84358-13-4 | Page 7 of 9 | Heterocyclic Building Blocks-piperidine

Iqbal, Zafar team published research on Beilstein Journal of Organic 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%.

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., 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. Application of C11H19NO4.

Iqbal, Zafar;Zhai, Lijuan;Gao, Yuanyu;Tang, Dong;Ma, Xueqin;Ji, Jinbo;Sun, Jian;Ji, Jingwen;Liu, Yuanbai;Jiang, Rui;Mu, Yangxiu;He, Lili;Yang, Haikang;Yang, Zhixiang research published 《 β-lactamase inhibition profile of new amidine-substituted diazabicyclooctanes》, the research content is summarized as follows. The diazabicyclooctane (DBO) scaffold is the backbone of non-β-lactam-based second generation β-lactamase inhibitors. A series of DBO derivatives containing amidine substituents at the C2 position of the bicyclic ring has been synthesized. These compounds, alone and in combination with meropenem, were tested against ten bacterial strains for their antibacterial activity in vitro. All compounds did not show antibacterial activity when tested alone (MIC >64 mg/L), however, they exhibited a moderate inhibition activity in the presence of meropenem by lowering its MIC values. The compound I proved most potent among the other counterparts against all bacterial species with MIC from <0.125 mg/L to 2 mg/L, and is comparable to avibactam against both E. coli strains with a MIC value of <0.125 mg/L.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Hu, Han-Wei team published research on Tetrahedron 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%.

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. COA of Formula: C11H19NO4.

Hu, Han-Wei;Zhang, Cairong;Yang, Yu-Ming;Deng, Hai-Qiang;Tang, Zhen-Yu research published 《 Photocatalytic decarboxylative alkylation of electron-rich heteroarenes with alkyl N-hydroxyphthalimide esters》, the research content is summarized as follows. A direct C-H alkylation of heteroarenes via photocatalytic decarboxylative couplings was reported. A series of primary, secondary, tertiary alkyl carboxylic acids and drug-derived N-hydroxyphthalimide esters were selectively coupled with various electron-rich heteroarenes, including furans, benzofurans and thiophenes. With advantages of mild reaction conditions, broad scopes of substrates and easy handling, this transformation represented a valuable method in organic synthesis.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Huang, Huan-Ming team published research on Nature Catalysis in 2020 | 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 of C11H19NO4.

Huang, Huan-Ming;Koy, Maximilian;Serrano, Eloisa;Pflueger, Philipp Miro;Schwarz, J. Luca;Glorius, Frank research published 《 Catalytic radical generation of π-allylpalladium complexes》, the research content is summarized as follows. A radical approach for the generation of π-allylpalladium complexes by employing N-hydroxyphthalimide esters e.g., I as bifunctional reagents in combination with 1,3-dienes RCH=CHCH=CH₂ (R = H, Me, 2-phenylethyl, cyclohexyl, etc.) and 1,3-cyclohexadiene was shown. Using this strategy, 1,4-aminoalkylation of dienes were reported. The remarkable scope and functional group tolerance of this redox-neutral and mild protocol were demonstrated across >60 examples e.g., II. The utility of this strategy was further demonstrated in radical cascade reactions and in the late-stage modification of drugs and natural products.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Jang, Eunbin team published research on Journal of Organic Chemistry in | 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. Application of C11H19NO4.

Jang, Eunbin;Kim, Hoe In;Jang, Hye Su;Sim, Jaehoon research published 《 Photoredox-Catalyzed Oxidative Radical-Polar Crossover Enables the Alkylfluorination of Olefins》, the research content is summarized as follows. The three-component alkylfluorination of olefins via an oxidative radical-polar crossover under visible light-induced photocatalysis is disclosed. A key feature of this reaction is the incorporation of two synthetically meaningful components involving a three-dimensional alkyl group and a fluorine atom using easily preparable N-hydroxyphthalimide esters as the alkyl donors and a low-cost hydrogen fluoride as the fluorine source. Furthermore, a one-step procedure using com. available carboxylic acids demonstrated the versatility of this new method.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Jiang, Bin team published research on Bioorganic & Medicinal Chemistry Letters in 2020 | 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%.

Jiang, Bin;Duan, James J.-W.;Stachura, Sylwia;Karmakar, Ananta;Hemagiri, Hemalatha;Raut, Dhanya Kumar;Gupta, Arun Kumar;Weigelt, Carolyn A.;Khan, Javed;Sack, John S.;Wu, Dauh-Rurng;Yarde, Melissa;Shen, Ding-Ren;Galella, Michael A.;Mathur, Arvind;Zhao, Qihong;Salter-Cid, Luisa M.;Carter, Percy H.;Dhar, T. G. Murali research published 《 Discovery of (3S,4S)-3-methyl-3-(4-fluorophenyl)-4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxyprop-2-yl)phenyl)pyrrolidines as novel RORγt inverse agonists》, the research content is summarized as follows. A novel series of cis-3,4-diphenylpyrrolidines were designed as RORγt inverse agonists based on the binding conformation of previously reported bicyclic sulfonamide I. Preliminary synthesis and structure-activity relationship (SAR) study established (3S,4S)-3-methyl-3-(4-fluorophenyl)-4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxyprop-2-yl)phenyl)pyrrolidine as the most effective scaffold. Subsequent SAR optimization led to identification of a piperidinyl carboxamide II, which was potent against RORγt (EC₅₀ of 61 nM in an inverse agonist assay), selective relative to RORα, RORβ, LXRα and LXRβ, and stable in human and mouse liver microsomes. Furthermore, compound II exhibited considerably lower PXR Y_max (46%) and emerged as a promising lead. The binding mode of the diphenylpyrrolidine series was established with an X-ray co-crystal structure of III/RORγt.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Jung, Young-Hwan team published research on Journal of Medicinal Chemistry in 2021 | 84358-13-4

Jung, Young-Hwan;Salmaso, Veronica;Wen, Zhiwei;Bennett, John M.;Phung, Ngan B.;Lieberman, David I.;Gopinatth, Varun;Randle, John C. R.;Chen, Zhoumou;Salvemini, Daniela;Karcz, Tadeusz P.;Cook, Donald N.;Jacobson, Kenneth A. research published 《 Structure-Activity Relationship of Heterocyclic P2Y₁₄ Receptor Antagonists: Removal of the Zwitterionic Character with Piperidine Bioisosteres》, the research content is summarized as follows. A known zwitterionic, heterocyclic P2Y₁₄R antagonist 3a was substituted with diverse groups on the central Ph and terminal piperidine moieties, following a computational selection process. The most potent analogs contained an uncharged piperidine bioisostere, prescreened in silico, while an aza-scan (central Ph ring) reduced P2Y₁₄R affinity. Piperidine amide 11, 3-aminopropynyl 19, and 5-(hydroxymethyl)isoxazol-3-yl) 29 congeners in the triazole series maintained moderate receptor affinity. Adaptation of 5-(hydroxymethyl)isoxazol-3-yl gave the most potent naphthalene-containing (32; MRS4654; IC₅₀, 15 nM) and less active phenylamide-containing (33) scaffolds. Thus, a zwitterion was nonessential for receptor binding, and mol. docking and dynamics probed the hydroxymethylisoxazole interaction with extracellular loops. Also, amidomethyl ester prodrugs were explored to reversibly block the conserved carboxylate group to provide neutral analogs, which were cleavable by liver esterase, and in vivo efficacy demonstrated. We have, in stages, converted zwitterionic antagonists into neutral mols. designed to produce potent P2Y₁₄R antagonists for in vivo application.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Kammer, Lisa Marie team published research on Chemical Science 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. HPLC of Formula: 84358-13-4.

Kammer, Lisa Marie;Badir, Shorouk O.;Hu, Ren-Ming;Molander, Gary A. research published 《 Photoactive electron donor-acceptor complex platform for Ni-mediated C(sp³)-C(sp²) bond formation》, the research content is summarized as follows. A dual photochem./nickel-mediated decarboxylative strategy for the assembly of C(sp₃)-C(sp₂) linkages was disclosed. Under light irradiation at 390 nm, com. available and inexpensive Hantzsch ester (HE) functions as a potent organic photoreductant to deliver catalytically active Ni(0) species through single-electron transfer (SET) manifolds. As part of its dual role, the Hantzsch ester effects a decarboxylative-based radical generation through electron donor-acceptor (EDA) complex activation. This homogeneous, net-reductive platform bypasses the need for exogenous photocatalysts, stoichiometric metal reductants, and additives. Under this cross-electrophile paradigm, the coupling of diverse C(sp₃)-centered radical architectures (including primary, secondary, stabilized benzylic, α-oxy, and α-amino systems) with (hetero)aryl bromides was accomplished. The protocol proceeded under mild reaction conditions in the presence of sensitive functional groups and pharmaceutically relevant cores.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Kapoor, Arun team published research on Journal of Medicinal Chemistry in 2020 | 84358-13-4

Kapoor, Arun;Ghosh, Ayan K.;Forman, Michael;Hu, Xin;Ye, Wenjuan;Southall, Noel;Marugan, Juan;Keyes, Robert F.;Smith, Brian C.;Meyers, David J.;Ferrer, Marc;Arav-Boger, Ravit research published 《 Validation and Characterization of Five Distinct Novel Inhibitors of Human Cytomegalovirus》, the research content is summarized as follows. The critical consequences of human cytomegalovirus (HCMV) infection in the transplant population and in congenitally infected infants, the limited treatment options for HCMV, and the rise of resistant mutants toward existing therapies has fueled the search for new anti-HCMV agents. A pp28-luciferase recombinant HCMV was used as a reporter system for high-throughput screening of HCMV inhibitors. Approx. 400 000 compounds from existing libraries were screened. Subsequent validation assays using resynthesized compounds, several virus strains, and detailed virol. assays resulted in the identification of five structurally unique and selective HCMV inhibitors, active at sub to low micromolar concentrations Further characterization revealed that each compound inhibited a specific stage of HCMV replication. One compound was also active against herpes simplex virus (HSV1 and HSV2), and another compound was active against Epstein-Barr virus (EBV). Drug combination studies revealed that all five compounds were additive with ganciclovir or letermovir. Future studies will focus on optimization of these new anti-HCMV compounds along with mechanistic studies.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Jiao, Ke-Jin team published research on Organic Chemistry Frontiers in 2021 | 84358-13-4

Jiao, Ke-Jin;Ma, Cong;Liu, Dong;Qiu, Hui;Cheng, Bin;Mei, Tian-Sheng research published 《 Nickel-catalyzed electrochemical reductive relay cross-coupling of alkyl halides with alkyl carboxylic acids》, the research content is summarized as follows. A highly regioselective Ni-catalyzed electrochem. (undivided cell) reductive relay cross-coupling between alkyl carboxylic acids and alkyl bromides was developed. This strategy allowed the direct acylation of benzylic C(sp³)-H bonds in good yields from com. available alkyl carboxylic acids, thus provided an alternative strategy for the synthesis of dialkyl ketones. Various functional groups were tolerated under mild reaction conditions.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Guo, Peng team published research on Organic Letters in 2022 | 84358-13-4

Guo, Peng;Tao, Maoling;Xu, Wen-Wen;Wang, An-Jun;Li, Weipiao;Yao, Qiuli;Tong, Jie;He, Chun-Yang research published 《 Synthesis of Secondary Trifluoromethylated Alkyl Bromides Using 2-Bromo-3,3,3-trifluoropropene as a Radical Acceptor》, the research content is summarized as follows. Herein, the first example using com. available 2-bromo-3,3,3-trifluoropropene (BTP) as a radical acceptor has been reported. Taking advantage of this strategy, a wide range of secondary trifluoromethylated alkyl bromides were synthesized in good to excellent yields with broad functional group tolerance by using redox-active esters as a radical precursor. The practicality of this protocol was further demonstrated by diverse derivations and direct modification of biol. active mols.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem