M.W=200-250 | Page 27 of 35 | 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

Yu, Haiyang team published research on Asian Journal of Organic Chemistry 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. Synthetic Route of 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

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.

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, 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

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

Zhang, Yanzhi team published research on Steroids in 2020 | 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

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

Yang, Qian team published research on ACS Sustainable Chemistry & Engineering in 2021 | 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