84358-13-4 | Heterocyclic Building Blocks-piperidine

Zhu, Mei team published research on European Journal of Medicinal Chemistry 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%.

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., Application In Synthesis 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. Application In Synthesis of 84358-13-4.

Zhu, Mei;Zhou, Huiyu;Ma, Ling;Dong, Biao;Zhou, Jinming;Zhang, Guoning;Wang, Minghua;Wang, Juxian;Cen, Shan;Wang, Yucheng research published 《 Design and evaluation of novel piperidine HIV-1 protease inhibitors with potency against DRV-resistant variants》, the research content is summarized as follows. A novel class of HIV-1 protease inhibitors with flexible piperidine as the P2 ligand was designed with the aim of improving extensive interactions with the active subsites. Many inhibitors exhibited good to excellent inhibitory effect on enzymic activity and viral infectivity. In particular, inhibitor 3a with (R)-piperidine-3-carboxamide as the P2 ligand and 4-methoxybenzenesulfonamide as the P2 ligand showed an enzyme Ki value of 29 pM and antiviral IC50 value of 0.13 nM, more than six-fold enhancement of activity compared to DRV. Furthermore, there was no significant change in potency against DRV-resistant mutations and HIV-1NL4-3 variant for 3a. Besides, inhibitor 3a exhibited potent antiviral activity against subtype C variants with low nanomole EC50 values. In addition, the mol. modeling revealed important hydrogen bonds and other favorable van der Waals interactions with the backbone atoms of the protease and provided insight for designing and optimizing more potent HIV-1 protease inhibitors.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Zhi, Zhuoer team published research on Journal of Medicinal Chemistry in 2020 | 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%.

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. Product Details of C11H19NO4.

Zhi, Zhuoer;Zhang, Wenting;Yao, Jingchun;Shang, Yanguo;Hao, Qingjing;Liu, Zhong;Ren, Yushan;Li, Jie;Zhang, Guimin;Wang, Jinxin research published 《 Discovery of Aryl Formyl Piperidine Derivatives as Potent, Reversible, and Selective Monoacylglycerol Lipase Inhibitors》, the research content is summarized as follows. Most of the current MAGL inhibitors function by an irreversible mechanism of action, causing a series of side effects. Herein, starting from irreversible inhibitors, 25 compounds were synthesized and evaluated in vitro for MAGL inhibition, among which, compound I showed the most potent inhibitory activity (IC50 = 15 nM). Crucially, docking studies demonstrated that the m-chlorine-substituted aniline fragment occupied a hydrophobic sub-pocket enclosed by side chains of Val191, Tyr194, Val270, and Lys273, which creatively identify a new key anchoring point for the development of new MAGL inhibitors. Furthermore, in vivo evaluation innovatively revealed that this reversible inhibitor I significantly displayed the depressive-like behaviors induced by reserpine. To the best of our knowledge, this is the first time that reversible inhibitors of MAGL were developed to support MAGL as a potential therapeutic target for depression.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Zhao, Yanmei team published research on Bioorganic & Medicinal Chemistry in 2021 | 84358-13-4

Zhao, Yanmei;Xu, Lei;Zhang, Jiankang;Zhang, Mengmeng;Lu, Jingyi;He, Ruoyu;Xi, Jianjun;Zhuang, Rangxiao;Li, Jia;Zhou, Yubo research published 《 Optimization of piperidine constructed peptidyl derivatives as proteasome inhibitors》, the research content is summarized as follows. A series of non-covalent piperidine-containing peptidyl derivatives with various substituents at side chains of different residues were designed, synthesized and evaluated as proteasome inhibitors. After proteasome inhibitory evaluations of all the synthesized target compounds, selected ones were tested for their anti-proliferation activities against three multiple myeloma (MM) cell lines. Eight analogs displayed more potent activities than carfilzomib, and the most promising compound 24 (I) showed IC₅₀ values of 0.8 ± 0.2 nM against 20S proteasome and 8.42 ± 0.74 nM, 7.14 ± 0.52 nM, 14.20 ± 1.08 nM for RPMI 8226, NCI-H929 and MM.1S cell lines, resp. Addnl., mechanisms of anti-cancer activity of representative compound 24 were further investigated. Apoptosis of RPMI-8226 cells were achieved through accumulating polyubiquitin and inducing the cleavage of caspase and PARP. Besides, half-life in rat plasma of compound 24 was prolonged after optimization, which would be helpful for increasing in vivo activities of this series of derivatives All the studies confirmed that piperidine-containing non-covalent proteasome inhibitors can be potential leads for anti-MM drug development.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Zhao, Haoqiang team published research on Organic Letters in 2020 | 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. Application of C11H19NO4.

Zhao, Haoqiang;Xu, Xin;Yu, Haiyang;Li, Bohan;Xu, Xingyu;Li, Huanrong;Xu, Lijin;Fan, Qinghua;Walsh, Patrick J. research published 《 Rh(I)-Catalyzed C6-Selective Decarbonylative Alkylation of 2-Pyridones with Alkyl Carboxylic Acids and Anhydrides》, the research content is summarized as follows. A Rh-catalyzed chelation-assisted C6-selective C-H activation/alkylation of 2-pyridones e.g., 1-(pyridin-2-yl)-1,2-dihydropyridin-2-one with readily available anhydrides RC(O)OC(O)R (R = Me, Et, 2-methylpropyl, etc.) or alkyl carboxylic acids R¹C(O)OH (R¹ = nonyl, cyanoethyl, cyclohexyl, etc.) is introduced. The reaction proceeds via substrate decarbonylation. This approach merges C-H functionalization with readily available anhydrides, allowing for the efficient synthesis of various C6-alkylated 2-pyridones e.g., 6-methyl-2H-[1,2′-bipyridin]-2-one with good functional group tolerance.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Zhang, Ziyi team published research on Fitoterapia in 2020 | 84358-13-4

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. Category: piperidines.

Zhang, Ziyi;Chen, Zhiguo;Zhang, Shengyu;Shao, Xiao;Zhou, Zhiwen research published 《 Antibacterial activity of the structurally novel ocotillol-type lactone and its analogues》, the research content is summarized as follows. A novel series of ocotillol-type lactone derivatives were designed and synthesized in order to study their antibacterial activity and structure-activity relationships. Among which, compounds 4j and 4 m were found to be the most active with min. inhibitory concentrations (MICs) of 1-4 μg/mL against Gram-pos. bacteria and showed low cytotoxicity against MCF-7, HEK-293 and HK-2 cells at their MICs. The antibacterial effect of compound 4 m was characterized further by SEM, cytoplasmic β-galactosidase leakage assay and UV-visible anal. The results showed that 4 m may exert its antibacterial effect by damaging bacterial cell membranes and disrupting the function of DNA, both of which could lead to rapid cell death.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Zhang, Benxiang team published research on Nature (London, United Kingdom) in 2022 | 84358-13-4

HPLC of Formula: 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. HPLC of Formula: 84358-13-4.

Zhang, Benxiang;Gao, Yang;Hioki, Yuta;Oderinde, Martins S.;Qiao, Jennifer X.;Rodriguez, Kevin X.;Zhang, Hai-Jun;Kawamata, Yu;Baran, Phil S. research published 《 Ni-electrocatalytic Csp³-Csp³ doubly decarboxylative coupling》, the research content is summarized as follows. Here, it was shown how a mildly reductive Ni-electrocatalytic system could couple two different carboxylates by means of in situ generated redox-active esters, termed doubly decarboxylative cross-coupling. This operationally simple method was used to heterocouple primary, secondary and even certain tertiary redox-active esters, thereby opening up a powerful new approach for synthesis. The reaction, which cannot be mimicked using stoichiometric metal reductants or photochem. conditions, tolerated a range of functional groups, was scalable and was used for the synthesis of 32 known compounds, reducing overall step counted by 73%.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Yu, Haiyang team published research on Asian Journal of Organic Chemistry in 2021 | 84358-13-4

Yu, Haiyang;Zhao, Haoqiang;Xu, Xin;Zhang, Xin;Yu, Zexin;Li, Lingchao;Wang, Peng;Shi, Qian;Xu, Lijin research published 《 Rhodium(I)-Catalyzed C2-Selective Decarbonylative C-H Alkylation of Indoles with Alkyl Carboxylic Acids and Anhydrides》, the research content is summarized as follows. A Rh(I)-catalyzed chelation-assisted C2-selective C-H decarbonylative alkylation of indoles with readily available, cheap, safe and structurally diverse alkyl carboxylic acids or anhydrides has been developed. A wide variety of primary and secondary alkyl carboxylic acids and differently substituted indoles are compatible with this transformation, allowing facile synthesis of various C2-alkylated indoles with high efficiency and broad tolerance of diverse functional groups. The reaction proceeds in the absence of any external oxidant, and the presence of readily installable and removable N-pyrimidyl directing group is critical for catalysis. The process is convenient and scalable, and avoids the use of a dried solvent and an inert atm. Moreover, selective C7-alkylation and C2, C7-dialkylation have also been achieved by slightly modifying the reaction conditions.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Yu, Wan-Lei team published research on Chemical Science in 2022 | 84358-13-4

Yu, Wan-Lei;Ren, Zi-Gang;Ma, Ke-Xing;Yang, Hui-Qing;Yang, Jun-Jie;Zheng, Haixue;Wu, Wangsuo;Xu, Peng-Fei research published 《 Cobalt-catalyzed chemoselective dehydrogenation through radical translocation under visible light》, the research content is summarized as follows. In this report, a straightforward and robust cobaloxime-catalyzed photochem. dehydrogenation strategy via intramol. HAT was described for the first time. The reaction proceeded through an intramol. radical translocation followed by the cobalt assisted dehydrogenation without needing any other external photosensitizers, noble-metals or oxidants. With this approach, a series of valuable unsaturated compounds such as α,β-unsaturated amides, enamides and allylic and homoallylic sulfonamides were obtained in moderate to excellent yields with good chemo- and regioselectivities, and the synthetic versatility was demonstrated by a range of transformations. And mechanistic studies of the method were discussed.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Zhang, Juan team published research on Chemical Papers in 2021 | 84358-13-4

Zhang, Juan;Ge, Yong-Xi;Fang, Lei;Zhu, Kong-Kai;Liu, Shan-Kui;Wang, Kai-Ming;Jiang, Cheng-Shi research published 《 Discovery of 3-(1H-indol-5-yl)-1,2,4-oxidizable derivatives as non-competitive α-glucosidase inhibitors》, the research content is summarized as follows. In this study, indolyl-1,2,4-oxidizable derivatives were synthesized and in vitro evaluated as new class of non-competitive α-glucosidase inhibitors. Most of the compounds showed better inhibitory activity than reference drug (acarbose), with compound 35 being the most potent inhibitor. Kinetic anal. indicated that compound 35 had non-competitive inhibition on α-glucosidase, and fluorescence quenching experiment confirmed the direct binding of 35 to α-glucosidase. Besides, some selected compounds had no effect on cell viability of human normal hepatocyte (LO2) and human liver cancer (HepG2) cells. Thus, this work provides a new chemotype for developing novel drugs against type 2 diabetes.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Zhang, Wenjuan team published research on Bioorganic & Medicinal Chemistry in 2020 | 84358-13-4

Zhang, Wenjuan;Wei, Zhao;Huang, Guozhi;Xie, Fei;Zheng, Zhibing;Li, Song research published 《 Study of triaryl-based sulfamic acid derivatives as HPTPβ inhibitors》, the research content is summarized as follows. A series of novel triaryl-based sulfamic acid analogs I [R = H, 3-FC₆H₄CH₂C(O), 4-MeOC₆H₄SO₂, etc.; Ar = Ph, 4-phenylthiazol-2-yl, 4-(2-thienyl)thiazol-2-yl] was designed, synthesized and evaluated as inhibitors of human protein tyrosine phosphatase beta (HPTPβ). A novel, easy and efficient synthetic method was developed for target compounds I, and the activity determination results showed that most of compounds were good HPTPβ inhibitors. Interestingly, the compounds I [R = 1-tert-butoxycarbonylpiperidine-4-carbonyl, Ar = Ph; R = H, Ar = 4-(2-thienyl)thiazol-2-yl] with simple structure not only showed potent inhibitory activity on HPTPβ but also had good inhibitory selectivity over other PTPs (PTP1B, SHP2, LAR and TC-PTP). The mol. docking simulation of compounds with the protein HPTPβ helped to understand the structure-activity relationship and clarified some confusing assay results. This research provided references for further drug design of HPTPβ and other PTPs inhibitors.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem