84358-13-4 | Page 2 of 9 | Heterocyclic Building Blocks-piperidine

Zhang, Yanzhi team published research on Steroids 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., SDS of cas: 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. SDS of cas: 84358-13-4.

Zhang, Yanzhi;Chen, Xubing;Zhou, Yang;Hou, Jinjun;Long, Huali;Zhang, Zijia;Lei, Min;Wu, Wanying research published 《 Synthesis of oleandrin derivatives and their cytotoxic activity》, the research content is summarized as follows. A series of oleandrin-4′-yl ester derivatives, e.g. I.HCl, were designed, synthesized, and evaluated for their proliferation inhibition activities against tumor cell lines. Cytotoxicity data revealed that the C₄‘ moiety had an important influence on cytotoxic activity. Several compounds that we designed and synthesized exhibit significant in vitro antiproliferative activity against the tested tumor cell lines. Among the derivatives of OL, I.HCl not only had good antitumor activity but also had good water solubility Furthermore, I.HCl can significantly inhibit tumor growth by 96.4% at a dose of 6 mg/kg/d by i.p.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Zhang, Zhucheng team published research on Organic & Biomolecular Chemistry in 2022 | 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. Quality Control of 84358-13-4.

Zhang, Zhucheng;He, Qian;Zhang, Xiaofei;Yang, Chunhao research published 《 Photoredox-catalysed regioselective synthesis of C-4-alkylated pyridines with N-(acyloxy)phthalimides》, the research content is summarized as follows. A method of direct C-4 selective alkylation of pyridines under visible light irradiation at room temperature was reported using simple maleate-derived pyridinium salts as pyridine precursors and the readily available carboxylic acid-derived N-(acyloxy)phthalimides as alkyl radical precursors, affording good to excellent yields without using stoichiometric oxidants and acids. A broad range of primary, secondary and tertiary carboxylates were used as alkylation reagents. Oxidant and acid-sensitive functional groups were tolerated well.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Yen-Pon, Expedite team published research on Journal of the American Chemical Society in 2022 | 84358-13-4

Quality Control 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 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. Quality Control of 84358-13-4.

Yen-Pon, Expedite;Li, Longbo;Levitre, Guillaume;Majhi, Jadab;McClain, Edward J.;Voight, Eric A.;Crane, Erika A.;Molander, Gary A. research published 《 On-DNA Hydroalkylation to Introduce Diverse Bicyclo[1.1.1]pentanes and Abundant Alkyls via Halogen Atom Transfer》, the research content is summarized as follows. A Giese addition to install highly functionalized bicyclo[1.1.1]pentanes (BCPs) using tricyclo[1.1.1.01,3]pentane (TCP) as a radical linchpin, as well as other diverse alkyl groups, on-DNA from the corresponding organohalides as non-stabilized radical precursors was reported. Telescoped procedures allow extension of the substrate pool by at least an order of magnitude to ubiquitous alcs. and carboxylic acids, allowing us to “upcycle” these abundant feedstocks to afford non-traditional libraries with different physicochem. properties for the small-mol. products (i.e., non-peptide libraries with acids). This approach is amenable to library production, as a DNA damage assessment revealed good PCR amplifiability and only 6% mutated sequences for a full-length DNA tag.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Yang, Qian team published research on ACS Sustainable Chemistry & Engineering in 2021 | 84358-13-4

Piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. This gave the compound its name. 84358-13-4, formula is C11H19NO4, Name is 1-(tert-Butoxycarbonyl)piperidine-4-carboxylic acid. Other examples are the fire ant toxin solenopsin, the nicotine analog anabasine of tree tobacco (Nicotiana glauca), lobeline of Indian tobacco. Related Products of 84358-13-4.

Yang, Qian;Pan, Guanglong;Wei, Jie;Wang, Wentao;Tang, Yurong;Cai, Yunfei research published 《 Remarkable Activity of Potassium-Modified Carbon Nitride for Heterogeneous Photocatalytic Decarboxylative Alkyl/Acyl Radical Addition and Reductive Dimerization of para-Quinone Methides》, the research content is summarized as follows. Heterogeneous photocatalysis has emerged as a green and sustainable technique in organic synthesis. Developing highly effective heterogeneous photocatalysts that outperformed classical ruthenium-/iridium-based homogeneous ones for the visible-light mediated organic transformations is actively pursued by chemists but remains challenging. Herein, a modified carbon nitride-based heterogeneous photocatalytic system for both decarboxylative addition and reductive dimerization of para-quinone methides has been developed. The potassium-intercalated carbon nitride (CN-K) facile prepared by the direct KCl-induced structure remodeling of bulk g-C₃N₄ exhibited remarkable catalytic activity. The catalyst loading can be decreased to 0.025-0.25 mg/mL, which is significantly lower than that in homogeneous photocatalysis. Studies on the structure characterizations and photoelec. properties of CN-K and g-C₃N₄ imply that the enhanced activity of CN-K was attributed to its K-intercalated poly(heptazine)-based structure and existed as small lamellar nanocrystallites, thus leading to enhanced optical absorption, improved electron-hole separation, and easy dispersion in polar solvents. The heterogeneous nature and mild reaction conditions of this protocol allow for good catalyst recyclability, broad substrate scope, scale-up in a continuous flow, and applications to the valued target synthesis.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Yamada, Kei team published research on Bioorganic & Medicinal Chemistry Letters in 2020 | 84358-13-4

Yamada, Kei;Matsumoto, Ryo;Suzuki, Yumiko;Mori, Suguru;Kitajima, Seiji research published 《 Design, synthesis and evaluation of unnatural peptides as T1R2/T1R3 PAMs》, the research content is summarized as follows. The sweet receptor T1R2/T1R3 is a member of G protein-coupled receptor family and recognizes diverse natural and synthetic sweeteners. Previously, we reported a novel class of pos. allosteric modulators (PAMs) of T1R2/T1R3 comprising an unnatural tripeptide structure. We classified the structure of these PAMs into three parts: “head”, “linker” and “tail”. Here, we report the design, synthesis and evaluation of various tail structures to obtain highly active unnatural peptide structure of PAM. In conclusion, we discovered the novel unnatural tetrapeptide with highly potent PAM activity on T1R2/T1R3 in a cell-based assay system.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Wang, Peng-Zi team published research on Angewandte Chemie, International Edition in 2021 | 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%.

Wang, Peng-Zi;Wu, Xue;Cheng, Ying;Jiang, Min;Xiao, Wen-Jing;Chen, Jia-Rong research published 《 Photoinduced Copper-Catalyzed Asymmetric Three-Component Coupling of 1,3-Dienes: An Alternative to Kharasch-Sosnovsky Reaction》, the research content is summarized as follows. Herein, an alternative to the asym. Kharasch-Sosnovsky reaction that utilized a chiral copper catalyst and purple-LED irradiation to enable the three-component coupling of 1,3-dienes RCH=CHC(R¹)=CHR² (R = H, Me; R¹ = H, Me; R² = Ph, 2-phenylethyl, furan-3-yl, etc.), oxime esters I (R³ = H, Me; R⁴ = H; R³R⁴ = -CH=CH-CH=CH-; R⁵ = H; R⁴R⁵ = -CH₂N(Boc)CH₂-, -(CH₂)₂N(Boc)(CH₂)₂-), and carboxylic acids R⁶C(O)OH (R⁵ = t-Bu, Ph, 2H-1,3-benzodioxol-5-yl, etc.) is reported. This protocol features mild conditions, remarkable scope and functional group tolerance as evidenced by >80 examples and utility in the late-stage modification of pharmaceuticals and natural products. Detailed mechanistic studies provide evidences for the radical-based reaction pathway.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Wang, Jiang team published research on Angewandte Chemie, International Edition in 2020 | 84358-13-4

Wang, Jiang;Hoerrner, Megan E.;Watson, Mary P.;Weix, Daniel J. research published 《 Nickel-Catalyzed Synthesis of Dialkyl Ketones from the Coupling of N-Alkyl Pyridinium Salts with Activated Carboxylic Acids》, the research content is summarized as follows. While ketones are among the most versatile functional groups, their synthesis remains reliant upon reactive and low-abundance starting materials. In contrast, amide formation is the most-used bond-construction method in medicinal chem. because the chem. is reliable and draws upon large and diverse substrate pools. A new method for the synthesis of ketones is presented here that draws from the same substrates used for amide bond synthesis: amines and carboxylic acids. A nickel terpyridine catalyst couples N-alkyl pyridinium salts with in situ formed carboxylic acid fluorides or 2-pyridyl esters under reducing conditions (Mn metal). The reaction has a broad scope, as demonstrated by the synthesis of 35 different ketones bearing a wide variety of functional groups with an average yield of 60±16%. This approach is capable of coupling diverse substrates, including pharmaceutical intermediates, to rapidly form complex ketones.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

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

Computed Properties 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. Computed Properties of 84358-13-4.

Wang, Junwei;Pan, Xiang;Song, Yi;Liu, Jian;Ma, Fei;Wang, Ping;Liu, Yan;Zhao, Lin;Kang, Di;Hu, Lihong research published 《 Discovery of a Potent and Selective FLT3 Inhibitor (Z)-N-(5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-4-methyl-1H-pyrrol-3-yl)-3-(pyrrolidin-1-yl)propanamide with Improved Drug-like Properties and Superior Efficacy in FLT3-ITD-Positive Acute Myeloid Leukemia》, the research content is summarized as follows. Overcoming the FLT3-ITD mutant has been a promising drug design strategy for treating acute myeloid leukemia (AML). Herein, we discovered a novel FLT3 inhibitor 17 (I), which displayed potent inhibitory activity against the FLT3-ITD mutant (IC₅₀ = 0.8 nM) and achieved good selectivity over c-KIT kinase (over 500-fold). Compound 17 selectively inhibited the proliferation of FLT3-ITD-pos. AML cell lines MV4-11 (IC₅₀ = 23.5 nM) and MOLM-13 (IC₅₀ = 35.5 nM) and exhibited potent inhibitory effects against associated acquired resistance mutations. In cellular mechanism studies, compound 17 strongly inhibited FLT3-mediated signaling pathways and induced apoptosis by arresting the cell cycle in the sub-G1 phase. In in vivo studies, compound 17 demonstrated a good bioavailability (73.6%) and significantly suppressed tumor growth in MV4-11 (10 mg/kg, TGI 93.4%) and MOLM-13 (20 mg/kg, TGI 98.0%) xenograft models without exhibiting obvious toxicity. These results suggested that compound 17 may be a promising drug candidate for treating FLT3-ITD-pos. AML.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Waybright, Jarod M. team published research on ACS Chemical Biology in 2021 | 84358-13-4

Waybright, Jarod M.;Clinkscales, Sarah E.;Barnash, Kimberly D.;Budziszewski, Gabrielle R.;Rectenwald, Justin M.;Chiarella, Anna M.;Norris-Drouin, Jacqueline L.;Cholensky, Stephanie H.;Pearce, Kenneth H.;Herring, Laura E.;McGinty, Robert K.;Hathaway, Nathaniel A.;James, Lindsey I. research published 《 A Peptidomimetic Ligand Targeting the Chromodomain of MPP8 Reveals HRP2’s Association with the HUSH Complex》, the research content is summarized as follows. The interpretation of histone post-translational modifications (PTMs), specifically lysine methylation, by specific classes of “reader” proteins marks an important aspect of epigenetic control of gene expression. Methyl-lysine (Kme) readers often regulate gene expression patterns through the recognition of a specific Kme PTM while participating in or recruiting large protein complexes that contain enzymic or chromatin remodeling activity. Understanding the composition of these Kme-reader-containing protein complexes can serve to further our understanding of the biol. roles of Kme readers, while small mol. chem. tools can be valuable reagents in interrogating novel protein-protein interactions. Here, we describe our efforts to target the chromodomain of M-phase phosphoprotein 8 (MPP8), a member of the human silencing hub (HUSH) complex and a histone 3 lysine 9 tri-Me (H3K9me3) reader that is vital for heterochromatin formation and has specific roles in cancer metastasis. Utilizing a one-bead, one-compound (OBOC) combinatorial screening approach, we identified UNC5246, a peptidomimetic ligand capable of interacting with the MPP8 chromodomain in the context of the HUSH complex. Addnl., a biotinylated derivative of UNC5246 facilitated chemoproteomics studies which revealed hepatoma-derived growth factor-related protein 2 (HRP2) as a novel protein associated with MPP8. HRP2 was further shown to colocalize with MPP8 at the E-cadherin gene locus, suggesting a possible role in cancer cell plasticity.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Wilt, Stephanie R. team published research on Chemical Biology & Drug Design in 2020 | 84358-13-4

Application 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%.

Wilt, Stephanie R.;Rodriguez, Mark;Le, Thanh N. H.;Baltodano, Emily V.;Salas, Adrian;Pecic, Stevan research published 《 Design, microwave-assisted synthesis, biological evaluation and molecular modeling studies of 4-phenylthiazoles as potent fatty acid amide hydrolase inhibitors》, the research content is summarized as follows. Endocannabinoids, anandamide (AEA) and 2-arachidonoylglycerol (2-AG), are endogenous lipids that activate cannabinoid receptors. Activation of these receptors produces anti-inflammatory and analgesic effects. Fatty acid amide hydrolase (FAAH) is a membrane enzyme that hydrolases endocannabinoids; thus, inhibition of FAAH represents an attractive approach to develop new therapeutics for treating inflammation and pain. Previously, potent rat FAAH inhibitors containing 2-naphthyl- and 4-phenylthiazole scaffolds were identified, but up to the present time, very little structure-activity relationship studies have been performed on these moieties. We designed and synthesized several analogs containing these structural motifs and evaluated their inhibition potencies against human FAAH enzyme. In addition, we built and validated a homol. model of human FAAH enzyme and performed docking experiments We identified several inhibitors in the low nanomolar range and calculated their ADME predicted values. These FAAH inhibitors represent promising drug candidates for future preclin. in vivo studies.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem