Category: piperidines

Discovery of Potent, Selective, and Orally Bioavailable Alkynylphenoxyacetic Acid CRTH2 (DP2) Receptor Antagonists for the Treatment of Allergic Inflammatory Diseases was written by Crosignani, Stefano;Pretre, Adeline;Jorand-Lebrun, Catherine;Fraboulet, Gaele;Seenisamy, Jeyaprakashnarayanan;Augustine, John Kallikat;Missotten, Marc;Humbert, Yves;Cleva, Christophe;Abla, Nada;Daff, Hamina;Schott, Olivier;Schneider, Manfred;Burgat-Charvillon, Fabienne;Rivron, Delphine;Hamernig, Ingrid;Arrighi, Jean-Francois;Gaudet, Marilene;Zimmerli, Simone C.;Juillard, Pierre;Johnson, Zoe. And the article was included in Journal of Medicinal Chemistry in 2011.Safety of 1-((3-Bromo-4-methylphenyl)sulfonyl)piperidine The following contents are mentioned in the article:

New phenoxyacetic acid antagonists of CRTH2 are described. Following the discovery of a hit compound, I, by a focused screening, high protein binding was identified as its main weakness. Optimization aimed at reducing serum protein binding led to the identification of several compounds that showed not only excellent affinities for the receptor (41 compounds with K_i < 10 nM) but also excellent potencies in a human whole blood assay (IC₅₀ < 100 nM; PGD2-induced eosinophil shape change). Addnl. optimization of the pharmacokinetic characteristics led to the identification of several compounds suitable for in vivo testing. Of these, II (R¹ = n-Pr, R² = Me; R¹ = n-Pr, R² = F) were tested in two different pharmacol. models (acute FITC-mediated contact hypersensitivity and ovalbumin-induced eosinophilia models) and found to be active after oral dosing (10 and 30 mg/kg). This study involved multiple reactions and reactants, such as 1-((3-Bromo-4-methylphenyl)sulfonyl)piperidine (cas: 850429-73-1Safety of 1-((3-Bromo-4-methylphenyl)sulfonyl)piperidine).

1-((3-Bromo-4-methylphenyl)sulfonyl)piperidine (cas: 850429-73-1) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. 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.Safety of 1-((3-Bromo-4-methylphenyl)sulfonyl)piperidine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Discovery of Potent, Selective, and Orally Bioavailable Alkynylphenoxyacetic Acid CRTH2 (DP2) Receptor Antagonists for the Treatment of Allergic Inflammatory Diseases was written by Crosignani, Stefano;Pretre, Adeline;Jorand-Lebrun, Catherine;Fraboulet, Gaele;Seenisamy, Jeyaprakashnarayanan;Augustine, John Kallikat;Missotten, Marc;Humbert, Yves;Cleva, Christophe;Abla, Nada;Daff, Hamina;Schott, Olivier;Schneider, Manfred;Burgat-Charvillon, Fabienne;Rivron, Delphine;Hamernig, Ingrid;Arrighi, Jean-Francois;Gaudet, Marilene;Zimmerli, Simone C.;Juillard, Pierre;Johnson, Zoe. And the article was included in Journal of Medicinal Chemistry in 2011.Recommanded Product: 850429-73-1 The following contents are mentioned in the article:

New phenoxyacetic acid antagonists of CRTH2 are described. Following the discovery of a hit compound, I, by a focused screening, high protein binding was identified as its main weakness. Optimization aimed at reducing serum protein binding led to the identification of several compounds that showed not only excellent affinities for the receptor (41 compounds with K_i < 10 nM) but also excellent potencies in a human whole blood assay (IC₅₀ < 100 nM; PGD2-induced eosinophil shape change). Addnl. optimization of the pharmacokinetic characteristics led to the identification of several compounds suitable for in vivo testing. Of these, II (R¹ = n-Pr, R² = Me; R¹ = n-Pr, R² = F) were tested in two different pharmacol. models (acute FITC-mediated contact hypersensitivity and ovalbumin-induced eosinophilia models) and found to be active after oral dosing (10 and 30 mg/kg). This study involved multiple reactions and reactants, such as 1-((3-Bromo-4-methylphenyl)sulfonyl)piperidine (cas: 850429-73-1Recommanded Product: 850429-73-1).

1-((3-Bromo-4-methylphenyl)sulfonyl)piperidine (cas: 850429-73-1) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. 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.Recommanded Product: 850429-73-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Construction of peptide macrocycles via radical-mediated intramolecular C-H alkylations was written by Hu, Xiafei;Chen, Xiangxiang;Li, Bo;He, Gang;Chen, Gong. And the article was included in Organic Letters in 2021.Quality Control of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid The following contents are mentioned in the article:

Enzyme-catalyzed radical-mediated C-H functionalization reactions allow nature to create natural products of unusual three-dimensional structures from simple linear peptide precursors. In comparison, chemist’s ability to harness radical C-H functionalization reactions for synthesis of complex peptides remains limited. In this work, new methods have been developed to construct peptide macrocycles via radical-mediated intramol. C-H alkylation reactions under photoredox catalysis. Linear peptide precursors equipped with a C-terminal N-(acyloxy)phthalimide ester can cyclize with the α C-H bond of N-terminal glycine or aryl C-H bond of N-heteroarene capping units in high yield and selectivity under mild conditions. The strategy uses the C-H cyclization step to incorporate lysine, homolysine, and various heteroarene-derived amino acid linchpins into peptide macrocycles, enabling convergent and flexible synthesis of complex peptide macrocycles from simple building blocks. 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. 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.Quality Control of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Construction of peptide macrocycles via radical-mediated intramolecular C-H alkylations was written by Hu, Xiafei;Chen, Xiangxiang;Li, Bo;He, Gang;Chen, Gong. And the article was included in Organic Letters in 2021.Application In Synthesis of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid The following contents are mentioned in the article:

Enzyme-catalyzed radical-mediated C-H functionalization reactions allow nature to create natural products of unusual three-dimensional structures from simple linear peptide precursors. In comparison, chemist’s ability to harness radical C-H functionalization reactions for synthesis of complex peptides remains limited. In this work, new methods have been developed to construct peptide macrocycles via radical-mediated intramol. C-H alkylation reactions under photoredox catalysis. Linear peptide precursors equipped with a C-terminal N-(acyloxy)phthalimide ester can cyclize with the α C-H bond of N-terminal glycine or aryl C-H bond of N-heteroarene capping units in high yield and selectivity under mild conditions. The strategy uses the C-H cyclization step to incorporate lysine, homolysine, and various heteroarene-derived amino acid linchpins into peptide macrocycles, enabling convergent and flexible synthesis of complex peptide macrocycles from simple building blocks. 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 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.Application In Synthesis of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Macrocyclic Peptides as a Novel Class of NNMT Inhibitors: A SAR Study Aimed at Inhibitory Activity in the Cell was written by Hayashi, Kyohei;Uehara, Shota;Yamamoto, Shiho;Cary, Douglas R.;Nishikawa, Junichi;Ueda, Taichi;Ozasa, Hiroki;Mihara, Kousuke;Yoshimura, Norito;Kawai, Taeko;Ono, Takashi;Yamamoto, Saki;Fumoto, Masataka;Mikamiyama, Hidenori. And the article was included in ACS Medicinal Chemistry Letters in 2021.Recommanded Product: 86069-86-5 The following contents are mentioned in the article:

Nicotinamide N-methyltransferase (NNMT), which catalyzes the methylation of nicotinamide, is a cytosolic enzyme that has attracted much attention as a therapeutic target for a variety of diseases. However, despite the considerable interest in this target, reports of NNMT inhibitors have still been limited to date. In this work, utilizing in vitro translated macrocyclic peptide libraries, we identified peptide 1 as a novel class of NNMT inhibitors. Further exploration based on the X-ray cocrystal structures of the peptides with NNMT provided a dramatic improvement in inhibitory activity (peptide 23: IC₅₀ = 0.15 nM). Furthermore, by balance of the peptides’ lipophilicity and biol. activity, inhibitory activity against NNMT in cell-based assay was successfully achieved (peptide 26: cell-based IC₅₀ = 770 nM). These findings illuminate the potential of cyclic peptides as a relatively new drug discovery modality even for intracellular targets. 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.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.Recommanded Product: 86069-86-5

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Macrocyclic Peptides as a Novel Class of NNMT Inhibitors: A SAR Study Aimed at Inhibitory Activity in the Cell was written by Hayashi, Kyohei;Uehara, Shota;Yamamoto, Shiho;Cary, Douglas R.;Nishikawa, Junichi;Ueda, Taichi;Ozasa, Hiroki;Mihara, Kousuke;Yoshimura, Norito;Kawai, Taeko;Ono, Takashi;Yamamoto, Saki;Fumoto, Masataka;Mikamiyama, Hidenori. And the article was included in ACS Medicinal Chemistry Letters in 2021.Formula: C21H21NO4 The following contents are mentioned in the article:

Nicotinamide N-methyltransferase (NNMT), which catalyzes the methylation of nicotinamide, is a cytosolic enzyme that has attracted much attention as a therapeutic target for a variety of diseases. However, despite the considerable interest in this target, reports of NNMT inhibitors have still been limited to date. In this work, utilizing in vitro translated macrocyclic peptide libraries, we identified peptide 1 as a novel class of NNMT inhibitors. Further exploration based on the X-ray cocrystal structures of the peptides with NNMT provided a dramatic improvement in inhibitory activity (peptide 23: IC₅₀ = 0.15 nM). Furthermore, by balance of the peptides’ lipophilicity and biol. activity, inhibitory activity against NNMT in cell-based assay was successfully achieved (peptide 26: cell-based IC₅₀ = 770 nM). These findings illuminate the potential of cyclic peptides as a relatively new drug discovery modality even for intracellular targets. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Formula: 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. 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: C21H21NO4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Effects of membrane transport activity and cell metabolism on the unbound drug concentrations in the skeletal muscle and liver of drugs: A microdialysis study in rats was written by Wang, Shuyao;Chen, Chun;Guan, Chi;Qiu, Liping;Zhang, Lei;Zhang, Shaofeng;Zhou, Hongyu;Du, Hongwen;Li, Chen;Wu, Yaqiong;Chang, Hang;Wang, Tao. And the article was included in Pharmacology Research & Perspectives in 2021.COA of Formula: C32H39NO4 The following contents are mentioned in the article:

The unbound concentrations of 14 com. drugs, including five non-efflux/uptake transporter substrates-Class I, five efflux transporter substrates-class II and four influx transporter substrates-Class III, were simultaneously measured in rat liver, muscle, and blood via microanal. Kpuu,liver and Kpuu,muscle were calculated to evaluate the membrane transport activity and cell metabolism on the unbound drug concentrations in the skeletal muscle and liver. For Class I compounds, represented by antipyrine, unbound concentrations among liver, muscle and blood are sym. distributed when compound hepatic clearance is low. And when compound hepatic clearance is high, unbound concentrations among liver, muscle and blood are asym. distributed, such as Propranolol. For Class II and III compounds, overall, the unbound concentrations among liver, muscle, and blood are asym. distributed due to a combination of hepatic metabolism and efflux and/or influx transporter activity. 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: 83799-24-0COA of Formula: C32H39NO4).

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. 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.COA of Formula: C32H39NO4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

TPPU, a sEH Inhibitor, Attenuates Corticosterone-Induced PC12 Cell Injury by Modulation of BDNF-TrkB Pathway was written by Wu, Qiong;Song, Jingfang;Meng, Danxin;Chang, Quanzhong. And the article was included in Journal of Molecular Neuroscience in 2019.Recommanded Product: 1222780-33-7 The following contents are mentioned in the article:

High level of corticosterone (CORT) is toxic to neurons and plays an important role in depression-like behavior and chronic stress. Our previous study showed that TPPU, a soluble epoxide hydrolase (sEH) inhibitor (sEHI), induces an antidepressant effect in animal models. However, the underlying mechanism is not clear. In this study, we investigated the protective effect of TPPU on PC12 cells against CORT-induced cytotoxicity and its underlying mechanism. We found that TPPU and the sEH substrate epoxyeicosatrienoic acids (EETs) protected PC12 cells from the CORT-induced injury by increasing cell viability and inhibiting apoptosis. Furthermore, TPPU and EETs also blocked the CORT-mediated downregulation of BDNF. Blocking the BDNF-TrkB pathway by the TrkB inhibitor K252a abolished the protective effect of TPPU. Taken together, our results suggest that sEHI could protect PC12 cells against the CORT-induced cytotoxicity via the BDNF-TrkB signaling pathway. This study involved multiple reactions and reactants, such as 1-(1-Propionylpiperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea (cas: 1222780-33-7Recommanded Product: 1222780-33-7).

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. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Recommanded Product: 1222780-33-7

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

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