September 2022 | Page 5 of 28 | Heterocyclic Building Blocks-piperidine

Yang, Qian team published research on ACS Sustainable Chemistry & Engineering 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., Related Products of 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. Related Products of 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

Yan, Guoyi team published research on Anti-Cancer Agents in Medicinal Chemistry in 2021 | 5382-16-1

Electric Literature of 5382-16-1, 4-Hydroxypiperidine is a molecule with a carbonyl group. It is the most active and selective CCR5 receptor antagonist that has been studied to date. 4-Hydroxypiperidine inhibits HIV infection by preventing the binding of HIV to its receptor on the surface of white blood cells, thereby preventing it from entering these cells. 4-Hydroxypiperidine also acts as an anti-inflammatory agent in chronic bronchitis patients, due to its ability to inhibit prostaglandin synthesis. The chemical ionization mass spectra of this molecule show peaks for methyl ethyl, malic acid, and hydroxyl groups. These properties make 4-hydroxypiperidine a useful candidate for drug development against inflammatory diseases and several cancers.
The molecular structure, vibrational spectra, NBO and UV-spectral analysis of 4-Hydroxypiperidine have been studied. The compounds with a substituted 4-piperidinol core have been found to be potent antagonists of the human H receptor., 5382-16-1.

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–). 5382-16-1, formula is C5H11NO, Name is 4-Piperidinol. It is a colorless liquid with an odor described as objectionable, and typical of amines. Electric Literature of 5382-16-1.

Yan, Guoyi;Luo, Jiang;Han, Xuan;Zhang, Wenjuan;Pu, Chunlan;Zhou, Meng;Zhong, Xinxin;Hou, Xueyan;Hou, Man Zhou;Li, Rui research published 《 Design, Synthesis and Biological Evaluation of 4, 6-Coumarin Derivatives as Anti- Cancer and Apoptosis-Inducing Agents》, the research content is summarized as follows. Coumarin structures were widely employed in anti-cancer drug design. Herein we focused on the modifications of C4 and C6 positions on coumarin scaffold to get novel anti-cancer agents. The objective of the current work was the synthesis and biol. evaluation of a series of 4, 6-coumarin derivatives to get novel anticancer agents. Thirty-seven coumarin derivatives were designed and synthesized, the antiproliferative activity of the compounds was evaluated against human cancer cell lines and non-cancerous cells by MTT assay. The bioactivities and underlying mechanisms of active mols. were studied and the ADMET characters were predicted. Among the compounds, 4-p-hydroxy phenol-6-pinacol borane coumarin (25) exhibited a promising anti-cancer activity to cancer cell lines in a dose-dependent manner and the toxicity to normal cells was low. The mechanism of action was observed by inducing G₂/M phase arrest and apoptosis which was further confirmed via western blot. In silico ADMET prediction revealed that compound 25 is a drug-like small mol. with a favorable safety profile. The findings in this work may give vital information for further development of 6-pinacol borane coumarin derivatives as novel anti-cancer agents.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Yamada, Kei team published research on Bioorganic & Medicinal Chemistry Letters 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. Safety of 1-(tert-Butoxycarbonyl)piperidine-4-carboxylic acid.

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

Xue, Ding team published research on Journal of Medicinal Chemistry in 2022 | 5382-16-1

5382-16-1, 4-Hydroxypiperidine is a molecule with a carbonyl group. It is the most active and selective CCR5 receptor antagonist that has been studied to date. 4-Hydroxypiperidine inhibits HIV infection by preventing the binding of HIV to its receptor on the surface of white blood cells, thereby preventing it from entering these cells. 4-Hydroxypiperidine also acts as an anti-inflammatory agent in chronic bronchitis patients, due to its ability to inhibit prostaglandin synthesis. The chemical ionization mass spectra of this molecule show peaks for methyl ethyl, malic acid, and hydroxyl groups. These properties make 4-hydroxypiperidine a useful candidate for drug development against inflammatory diseases and several cancers.
The molecular structure, vibrational spectra, NBO and UV-spectral analysis of 4-Hydroxypiperidine have been studied. The compounds with a substituted 4-piperidinol core have been found to be potent antagonists of the human H receptor., Name: 4-Piperidinol

Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst: C5H5N + 3 H2 → C5H10NH. 5382-16-1, formula is C5H11NO, Name is 4-Piperidinol. Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol. Name: 4-Piperidinol.

Xue, Ding;Xu, Yibin;Kyani, Armita;Roy, Joyeeta;Dai, Lipeng;Sun, Duxin;Neamati, Nouri research published 《 Multiparameter Optimization of Oxidative Phosphorylation Inhibitors for the Treatment of Pancreatic Cancer》, the research content is summarized as follows. Targeting oxidative phosphorylation (OXPHOS) complexes is an emerging strategy to disrupt the metabolism of select cancer subtypes and to overcome resistance to targeted therapies. Here, we describe our lead optimization campaign on a series of benzene-1,4-disulfonamides as novel OXPHOS complex I inhibitors. This effort led to the discovery of compound 23 (DX3-213B)(I) as one of the most potent complex I inhibitors reported to date. DX3-213B disrupts ATP generation, inhibits complex I function, and results in the growth inhibition of pancreatic cancer cells in the low nanomolar range. Importantly, the oral administration of DX3-213B resulted in significant in vivo efficacy in a pancreatic cancer syngeneic model without obvious toxicity. Our data clearly demonstrate that OXPHOS inhibition can be a safe and efficacious strategy to treat pancreatic cancer.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Xu, Qinlong team published research on European Journal of Medicinal Chemistry in 2022 | 5382-16-1

Quality Control of 5382-16-1, 4-Hydroxypiperidine is a molecule with a carbonyl group. It is the most active and selective CCR5 receptor antagonist that has been studied to date. 4-Hydroxypiperidine inhibits HIV infection by preventing the binding of HIV to its receptor on the surface of white blood cells, thereby preventing it from entering these cells. 4-Hydroxypiperidine also acts as an anti-inflammatory agent in chronic bronchitis patients, due to its ability to inhibit prostaglandin synthesis. The chemical ionization mass spectra of this molecule show peaks for methyl ethyl, malic acid, and hydroxyl groups. These properties make 4-hydroxypiperidine a useful candidate for drug development against inflammatory diseases and several cancers.
The molecular structure, vibrational spectra, NBO and UV-spectral analysis of 4-Hydroxypiperidine have been studied. The compounds with a substituted 4-piperidinol core have been found to be potent antagonists of the human H receptor., 5382-16-1.

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. 5382-16-1, formula is C5H11NO, Name is 4-Piperidinol. Other examples are the fire ant toxin solenopsin, the nicotine analog anabasine of tree tobacco (Nicotiana glauca), lobeline of Indian tobacco. Quality Control of 5382-16-1.

Xu, Qinlong;Hu, Mengqi;Li, Jiaming;Ma, Xiaodong;Chu, Zhaoxing;Zhu, Qihua;Zhang, Yanchun;Zhu, Panhu;Huang, Yuanzheng;He, Guangwei research published 《 Discovery of novel brain-penetrant GluN2B NMDAR antagonists via pharmacophore-merging strategy as anti-stroke therapeutic agents》, the research content is summarized as follows. In this work, a novel structural series of brain-penetrant GluN2B NMDAR antagonists were designed, synthesized and biol. evaluated as anti-stroke therapeutic agents via merging the structures of NBP and known GluN2B ligands. Approx. half of them exhibited superior neuroprotective activity to NBP against NMDA-induced neurotoxicity in hippocampal neurons at 10 μM, and compound 3-(3-(4-(4-Trifluoromethylbenzyl)piperazin-1-yl)propyl)isobenzofuran-1(3H)-one hydrochloride and 3-(3-(4-(4-Nitrobenzyl)piperazin-1-yl)propyl) isobenzofuran-1(3H)-one hydrochloride exerted equipotent activity to ifenprodil, an approved GluN2B- selective NMDAR antagonist. In particular, 3-(3-(4-(4-Trifluoromethylbenzyl)piperazin-1-yl)propyl)isobenzofuran-1(3H)-one hydrochloride, with the most potent neuroprotective activity throughout this series, displayed dramatically enhanced activity (K_i = 3.26 nM) compared to ifenprodil (K_i = 14.80 nM) in Radioligand Competitive Binding Assay, and remarkable inhibition (IC50 = 79.32 nM) against GluN1/GluN2B receptor-mediated current in Patch Clamp Assay. Meanwhile, 3-(3-(4-(4-Trifluoromethylbenzyl)piperazin-1-yl)propyl)isobenzofuran-1(3H)-one hydrochloride and its enantiomers exhibited low inhibition rate against the current mediated by other investigated receptors at the concentration of 10 μM, indicating their favorable selectivity for GluN1/GluN2B. In the rat model of middle cerebral artery ischemia (MCAO), 3-(3-(4-(4-Trifluoromethylbenzyl)piperazin-1-yl)propyl)isobenzofuran-1(3H)-one hydrochloride exerted comparable therapeutic efficacy to ifenprodil at the same dosage. In addition to the attractive in vitro and in vivo potency, 3-(3-(4-(4-Trifluoromethylbenzyl)piperazin-1-yl)propyl)isobenzofuran-1(3H)-one hydrochloride displayed a favorable bioavailability (F = 63.37%) and an excellent brain exposure. In further repeated dose toxicity experiments, compound 3-(3-(4-(4-Trifluoromethylbenzyl)piperazin-1-yl)propyl)isobenzofuran-1(3H)-one hydrochloride demonstrated an acceptable safety profile. With the above merits, 3-(3-(4-(4-Trifluoromethylbenzyl)piperazin-1-yl)propyl)isobenzofuran-1(3H)-one hydrochloride is worthy of further functional investigation as a novel anti-stroke therapeutic agent.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Xu, Lijuan team published research on Chinese Chemical Letters in 2022 | 84358-13-4

Xu, Lijuan;Tu, Ye;Li, Jiao;Zhang, Wannian;Wang, Zhibin;Zhuang, Chunlin;Xue, Lei research published 《 Structure-based optimizations of a necroptosis inhibitor (SZM594) as novel protective agents of acute lung injury》, the research content is summarized as follows. Targeting RIPK1 is a promising strategy for the treatment or alleviation of acute lung injury (ALI). SZM594, a benzothiazole compound previously developed by our research group, possessed good dual-targeting receptor-interacting protein kinase 1 (RIPK1) and RIPK3 activity and anti-necroptosis activity as well as acceptable in vivo efficacy. In this study, the cyclopropyl moiety of SZM594 was modified based on a structure-based design strategy. The resulting cyclohexanone-containing analog 41 improved the selectivity toward RIPK1 over RIPK3 and the anti-necroptosis activity was also increased compared with those of SZM594. More importantly, compound 41 could inhibit the tumor necrosis factor-α (TNF-α) expression in lipopolysaccharide (LPS)-induced peritoneal macrophage cell model, and significantly alleviate LPS-induced ALI in a mouse model. This compound could significantly inhibit the expressions of the phosphorylation of RIPK1 and down-stream RIPK3 and mixed lineage kinase domain-like protein (MLKL). Thus, these cyclohexanone-containing benzothiazole analogs represent promising lead structures for the discovery of novel protective agents of ALI.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Xi, Xiaoxiang team published research on Angewandte Chemie, International Edition in 2022 | 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%.

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. Recommanded Product: 1-(tert-Butoxycarbonyl)piperidine-4-carboxylic acid.

Xi, Xiaoxiang;Luo, Yixin;Li, Weirong;Xu, Minghao;Zhao, Hongping;Chen, Yukun;Zheng, Songlin;Qi, Xiaotian;Yuan, Weiming research published 《 From Esters to Ketones via a Photoredox-Assisted Reductive Acyl Cross-Coupling Strategy》, the research content is summarized as follows. A method was developed for ketone synthesis via a photoredox-assisted reductive acyl cross-coupling (PARAC) using a nickel/photoredox dual-catalyzed cross-electrophile coupling of two different carboxylic acid esters. A variety of aryl, 1°, 2°, 3°-alkyl 2-pyridyl esters could act as acyl electrophiles while N-(acyloxy)phthalimides (NHPI esters) act as 1°, 2°, 3°-radical precursors. Our PARAC strategy provides an alternative and reliable way to synthesize various sterically congested 3°-3°, 3°-2°, and aryl-3° ketones under mild and highly unified conditions, which have been otherwise difficult to access. The combined exptl. and computational studies identified a Ni0/NiI/NiIII pathway for ketone formation.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Xi, Ji-Ming team published research on Organic Letters in 2022 | 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. Electric Literature of 84358-13-4.

Xi, Ji-Ming;Sun, Yun-Hai;Li, Wen-Cheng;Wu, Yu-Heng;Wei, Zhong-Lin;Liao, Wei-Wei research published 《 Radical Alkene-Trifluoromethylation-Triggered Nitrile Insertion/Remote Functionalization Relay Processes: Diverse Synthesis of Trifluoromethylated Azaheterocycles Enabled by Copper Catalysis》, the research content is summarized as follows. A copper-catalyzed trifluoromethylation-of-alkenes-triggered nitrile insertion/remote functionalization relay process has been achieved, in which an “interrupted” remote 1, n-difunctionalizations of alkenes with a nitrile insertion, can deliver iminyl radical intermediate, followed by subsequent 1, n-HAT to furnish corresponding remote functionalization, instead of C-based radical. This relay protocol enabled a straightforward approach to streamline the assembly of structurally diverse trifluoromethylated azaheterocycles.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Wu, Yu team published research on Bioorganic & Medicinal Chemistry in 2021 | 5382-16-1

Piperidine the name comes from the genus name Piper, which is the Latin word for pepper. 5382-16-1, formula is C5H11NO, Name is 4-Piperidinol. 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. Quality Control of 5382-16-1.

Wu, Yu;Cheung, Chen-Yi;Zhou, Yang;Wang, Zhen;Tu, Zhengchao;Cook, Gregory M.;Lu, Xiaoyun research published 《 Discovery of 5-methylpyrimidopyridone analogues as selective antimycobacterial agents》, the research content is summarized as follows. With the emergence of multidrug-resistant strains of Mycobacterium tuberculosis (MDR-TB) and extensive drug-resistant strains (XDR-TB), there is an urgent need to develop novel drugs for the treatment of tuberculosis. Here, the authors designed and synthesized a series of 5-methylpyrimidopyridone analogs I [R¹ = NHEt, cyclopropylamino, 4-methylpiperidino, etc., R² = (3s,5S,7s)-adamant-1-yl, cyclopentyl, cyclohexyl, R³ = 2-Cl, 4-Cl, H, 2-CN, etc.] as potential antitubercular agents. The most potent compound II exhibited a MIC value of 4μM in vitro against Mycobacterium tuberculosis. The antitubercular activities of the synthesized compounds were impacted by the amantadine and 2-chlorophenyl groups, and were enhanced by the presence of 3-methyl(4-dimethylamino)piperidinylphenyl. Mol. modeling and binding studies suggest that PknB is the potential mol. target of 5-methylpyrimidopyridone compounds This study provides insights for the future development of new antimycobacterial agents with novel mechanisms of action.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Wu, Qingmei team published research on Journal of Molecular Structure in 2022 | 5382-16-1

Wu, Qingmei;Zheng, Zhaopeng;Ye, Wenjun;Guo, Qian;Liao, Tianhui;Yang, Di;Zhao, Chunshen;Liao, Weike;Chai, Huifang;Zhou, Zhixu research published 《 Synthesis, crystal and molecular structure, vibrational spectroscopic, DFT and molecular docking of 4-(2-chlorobenzyl)-1-(4-hydroxy-3- ((4-hydroxypiperidin-1-yl) methyl-5-methoxyphenyl)-[1,2,4] triazolo [4,3-a] quinazolin-5(4H)-one》, the research content is summarized as follows. In current work, triazolo[4,3-a]quinazolinone I was synthesized. The structural properties of I were explored using spectroscopy (1H NMR, 13C NMR, MS and FT-IR) and X-ray crystallog. method. The single-crystal structure confirmed by X-ray diffraction was consistent with the mol. structure optimized by d. functional theory (DFT) calculation at B3LYP/6-311 G (2d, p) level of theory. The geometrical parameters, mol. electrostatic potential (MEP) and frontier MO (FMO) anal. were performed by DFT using the B3LYP/6-311 G (2d, p) method. Mol. docking may suggest a favorable interaction between I and SHP2 protein. The mol. dynamics (MD) simulation results shown that there are hydrogen bonds, electrostatic interactions and Pi interactions between compound I and SHP2 proteins. The inhibitory activity of I on SHP2 protein was better than the reference compound (SHP244).

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem