84358-13-4 | Page 9 of 9 | Heterocyclic Building Blocks-piperidine

Adu-Ampratwum, Daniel team published research on ACS Omega in 2022 | 84358-13-4

Product Details of C11H19NO4, N-BOC-piperidine-4-carboxylic acid, also known asN-Boc-isonipecotic acid , is a useful research compound. Its molecular formula is C11H19NO4 and its molecular weight is 229,28 g/mole. The purity is usually 95%.

N-Boc-isonipecotic acid is a potent antitumor agent that has been clinically shown to be effective against leukemia and lymphoma. It has potent antibacterial activity against Gram-positive bacteria such as Staphylococcus aureus and Streptococcus pyogenes. N-Boc-isonipecotic acid binds to the gyrase enzyme, which is used by these bacteria to maintain the integrity of their DNA, inhibiting protein synthesis and cell division. This drug also has anti-inflammatory properties. N-Boc-isonipecotic acid inhibits prostaglandin synthesis in cells, which may be due to its ability to inhibit the production of tumor necrosis factor α (TNFα) in macrophages., 84358-13-4.

Piperidine was first reported in 1850 by the Scottish chemist Thomas Anderson and again, independently, in 1852 by the French chemist 84358-13-4, formula is C11H19NO4, Name is 1-(tert-Butoxycarbonyl)piperidine-4-carboxylic acid. Auguste Cahours, who named it. Both of them obtained piperidine by reacting piperine with nitric acid. Product Details of C11H19NO4.

Adu-Ampratwum, Daniel;Pan, Yuhan;Koneru, Pratibha C.;Antwi, Janet;Hoyte, Ashley C.;Kessl, Jacques;Griffin, Patrick R.;Kvaratskhelia, Mamuka;Fuchs, James R.;Larue, Ross C. research published 《 Identification and Optimization of a Novel HIV-1 Integrase Inhibitor》, the research content is summarized as follows. Human immunodeficiency virus-1 (HIV-1) is the causative agent of acquired immunodeficiency syndrome (AIDS). HIV-1, like all retroviruses, stably integrates its vDNA copy into host chromatin, a process allowing for permanent infection. This essential step for HIV-1 replication is catalyzed by viral integrase (IN) and aided by cellular protein LEDGF/p75. In addition, IN is also crucial for proper virion maturation as it interacts with the viral RNA genome to ensure encapsulation of ribonucleoprotein complexes within the protective capsid core. These key functions make IN an attractive target for the development of inhibitors with various mechanisms of action. We conducted a high-throughput screen (HTS) of ~370,000 compounds using a homogeneous time-resolved fluorescence-based assay capable of capturing diverse inhibitors targeting multifunctional IN. Our approach revealed chem. scaffolds containing diketo acid moieties similar to IN strand transfer inhibitors (INSTIs) as well as novel compounds distinct from all current IN inhibitors including INSTIs and allosteric integrase inhibitors (ALLINIs). Specifically, our HTS resulted in the discovery of compound I, with a novel IN inhibitor scaffold amenable for chem. modification. Its more potent derivative II similarly inhibited catalytic activities of WT and mutant INs containing archetypical INSTI- and ALLINI-derived resistant substitutions. Further SAR-based optimization resulted in compound III with an antiviral EC₅₀ of ~58μM and a selectivity index of >8500. Thus, our studies identified a novel small-mol. scaffold for inhibiting HIV-1 IN, which provides a promising platform for future development of potent antiviral agents to complement current HIV-1 therapies.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Bay, Anna V. team published research on Angewandte Chemie, International Edition in 2021 | 84358-13-4

84358-13-4, N-BOC-piperidine-4-carboxylic acid, also known asN-Boc-isonipecotic acid , is a useful research compound. Its molecular formula is C11H19NO4 and its molecular weight is 229,28 g/mole. The purity is usually 95%.

Piperidine the name comes from the genus name Piper, which is the Latin word for pepper. 84358-13-4, formula is C11H19NO4, Name is 1-(tert-Butoxycarbonyl)piperidine-4-carboxylic acid. Although piperidine is a common organic compound, it is best known as a representative structure element within many pharmaceuticals and alkaloids, such as natural-occurring solenopsins. Formula: C11H19NO4.

Bay, Anna V.;Fitzpatrick, Keegan P.;Gonzalez-Montiel, Gisela A.;Farah, Abdikani Omar;Cheong, Paul Ha-Yeon;Scheidt, Karl A. research published 《 Light-Driven Carbene Catalysis for the Synthesis of Aliphatic and α-Amino Ketones》, the research content is summarized as follows. Single-electron N-heterocyclic carbene (NHC) catalysis has gained attention recently for the synthesis of C-C bonds. Guided by d. functional theory and mechanistic analyses, authors report the light-driven synthesis of aliphatic and α-amino ketones using single-electron NHC operators. Computational and exptl. results reveal that the reactivity of the key radical intermediate is substrate-dependent and can be modulated through steric and electronic parameters of the NHC. Catalyst potential is harnessed in the visible-light driven generation of an acyl azolium radical species that underwent selective coupling with various radical partners to afford diverse ketone products. This methodol. is showcased in the direct late-stage functionalization of amino acids and pharmaceutical compounds, highlighting the utility of single-electron NHC operators.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Bay, Anna V. team published research on Angewandte Chemie, International Edition in 2020 | 84358-13-4

Related Products of 84358-13-4, N-BOC-piperidine-4-carboxylic acid, also known asN-Boc-isonipecotic acid , is a useful research compound. Its molecular formula is C11H19NO4 and its molecular weight is 229,28 g/mole. The purity is usually 95%.

Bay, Anna V.;Fitzpatrick, Keegan P.;Betori, Rick C.;Scheidt, Karl A. research published 《 Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids》, the research content is summarized as follows. As a key element in the construction of complex organic scaffolds, the formation of C-C bonds remains a challenge in the field of synthetic organic chem. Recent advancements in single-electron chem. have enabled new methods for the formation of various C-C bonds. Disclosed herein is the development of a novel single-electron reduction of acyl azoliums for the formation of ketones from carboxylic acids. Facile construction of the acyl azolium in situ followed by a radical-radical coupling was made possible merging N-heterocyclic carbene (NHC) and photoredox catalysis. The utility of this protocol in synthesis was showcased in the late-stage functionalization of a variety of pharmaceutical compounds Preliminary studies using chiral NHCs demonstrate that enantioselectivity can be achieved, showcasing the advantages of this protocol over alternative methodologies.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Barthels, Fabian team published research on ChemMedChem in 2020 | 84358-13-4

Barthels, Fabian;Marincola, Gabriella;Marciniak, Tessa;Konhaeuser, Matthias;Hammerschmidt, Stefan;Bierlmeier, Jan;Distler, Ute;Wich, Peter R.;Tenzer, Stefan;Schwarzer, Dirk;Ziebuhr, Wilma;Schirmeister, Tanja research published 《 Asymmetric Disulfanylbenzamides as Irreversible and Selective Inhibitors of Staphylococcus aureus Sortase A》, the research content is summarized as follows. Staphylococcus aureus is one of the most frequent causes of nosocomial and community-acquired infections, with drug-resistant strains being responsible for tens of thousands of deaths per yr. S. aureus sortase A inhibitors are designed to interfere with virulence determinants. We have identified disulfanylbenzamides as a new class of potent inhibitors against sortase A that act by covalent modification of the active-site cysteine. A broad series of derivatives were synthesized to derive structure-activity relationships (SAR). In vitro and in silico methods allowed the exptl. observed binding affinities and selectivities to be rationalized. The most active compounds were found to have single-digit micromolar K_i values and caused up to a 66% reduction of S. aureus fibrinogen attachment at an effective inhibitor concentration of 10μM. This new mol. class exhibited minimal cytotoxicity, low bacterial growth inhibition and impaired sortase-mediated adherence of S. aureus cells.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Barlaam, Bernard team published research on Journal of Medicinal Chemistry in 2021 | 84358-13-4

Barlaam, Bernard;De Savi, Chris;Dishington, Allan;Drew, Lisa;Ferguson, Andrew D.;Ferguson, Douglas;Gu, Chungang;Hande, Sudhir;Hassall, Lorraine;Hawkins, Janet;Hird, Alexander W.;Holmes, Jane;Lamb, Michelle L.;Lister, Andrew S.;McGuire, Thomas M.;Moore, Jane E.;O’Connell, Nichole;Patel, Anil;Pike, Kurt G.;Sarkar, Ujjal;Shao, Wenlin;Stead, Darren;Varnes, Jeffrey G.;Vasbinder, Melissa M.;Wang, Lei;Wu, Liangwei;Xue, Lin;Yang, Bin;Yao, Tieguang research published 《 Discovery of a Series of 7-Azaindoles as Potent and Highly Selective CDK9 Inhibitors for Transient Target Engagement》, the research content is summarized as follows. Optimization of a series of azabenzimidazole54387894As identified from screening hit 2 and the information gained from a co-crystal structure of the azabenzimidazole-based lead 6 bound to CDK9 led to the discovery of azaindoles as highly potent and selective CDK9 inhibitors. With the goal of discovering a highly selective and potent CDK9 inhibitor administered i.v. that would enable transient target engagement of CDK9 for the treatment of hematol. malignancies, further optimization focusing on physicochem. and pharmacokinetic properties led to azaindoles 38 (I) and 39 (II). These compounds are highly potent and selective CDK9 inhibitors having short half-lives in rodents, suitable phys. properties for i.v. administration, and the potential to achieve profound but transient inhibition of CDK9 in vivo.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Bao, Qiao-Fei team published research on Organic Letters in 2021 | 84358-13-4

Bao, Qiao-Fei;Li, Ming;Xia, Yu;Wang, Yu-Zhao;Zhou, Zhao-Zhao;Liang, Yong-Min research published 《 Visible-Light-Mediated Decarboxylative Radical Addition Bifunctionalization Cascade for the Production of 1,4-Amino Alcohols》, the research content is summarized as follows. A photocatalytic decarboxylative radical addition bifunctionalization cascade for the synthesis of functionalized alcs. e.g., 2-(cyclohexylmethyl)-2-methylpent-4-enoic acid is described. The catalytic cycle is completed through single-electron transfer. The advantages of this reaction are the com. available materials, wide functional group compatibility, and mild conditions. Notably, some amino acids and bioactive carboxylic acids e.g., gemfibrozil can provide corresponding products e.g., 7-(2,5-dimethylphenoxy)-4,4-dimethyl-1,2,2-triphenylheptan-1-ol in moderate to good yields, reflecting the potential value in drug development.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Aspnes, Gary E. team published research on Bioorganic & Medicinal Chemistry Letters in 2021 | 84358-13-4

Aspnes, Gary E.;Menhaji-Klotz, Elnaz;Boehm, Markus;Londregan, Allyn T.;Lee, Esther C. Y.;Limberakis, Chris;Coffey, Steven B.;Brown, Janice A.;Jones, Rhys M.;Hesp, Kevin D. research published 《 Discovery and evaluation of non-basic small molecule modulators of the atypical chemokine receptor CXCR7》, the research content is summarized as follows. The atypical chemokine receptor C-X-C chemokine receptor type 7 (CXCR7) is an attractive therapeutic target for a variety of cardiac and immunol. diseases. As a strategy to mitigate known risks associated with the development of higher mol. weight, basic compounds, a series of pyrrolidinyl-azolopyrazines were identified as promising small-mol. CXCR7 modulators. Using a highly enabled parallel medicinal chem. strategy, structure-activity relationship studies geared towards a reduction in lipophilicity and incorporation of saturated heterocycles led to the identification of representative tool compound 20. Notably, compound 20 maintained good potency against CXCR7 with a suitable balance of physicochem. properties to support in vivo pharmacokinetic studies.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Alverez, Celeste N. team published research on Journal of Medicinal Chemistry in 2020 | 84358-13-4

Alverez, Celeste N.;Park, Jung-Eun;Toti, Kiran S.;Xia, Yangliu;Krausz, Kristopher W.;Rai, Ganesha;Bang, Jeong K.;Gonzalez, Frank J.;Jacobson, Kenneth A.;Lee, Kyung S. research published 《 Identification of a New Heterocyclic Scaffold for Inhibitors of the Polo-Box Domain of Polo-like Kinase 1》, the research content is summarized as follows. As a mitotic-specific target widely deregulated in various human cancers, polo-like kinase 1 (Plk1) has been extensively explored for anticancer activity and drug discovery. Although multiple catalytic domain inhibitors were tested in preclin. and clin. studies, their efficacies are limited by dose-limiting cytotoxicity, mainly from off-target cross reactivity. The C-terminal noncatalytic polo-box domain (PBD) of Plk1 has emerged as an attractive target for generating new protein-protein interaction inhibitors. Here, we identified a 1-thioxo-2,4-dihydro-[1,2,4]triazolo[4,3-a]quinazolin-5(1H)-one scaffold that efficiently inhibits Plk1 PBD but not its related Plk2 and Plk3 PBDs. Structure-activity relationship studies led to multiple inhibitors having ≥10-fold higher inhibitory activity than the previously characterized Plk1 PBD-specific phosphopeptide, PLHSpT (K_d ~450 nM). In addition, S-Me prodrugs effectively inhibited mitotic progression and cell proliferation and their metabolic stability was determined These data describe a novel class of small-mol. inhibitors that offer a promising avenue for future drug discovery against Plk1-addicted cancers.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

AlNajjar, Yasmeen T. team published research on European Journal of Medicinal Chemistry in 2022 | 84358-13-4

Reference of 84358-13-4, N-BOC-piperidine-4-carboxylic acid, also known asN-Boc-isonipecotic acid , is a useful research compound. Its molecular formula is C11H19NO4 and its molecular weight is 229,28 g/mole. The purity is usually 95%.

Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). 84358-13-4, formula is C11H19NO4, Name is 1-(tert-Butoxycarbonyl)piperidine-4-carboxylic acid. It is a colorless liquid with an odor described as objectionable, and typical of amines. Reference of 84358-13-4.

AlNajjar, Yasmeen T.;Gabr, Moustafa;ElHady, Ahmed K.;Salah, Mohamed;Wilms, Gerrit;Abadi, Ashraf H.;Becker, Walter;Abdel-Halim, Mohammad;Engel, Matthias research published 《 Discovery of novel 6-hydroxybenzothiazole urea derivatives as dual Dyrk1A/α-synuclein aggregation inhibitors with neuroprotective effects》, the research content is summarized as follows. A role of Dyrk1A in the progression of Down syndrome-related Alzheimer’s disease (AD) is well supported. However, the involvement of Dyrk1A in the pathogenesis of Parkinson’s disease (PD) was much less studied, and it is not clear whether it would be promising to test Dyrk1A inhibitors in relevant PD models. Herein, we modified our previously published 1-(6-hydroxybenzo[d]thiazol-2-yl)-3-phenylurea scaffold of Dyrk1A inhibitors to obtain a new series of analogs with higher selectivity for Dyrk1A on the one hand, but also with a novel, addnl. activity as inhibitors of α-synuclein (α-syn) aggregation, a major pathogenic hallmark of PD. The Ph acetamide derivative b27 displayed the highest potency against Dyrk1A with an IC₅₀ of 20 nM and high selectivity over closely related kinases. Furthermore, b27 was shown to successfully target intracellular Dyrk1A and to inhibit SF3B1 phosphorylation in HeLa cells with an IC₅₀ of 690 nM. In addition, two compounds among the Dyrk1A inhibitors, b1 and b20, also suppressed the aggregation of α-synuclein (α-syn) oligomers (with IC₅₀ values of 10.5μM and 7.8μM, resp.). Both compounds but not the Dyrk1A reference inhibitor harmine protected SH-SY5Y neuroblastoma cells against α-syn-induced cytotoxicity, with b20 exhibiting a higher neuroprotective effect. Compound b1 and harmine were more efficient in protecting SH-SY5Y cells against 6-hydroxydopamine-induced cell death, an effect that was previously correlated to Dyrk1A inactivation in cells but not yet verified using chem. inhibitors. The presented dual inhibitors exhibited a novel activity profile encouraging for further testing in neurodegenerative disease models.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem