M.W=200-250 | Page 34 of 35 | Heterocyclic Building Blocks-piperidine

Cox, Brian team published research on ACS Medicinal Chemistry Letters in 2020 | 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%.

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., Synthetic Route of 84358-13-4

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. Synthetic Route of 84358-13-4.

Cox, Brian;Duffy, James;Zdorichenko, Victor;Bellanger, Corentin;Hurcum, Jessica;Laleu, Benoit;Booker-Milburn, Kevin I.;Elliott, Luke D.;Robertson-Ralph, Michael;Swain, Christopher J.;Bishop, Stephen J.;Hallyburton, Irene;Anderson, Mark research published 《 Escaping from Flatland: Antimalarial Activity of sp³-Rich Bridged Pyrrolidine Derivatives》, the research content is summarized as follows. Synthetic photochem. to generate novel sp3-rich scaffolds and report the design, synthesis, and biol. testing of a diverse series of amides based on the 1-(amino-methyl)-2-benzyl-2-aza-bicyclo[2.1.1]hexane scaffold was utilized . Preliminary antimalarial screening of the library provided promising compounds with activity in the 1-5μM range with an enhanced hit rate. Further evaluation (solubility, drug metabolism and pharmacokinetics (DMPK), and toxicity) of a selected compound (9) suggested that this series represents an excellent opportunity for further optimization with the framework offering multiple opportunities for the addition of uniquely vectorally positioned extra functionality.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Dai, Jian-Jun team published research on Chinese Chemical Letters in 2022 | 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%.

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. Related Products of 84358-13-4.

Dai, Jian-Jun;Teng, Xin-Xin;Fang, Wen;Xu, Jun;Xu, Hua-Jian research published 《 Electrochemically promoted decarboxylative borylation of alkyl N-hydroxyphthalimide esters》, the research content is summarized as follows. An electrochem. promoted decarboxylative borylation reaction is reported. The reaction proceeds under mild conditions in an undivided cell without use of transition metal- or photo-catalysts. The key feature of the reaction is the compatibility of diboron reagents with the electrochem. conditions. This reaction exhibits broad substrate scope, good functional group tolerability, and easy scalability.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Delgado, Jose A. C. team published research on Organic Letters in 2021 | 84358-13-4

Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst: C5H5N + 3 H2 → C5H10NH. 84358-13-4, formula is C11H19NO4, Name is 1-(tert-Butoxycarbonyl)piperidine-4-carboxylic acid. Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol. Related Products of 84358-13-4.

Delgado, Jose A. C.;Correia, Jose T. M.;Pissinati, Emanuele F.;Paixao, Marcio W. research published 《 Biocompatible photoinduced alkylation of dehydroalanine for the synthesis of unnatural α-amino acids》, the research content is summarized as follows. A site-selective alkylation of dehydroalanine to access protected unnatural amino acids is described. The protocol is characterized by the wide nature of alkyl radicals employed, mild conditions, and functional group compatibility. This protocol is further extended to access peptides, late-stage functionalization of pharmaceuticals, and enantioenriched amino acids.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Deng, Xiao-Jun team published research on Journal of Organic Chemistry in 2021 | 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%.

Deng, Xiao-Jun;Liu, Hui-Xia;Zhang, Lu-Wen;Zhang, Guan-Yu;Yu, Zhi-Xiang;He, Wei research published 《 Iodoarene-Catalyzed Oxyamination of Unactivated Alkenes to Synthesize 5-Imino-2-Tetrahydrofuranyl Methanamine Derivatives》, the research content is summarized as follows. Reported here is the room-temperature metal-free iodoarene-catalyzed oxyamination of unactivated alkenes. In this process, the alkenes are difunctionalized by the oxygen atom of the amide group and the nitrogen in an exogenous HNTs₂ mol. This mild and open-air reaction provided an efficient synthesis to N-bistosyl-substituted 5-imino-2-tetrahydrofuranyl methanamine derivatives, which are important motifs in drug development and biol. studies. Mechanistic study based on experiments and d. functional theory calculations showed that this transformation proceeds via activation of the substrate alkene by an in situ generated cationic iodonium(III) intermediate, which is subsequently attacked by an oxygen atom (instead of nitrogen) of amides to form a five-membered ring intermediate. Finally, this intermediate undergoes an S_N2 reaction by NTs₂ as the nucleophile to give the oxygen and nitrogen difunctionalized 5-imino-2-tetrahydrofuranyl methanamine product. An asym. variant of the present alkene oxyamination using chiral iodoarenes as catalysts also gave promising results for some of the substrates.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Dombrowski, Amanda W. team published research on ACS Medicinal Chemistry Letters in 2020 | 84358-13-4

Recommanded Product: 1-(tert-Butoxycarbonyl)piperidine-4-carboxylic acid, 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%.

Dombrowski, Amanda W.;Gesmundo, Nathan J.;Aguirre, Ana L.;Sarris, Katerina A.;Young, Jonathon M.;Bogdan, Andrew R.;Martin, M. Cynthia;Gedeon, Shasline;Wang, Ying research published 《 Expanding the Medicinal Chemist Toolbox: Comparing Seven C(sp²)-C(sp³) Cross-Coupling Methods by Library Synthesis》, the research content is summarized as follows. Despite recent advances in the field of C(sp²)-C(sp³) cross-couplings and the accompanying increase in publications, it can be hard to determine which method is appropriate for a given reaction when using the highly functionalized intermediates prevalent in medicinal chem. Thus a study was done comparing the ability of seven methods to directly install a diverse set of alkyl groups on “drug-like” aryl structures via parallel library synthesis. Each method showed substrates that it excelled at coupling compared with the other methods. When analyzing the reactions run across all of the methods, a reaction success rate of 50% was achieved. Whereas this is promising, there are still gaps in the scope of direct C(sp²)-C(sp³) coupling methods, like tertiary group installation. The results reported herein should be used to inform future syntheses, assess reaction scope, and encourage medicinal chemists to expand their synthetic toolbox.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Duan, Shengzu team published research on Chemical Science in 2022 | 84358-13-4

Duan, Shengzu;Zi, Yujin;Wang, Lingling;Cong, Jielun;Chen, Wen;Li, Minyan;Zhang, Hongbin;Yang, Xiaodong;Walsh, Patrick J. research published 《 α-Branched amines through radical coupling with 2-azaallyl anions, redox active esters and alkenes》, the research content is summarized as follows. Herein, a unique cascade reaction that enables the preparation of α-branched amines I (R = Me, Ad, oxan-4-ylmethyl, etc.; R¹ = H, Me, Ph; R² = Ph; R¹R² = -(CH₂)₂CH(Ph)(CH₂)₂-; R³ = H, Me; R⁴ = Ph, 4-chlorophenyl, furan-3-yl, etc.) and 3-methyl-1,2,2-triphenylpentan-1-amine bearing aryl or alkyl groups at the β- or γ-positions is reported. The cascade is initiated by reduction of redox active esters II to alkyl radicals. The resulting alkyl radicals are trapped by styrene derivatives, R¹C(R²)=CHR³ leading to benzylic radicals. The persistent 2-azaallyl radicals and benzylic radicals are proposed to undergo a radical-radical coupling leading to functionalized amine products I and 3-methyl-1,2,2-triphenylpentan-1-amine. Evidence is provided that the role of the nickel catalyst is to promote formation of the alkyl radical from the redox active ester and not promote the C-C bond formation. The synthetic method introduced herein tolerates a variety of imines III and redox active esters II, allowing for efficient construction of amine building blocks.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

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%.

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

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

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

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