Category: piperidines

Development of Human Calcitonin Gene-Related Peptide (CGRP) Receptor Antagonists. Potent and Selective Small Molecule CGRP Antagonists. 1-[N²-[3,5-Dibromo-N-[[4-(3,4-dihydro-2(1H)-oxoquinazolin-3-yl)-1- piperidinyl]carbonyl]-D-tyrosyl]-L-lysyl]-4-(4-pyridinyl)piperazine: The First CGRP Antagonist for Clinical Trials in Acute Migraine was written by Rudolf, Klaus;Eberlein, Wolfgang;Engel, Wolfhard;Pieper, Helmut;Entzeroth, Michael;Hallermayer, Gerhard;Doods, Henri. And the article was included in Journal of Medicinal Chemistry in 2005.Recommanded Product: 58333-75-8 This article mentions the following:

Although the triptans have greatly improved the acute treatment of migraine headache, there are yet many shortcomings. Therefore, new strategies for the treatment of migraine are needed which offer advantages over current therapy, e.g. triptans. Our novel approach was based on the hypothesis that the release of calcitonin gene-related peptide (CGRP) could play a causative role in migraine headache. Thus the authors initiated a program aimed at the design and synthesis of small mol. CGRP receptor antagonists. High throughput screening led to the identification of (R)-Tyr-(S)-Lys dipeptide-like compounds that showed weak but unequivocal binding to the human CGRP receptor. Lead optimization afforded highly potent CGRP antagonists, the prototype being compound (I) (BIBN4096). This compound exhibiting a favorable biol. profile was selected for initial clin. trials. A proof of concept study indicated that i.v. application of I was effective in the treatment of acute migraine headache. This finding strongly supports our initial working hypothesis that CGRP plays an important role in the pathophysiol. of migraine. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Recommanded Product: 58333-75-8).

4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. 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: 58333-75-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Discovery of 3-Methyl-N-(1-oxy-3′,4′,5′,6′-tetrahydro-2’H-[2,4′-bipyridine]-1′-ylmethyl)benzamide (ABT-670), an Orally Bioavailable Dopamine D₄ Agonist for the Treatment of Erectile Dysfunction was written by Patel, Meena V.;Kolasa, Teodozyj;Mortell, Kathleen;Matulenko, Mark A.;Hakeem, Ahmed A.;Rohde, Jeffrey J.;Nelson, Sherry L.;Cowart, Marlon D.;Nakane, Masaki;Miller, Loan N.;Uchic, Marie E.;Terranova, Marc A.;El-Kouhen, Odile F.;Donnelly-Roberts, Diana L.;Namovic, Marian T.;Hollingsworth, Peter R.;Chang, Renjie;Martino, Brenda R.;Wetter, Jill M.;Marsh, Kennan C.;Martin, Ruth;Darbyshire, John F.;Gintant, Gary;Hsieh, Gin C.;Moreland, Robert B.;Sullivan, James P.;Brioni, Jorge D.;Stewart, Andrew O.. And the article was included in Journal of Medicinal Chemistry in 2006.Category: piperidines This article mentions the following:

The goal of this study was to identify a structurally distinct D₄-selective agonist with superior oral bioavailability to our first-generation clin. candidate 1a (ABT-724) for the potential treatment of erectile dysfunction. Arylpiperazines such as (heteroarylmethyl)piperazine 1a, benzamide 2, and acetamides such as 3a,b exhibit poor oral bioavailability. Structure-activity relationship (SAR) studies with the arylpiperidine template provided potent partial agonists such as 4d and 5k that demonstrated no improvement in oral bioavailability. Further optimization with the (N-oxy-2-pyridinyl)piperidine template led to the discovery of compound 6b (ABT-670), which exhibited excellent oral bioavailability in rat, dog, and monkey (68%, 85%, and 91%, resp.) with comparable efficacy, safety, and tolerability to 1a. The N-oxy-2-pyridinyl moiety not only provided the structural motif required for agonist function but also reduced metabolism rates. The SAR study leading to the discovery of 6b is described herein. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Category: piperidines).

4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8) 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.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Cyano phosphate: an efficient intermediate for the chemoselective conversion of carbonyl compounds to nitriles was written by Yoneda, Ryuji;Harusawa, Shinya;Kurihara, Takushi. And the article was included in Journal of Organic Chemistry in 1991.Application In Synthesis of 1-Benzylpiperidine-4-carbonitrile This article mentions the following:

Cyanohydrin di-Et phosphates, readily obtained from various ketones and aldehydes by reaction with di-Et phosphorocyanidate and lithium cyanide, reacted chemoselectively with SmI₂ in THF to give the corresponding nitriles in excellent yields. This method was also found applicable to α,β-unsaturated carbonyl compounds via cyano phosphates to give β,γ-unsaturated nitriles, not obtainable by standard methods, without isomerization of the double bonds. In the experiment, the researchers used many compounds, for example, 1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4Application In Synthesis of 1-Benzylpiperidine-4-carbonitrile).

1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. 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 In Synthesis of 1-Benzylpiperidine-4-carbonitrile

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Tetrahydro-isoquinoline-Based Factor Xa Inhibitors was written by Kucznierz, Ralf;Grams, Frank;Leinert, Herbert;Marzenell, Klaus;Engh, Richard A.;von Saal, Wolfgang. And the article was included in Journal of Medicinal Chemistry in 1998.Synthetic Route of C7H13NO2 This article mentions the following:

(Amidinotetrahydroisoquinolinyloxy)phenylacetic acids were prepared as inhibitors of Factor Xa (fXa). The compounds were prepared using 15 synthetic steps on average The most potent compounds I (R = H, Et) and II (R = H, Et; R¹ = Me, 4-MeOC₆H₄, Et) display inhibition constants of K_i = 21-55 nM but do not inhibit thrombin and only weakly inhibit trypsin. They bear a second basic moiety, e.g., substituted 1-(iminomethyl)piperidines, which is linked to C-4 of the Ph group via an oxygen atom. The inhibition constants of these compounds are almost independent of the size of the (iminomethyl)piperidine substituent. Due to the fact that fXa displays two cation binding sites, namely, the S1 and S4 sites, in principle two binding modes are conceivable for the novel dibasic fXa inhibitors. Mol. modeling experiments based on the X-ray structures of uninhibited fXa and the DX-9065a/fXa complex were carried out. The results, taken together with the inhibition constants, favor one binding mode: the tetrahydro-isoquinoline fills the S1 pocket even better than the naphthalene moiety of DX-9065a, and the (iminomethyl)piperidine residues occupy the S4 site. In the experiment, the researchers used many compounds, for example, 1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1Synthetic Route of C7H13NO2).

1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. 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.Synthetic Route of C7H13NO2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Towards metabolically stable 5-HT₇ receptor ligands: a study on 1-arylpiperazine derivatives and related isosters was written by Lacivita, Enza;De Giorgio, Paola;Patarnello, Daniela;Niso, Mauro;Colabufo, Nicola A.;Berardi, Francesco;Perrone, Roberto;Satala, Grzegorz;Duszynska, Beata;Bojarski, Andrzej J.;Leopoldo, Marcello. And the article was included in Experimental Brain Research in 2013.Safety of 4-(2-Methoxyphenyl)piperidine This article mentions the following:

Serotonin 7 (5-hydroxytryptamine7 or 5-HT₇) is the most recently identified serotonin receptor. It is involved in mood disorders and is studied as a target for antidepressants. Here, we report on the structural manipulation of the 5-HT₇ receptor ligand 4-[2-(3-methoxyphenyl)ethyl]-1-(2-methoxyphenyl)piperazine (1a) aimed at obtaining 5-HT₇ receptor ligands endowed with good in vitro metabolic stability. A set of N-[3-methoxyphenyl)ethyl-substituted] 1-arylpiperazine, 4-arylpiperidine and 1-aryl-4-aminopiperidine was synthesized and tested in radioligand binding assays at human cloned 5-HT₇ and 5-HT_1A receptors. In vitro metabolic stability of the target compounds was assessed after incubation with rat hepatic S9 microsomal fraction. Among the new compounds, 1-(2-biphenyl)-4-[2-(3-methoxyphenyl)ethyl]piperazine (1d) and 4-(2-biphenyl)-1-[2-(3-methoxyphenyl)ethyl]piperidine (2d) showed a good compromise between affinity at 5-HT₇ receptor (K_i = 7.5 nM and 13 nM, resp.) and in vitro metabolic stability (26 and 65 % recovery of parent compound, resp.) but were poorly selective over 5-HT_1A receptor. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Safety of 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. 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.Safety of 4-(2-Methoxyphenyl)piperidine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

6-Amino-4-(pyrimidin-4-yl)pyridones: Novel glycogen synthase kinase-3β inhibitors was written by Coffman, Karen;Brodney, Michael;Cook, James;Lanyon, Lorraine;Pandit, Jayvardhan;Sakya, Subas;Schachter, Joel;Tseng-Lovering, Elaine;Wessel, Matthew. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Name: 4-(2-Methoxyphenyl)piperidine This article mentions the following:

The synthesis and structure-activity relationships for a novel series of 6-amino-4-(pyrimidin-4-yl)pyridones e. g., I derived from a high throughput screening hit are discussed. Optimization of lead matter afforded compounds with good potency, selectivity and central nervous system (CNS) exposure. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Name: 4-(2-Methoxyphenyl)piperidine).

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 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.Name: 4-(2-Methoxyphenyl)piperidine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Ligand and Target Discovery by Fragment-Based Screening in Human Cells was written by Parker, Christopher G.;Galmozzi, Andrea;Wang, Yujia;Correia, Bruno E.;Sasaki, Kenji;Joslyn, Christopher M.;Kim, Arthur S.;Cavallaro, Cullen L.;Lawrence, R. Michael;Johnson, Stephen R.;Narvaiza, Inigo;Saez, Enrique;Cravatt, Benjamin F.. And the article was included in Cell (Cambridge, MA, United States) in 2017.Safety of 4-(2-Methoxyphenyl)piperidine This article mentions the following:

Advances in the synthesis and screening of small-mol. libraries have accelerated the discovery of chem. probes for studying biol. processes. Still, only a small fraction of the human proteome has chem. ligands. Here, we describe a platform that marries fragment-based ligand discovery with quant. chem. proteomics to map thousands of reversible small mol.-protein interactions directly in human cells, many of which can be site-specifically determined We show that fragment hits can be advanced to furnish selective ligands that affect the activity of proteins heretofore lacking chem. probes. We further combine fragment-based chem. proteomics with phenotypic screening to identify small mols. that promote adipocyte differentiation by engaging the poorly characterized membrane protein PGRMC2. Fragment-based screening in human cells thus provides an extensive proteome-wide map of protein ligandability and facilitates the coordinated discovery of bioactive small mols. and their mol. targets. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Safety of 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. 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 4-(2-Methoxyphenyl)piperidine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Rapid Synthesis of Polycyclic Aromatic Compounds by Iodocyclization of Ynamides was written by Okitsu, Takashi;Itoh, Maho;Inui, Ayaka;Muta, Emiko;Nakamoto, Ryota;Adachi, Yuta;Wada, Akimori;Hatano, Manabu. And the article was included in Asian Journal of Organic Chemistry in 2022.Application In Synthesis of 1-Tosylpiperidin-4-one This article mentions the following:

The iodocyclization of ene-ynamides, e.g., N-((2-(Cyclohept-1-en-1-yl)phenyl)ethynyl)-N,4-dimethylbenzenesulfonamide leading to naphthalenes, e.g., I and phenanthrenes, e.g., II has been described. These reactions were completed within 3 s by using I(coll)₂PF₆ as an iodonium reagent, and cyclized products were obtained in good to high yields. This method is the most rapid synthesis known to date of polycyclic aromatic compounds In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Application In Synthesis of 1-Tosylpiperidin-4-one).

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

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Catalytic Oxygenative Allylic Transposition of Alkenes into Enones with an Azaadamantane-Type Oxoammonium Salt Catalyst was written by Nagasawa, Shota;Sasano, Yusuke;Iwabuchi, Yoshiharu. And the article was included in Chemistry – A European Journal in 2017.Category: piperidines This article mentions the following:

The first catalytic oxygenative allylic transposition of unactivated alkenes, e.g., Me₂C:CH₂(CH₂)₃OCOPh, into enones, e.g., H₂C:C(Me)CO(CH₂)₃OCOPh, has been developed using an oxoammonium salt, azaadamantane I, as the catalyst. This reaction converts various tri- and trans-disubstituted alkenes into their corresponding enones with transposition of their double bonds at ambient temperature in good yields. The use of a less-hindered azaadamantane-type oxoammonium salt as the catalyst and a combination of two distinct stoichiometric oxidants, namely, iodobenzene diacetate and magnesium monoperoxyphthalate hexahydrate (MMPP·6H₂O) are essential to facilitate the enone formation efficiently. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Category: piperidines).

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 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

Eliminative Deoxofluorination Using XtalFluor-E: A One-Step Synthesis of Monofluoroalkenes from Cyclohexanone Derivatives was written by Vandamme, Mathilde;Paquin, Jean-Francois. And the article was included in Organic Letters in 2017.SDS of cas: 33439-27-9 This article mentions the following:

The eliminative deoxofluorination of cyclohexanone derivatives using XtalFluor-E is described. The corresponding monofluoroalkenes are obtained in up to 79% yield. Notably, this one-step procedure occurs at room temperature using readily accessible and cost-effective reagents. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9SDS of cas: 33439-27-9).

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

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem