Tag: 100-200

New CNS agent precursors. A simple and efficient route for synthesis of 6-aminomethyl-4,5,6,7-tetrahydrobenzofuran-4-ones as conformationally constrained butyrophenone analogs was written by Casariego, Isabel;Masaguer, Christian F.;Ravina, Enrique. And the article was included in Tetrahedron Letters in 1997.Application In Synthesis of 4-(2-Methoxyphenyl)piperidine This article mentions the following:

Starting from 3,4,5-trimethoxybenzoic acid, we described a practical and efficient five-step synthesis of 6-aminomethyl-4,5,6,7-tetrahydrobenzofuran-4-ones as new CNS agent precursors in an overall yield of 20%. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Application In Synthesis of 4-(2-Methoxyphenyl)piperidine).

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 bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Application In Synthesis of 4-(2-Methoxyphenyl)piperidine

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

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

Syntheses in the piperidine series. I. A facile synthesis of 4-piperidinol and the preparation of related compounds was written by Bowden, K.;Green, P. N.. And the article was included in Journal of the Chemical Society in 1952.Recommanded Product: 4045-22-1 This article mentions the following:

(ClCH₂)₂CHOH (65 g.) and 54 g. NaCN in 60 ml. H₂O, warmed 40 min. at 50-5° and kept overnight, give 6.3 g. ClCH₂CH(OH)CH₂CN and 23.3 g. (NCCH₂)₂CHOH (I). I (45 g.) in 400 ml. EtOH, hydrogenated over 10 g. Raney Ni at 50°/50 atm. (2 hrs.), gives 17.6 g. 4-piperidinol (II), b₁₀ 110-15°; chloroplatinate, m. 195° (decomposition) [Koenigs and Neumann, C.A. 9, 2254, gave 184-7° (decomposition)]; II and dilute H₂SO₄ give the sulfate, m. 272-4° (K. and N. gave 263-6°); with 4 mols. H₂O, m. 66-8°. The EtOH-insoluble matter from II yields the dipicrate, yellow, m. 238° (decomposition), of (CH₂)₅(NH₂)₂. II (3 g.) in 10 g. 47% HBr, evaporated to dryness in vacuo, the residue in 10 ml. hot EtOH evaporated in vacuo, and the product refluxed 10 min. with 5 g. PBr₃, gives 2.8 g. 4-bromopiperidinium bromide (III), m. 192-3° (decomposition); picrate, yellow, m. 162-3°; sulfate, m. 163-4°. III (2.45 g.) in 15 ml. H₂O, added to 1.54 g. BzCl in 5 ml. C₆H₆, followed dropwise with 1.27 g. Na₂CO₃ in 12.7 ml. H₂O at 5°, gives 2 g. 1-benzoyl-4-bromopiperidine, m. 67-9°. II (5 g.) in 6 ml. AcOMe, refluxed 78 hrs., gives 3 g. 1-acetyl-4-piperidinol (IV), m. 66-7°; 2.5 g. II, 1.5 AcONH₂, and 5 g. cyclohexanol, refluxed 6 hrs., give 1.5 g. IV. (ClCH₂CH₂)₂CO (4.65 g.) in 30 ml. absolute EtOH, treated dropwise (45 min.) with 6.3 g. Na₂CO₃ in 70 ml. H₂O and simultaneously with MeNH₂, and refluxed 1 hr., give 0.75 g. 4-methylpiperidone, b₁₄ 55-9°. II (5 g.) in 8 g. 90% HCO₂H, treated with 5 g. 40% aqueous HCHO, heated 8 hrs. on the steam bath, treated the next day with 10 ml. concentrated HCl, and refluxed 5 min., gives 4.3 g. 1-methyl-4-piperidinol, b₁₀ 95-6° [methiodide, m. 327° (decomposition)]. In the experiment, the researchers used many compounds, for example, 1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1Recommanded Product: 4045-22-1).

1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1) 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.Recommanded Product: 4045-22-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis and in vitro evaluation of three novel radiotracers for imaging of metabotropic glutamate receptor subtype 2 in rat brain was written by Kumata, Katsushi;Yamasaki, Tomoteru;Hatori, Akiko;Zhang, Yiding;Mori, Wakana;Fujinaga, Masayuki;Xie, Lin;Okubo, Takayuki;Nengaki, Nobuki;Zhang, Ming-Rong. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.Product Details of 58333-75-8 This article mentions the following:

The purpose of this study was to develop three new radiotracers, 1-(cyclopropylmethyl)-4-([¹¹C/¹⁸F]substituted-phenyl)piperidin-1-yl-2-oxo-1,2-dihydropyridine-3-carbonitrile I [R = 2-O¹¹CH₃ (II), 3-O¹¹CH₃ (III), 2-OCH₂CH₂¹⁸F (IV)], and to examine their specific bindings with metabotropic glutamate receptor subtype 2 (mGluR2) in rat brain sections by using in vitro autoradiog. These compounds were found to possess potent in vitro binding affinities (K_i: 8.0-34.1 nM) for mGluR2 in rat brain homogenate. II, III, and IV were synthesized by [¹¹C/¹⁸F]alkylation of the corresponding phenol precursors with [¹¹C]methyl iodide or [¹⁸F]fluoroethyl bromide with >98% radiochem. purity and 80-130 GBq/μmol specific activity at the end of synthesis. In vitro autoradiog. indicated that these radiotracers showed heterogeneous specific bindings in mGluR2-rich brain regions, such as the cerebral cortex, striatum, hippocampus, and granular layer of the cerebellum. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Product Details of 58333-75-8).

4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8) 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.Product Details of 58333-75-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

New μ-opioid receptor agonists with a phenoxyacetic acid moiety was written by Sato, Susumu;Komoto, Teruo;Kanamaru, Yoshihiko;Kawamoto, Noriyuki;Okada, Tomomi;Kaiho, Terurnitsu;Mogi, Kinichi;Morimoto, Shinichi;Umehara, Norimitsu;Koda, Tadayuki;Miyashita, Akira;Sakamoto, Takao;Niino, Yasuhiro;Oka, Tetsuo. And the article was included in Chemical & Pharmaceutical Bulletin in 2002.Synthetic Route of C12H17NO This article mentions the following:

New μ-opioid receptor (MOR) agonists containing 4-hydroxypiperidine, piperidine and piperazine moieties were synthesized and evaluated to find a peripheral opioid analgesic. Among the synthesized compounds, I showed the highest agonist potency on the MOR in an isolated guinea-pig ileum preparation, and it also had selectivity to the human MOR expressed in Chinese hamster ovary (CHO)-K1 cells compared with the same types of δ- and κ-opioid receptors. In addition, compound I showed 10 times more potent MOR agonist activity than loperamide. Furthermore, compound I showed a peripheral analgesic activity in the rat. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Synthetic Route 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. 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.Synthetic Route of C12H17NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Structure and activity relationship of 2-(substituted benzoyl)-hydroxyindoles as novel CaMKII inhibitors was written by Komiya, Masafumi;Asano, Shigehiro;Koike, Nobuyuki;Koga, Erina;Igarashi, Junetsu;Nakatani, Shogo;Isobe, Yoshiaki. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Product Details of 4045-22-1 This article mentions the following:

A series of novel 2-substituted-5-hydroxyindoles were synthesized and evaluated for their inhibitory activity against CaMKII. Structure and activity relationship results indicated that potent inhibitory activity could be achieved by modification at the para-position of the Ph ring of the high throughput screening hit compound I. Among the prepared compounds, we identified II as a novel CaMKII inhibitor with an activity stronger than that of KN-93, a known CaMKII inhibitor. In the experiment, the researchers used many compounds, for example, 1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1Product Details of 4045-22-1).

1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. 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.Product Details of 4045-22-1

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. [Erratum to document cited in CA149:000438] 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.Synthetic Route of C12H17NO This article mentions the following:

In Tables 1 (pages 2855-2858), 2 (page 2859-2860), and 3 (page 2861), the second column heading, “R¹/R³“, was incorrectly given, and should read: “R³/R¹“. On page 2858, in Table 2, for compound 58, in the second column, “(CH₃)₂CHCH₂/Pr”, was incorrectly given, and should read “CH₃/(CH₃)₂CHCH₂“. On page 2861, in Table 3, for compound 87, in the second column, “CH₃/Pr” was incorrectly given, and should read “Pr/CH₃“. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Synthetic Route of C12H17NO).

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. 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.Synthetic Route of C12H17NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Liquid-crystalline side chain polysiloxanes with 4-amino-4′-stilbenecarboxylic ester mesogens was written by Bautista, Marietta O.;Duran, Randolph S.;Ford, Warren T.. And the article was included in Macromolecules in 1993.HPLC of Formula: 4045-22-1 This article mentions the following:

Side chain polysiloxanes with 4-(dimethylamino)- and 4-[4-(hexyloxy)piperidino]-4′-stilbenecarboxylic ester mesogens were synthesized from poly(hydromethylsiloxane) and poly(hydromethylsiloxane-co-dimethylsiloxane) and the 10-undecen-1-yl esters. Size-exclusion chromatog. (SEC) underestimated M_n of the (dimethylamino)stilbene homopolymer by a factor of 4 and M_n of the piperidinostilbene homopolymer by a factor of 2 compared with ¹H NMR end group analyses. SEC and NMR values of M_n approx. agreed for the copolymers. The phases of the monomers and polysiloxanes were assigned by polarizing microscopy and x-ray diffraction. The copolysiloxanes had T_g near -40° by DSC, but T_g was not detected for the homopolysiloxanes. Both homopolysiloxanes have nematic phases, and both copolymers have S_A phases. The [(hexyloxy)piperidino]silbene polymers have more ordered phases, assigned as S_B of the copolymer and either S_B or hexagonal nematic of the homopolymer. The isotropic transitions were detected by polarizing microscopy but not by DSC. All of the polysiloxanes form stable monolayers on water that can be compressed to mean areas per stilbene repeat unit ranging from 23 to 34 Ų and to pressure of â‰?0 mN/m. In the experiment, the researchers used many compounds, for example, 1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1HPLC of Formula: 4045-22-1).

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.HPLC of Formula: 4045-22-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

2,4-Diamino-6,7-dimethoxyquinazolines. 4. 2-[4-(Substituted oxyethoxy)piperidino] derivatives as α₁-adrenoceptor antagonists and antihypertensive agents was written by Campbell, Simon F.;Danilewicz, John C.;Greengrass, Colin W.;Plews, Rhona M.. And the article was included in Journal of Medicinal Chemistry in 1988.Application of 4045-22-1 This article mentions the following:

A series of piperidinoquinazolines I (R = H, Ph, R¹ = H, Me, R² = H, Me, Ph, R³ = H, Me, Ph, Bu, CHMe₂, cyclopentyl) were prepared and evaluated for α-adrenoceptor affinity and antihypertensive activity. Most I showed binding affinities within the nM range for α₁-receptors, although I (R = R¹ = R³ = H, R² = Ph; R = H, R¹ = Me, R² = Ph, R³ = Et) showed enhanced potency (K_i, ca. 1.5 × 10^-10M), equivalent to that of prazosin. I also displaced [³H]clonidine from α₂-adrenoceptors, but at relatively high doses of 10^-6M, and selectivity for α₁ sites still predominated. In a rabbit pulmonary artery preparation, I (R = R¹ = R² = H, R³ = Et, Ph; R = H, R¹ = Me, R² = Ph, R³ = Et) were potent antagonists of the α₁-mediated, postjunctional vasoconstrictor activity of norepinephrine with no effect at the prejunctional α₂ sites which modulate transmitter release. Physicochem. measurements gave a pK_a of 7.63 ± 0.10 for I (R = R¹ = R² = H, R³ = Et) and N-1 protonation will be favored (60%) at physiol. pH to provide the α₁-adrenoceptor pharmacophore. Antihypertensive activity of I was evaluated following oral administration to spontaneously hypertensive rats, and blood pressure was measured after 1 and 6 h. I (R = R¹ = R² = H, R³ = Et, Bu, Ph; R = R³ = H, R¹ = Me, R² = Ph; R = Ph, R¹ = R² = H, R³ = Et) displayed moderate efficacy and duration of action in lowering blood pressure, but the plasma half-life (ca. 2 h) of I (R = R¹ = R² = H, R³ = Ph) in dogs was not compatible with potential once-daily administration in humans. In the experiment, the researchers used many compounds, for example, 1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1Application of 4045-22-1).

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. 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.Application of 4045-22-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem