, we replaced the potentially labile pipecolic ester group of previous FKBP51 ligands by various low mol. weight amides. This resulted in the first series of pipecolic acid amides, which had much lower mol. weights without affecting FKBP51 selectivity. We discovered a geminally substituted cyclopentyl amide as a preferred FKBP51-binding motif and elucidated its binding mode to provide a new lead structure for future drug optimization. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Synthetic Route of C21H21NO4).

(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 ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Synthetic Route of C21H21NO4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Extending Foldamer Design beyond α-Helix Mimicry: α/β-Peptide Inhibitors of Vascular Endothelial Growth Factor Signaling was written by Haase, Holly S.;Peterson-Kaufman, Kimberly J.;Lan Levengood, Sheeny K.;Checco, James W.;Murphy, William L.;Gellman, Samuel H.. And the article was included in Journal of the American Chemical Society in 2012.HPLC of Formula: 86069-86-5 The following contents are mentioned in the article:

Diverse strategies have been explored to mimic the surface displayed by an α-helical segment of a protein, with the goal of creating inhibitors of helix-mediated protein-protein interactions. Many recognition surfaces on proteins, however, are topol. more complex and less regular than a single α-helix. We describe efforts to develop peptidic foldamers that bind to the irregular receptor-recognition surface of vascular endothelial growth factor (VEGF). Our approach begins with a 19-residue α-peptide previously reported by Fairbrother et al. (Biochem.1998, 37, 17754) to bind to this surface on VEGF. Systematic evaluation of α→β replacements throughout this 19-mer sequence enabled us to identify homologs that contain up to ∼30% β residues, retain significant affinity for VEGF, and display substantial resistance to proteolysis. These α/β-peptides can block VEGF-stimulated proliferation of human umbilical vein endothelial cells. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5HPLC of Formula: 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 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.HPLC of Formula: 86069-86-5

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Extending Foldamer Design beyond α-Helix Mimicry: α/β-Peptide Inhibitors of Vascular Endothelial Growth Factor Signaling was written by Haase, Holly S.;Peterson-Kaufman, Kimberly J.;Lan Levengood, Sheeny K.;Checco, James W.;Murphy, William L.;Gellman, Samuel H.. And the article was included in Journal of the American Chemical Society in 2012.Category: piperidines The following contents are mentioned in the article:

Diverse strategies have been explored to mimic the surface displayed by an α-helical segment of a protein, with the goal of creating inhibitors of helix-mediated protein-protein interactions. Many recognition surfaces on proteins, however, are topol. more complex and less regular than a single α-helix. We describe efforts to develop peptidic foldamers that bind to the irregular receptor-recognition surface of vascular endothelial growth factor (VEGF). Our approach begins with a 19-residue α-peptide previously reported by Fairbrother et al. (Biochem.1998, 37, 17754) to bind to this surface on VEGF. Systematic evaluation of α→β replacements throughout this 19-mer sequence enabled us to identify homologs that contain up to ∼30% β residues, retain significant affinity for VEGF, and display substantial resistance to proteolysis. These α/β-peptides can block VEGF-stimulated proliferation of human umbilical vein endothelial cells. 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. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Category: piperidines

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

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

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

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

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

Analogues of AVP modified in the N-terminal part of the molecule with Pip isomers: TFA-catalyzed peptide bond hydrolysis was written by Sobolewski, Dariusz;Prahl, Adam;Kwiatkowska, Anna;Slaninova, Jirina;Lammek, Bernard. And the article was included in Journal of Peptide Science in 2009.Category: piperidines The following contents are mentioned in the article:

Using SPPS techniques, six new analogs of AVP (arginine vasopressin) and some of its agonists were synthesized. The peptides were designed by substitution of Phe at position 3 of AVP, [Mpa¹] AVP (dAVP) and [Mpa¹,Val⁴,D-Arg⁸]VP (dVDAVP) with L– or D-Pip (Mpa = 3-mercaptopropionic acid; Pip = pipecolic acid, a non-coded α-imino acid, also known as homoproline). Surprisingly enough, both the analogs of AVP and [Mpa¹]AVP with identical substituents at position 2 turned out to be highly sensitive to TFA used for the deprotection and resin cleavage step, and it was the reason why the authors were not able to obtain these four peptides. The mechanisms of their fragmentation were proposed in this study. Unfortunately, all the new analogs were inactive in bioassays for the pressor, antidiuretic and uterotonic in vitro activities in the rat. 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. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Analogues of AVP modified in the N-terminal part of the molecule with Pip isomers: TFA-catalyzed peptide bond hydrolysis was written by Sobolewski, Dariusz;Prahl, Adam;Kwiatkowska, Anna;Slaninova, Jirina;Lammek, Bernard. And the article was included in Journal of Peptide Science in 2009.Recommanded Product: (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid The following contents are mentioned in the article:

Using SPPS techniques, six new analogs of AVP (arginine vasopressin) and some of its agonists were synthesized. The peptides were designed by substitution of Phe at position 3 of AVP, [Mpa¹] AVP (dAVP) and [Mpa¹,Val⁴,D-Arg⁸]VP (dVDAVP) with L– or D-Pip (Mpa = 3-mercaptopropionic acid; Pip = pipecolic acid, a non-coded α-imino acid, also known as homoproline). Surprisingly enough, both the analogs of AVP and [Mpa¹]AVP with identical substituents at position 2 turned out to be highly sensitive to TFA used for the deprotection and resin cleavage step, and it was the reason why the authors were not able to obtain these four peptides. The mechanisms of their fragmentation were proposed in this study. Unfortunately, all the new analogs were inactive in bioassays for the pressor, antidiuretic and uterotonic in vitro activities in the rat. 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 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.Recommanded Product: (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem