M.W=200-250 | Page 31 of 35 | Heterocyclic Building Blocks-piperidine

Oh, Sangmi team published research on ACS Medicinal Chemistry Letters 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 of C11H19NO4

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.

Oh, Sangmi;Kwon, Do Yoon;Choi, Inhee;Kim, Young Mi;Lee, Ji Young;Ryu, Jiyoung;Jeong, Hangyeol;Kim, Myung Jin;Song, Rita research published 《 Identification of Piperidine-3-carboxamide Derivatives Inducing Senescence-like Phenotype with Antimelanoma Activities》, the research content is summarized as follows. This study evaluated the potential use of senescence-inducing small mols. in the treatment of melanoma. We screened com. available small-mol. libraries with high-throughput screening and high-content screening image-based technol. Our findings showed an initial hit with the embedded N-arylpiperidine-3-carboxamide scaffold induced senescence-like phenotypic changes in human melanoma A375 cells without serious cytotoxicity against normal cells. A focused library containing diversely modified analogs were constructed and examined to evaluate the structure-activity relationship of N-arylpiperidine-3-carboxamide derivatives starting from hit 1. This work identified a novel compound with remarkable antiproliferative activity in vitro and demonstrated the key structural moieties within.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Park, Sang-Hyun team published research on Analytical Chemistry (Washington, DC, United States) 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%.

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. HPLC of Formula: 84358-13-4.

Park, Sang-Hyun;Shin, Insu;Kim, Young-Hyun;Shin, Injae research published 《 Mitochondrial Cl^–-Selective Fluorescent Probe for Biological Applications》, the research content is summarized as follows. Herein the authors describe the development of the first mitochondrial Cl^–-selective fluorescent probe, Mito-MQAE(I), and its applications in biol. systems. Fluorescence of Mito-MQAE is insensitive to pH over the physiol. pH range and is quenched by Cl^– with a Stern-Volmer quenching constant of 201 M^-1 at pH 7.0. The results of cell studies using Mito-MQAE show that substances with the ability to disrupt mitochondrial membranes cause increases in the mitochondrial Cl^– concentration

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Piticari, Amalia-Sofia team published research on Advanced Synthesis & Catalysis in 2022 | 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%.

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. Formula: C11H19NO4.

Piticari, Amalia-Sofia;Antermite, Daniele;Higham, Joe I.;Moore, J. Harry;Webster, Matthew P.;Bull, James A. research published 《 Stereoselective Palladium-Catalyzed C(sp³)-H Mono-Arylation of Piperidines and Tetrahydropyrans with a C(4) Directing Group》, the research content is summarized as follows. A selective Pd-catalyzed C(3)-H cis-functionalization of piperidine and tetrahydropyran carboxylic acids is achieved using a C(4) aminoquinoline amide auxiliary. High mono- and cis-selectivity is attained by using mesityl carboxylic acid as an additive. Conditions are developed with significantly lower reaction temperatures (≤50°C) than other reported heterocycle C(sp³)-H functionalization reactions, which is facilitated by a DoE optimization. A one-pot C-H functionalization-epimerization procedure provides the trans-3,4-disubstituted isomers directly. Divergent aminoquinoline removal is accomplished with the installation of carboxylic acid, alc., amide and nitrile functional groups. Overall, fragment compounds suitable for screening are generated in 3-4 steps from readily-available heterocyclic carboxylic acids.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

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

Liu, Yao;Hao, Mingfeng;Leggett, Alan L.;Gao, Yang;Ficarro, Scott B.;Che, Jianwei;He, Zhixiang;Olson, Calla M.;Marto, Jarrod A.;Kwiatkowski, Nicholas P.;Zhang, Tinghu;Gray, Nathanael S. research published 《 Discovery of MFH290: A Potent and Highly Selective Covalent Inhibitor for Cyclin-Dependent Kinase 12/13》, the research content is summarized as follows. Genetic depletion of cyclin-dependent kinase 12 (CDK12) or selective inhibition of an analog-sensitive CDK12 reduces DNA damage repair gene expression, but selective inhibition of endogenous CDK12 is difficult. Here, we report the development of MFH290(I), a novel cysteine (Cys)-directed covalent inhibitor of CDK12/13. MFH290 forms a covalent bond with Cys-1039 of CDK12, exhibits excellent kinome selectivity, inhibits the phosphorylation of serine-2 in the C-terminal domain (CTD) of RNA-polymerase II (Pol II), and reduces the expression of key DNA damage repair genes. Importantly, these effects were demonstrated to be CDK12-dependent as mutation of Cys-1039 rendered the kinase refractory to MFH290 and restored Pol II CTD phosphorylation and DNA damage repair gene expression. Consistent with its effect on DNA damage repair gene expression, MFH290 augments the antiproliferative effect of the PARP inhibitor olaparib.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Lu, Xiao-Yu team published research on Journal of Organic Chemistry in 2022 | 84358-13-4

Related Products 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%.

Lu, Xiao-Yu;Gao, Ang;Ge, Meng-Yuan;Xia, Ze-Jie;Liu, Qi-Le;Tao, Ting-Hua;Sun, Xiao-Mei research published 《 Stereoconvergent Synthesis of Monofluoroalkenes via Photoinduced Dual Decarboxylative Cross-Coupling of α-Fluoroacrylic Acids with Redox-Active Esters》, the research content is summarized as follows. Herein, a new strategy for the synthesis of monofluoroalkenes via employing α-fluoroacrylic acids and N-hydroxyphthalimide (NHPI) redox-active esters as coupling partners has been developed. This decarboxylative reaction enabled the formation of C(sp²)-C(sp³) bonds to provide a practical and efficient approach for the construction of a variety of monofluoroalkenes, which are key structural motifs in organic chem., under mild reaction conditions. The protocol exhibited excellent functional group compatibility and delivered monofluoroalkene products with excellent Z-stereoselectivity. This work also provides a platform for the modification of complex biol. active mols. containing carboxylic acids.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Lu, Zhichao team published research on Angewandte Chemie, International Edition in 2021 | 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. HPLC of Formula: 84358-13-4.

Lu, Zhichao;Kumon, Tatsuya;Hammond, Gerald B.;Umemoto, Teruo research published 《 Trifluoromethyl Nonaflate: A Practical Trifluoromethoxylating Reagent and its Application to the Regio- and Stereoselective Synthesis of Trifluoromethoxylated Alkenes》, the research content is summarized as follows. Trifluoromethyl nonafluorobutanesulfonate (nonaflate), TFNf, an easy-to-handle, bench-stable, reactive, and scalable trifluoromethoxylating reagent was developed. TFNf was easily and safely prepared in a simple process in large scale and the nonaflyl part of TFNf could easily be recovered as nonaflyl fluoride after usage and recycled. The synthetic potency of TFNf was showcased with the underexplored synthesis of various trifluoromethoxylated alkenes, through a high regio- and stereoselective hydro(halo)trifluoromethoxylation of alkyne derivatives such as haloalkynes, alkynyl esters, and alkynyl sulfones. The synthetic merits of TFNf were further underscored with a high-yielding and smooth nucleophilic trifluoromethoxylation of alkyl triflates/bromides and primary/secondary alcs.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Mao, Runze team published research on Journal of the American Chemical Society in 2021 | 84358-13-4

Mao, Runze;Bera, Srikrishna;Turla, Aurelya Christelle;Hu, Xile research published 《 Copper-Catalyzed Intermolecular Functionalization of Unactivated C(sp³)-H Bonds and Aliphatic Carboxylic Acids》, the research content is summarized as follows. A Cu-catalyzed process for the diverse functionalization of both unactivated C(sp³)-H bonds RH (cyclododecyl, n-hexyl, tetrahydrofuran-2-yl, etc.) and aliphatic carboxylic acids R¹C(O)OH (R¹ = 1-phenylethyl, tetrahydro-2H-pyran-4-yl, 4-oxocyclohexyl, etc.) was described. The process is enabled by trapping of alkyl radicals generated through hydrogen atom abstraction by arylsulfonyl-based SOMO-philes, which introduces a large array of C, N, S, Se, and halide-based functional groups. The chemoselectivity can be switched from C-H functionalization to decarboxylative functionalization by matching the bond dissociation energy of the hydrogen atom transfer reagent with that of the target C-H or O-H bond.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Meden, Anze team published research on European Journal of Medicinal Chemistry in 2020 | 84358-13-4

Category: piperidines, 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%.

Meden, Anze;Knez, Damijan;Malikowska-Racia, Natalia;Brazzolotto, Xavier;Nachon, Florian;Svete, Jurij;Salat, Kinga;Groselj, Uros;Gobec, Stanislav research published 《 Structure-activity relationship study of tryptophan-based butyrylcholinesterase inhibitors》, the research content is summarized as follows. A series of tryptophan-based selective nanomolar butyrylcholinesterase (BChE) inhibitors was designed and synthesized. Compounds were optimized in terms of potency, selectivity, and synthetic accessibility. The crystal structure of the inhibitor (I) in complex with BChE revealed the mol. basis for its low nanomolar inhibition (IC₅₀ = 2.8 nM). The favorable in vitro results enabled a first-in-animal in vivo efficacy and safety trial, which demonstrated a pos. impact on fear-motivated and spatial long-term memory retrieval without any concomitant adverse motor effects. Altogether, this research culminated in a handful of new lead compounds with promising potential for symptomatic treatment of patients with Alzheimer’s disease.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Merkens, Kay team published research on Advanced Synthesis & Catalysis in 2020 | 84358-13-4

Merkens, Kay;Aguilar Troyano, Francisco Jose;Djossou, Jonas;Gomez-Suarez, Adrian research published 《 Synthesis of unnatural α-amino acid derivatives via light-mediated radical decarboxylative processes》, the research content is summarized as follows. Unnatural amino acids (UAAs) are key building blocks with widespread application across several scientific fields. Therefore, it is highly attractive to develop straightforward and simple methodologies capable of granting quick access to these species. Herein we report a light-mediated protocol for the synthesis of UAA via radical decarboxylative processes. This methodol., which employs readily available and abundant starting materials – such as carboxylic and α-keto acids – proceeds under very mild reaction conditions and shows a high functional group tolerance. In addition, the products of the radical reaction can be readily derivatized to grant rapid access to complex UAAs.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Li, Xuemei team published research on European Journal of Medicinal Chemistry in 2021 | 84358-13-4

Li, Xuemei;Hong, Duidui;Zhang, Mengmeng;Xu, Lei;Zhou, Yubo;Li, Jia;Liu, Tao research published 《 Development of peptide epoxyketones as selective immunoproteasome inhibitors》, the research content is summarized as follows. A series of epoxyketone analogs with varying N-caps and P3-configurations were designed, synthesized and evaluated. We found that D-Ala in P3 was crucial for β5i selectivity over β5c. Notably, compounds (I) (R¹ = II) (β5i IC₅₀ = 26.0 nM, 25-fold selectivity) and I (r¹ = III) (β5i IC₅₀ = 25.1 nM, 24-fold selectivity) with the D-configuration at P3 were the most selective inhibitors. Although I (R¹ = II and III) showed only moderate anti-proliferative activity against RPMI-8226 and MM.1S cell lines, based on our experiments, it indicates that the inhibition of β5i alone is not sufficient to exert anticancer effects and may rely on the complementary inhibition of β1i, β5c and β5i. These data further increase our understanding of immunoproteasome inhibitors in hematol. malignancies.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem