84358-13-4 | Page 3 of 9 | Heterocyclic Building Blocks-piperidine

Xi, Ji-Ming team published research on Organic Letters in 2022 | 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., Electric Literature of 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. Electric Literature of 84358-13-4.

Xi, Ji-Ming;Sun, Yun-Hai;Li, Wen-Cheng;Wu, Yu-Heng;Wei, Zhong-Lin;Liao, Wei-Wei research published 《 Radical Alkene-Trifluoromethylation-Triggered Nitrile Insertion/Remote Functionalization Relay Processes: Diverse Synthesis of Trifluoromethylated Azaheterocycles Enabled by Copper Catalysis》, the research content is summarized as follows. A copper-catalyzed trifluoromethylation-of-alkenes-triggered nitrile insertion/remote functionalization relay process has been achieved, in which an “interrupted” remote 1, n-difunctionalizations of alkenes with a nitrile insertion, can deliver iminyl radical intermediate, followed by subsequent 1, n-HAT to furnish corresponding remote functionalization, instead of C-based radical. This relay protocol enabled a straightforward approach to streamline the assembly of structurally diverse trifluoromethylated azaheterocycles.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Xi, Xiaoxiang team published research on Angewandte Chemie, International Edition in 2022 | 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%.

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

Xi, Xiaoxiang;Luo, Yixin;Li, Weirong;Xu, Minghao;Zhao, Hongping;Chen, Yukun;Zheng, Songlin;Qi, Xiaotian;Yuan, Weiming research published 《 From Esters to Ketones via a Photoredox-Assisted Reductive Acyl Cross-Coupling Strategy》, the research content is summarized as follows. A method was developed for ketone synthesis via a photoredox-assisted reductive acyl cross-coupling (PARAC) using a nickel/photoredox dual-catalyzed cross-electrophile coupling of two different carboxylic acid esters. A variety of aryl, 1°, 2°, 3°-alkyl 2-pyridyl esters could act as acyl electrophiles while N-(acyloxy)phthalimides (NHPI esters) act as 1°, 2°, 3°-radical precursors. Our PARAC strategy provides an alternative and reliable way to synthesize various sterically congested 3°-3°, 3°-2°, and aryl-3° ketones under mild and highly unified conditions, which have been otherwise difficult to access. The combined exptl. and computational studies identified a Ni0/NiI/NiIII pathway for ketone formation.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Xu, Lijuan team published research on Chinese Chemical Letters in 2022 | 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. Formula: C11H19NO4.

Xu, Lijuan;Tu, Ye;Li, Jiao;Zhang, Wannian;Wang, Zhibin;Zhuang, Chunlin;Xue, Lei research published 《 Structure-based optimizations of a necroptosis inhibitor (SZM594) as novel protective agents of acute lung injury》, the research content is summarized as follows. Targeting RIPK1 is a promising strategy for the treatment or alleviation of acute lung injury (ALI). SZM594, a benzothiazole compound previously developed by our research group, possessed good dual-targeting receptor-interacting protein kinase 1 (RIPK1) and RIPK3 activity and anti-necroptosis activity as well as acceptable in vivo efficacy. In this study, the cyclopropyl moiety of SZM594 was modified based on a structure-based design strategy. The resulting cyclohexanone-containing analog 41 improved the selectivity toward RIPK1 over RIPK3 and the anti-necroptosis activity was also increased compared with those of SZM594. More importantly, compound 41 could inhibit the tumor necrosis factor-α (TNF-α) expression in lipopolysaccharide (LPS)-induced peritoneal macrophage cell model, and significantly alleviate LPS-induced ALI in a mouse model. This compound could significantly inhibit the expressions of the phosphorylation of RIPK1 and down-stream RIPK3 and mixed lineage kinase domain-like protein (MLKL). Thus, these cyclohexanone-containing benzothiazole analogs represent promising lead structures for the discovery of novel protective agents of ALI.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Wilt, Stephanie team published research on Bioorganic Chemistry in 2020 | 84358-13-4

Name: 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%.

Wilt, Stephanie;Kodani, Sean;Le, Thanh N. H.;Nguyen, Lato;Vo, Nghi;Ly, Tanya;Rodriguez, Mark;Hudson, Paula K.;Morisseau, Christophe;Hammock, Bruce D.;Pecic, Stevan research published 《 Development of multitarget inhibitors for the treatment of pain: Design, synthesis, biological evaluation and molecular modeling studies》, the research content is summarized as follows. Multitarget-directed ligands are a promising class of drugs for discovering innovative new therapies for difficult to treat diseases. In this study, we designed dual inhibitors targeting the human fatty acid amide hydrolase (FAAH) enzyme and human soluble epoxide hydrolase (sEH) enzyme. Targeting both of these enzymes concurrently with single target inhibitors synergistically reduces inflammatory and neuropathic pain; thus, dual FAAH/sEH inhibitors are likely to be powerful analgesics. Here, we identified the piperidinyl-sulfonamide moiety as a common pharmacophore and optimized several inhibitors to have excellent inhibition profiles on both targeted enzymes simultaneously. In addition, several inhibitors show good predicted pharmacokinetic properties. These results suggest that this series of inhibitors has the potential to be further developed as new lead candidates and therapeutics in pain management.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Wang, Hao team published research on Nature Chemistry in 2021 | 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%.

Wang, Hao;Jung, Hoimin;Song, Fangfang;Zhu, Shiyang;Bai, Ziqian;Chen, Danye;He, Gang;Chang, Sukbok;Chen, Gong research published 《 Nitrene-mediated intermolecular N-N coupling for efficient synthesis of hydrazides》, the research content is summarized as follows. N-N linkages are found in many natural compounds and endow fascinating structural and functional properties. In comparison to the myriad methods for the construction of C-N bonds, chem. for N-N coupling, especially in an intermol. fashion, remains underdeveloped. Here, we report a nitrene-mediated intermol. N-N coupling of dioxazolones and arylamines under iridium or iron catalysis. These reactions offer a simple and efficient method for the synthesis of various hydrazides from readily available carboxylic acid and amine precursors. Although the Ir-catalyzed conditions usually give higher N-N coupling yield than the Fe-catalyzed conditions, the reactions of sterically more demanding dioxazolones derived from α-substituted carboxylic acids work much better under the Fe-catalyzed conditions. Mechanistic studies revealed that the nitrogen atom of Ir acyl nitrene intermediates has strong electrophilicity and can undergo nucleophilic attack with arylamines with the assistance of Cl···HN hydrogen bonding to form the N-N bond with high efficiency and chemoselectivity.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Walczak, Maciej team published research on Chemistry & Biodiversity in 2021 | 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 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. Quality Control of 84358-13-4.

Walczak, Maciej;Chryplewicz, Agnieszka;Olewinska, Sandra;Psurski, Mateusz;Winiarski, Lukasz;Torzyk, Karolina;Oleksyszyn, Jozef;Sienczyk, Marcin research published 《 Phosphonic Analogs of Alanine as Acylpeptide Hydrolase Inhibitors》, the research content is summarized as follows. Acylpeptide hydrolase is a serine protease, which, together with prolyl oligopeptidase, dipeptidyl peptidase IV and oligopeptidase B, belongs to the prolyl oligopeptidase family. Its primary function is associated with the removal of N-acetylated amino acid residues from proteins and peptides. Although the N-acylation occurs in 50-90% of eukaryotic proteins, the precise functions of this modification remains unclear. Recent findings have indicated that acylpeptide hydrolase participates in various events including oxidized proteins degradation, amyloid β-peptide cleavage, and response to DNA damage. Considering the protein degradation cycle cross-talk between acylpeptide hydrolase and proteasome, inhibition of the first enzyme resulted in down-regulation of the ubiquitin-proteasome system and induction of cancer cell apoptosis. Acylpeptide hydrolase has been proposed as an interesting target for the development of new potential anticancer agents. Here, we present the synthesis of simple derivatives of (1-aminoethyl)phosphonic acid diaryl esters, phosphonic analogs of alanine diversified at the N-terminus and ester rings, as inhibitors of acylpeptide hydrolase and discuss the ability of the title compounds to induce apoptosis of U937 and MV-4-11 tumor cell lines.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Vimala, M. team published research on Journal of Molecular Liquids in 2021 | 84358-13-4

Vimala, M.;Stella Mary, S.;Ramalakshmi, R.;Muthu, S.;Irfan, Ahmad research published 《 Computational prediction of polar and non-polar solvent effect on the electronic property of N-BOC- Piperidine-4-Carboxylic acid》, the research content is summarized as follows. Geometrical parameters and vibrational anal. of N-BOC-Piperidine-4-Carboxylic acid were computed using Hartree – Fock and D. functional theory with 6-311++G(d,p) basis set. Apparent change occurs in electronic property due to polar and non-polar solvents were investigated. The stabilization energy and mol. bonding interactions were calculated in NBO anal. Global descriptors and NLO parameters were predicted. Fukui functions, mol. electrostatic potential, reduced d. gradient isosurface, electron d. at bonding and antibonding were visualized. Total, partial and overall DOS spectrum were intricated to study the bonds overlapping interactions in the mol. Mol. docking was performed to reveal the protein interaction with BP4C.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Trammel, Grace L. team published research on Journal of the American Chemical Society in 2021 | 84358-13-4

Formula: 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%.

Trammel, Grace L.;Kuniyil, Rositha;Crook, Phillip F.;Liu, Peng;Brown, M. Kevin research published 《 Nickel-Catalyzed Dearomative Arylboration of Indoles: Regioselective Synthesis of C2- and C3-Borylated Indolines》, the research content is summarized as follows. Indole dearomatization is an important strategy to access indolines: a motif present in a variety of natural products and biol. active mols. Herein, a method for transition-metal catalyzed regioselective dearomative arylboration of indoles to generate diverse indolines is presented. The method accomplishes intermol. dearomatization of simple indoles through a migratory insertion pathway on substrates that lack activating or directing groups on the C2- or C3-positions. Synthetically useful C2- and C3-borylated indolines can be accessed through a simple change in N-protecting group in high regio- and diastereoselectivities (up to >40:1 rr and >40:1 dr) from readily available starting materials. Addnl., the origin of regioselectivity was explored exptl. and computationally to uncover the remarkable interplay between carbonyl orientation of the N-protecting group on indole, electronics of the C2-C3 π-bond, and sterics. The method enabled the 1st enantioselective synthesis of (-)-azamedicarpin.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Thomson, Christopher G. team published research on Bioorganic & Medicinal Chemistry Letters in 2021 | 84358-13-4

Application In Synthesis 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%.

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. Application In Synthesis of 84358-13-4.

Thomson, Christopher G.;Le Grand, Darren;Dowling, Mark;Beattie, David;Elphick, Lucy;Faller, Michael;Freeman, Mark;Hardaker, Elizabeth;Head, Victoria;Hemmig, Rene;Hill, Johan;Lister, Andrew;Pascoe, David;Rieffel, Sebastien;Shrestha, Binesh;Steward, Oliver;Zink, Florence research published 《 Development of autotaxin inhibitors: A series of tetrazole cinnamides》, the research content is summarized as follows. A series of inhibitors of autotaxin (ATX) have been developed from a high throughput screening hit, 1a (I), which shows an alternative binding mode to known catalytic site inhibitors. Selectivity over the hERG channel and microsomal clearance were dependent on the lipophilicity of the compounds, and this was optimized by reduction of clogD while maintaining high affinity ATX inhibition. Compound 15a (II) shows good oral exposure, and concentration dependent inhibition of formation of LPA in vivo, as shown in pharmacokinetic-pharmacodynamic (PK/PD) experiments

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Tang, Zi-Liang team published research on Organic Letters in 2021 | 84358-13-4

Tang, Zi-Liang;Ouyang, Xuan-Hui;Song, Ren-Jie;Li, Jin-Heng research published 《 Decarboxylative C(sp³)-N Cross-Coupling of Diacyl Peroxides with Nitrogen Nucleophiles》, the research content is summarized as follows. A new radical-mediated decarboxylative C(sp³)-N cross-coupling of diacyl peroxides with nitrogen nucleophiles has been disclosed. The primary and secondary alkyl radicals derived from corresponding diacyl peroxides were generated by copper catalysis or by merging copper catalysis and photoredox catalysis, resp. Various N-alkyl nitrogen nucleophiles, including indazoles, triazoles, indoles, purine, carbazole, anilines, and sulfonamide, were provided with a broad substrate scope and good functional group tolerance.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem