Month: January 2023

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

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

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

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

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

Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C-H Activation was written by Romanov-Michailidis, Fedor;Sedillo, Kassandra F.;Neely, Jamie M.;Rovis, Tomislav. And the article was included in Journal of the American Chemical Society in 2015.Quality Control of 1-Tosylpiperidin-4-one This article mentions the following:

α,β-Unsaturated oxime pivalates are proposed to undergo reversible C(sp²)-H insertion with cationic Rh(III) complexes to furnish five-membered metallacycles. In the presence of 1,1-disubstituted olefins, these species participate in irreversible migratory insertion to give, after reductive elimination, 2,3-dihydropyridine products in good yields. Catalytic hydrogenation can then be used to convert these mols. into piperidines, which are important structural components of numerous pharmaceuticals. Thus, e.g., heterocyclization of unsaturated oxime pivalate I with alkene II in presence of [Rh(MeCN)₃(C₅Me₄CF₃)](SbF₆)₂ afforded dihydropyridine III (99%). In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Quality Control of 1-Tosylpiperidin-4-one).

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

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

New Pyrimido[5,4-b]indoles as Ligands for α₁-Adrenoceptor Subtypes was written by Romeo, Giuseppe;Materia, Luisa;Manetti, Fabrizio;Cagnotto, Alfredo;Mennini, Tiziana;Nicoletti, Ferdinando;Botta, Maurizio;Russo, Filippo;Minneman, Kenneth P.. And the article was included in Journal of Medicinal Chemistry in 2003.Recommanded Product: 58333-75-8 This article mentions the following:

Tricyclic 5H-pyrimido[5,4-b]indoles I (R¹ = H, Me, Et; n = 2, 3; R² = 2-MeO, 2-EtO, 4-Me₂CH, 4-Me₃C) and II (R³ = NCCH₂, Me₂CH, Bu, Me₃C, EtCHMe, cyclohexyl) bearing a piperazine moiety connected through an alkyl chain were designed as structural analogs of the α₁-AR ligand RN5. I and II were synthesized and tested in binding assays on human α_1A-AR, α_1B-AR, and α_1D-AR subtypes expressed in HEK293 cells, with many of the new mols. showing a preferential affinity for the α_1D-AR subtype. Some compounds, including II (R³ = Me₂CH, Me₃C), displayed substantial α_1D-AR selectivity with respect to α_1A-AR, α_1B-AR, serotonergic 5-HT_1A, 5-HT_1B, 5-HT_2A, and dopaminergic D₁ and D₂ receptors. Two conformationally rigid analogs of RN5, useful for studying the architecture of the receptor/ligand complex, were also prepared and tested. A subset of the new compounds was then used to evolve a preliminary pharmacophore model for α_1D-AR antagonists, based on a more generalized model developed for α₁-AR antagonists. This new model rationalized the relationships between structural properties and biol. data of the pyrimido[5,4-b]indole compounds, as well as other compounds 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. 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.Recommanded Product: 58333-75-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Design and synthesis of 4-(heterocyclic substituted amino)-1H-pyrazole-3-carboxamide derivatives and their potent activity against acute myeloid leukemia (AML) was written by Zhi, Yanle;Wang, Zhijie;Yao, Chao;Li, Baoquan;Heng, Hao;Cai, Jiongheng;Xiang, Li;Wang, Yue;Lu, Tao;Lu, Shuai. And the article was included in International Journal of Molecular Sciences in 2019.Synthetic Route of C9H19N3O2 This article mentions the following:

Fms-like receptor tyrosine kinase 3 (FLT3) has been emerging as an attractive target for the treatment of acute myeloid leukemia (AML). By modifying the structure of FN-1501, a potent FLT3 inhibitor, 24 novel 1H-pyrazole-3-carboxamide derivatives I [R = Ph, pyridin-4-yl, 1-(tert-butoxycarbonyl)piperidine-4-yl, piperidin-4-yl] and II [R¹ = H, (morpholin-4-yl)carbonyl, (4-methylpiperazin-1-yl)carbonyl, piperazin-1-yl, etc.; R² = H, 4-methyl-1,4-diazepan-1-yl; X = CH, N; R³ = thieno[2,3-d]pyrimidin-4-yl, 7H-pyrrolo[2,3-d]pyrimidin-4-yl, etc.] were designed and synthesized. Compound II [R¹ = piperazin-1-yl, R² = H, X = CH, R³ = 7-thia-9,11-diazatricyclo[6.4.0.0(2,6)]dodeca-1(8),2(6),9,11-tetraen-12-yl (III)] showed strong activity against FLT3 (IC⁵⁰: 0.089 nM) and CDK2/4 (IC⁵⁰: 0.719/0.770 nM), which is more efficient than FN-1501(FLT3, IC⁵⁰: 2.33 nM; CDK2/4, IC⁵⁰: 1.02/0.39 nM). Compound III also showed excellent inhibitory activity against a variety of FLT3 mutants (IC⁵⁰ >5 nM), and potent anti-proliferative effect within the nanomolar range on acute myeloid leukemia (MV4-11, IC⁵⁰: 1.22 nM). In addition, compound III significantly inhibited the proliferation of most human cell lines of NCI60 (GI⁵⁰ < 1μ M for most cell lines). Taken together, these results demonstrated the potential of III as a novel compound for further development into a kinase inhibitor applied in cancer therapeutics. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-aminopiperazine-1-carboxylate (cas: 118753-66-5Synthetic Route of C9H19N3O2).

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

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Antagonists of the human CCR5 receptor as anti-HIV-1 agents. Part 3: A proposed pharmacophore model for 1-[N-(methyl)-N-(phenylsulfonyl)amino]-2-(phenyl)-4-[4-(substituted)piperidin-1-yl]butanes was written by Finke, P. E.;Meurer, L. C.;Oates, B.;Shah, S. K.;Loebach, J. L.;Mills, S. G.;MacCoss, M.;Castonguay, L.;Malkowitz, L.;Springer, M. S.;Gould, S. L.;DeMartino, J. A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2001.Recommanded Product: 4-(2-Methoxyphenyl)piperidine This article mentions the following:

Structure-activity relationship studies directed toward the optimization of (2S)-2-(3-chlorophenyl)-1-[N-(methyl)-N-(phenylsulfonyl)amino]-4-[4-(substituted)piperidin-1-yl]butanes as CCR5 antagonists resulted in the synthesis of the spiro-indanone derivative I (IC₅₀=5 nM). These and previous results are summarized in a proposed pharmacophore model for this class of CCR5 antagonist. 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 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.Recommanded Product: 4-(2-Methoxyphenyl)piperidine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Au-Catalyzed Formation of Functionalized Quinolines from 2-Alkynyl Arylazide Derivatives was written by Gronnier, Colombe;Boissonnat, Guillaume;Gagosz, Fabien. And the article was included in Organic Letters in 2013.SDS of cas: 33439-27-9 This article mentions the following:

A new method for converting 2-alkynyl arylazide derivatives into functionalized polysubstituted quinolines following a gold-catalyzed 1,3-acetoxy shift/cyclization/1,2-group shift sequence has been developed (e.g., I → II). This transformation proceeds under mild reaction conditions, is efficient, and tolerates a large variety of functional groups. 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. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.SDS of cas: 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem