Heterocyclic Building Blocks-piperidine

Biomimetic Oxidative Coupling Cyclization Enabling Rapid Construction of Isochromanoindolenines was written by Ye, Jinxiang;Lin, Yuqi;Liu, Qing;Xu, Dekang;Wu, Fan;Liu, Bin;Gao, Yu;Chen, Haijun. And the article was included in Organic Letters in 2018.Application In Synthesis of 1-Tosylpiperidin-4-one This article mentions the following:

Herein, we report a biomimetic oxidative coupling cyclization strategy for the highly efficient functionalization of tetrahydrocarbolines (THCs). This process enables rapid access to complex isochromanoindolenine scaffolds I (X = N, Y-R¹ = CH₂; Y = N, X-R² = CH₂; R¹= R²= Ts, SO₂Ph, Ac, etc.; R³ = H, 10-Cl, 9-F, 10-MeO, etc.) in moderate to excellent yields. The reaction proceeds smoothly and rapidly (complete within minutes) in an open flask. This operationally simple protocol is scalable and compatible with a wide range of functional groups. Late-stage functionalization of a pharmacol. relevant mol. is also demonstrated. 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. 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. 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 In Synthesis of 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

A library of conformationally restricted saturated heterocyclic sulfonyl chlorides was written by Zhersh, Sergey;Buryanov, Volodymyr V.;Karpenko, Oleksandr V.;Grygorenko, Oleksandr O.;Tolmachev, Andrey A.. And the article was included in Synthesis in 2011.Application of 95798-22-4 This article mentions the following:

An approach to the synthesis of conformationally restricted saturated heterocyclic sulfonyl chlorides is described. Being guided by the principle of diversity-oriented conformational restriction, a mini-library of saturated heterocyclic sulfonyl chlorides was designed and synthesized. The library consists of nine members that are derivatives of azetidine, pyrrolidine, and piperidine. These compounds were prepared in 19-88% total yields on multigram scale starting from the corresponding Cbz-protected amino alcs. In the experiment, the researchers used many compounds, for example, Benzyl 3-hydroxypiperidine-1-carboxylate (cas: 95798-22-4Application of 95798-22-4).

Benzyl 3-hydroxypiperidine-1-carboxylate (cas: 95798-22-4) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. 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 of 95798-22-4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Design, synthesis, and pharmacological evaluation of mefloquine-based ligands as novel antituberculosis agents was written by Mao, Jialin;Wang, Yuehong;Wan, Baojie;Kozikowski, Alan P.;Franzblau, Scott G.. And the article was included in ChemMedChem in 2007.Related Products of 118753-66-5 This article mentions the following:

Tuberculosis (TB) is presently regarded as one of the most dangerous infective diseases worldwide and one of the major AIDS-associated infections. To shorten the current treatment regimen, there is an urgent need to identify new anti-TB agents which are active against both replicating TB (R-TB) and nonreplicating TB (NRP-TB). Mefloquine, a well-known antimalarial drug was found to possess reasonable activity against NRP-TB, and accordingly, 30 new analogs were synthesized and evaluated for their anti-TB activity against Mycobacterium tuberculosis H₃₇Rv. As the target of mefloquine in Mycobacterium tuberculosis remains unknown, we resorted to modifying mefloquine in a variety of chem. convenient ways, which led us in turn to the active hydrazone 10a. Further modifications of 10a led to compound 7f, with an improved anti-TB activity/selectivity profile with both less cytotoxicity and less predicted CNS side effects compared with mefloquine. The clear structure-activity relationships (SARs) derived from this study should facilitate our ultimate goal of identifying improved anti-TB agents. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-aminopiperazine-1-carboxylate (cas: 118753-66-5Related Products of 118753-66-5).

tert-Butyl 4-aminopiperazine-1-carboxylate (cas: 118753-66-5) 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.Related Products of 118753-66-5

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis, characterization and antimicrobial activity of substituted tricyclic compounds: 5,6,7,8-tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidines was written by Mittal, Manish;Sarode, Suraj M.;Vidyasagar, G.. And the article was included in International Journal of Pharma and Bio Sciences in 2011.Formula: C12H15NO3S This article mentions the following:

7-(Arylsulfonyl)-N-aryl-5,6,7,8-tetrahydropyrido[4,3′:4,5]thieno[2,3-d]pyrimidin-4-amines were synthesized from 7-(arylsulfonyl)-4-chloro-5,6,7,8-tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidines using piperidin-4-one.HCl and arenesulfonyl chloride as the starting material. All the synthesized products were evaluated for antibacterial activity against B. subtilis, E. coli, K. pneumoniae, and S. aureus as well as for antifungal activity against A. niger, A. flavus, F. oxysporum, and T. viride. Most of the synthesized compounds exhibited antibacterial and antifungal activity. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Formula: C12H15NO3S).

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. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Formula: C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Catalytic Asymmetric Dearomatizing Redox Cross Coupling of Ketones with Aryl Hydrazines Giving 1,4-Diketones was written by Huang, Shenlin;Koetzner, Lisa;De, Chandra Kanta;List, Benjamin. And the article was included in Journal of the American Chemical Society in 2015.Category: piperidines This article mentions the following:

;An asym. Bronsted acid catalyzed dearomatizing redox cross coupling reaction has been realized, in which aryl hydrazines react with ketones to deliver 1,4-diketones, bearing an all-carbon quaternary stereocenter in high enantiopurity [e.g., (2-methylnaphthalen-1-yl)hydrazine + cyclohexanone in presence of Amberlite CG50 and SPINOL-derived phosphoric acid afforded diketone I (72%, 96:4 er, optimized)]. 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 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. 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.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of Aminoethyl-Substituted Piperidine Derivatives as σ₁ Receptor Ligands with Antiproliferative Properties was written by Holtschulte, Catharina;Borgel, Frederik;Westphalinger, Stefanie;Schepmann, Dirk;Civenni, Gianluca;Laurini, Erik;Marson, Domenico;Catapano, Carlo V.;Pricl, Sabrina;Wuensch, Bernhard. And the article was included in ChemMedChem in 2022.SDS of cas: 33439-27-9 This article mentions the following:

A series of novel σ₁ receptor ligands with a 4-(2-aminoethyl)piperidine scaffold I [ R¹ = H,methyl, ethyl; R² = benzylamino, cyclohexylmethylamino etc] were prepared and biol. evaluated. The underlying concept of project were the improvement of the lipophilic ligand efficiency of previously synthesized potent σ₁ ligands. The key steps of the synthesis comprise the conjugate addition of phenylboronic acid at dihydropyridin-4(1H)-ones, homologation of the ketones and introduction of diverse amino moieties and piperidine N-substituents. 1-Methylpiperidines showed particular high σ₁ receptor affinity and selectivity over the σ₂ subtype, while piperidines with a proton, a tosyl moiety or an Et moiety exhibited considerably lower σ₁ affinity. Mol. dynamics simulations with per-residue binding free energy deconvolution demonstrated that different interactions of the basic piperidine-N-atom and its substituents (or the cyclohexane ring) with the lipophilic binding pocket consisting of Leu105, Thr181, Leu182, Ala185, Leu186, Thr202 and Tyr206 were responsible for the different σ₁ receptor affinities. Recorded logD_7.4 and calculated clogP values of I [ R¹ = H,methyl; R² = benzylamino] indicated low lipophilicity and thus high lipophilic ligand efficiency. Piperidine I [ R¹ = H; R² = benzylamino] inhibited the growth of human non-small cell lung cancer cells A427 to a similar extent as the σ₁ antagonist haloperidol. 1-Methylpiperidines I [ R¹ = methyl; R² = cyclohexylmethylamino, benzyl(methyl)amino, 4-phenylpiperazin-1-yl] showed stronger antiproliferative effects on androgen neg. human prostate cancer cells DU145 than the σ₁ ligands NE100 and S1RA. 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

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

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

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

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