M.W=200-250 | Page 32 of 35 | Heterocyclic Building Blocks-piperidine

Li, Zhan team published research on Nature Communications in 2020 | 84358-13-4

Synthetic Route 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%.

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.

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. Synthetic Route of 84358-13-4.

Li, Zhan;Wang, Ke-Feng;Zhao, Xin;Ti, Huihui;Liu, Xu-Ge;Wang, Honggen research published 《 Manganese-mediated reductive functionalization of activated aliphatic acids and primary amines》, the research content is summarized as follows. In this work, a Mn-mediated reductive decarboxylative/deaminative functionalization of activated aliphatic acids and primary amines was disclosed. A series of C-X (X = S, Se, Te, H, P) and C-C bonds were efficiently constructed under simple and mild reaction conditions. The protocol was applicable to the late-stage modification of some structurally complex natural products or drugs. Preliminary mechanistic studies suggest the involvement of radicals in the reaction pathway.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Liu, Can team published research on Organic Chemistry Frontiers 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%.

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. SDS of cas: 84358-13-4.

Liu, Can;Shen, Ni;Shang, Rui research published 《 Photocatalytic decarboxylative alkylation of silyl enol ether and enamide with N-(acyloxy)phthalimide using ammonium iodide》, the research content is summarized as follows. Enamides and silyl enol ethers were alkylated to deliver products of N-acyl imines and ketones in the presence of a catalytic amount of N-tetrabutylammonium iodide (TBAI) under irradiation with purple light-emitting diodes (427 nm) at room temperature A broad scope of tertiary, secondary, and primary alkylation products was achieved with good yields and tolerance of a variety of functional groups. The reactions proceed through the photoactivation of a transiently assembled electron donor-acceptor complex formed between iodide and N-(acyloxy)phthalimide to generate alkyl radicals. The simplicity and low-cost nature of these methods without using metal catalysts demonstrate the practicality of the use of alkyl carboxylates as alkyl sources in organic synthesis.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Liu, Hui-Yuan team published research on Organic Letters in 2020 | 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%.

Liu, Hui-Yuan;Lu, Yuan;Li, Yang;Li, Jin-Heng research published 《 Photocatalytic Decarboxylative [2 + 2 + m] Cyclization of 1,7-Enynes Mediated by Tricyclohexylphosphine and Potassium Iodide》, the research content is summarized as follows. A novel photocatalytic decarboxylative [2 + 2 + m] cyclization of 1,7-enynes [N-(o-alkynylphenyl)acrylamides] with alkyl N-hydroxyphthalimide (NHP) esters, using tricyclohexylphosphine (PCy₃) and potassium iodide as redox catalysts, is reported for the construction of functional polycyclic compounds such as phenanthridinone I and fused quinolinones such as II (with the formed ring system dependent on the presence or absence of α-hydrogen atoms in the N-acyloxyphthalimide). This protocol tolerates primary, secondary, and tertiary alkyl NHP esters through a single reaction via decarbonylation, radical addition, C-H functionalization, and cyclization under mild conditions.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Kuehl, Nikos team published research on Journal of Medicinal Chemistry in 2021 | 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%.

Kuehl, Nikos;Leuthold, Mila M.;Behnam, Mira A. M.;Klein, Christian D. research published 《 Beyond Basicity: Discovery of Nonbasic DENV-2 Protease Inhibitors with Potent Activity in Cell Culture》, the research content is summarized as follows. The viral serine protease NS2B-NS3 is one of the promising targets for drug discovery against dengue virus and other flaviviruses. The mol. recognition preferences of the protease favor basic, pos. charged moieties as substrates and inhibitors, which leads to pharmacokinetic liabilities and off-target interactions with host proteases such as thrombin. We here present the results of efforts that were aimed specifically at the discovery and development of noncharged, small-mol. inhibitors of the flaviviral proteases. A key factor in the discovery of these compounds was a cellular reporter gene assay for the dengue protease, the DENV2proHeLa system. Extensive structure-activity relationship explorations resulted in novel benzamide derivatives with submicromolar activities in viral replication assays (EC₅₀ 0.24μM), selectivity against off-target proteases, and negligible cytotoxicity. This structural class has increased drug-likeness compared to most of the previously published active-site-directed flaviviral protease inhibitors and includes promising candidates for further preclin. development.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Li, Jiacheng team published research on Journal of Medicinal Chemistry in | 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. Name: 1-(tert-Butoxycarbonyl)piperidine-4-carboxylic acid.

Li, Jiacheng;Liu, Ting;Song, Yuanli;Wang, Mingyu;Liu, Liping;Zhu, Hongwen;Li, Qi;Lin, Jin;Jiang, Hualiang;Chen, Kaixian;Zhao, Kehao;Wang, Mingliang;Zhou, Hu;Lin, Hua;Luo, Cheng research published 《 Discovery of Small-Molecule Degraders of the CDK9-Cyclin T1 Complex for Targeting Transcriptional Addiction in Prostate Cancer》, the research content is summarized as follows. Aberrant hyperactivation of cyclins results in carcinogenesis and therapy resistance in cancers. Direct degradation of the specific cyclin or cyclin-dependent kinase (CDK)-cyclin complex by small-mol. degraders remains a great challenge. Here, we applied the first application of hydrophobic tagging to induce degradation of CDK9-cyclin T1 heterodimer, which is required to keep productive transcription of oncogenes in cancers. LL-K9-3 (I) was identified as a potent small-mol. degrader of CDK9-cyclin T1. Quant. and time-resolved proteome profiling exhibited LL-K9-3-induced selective and synchronous degradation of CDK9 and cyclin T1. The expressions of androgen receptor (AR) and cMyc were reduced by LL-K9-3 (I) in 22RV1 cells. LL-K9-3 (I) exhibited enhanced anti-proliferative and pro-apoptotic effects compared with its parental CDK9 inhibitor SNS032 and suppressed downstream signaling of CDK9 and AR more effectively than SNS032. Moreover, LL-K9-3 (I) inhibited AR and Myc-driven oncogenic transcriptional programs and exerted stronger inhibitory effects on several intrinsic target genes of AR than the monomeric CDK9 PROTAC (Thal-SNS032).

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Li, Shunyao team published research on Organic & Biomolecular Chemistry in 2021 | 84358-13-4

Reference 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%.

Li, Shunyao;Zhang, Lanfei;He, Qian;Zhang, Xiaofei;Yang, Chunhao research published 《 Synthesis of 2-alkyl-chroman-4-ones via cascade alkylation-dechlorination of 3-chlorochromones》, the research content is summarized as follows. An efficient and mild synthetic approach for 2-alkyl-substituted chroman-4-ones via zinc-mediated cascade decarboxylative β-alkylation and dechlorination of 3-chlorochromones was developed. This transformation employed com. available starting materials and was performed under mild conditions without heat, visible light, peroxide or heavy metals. Moreover, various alkyl NHPI esters with functional groups and differently substituted 3-chlorochromones were tolerated, affording the targeted products with moderate to excellent yields. This protocol could be utilized to construct a diverse library of 2-substituted chroman-4-one derivatives, which could be useful in the discovery of lead compounds for drug discovery in the future.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Hu, Han-Wei team published research on Tetrahedron Letters in 2022 | 84358-13-4

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

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

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

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