Category: piperidines

The Witkop-Winterfeldt oxidation converts tetrahydropyridoindoles into pyrroloquinolones and cinnolines by an unprecedented scaffold rearrangement was written by Mentel, Matthias;Peters, Martin;Albering, Joerg;Breinbauer, Rolf. And the article was included in Tetrahedron in 2011.Application of 33439-27-9 This article mentions the following:

The Fischer indole reaction between phenylhydrazines and N-tosyl-4-piperidone furnishes tetrahydropyrido[4,3-b]indoles. In a Witkop-Winterfeldt oxidation using ozone, such indole derivatives are converted into medium-sized dicarbonyl ring systems, which cyclize to pyrroloquinolones. A detailed study of the reaction intermediates and the characterization of a cinnoline betaine side product formed by an unprecedented ring closure mechanism are reported. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Application of 33439-27-9).

1-Tosylpiperidin-4-one (cas: 33439-27-9) 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.Application of 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

6-Benzhydryl-4-amino-quinolin-2-ones as Potent Cannabinoid Type 1 (CB₁) Receptor Inverse Agonists and Chemical Modifications for Peripheral Selectivity was written by Zhang, Yue-Mei;Greco, Michael N.;Macielag, Mark J.;Teleha, Christopher A.;DesJarlais, Renee L.;Tang, Yuting;Ho, George;Hou, Cuifen;Chen, Cailin;Zhao, Shuyuan;Kauffman, Jack;Camacho, Raul;Qi, Jenson;Murray, William;Demarest, Keith;Leonard, James. And the article was included in Journal of Medicinal Chemistry in 2018.Application In Synthesis of 1-(Methylsulfonyl)piperidin-4-amine hydrochloride This article mentions the following:

A novel series of 6-benzhydryl-4-amino-quinolin-2-ones was discovered as cannabinoid type 1 receptor (CB₁R) inverse agonists based on the high-throughput screening hit, compound 1a. Structure-activity relationships were studied to improve in vitro/in vivo pharmacol. and restrict distribution to the peripheral circulation. We adopted several strategies such as increasing topol. polar surface area, incorporating discrete polyethylene glycol side chains, and targeting P-glycoprotein (P-gp) to minimize access to the brain. Compound 6a is a P-gp substrate and a potent and highly selective CB₁R inverse agonist, demonstrating excellent in vivo metabolic stability and a low brain to plasma ratio. However, brain receptor occupancy studies showed that compound 6a may accumulate in brain with repeat dosing. This was evidenced by compound 6a inhibiting food intake and inducing weight loss in diet-induced obese mice. Thus, a strategy based on P-gp efflux may not be adequate for peripheral restriction of the disclosed quinolinone series. In the experiment, the researchers used many compounds, for example, 1-(Methylsulfonyl)piperidin-4-amine hydrochloride (cas: 651057-01-1Application In Synthesis of 1-(Methylsulfonyl)piperidin-4-amine hydrochloride).

1-(Methylsulfonyl)piperidin-4-amine hydrochloride (cas: 651057-01-1) 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.Application In Synthesis of 1-(Methylsulfonyl)piperidin-4-amine hydrochloride

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Catalytic C(sp²)-C(sp³) Bond Formation of Methoxyarenes by the Organic Superbase t-Bu-P4 was written by Shigeno, Masanori;Hayashi, Kazutoshi;Nozawa-Kumada, Kanako;Kondo, Yoshinori. And the article was included in Organic Letters in 2020.COA of Formula: C13H16N2 This article mentions the following:

The organic superbase catalyst t-Bu-P4 achieves nucleophilic aromatic substitution of methoxyarenes with alkanenitrile pronucleophiles. A variety of functional groups [cyano, nitro, (non)enolizable ketone, chloride, and amide moieties] are allowed on methoxyarenes. Moreover, an array of alkanenitriles with/without an aryl moiety at the nitrile α-position can be employed. The system also features no requirement of a stoichiometric base, MeOH (not salt waste) formation as a byproduct, and the production of congested quaternary carbon centers. In the experiment, the researchers used many compounds, for example, 1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4COA of Formula: C13H16N2).

1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.COA of Formula: C13H16N2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Discovery of GS-9973, a Selective and Orally Efficacious Inhibitor of Spleen Tyrosine Kinase was written by Currie, Kevin S.;Kropf, Jeffrey E.;Lee, Tony;Blomgren, Peter;Xu, Jianjun;Zhao, Zhongdong;Gallion, Steve;Whitney, J. Andrew;Maclin, Deborah;Lansdon, Eric B.;Maciejewski, Patricia;Rossi, Ann Marie;Rong, Hong;Macaluso, Jennifer;Barbosa, James;Di Paolo, Julie A.;Mitchell, Scott A.. And the article was included in Journal of Medicinal Chemistry in 2014.Safety of 4-Methylpiperidin-4-ol hydrochloride This article mentions the following:

Spleen tyrosine kinase (Syk) is an attractive drug target in autoimmune, inflammatory, and oncol. disease indications. The most advanced Syk inhibitor, R406, (or its prodrug form fostamatinib), has shown efficacy in multiple therapeutic indications, but its clin. progress has been hampered by dose-limiting adverse effects that have been attributed, at least in part, to the off-target activities of R406. It is expected that a more selective Syk inhibitor would provide a greater therapeutic window. Herein the authors report the discovery and optimization of a novel series of imidazo[1,2-a]pyrazine Syk inhibitors. This work culminated in the identification of GS-9973, a highly selective and orally efficacious Syk inhibitor which is currently undergoing clin. evaluation for autoimmune and oncol. indications. In the experiment, the researchers used many compounds, for example, 4-Methylpiperidin-4-ol hydrochloride (cas: 586375-35-1Safety of 4-Methylpiperidin-4-ol hydrochloride).

4-Methylpiperidin-4-ol hydrochloride (cas: 586375-35-1) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Safety of 4-Methylpiperidin-4-ol hydrochloride

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Design and synthesis of 4-arylpiperidinyl amide and N-arylpiperidin-3-yl-cyclopropanecarboxamide derivatives as novel melatonin receptor ligands was written by Li, Guiying;Zhou, Hao;Jiang, Yu;Keim, Holger;Topiol, Sidney W.;Poda, Suresh B.;Ren, Yong;Chandrasena, Gamini;Doller, Dario. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.HPLC of Formula: 58333-75-8 This article mentions the following:

Two series of 4-aryl-1-cyclopropanecarbonylpiperidines (I) and 1-arylpiperidin-3-ylcyclopropanecarboxamides (II), exhibiting diverse functionality at rat MT₁ and MT₂ receptors, are reported. I and (S)-II [aryl = 3-MeOC₆H₄] (MT₁/MT₂ agonist) have human microsomal intrinsic clearance comparable to ramelteon. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8HPLC of Formula: 58333-75-8).

4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8) 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 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.HPLC of Formula: 58333-75-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Silyl enol etherification by a Tf₂NH/amine co-catalytic system for minimizing hazardous waste generation was written by Kurahashi, Kei;Yamaoka, Yousuke;Takemoto, Yoshiji;Takasu, Kiyosei. And the article was included in Reaction Chemistry & Engineering in 2018.Computed Properties of C12H15NO3S This article mentions the following:

A practical silyl enol etherification of ketones with allylsilanes catalyzed by a Tf₂NH-amine co-catalyst under mild conditions has been developed. The reaction generated only volatile isobutene gas as waste. Moreover, a multi-gram synthesis using a microfluidic system and a domino silyl enol etherification-(2 + 2) cycloaddition reaction were demonstrated. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Computed Properties of C12H15NO3S).

1-Tosylpiperidin-4-one (cas: 33439-27-9) 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 are being utilized in different ways as anticancer, antiviral, antimalarial, antimicrobial, antifungal, antihypertension, analgesic, anti-inflammatory, anti-Alzheimer, antipsychotic and/or anticoagulant agents.Computed Properties of C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Discovery of MAP855, an Efficacious and Selective MEK1/2 Inhibitor with an ATP-Competitive Mode of Action was written by Poddutoori, Ramulu;Aardalen, Kimberly;Aithal, Kiran;Barahagar, Sanjeev Surendranath;Belliappa, Charamanna;Bock, Mark;Chelur, Shekar;Gerken, Andrea;Gopinath, Sreevalsam;Gruenenfelder, Bjoern;Kiffe, Michael;Krishnaswami, Maithreyi;Langowski, John;Madapa, Sudharshan;Narayanan, Kishore;Pandit, Chetan;Panigrahi, Sunil Kumar;Perrone, Mark;Potakamuri, Ravi Kumar;Ramachandra, Murali;Ramanathan, Anuradha;Ramos, Rita;Sager, Emine;Samajdar, Susanta;Subramanya, Hosahalli S.;Thimmasandra, Devaraja Seethappa;Venetsanakos, Eleni;Mobitz, Henrik. And the article was included in Journal of Medicinal Chemistry in 2022.Formula: C9H19N3O2 This article mentions the following:

Mutations in MEK1/2 have been described as a resistance mechanism to BRAF/MEK inhibitor treatment. We report the discovery of a novel ATP-competitive MEK1/2 inhibitor with efficacy in wildtype (WT) and mutant MEK12 models. Starting from a HTS hit, we obtained selective, cellularly active compounds that showed equipotent inhibition of WT MEK1/2 and a panel of MEK1/2 mutant cell lines. Using a structure-based approach, the optimization addressed the liabilities by systematic anal. of mol. matched pairs (MMPs) and ligand conformation. Addition of only three heavy atoms to early tool compound 6 removed Cyp3A4 liabilities and increased the cellular potency by 100-fold, while reducing log P by 5 units. Profiling of MAP855, compound 30, in pharmacokinetic-pharmacodynamic and efficacy studies in BRAF-mutant models showed comparable efficacy to clin. MEK1/2 inhibitors. Compound 30 is a novel highly potent and selective MEK1/2 kinase inhibitor with equipotent inhibition of WT and mutant MEK1/2, whose drug-like properties allow further investigation in the mutant MEK setting upon BRAF/MEK therapy. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-aminopiperazine-1-carboxylate (cas: 118753-66-5Formula: C9H19N3O2).

tert-Butyl 4-aminopiperazine-1-carboxylate (cas: 118753-66-5) 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. 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.Formula: C9H19N3O2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

1-, 3- And 8-substituted-9-deazaxanthines as potent and selective antagonists at the human A_2B adenosine receptor was written by Stefanachi, Angela;Brea, Jose Manuel;Cadavid, Maria Isabel;Centeno, Nuria B.;Esteve, Cristina;Loza, Maria Isabel;Martinez, Ana;Nieto, Rosa;Ravina, Enrique;Sanz, Ferran;Segarra, Victor;Sotelo, Eddy;Vidal, Bernat;Carotti, Angelo. And the article was included in Bioorganic & Medicinal Chemistry in 2008.Recommanded Product: 4-(2-Methoxyphenyl)piperidine This article mentions the following:

A large series of piperazin-, piperidin- and tetrahydroisoquinolinamides of 4-(1,3-dialkyl-9-deazaxanthin-8-yl)phenoxyacetic acid were prepared through conventional or multiple parallel syntheses and evaluated for their binding affinity at the recombinant human adenosine receptors, chiefly at the hA_2B and hA_2A receptor subtypes. Several ligands endowed with high binding affinity at hA_2B receptors, excellent selectivity over hA_2A and hA₃ and a significant, but lower, selectivity over hA₁ were identified. Among them, piperazinamide derivatives (I and II), and piperidinamide derivative (III) proved highly potent at hA_2B (K_i = 11, 2 and 5.5 nM, resp.) and selective towards hA_2A (hA_2A/hA_2B SI = 912, 159 and 630, resp.), hA₃ (hA₃/hA_2B SI = > 100, 3090 and >180, resp.) and hA₁ (hA₁/hA_2B SI = > 100, 44 and 120, resp.), SI being the selectivity index. A number of selected ligands tested in functional assays in vitro showed very interesting antagonist activities and efficacies at both A_2A and A_2B receptor subtypes, with pA₂ values close to the corresponding pK_is. Structure-affinity and structure-selectivity relationships suggested that the binding potency at the hA_2B receptor may be increased by lipophilic substituents at the N4-position of piperazinamides and that an ortho-methoxy substituent at the 8-Ph ring and alkyl groups at N1 larger than the ones at N3, in the 9-deazaxanthine ring, may strongly enhance the hA_2A/hA_2B SI. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Recommanded Product: 4-(2-Methoxyphenyl)piperidine).

4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8) 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. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Recommanded Product: 4-(2-Methoxyphenyl)piperidine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Orally bioavailable dual MMP-1/MMP-14 sparing, MMP-13 selective α-sulfone hydroxamates was written by Kolodziej, Stephen A.;Hockerman, Susan L.;Boehm, Terri L.;Carroll, Jeffery N.;DeCrescenzo, Gary A.;McDonald, Joseph J.;Mischke, Debbie A.;Munie, Grace E.;Fletcher, Theresa R.;Rico, Joseph G.;Stehle, Nathan W.;Swearingen, Craig;Becker, Daniel P.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.Electric Literature of C12H17NO This article mentions the following:

A series of Ph piperidine α-sulfone hydroxamate derivatives, e.g., I, has been prepared utilizing a combination of solution-phase and resin-bound library technologies to afford compounds that are potent and highly selective for MMP-13, are dual-sparing of MMP-1 and MMP-14 (MT1-MMP) and exhibit oral bioavailability in rats. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Electric Literature of C12H17NO).

4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. 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.Electric Literature of C12H17NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Ni-catalyzed cross-electrophile coupling between vinyl/aryl and alkyl sulfonates: synthesis of cycloalkenes and modification of peptides was written by Duan, Jicheng;Du, Yun-Fei;Pang, Xiaobo;Shu, Xing-Zhong. And the article was included in Chemical Science in 2019.Application of 33439-27-9 This article mentions the following:

The coupling reactions between vinyl/aryl and alkyl C-O electrophiles that can be derived from chem. feedstocks and naturally occurring functional groups was reported. This method provided an efficient approach to the synthesis of a wide range of functionalized, and/or secondary alkyl substituted cycloalkenes that are difficult to synthesize by conventional methods. The reaction proceeded with broad substrate scope, and tolerated various functional groups such as alc., aldehyde, ketone, ester, amide, alkene, alkyne, heterocycles, organotin and organosilicon compounds The synthetic utility of this method was demonstrated by providing facile access to important building blocks. The possibility to apply this method for late-stage modification of peptides was also demonstrated. A broad range of functionalized alkyl groups was selectively introduced into tyrosine in peptides via C-C bond formation, which was a challenge to the existing procedures. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Application of 33439-27-9).

1-Tosylpiperidin-4-one (cas: 33439-27-9) 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 bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Application of 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem