Category: piperidines

In 2014,Iwasaki, Takanori; Imanishi, Reiko; Shimizu, Ryohei; Kuniyasu, Hitoshi; Terao, Jun; Kambe, Nobuaki published 《Copper-Catalyzed Alkyl-Alkyl Cross-Coupling Reactions Using Hydrocarbon Additives: Efficiency of Catalyst and Roles of Additives》.Journal of Organic Chemistry published the findings.COA of Formula: C7H15NO The information in the text is summarized as follows:

Cross-coupling of alkyl halides with alkyl Grignard reagents proceeds with extremely high TONs of up to 1230000 using a Cu/unsaturated hydrocarbon catalytic system. Alkyl fluorides, chlorides, bromides, and tosylates are all suitable electrophiles, and a TOF as high as 31200 h-1 was attained using an alkyl iodide. Side reactions of this catalytic system, i.e., reduction, dehydrohalogenation (elimination), and the homocoupling of alkyl halides, occur in the absence of additives. It appears that the reaction involves the β-hydrogen elimination of alkylcopper intermediates, giving rise to olefins and Cu-H species, and that this process triggers both side reactions and the degradation of the Cu catalyst. The formed Cu-H promotes the reduction of alkyl halides to give alkanes and Cu-X or the generation of Cu(0), probably by disproportionation, which can oxidatively add to alkyl halides to yield olefins and, in some cases, homocoupling products. Unsaturated hydrocarbon additives such as 1,3-butadiene and phenylpropyne play important roles in achieving highly efficient cross-coupling by suppressing β-hydrogen elimination, which inhibits both the degradation of the Cu catalyst and undesirable side reactions. The experimental part of the paper was very detailed, including the reaction process of 2-(Piperidin-4-yl)ethanol(cas: 622-26-4COA of Formula: C7H15NO)

2-(Piperidin-4-yl)ethanol(cas: 622-26-4) can be used to synthese ursolic acid derivatives, spiroimidazolidinone NPC1L1 inhibitors, neurokinin-2 receptor antagonists, antagonists for inhibition of platelet aggregation.COA of Formula: C7H15NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Xing, Hongjie; Gao, Shitao; Zhang, Jingji; Xu, Yu; Du, Huiwei; Zhu, Zejie; Wang, Jiangying; Yao, Yaxuan; Zhang, Suwei; Ren, Lingling published an article on February 15 ,2021. The article was titled 《Ultrasound-assisted synthesized BiFeO3 as FeOH+ promoted peroxymonosulfate activator for highly efficient degradation of tetracycline》, and you may find the article in Journal of Alloys and Compounds.SDS of cas: 826-36-8 The information in the text is summarized as follows:

A multiferroic BiFeO3 (BFO) catalyst was fabricated through a mild one-pot hydrothermal process with a bath-ultrasound assisted dissolution of Fe(NO3)3·9H2O for 30 min. X-ray photoemission spectroscopy revealed that the BFO (BFO-u) catalyst with US assisted dissolution of Fe(NO3)3·9H2O in the synthetic process exhibited high Fe2+ and OH- levels, which could be explained to be Fe3+ + H2O → Fe2+ + H+ + •OH. As a result, BFO-u catalyst activated potassium peroxymonosulfate (PMS) efficiently for degrading tetracycline hydrochloride. In particular, visible-light assisted activation of PMS over BFO-u catalyst exhibited the highest degradation rate constant, at 0.352 min-1. Species-trapping experiments revealed that the presence of PMS promoted the generation of •OH, •O-2 and 1O2 that all participated in degrading TCH, in which 1O2 was primarily contributed to the degradation Also, BFO-u catalyst was stable and recyclable and thus suitable for practical applications. In the part of experimental materials, we found many familiar compounds, such as Triacetonamine(cas: 826-36-8SDS of cas: 826-36-8)

Triacetonamine(cas: 826-36-8) is a member of piperidine. Piperidine is ubiquitous structural motif widely occurred in diverse synthetically and naturally occurring bioactive molecules. Piperidines are an immensely important class of compounds medicinally: the piperidine ring is the most common heterocyclic subunit among FDA approved drugs.SDS of cas: 826-36-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Kumar, Aditya; Prasad, Ankush; Sedlarova, Michaela; Pospisil, Pavel published an article on January 31 ,2019. The article was titled 《Organic radical imaging in plants: Focus on protein radicals》, and you may find the article in Free Radical Biology & Medicine.Formula: C9H17NO The information in the text is summarized as follows:

Biomol. (lipid and protein) oxidation products formed in plant cells exposed to photooxidative stress play a crucial role in the retrograde signaling and oxidative damage. The oxidation of biomols. initiated by reactive oxygen species is associated with formation of organic (alkyl, peroxyl and alkoxyl) radicals. Currently, there is no selective and sensitive technique available for the detection of organic radicals in plant cells. Here, based on the analogy with animal cells, immuno-spin trapping using spin trap, 5,5-dimethyl-1-pyrroline N-oxide (DMPO) was used to image organic radicals in Arabidopsis leaves exposed to high light. Using antibody raised against the DMPO nitrone adduct conjugated with the fluorescein isothiocyanate, organic radicals were imaged by confocal laser scanning microscopy. Organic radicals are formed predominantly in the chloroplasts located at the periphery of the cells and distributed uniformly throughout the grana stack. Characterization of protein radicals by standard immunol. techniques using anti-DMPO antibody shows protein bands with apparent mol. weights of 32 and 34 kDa assigned to D1 and D2 proteins and two protein bands below the D1/D2 band with apparent mol. weights of 23 and 18 kDa and four protein bands above the D1/D2 band with apparent mol. weights of 41, 43, 55 and 68 kDa. In summary, imaging of organic radicals by immuno-spin trapping represents selective and sensitive technique for the detection of organic radicals that might help to clarify mechanistic aspects on the role of organic radicals in the retrograde signaling and oxidative damage in plant cell. The experimental part of the paper was very detailed, including the reaction process of Triacetonamine(cas: 826-36-8Formula: C9H17NO)

Triacetonamine(cas: 826-36-8) is a member of piperidine. Piperidine-containing compounds are also frequently employed in synthesis as ligands or auxiliaries. Accordingly, many efforts have been devoted to the development of novel methods for the synthesis of these compounds over the years.Formula: C9H17NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Insights on the nitrate reduction and norfloxacin oxidation over a novel nanoscale zero valent iron particle: Reactivity, products, and mechanism》 was written by Diao, Zeng-Hui; Qian, Wei; Lei, Ze-Xiang; Kong, Ling-Jun; Du, Jian-Jun; Liu, Hui; Yang, Jie-Wen; Pu, Sheng Yan. SDS of cas: 826-36-8 And the article was included in Science of the Total Environment on April 10 ,2019. The article conveys some information:

Herein, the application of a novel acid mine drainage-based nanoscale zero valent iron (AMD-based nZVI) for the remediation of nitrate and norfloxacin (NOR) was studied. Exptl. results indicated that the catalytic reactivity of AMD-based nZVI toward nitrate reduction was superior to that of iron salt-based nanoscale zero valent iron (Iron salt-based nZVI). The presence of ultrasound irradiation could significantly enhance the reactivity toward both the nitrate reduction and NOR oxidation processes. The optimal efficiencies of nitrate and NOR by AMD-based nZVI/US process could be kept 96 and 94% within 120 min, resp. Ammonia was identified as a major product in nitrate reduction process, while three oxidation products were observed in NOR degradation process. Both reduction reaction of nitrate from AMD-based nZVI and oxidation reaction of NOR from US-assisted Fenton system might be involved in AMD-based nZVI/US process. The AMD-based nZVI/US process showed a better performance on the removal of NOR compared with that of nitrate. The findings of the present work could be as a guide and show that AMD-based nZVI/US process is feasible for the remediation of both nitrate and NOR in real wastewater. After reading the article, we found that the author used Triacetonamine(cas: 826-36-8SDS of cas: 826-36-8)

Triacetonamine(cas: 826-36-8) is a member of piperidine. Piperidine is a key saturated heterocyclic scaffold found in several of the top-selling small molecule pharmaceuticals and natural alkaloids, with a diverse range of biological activities. Hence, continuous efforts have been made to develop convenient methods to prepare piperidine derivatives.SDS of cas: 826-36-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Safety of tert-Butyl 4-hydroxypiperidine-1-carboxylateIn 2021 ,《Design and Synthesis of Novel Spiro Derivatives as Potent and Reversible Monoacylglycerol Lipase (MAGL) Inhibitors: Bioisosteric Transformation from 3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl Moiety》 was published in Journal of Medicinal Chemistry. The article was written by Ikeda, Shuhei; Sugiyama, Hideyuki; Tokuhara, Hidekazu; Murakami, Masataka; Nakamura, Minoru; Oguro, Yuya; Aida, Jumpei; Morishita, Nao; Sogabe, Satoshi; Dougan, Douglas R.; Gay, Sean C.; Qin, Ling; Arimura, Naoto; Takahashi, Yasuko; Sasaki, Masako; Kamada, Yusuke; Aoyama, Kazunobu; Kimoto, Kouya; Kamata, Makoto. The article contains the following contents:

The therapeutic potential of monoacylglycerol lipase (MAGL) inhibitors in central nervous system-related diseases has attracted attention worldwide. However, the availability of reversible-type inhibitor is still limited to clarify the pharmacol. effect. Herein, we report the discovery of novel spiro chem. series as potent and reversible MAGL inhibitors with a different binding mode to MAGL using Arg57 and His121. Starting from hit compound 1 and its co-crystal structure with MAGL, structure-based drug discovery (SBDD) approach enabled us to generate various spiro scaffolds like 2a (azetidine-lactam), 2b (cyclobutane-lactam), and 2d (cyclobutane-carbamate) as novel bioisosteres of 3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl moiety in 1 with higher lipophilic ligand efficiency (LLE). Optimization of the left hand side afforded 4f (I) as a promising reversible MAGL inhibitor, which showed potent in vitro MAGL inhibitory activity (IC50 6.2 nM), good oral absorption, blood-brain barrier penetration, and significant pharmacodynamic changes (2-arachidonoylglycerol increase and arachidonic acid decrease) at 0.3-10 mg/kg, po. in mice. In the part of experimental materials, we found many familiar compounds, such as tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas: 109384-19-2Safety of tert-Butyl 4-hydroxypiperidine-1-carboxylate)

tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas:109384-19-2) is a 4-hydroxypyridine with a boc protecting group used in the preparation of neurologically active agents and other pharmaceutical compounds.Safety of tert-Butyl 4-hydroxypiperidine-1-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Electric Literature of C10H20N2O2In 2022 ,《Exploratory studies on soluble small molecule CD4 mimics as HIV entry inhibitors》 appeared in Bioorganic & Medicinal Chemistry. The author of the article were Tsuji, Kohei; Kobayakawa, Takuya; Konno, Kiju; Masuda, Ami; Takahashi, Kohei; Ohashi, Nami; Yoshimura, Kazuhisa; Kuwata, Takeo; Matsushita, Shuzo; Harada, Shigeyoshi; Tamamura, Hirokazu. The article conveys some information:

Several small mol. CD4 mimics, which inhibit the interaction of gp120 with CD4, have been developed. Original CD4 mimics such as NBD-556, which has an aromatic ring, an oxalamide linker and a piperidine moiety, possess significant anti-HIV activity but with their hydrophobic aromatic ring-containing structures are poorly soluble in water. We have developed derivatives with a halopyridinyl group in place of the Ph group, such as KKN-134, and found them to have excellent aqueous solubility Other leads that were examined are YIR-821, a compound with a cyclohexane group in a spiro attachment to a piperidine ring and a guanidino group on the piperidine nitrogen atom, and its PEGylated derivative, TKB-002. YIR-821 and TKB-002 retain potent anti-HIV activity. Here, new CD4 mimics, in which the Ph group was replaced by a halopyridinyl group with the halogen atoms in different positions, their derivatives without a cyclohexane group on the piperidine ring and their hybrid mols. with PEG units were designed and synthesized. Some of these compounds show significantly higher aqueous solubility with maintenance of certain levels of anti-HIV activity. The present data should be useful in the future design of CD4 mimic mols. The experimental process involved the reaction of tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7Electric Literature of C10H20N2O2)

tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7) belongs to anime. Aniline, ethanolamines, and several other amines are major industrial commodities used in making rubber, dyes, pharmaceuticals, and synthetic resins and fibres and for a host of other applications. Most of the numerous methods for the preparation of amines may be broadly divided into two groups: (1) chemical reduction (replacement of oxygen with hydrogen atoms in the molecule) of members of several other classes of organic nitrogen compounds and (2) reactions of ammonia or amines with organic compounds.Electric Literature of C10H20N2O2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2022,Zhang, Jingyu; Che, Jinxin; Luo, Xiaomin; Wu, Mingfei; Kan, Weijuan; Jin, Yuheng; Wang, Hanlin; Pang, Ao; Li, Cong; Huang, Wenhai; Zeng, Shenxin; Zhuang, Weihao; Wu, Yizhe; Xu, Yongjin; Zhou, Yubo; Li, Jia; Dong, Xiaowu published an article in Journal of Medicinal Chemistry. The title of the article was 《Structural Feature Analyzation Strategies toward Discovery of Orally Bioavailable PROTACs of Bruton’s Tyrosine Kinase for the Treatment of Lymphoma》.HPLC of Formula: 109384-19-2 The author mentioned the following in the article:

Bruton’s tyrosine kinase proteolysis-targeting chimeras (BTK-PROTACs) have emerged as a promising approach to address the limitations of BTK inhibitors. However, conducting the rational discovery of orally bioavailable BTK-PROTACs presents significant challenges. In this study, dimensionality reduction anal. and model mol. validation were utilized to identify some key structural features for improving the oral absorption of BTK-PROTACs. The results were applied to optimize the newly discovered BTK-PROTACs B1 and B2. Compound C13 (I) was discovered with improved oral bioavailability, high BTK degradation activity, and selectivity. It exhibited inhibitory effects against different hematol. cancer cells and attenuated the BTK-related signaling pathway. The oral administration of C13 effectively reduced BTK protein levels and suppressed tumor growth. This study led to the discovery of a new orally bioavailable BTK-PROTAC for the treatment of lymphoma, and we hope that the strategy will find wide utility. After reading the article, we found that the author used tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas: 109384-19-2HPLC of Formula: 109384-19-2)

tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas:109384-19-2) is a 4-hydroxypyridine with a boc protecting group used in the preparation of neurologically active agents and other pharmaceutical compounds.HPLC of Formula: 109384-19-2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Frolov, Andriy I.; Ostapchuk, Eugeniy N.; Pashenko, Alexander E.; Chuchvera, Yaroslav O.; Rusanov, Eduard B.; Volochnyuk, Dmitriy M.; Ryabukhin, Sergey V. published an article in 2021. The article was titled 《Selective α-Methylation of Ketones》, and you may find the article in Journal of Organic Chemistry.Reference of 1-Methyl-4-piperidone The information in the text is summarized as follows:

The convenient and scalable preparative approach for the two-step α-methylation of ketones was described. The optimized protocols for regioselective preparation of enaminones with further diastereoselective and functional groups tolerant hydrogenation to α-methylketones was developed. The scope and limitations of the proposed methodol. were discussed. The advantages compared to known procedures were demonstrated. The unexpected role of acetone in the hydrogenation was suggested. The evaluation of the method for both early building block synthesis and late-stage CH-functionalization was shown. The elaborate procedures preparability and scalability were demonstrated by the synthesis of several α-Me ketones up to 100 g amount The results came from multiple reactions, including the reaction of 1-Methyl-4-piperidone(cas: 1445-73-4Reference of 1-Methyl-4-piperidone)

1-Methyl-4-piperidone(cas: 1445-73-4) is a member of piperidine. Piperidine-containing compounds are also frequently employed in synthesis as ligands or auxiliaries. Accordingly, many efforts have been devoted to the development of novel methods for the synthesis of these compounds over the years.Reference of 1-Methyl-4-piperidone

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Klug, Dana M.; Mavrogiannaki, Eftychia M.; Forbes, Katherine C.; Silva, Lisseth; Diaz-Gonzalez, Rosario; Perez-Moreno, Guiomar; Ceballos-Perez, Gloria; Garcia-Hernandez, Raquel; Bosch-Navarrete, Cristina; Cordon-Obras, Carlos; Gomez-Linan, Claudia; Saura, Andreu; Momper, Jeremiah D.; Martinez-Martinez, Maria Santos; Manzano, Pilar; Syed, Ali; El-Sakkary, Nelly; Caffrey, Conor R.; Gamarro, Francisco; Ruiz-Perez, Luis Miguel; Gonzalez Pacanowska, Dolores; Ferrins, Lori; Navarro, Miguel; Pollastri, Michael P. published an article in 2021. The article was titled 《Lead Optimization of 3,5-Disubstituted-7-Azaindoles for the Treatment of Human African Trypanosomiasis》, and you may find the article in Journal of Medicinal Chemistry.Application of 109384-19-2 The information in the text is summarized as follows:

Neglected tropical diseases such as human African trypanosomiasis (HAT) are prevalent primarily in tropical climates and among populations living in poverty. Historically, the lack of economic incentive to develop new treatments for these diseases has meant that existing therapeutics have serious shortcomings in terms of safety, efficacy, and administration, and better therapeutics are needed. We now report a series of 3,5-disubstituted-7-azaindoles identified as growth inhibitors of Trypanosoma brucei, the parasite that causes HAT, through a high-throughput screen. We describe the hit-to-lead optimization of this series and the development and preclin. investigation of 29d (I), a potent antitrypanosomal compound with promising pharmacokinetic (PK) parameters. This compound was ultimately not progressed beyond in vivo PK studies due to its inability to penetrate the blood-brain barrier (BBB), critical for stage 2 HAT treatments. In the experiment, the researchers used tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas: 109384-19-2Application of 109384-19-2)

tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas:109384-19-2) is a 4-hydroxypyridine with a boc protecting group used in the preparation of neurologically active agents and other pharmaceutical compounds.Application of 109384-19-2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Poly(meta/para-terphenylene-methyl piperidinium)-based anion exchange membranes: the effect of backbone structure in AEMFC application》 was written by Mayadevi, T. S.; Sung, Seounghwa; Varghese, Listo; Kim, Tae-Hyun. Synthetic Route of C6H11NO And the article was included in Membranes (Basel, Switzerland) in 2020. The article conveys some information:

A series of poly( meta/para-terphenylene-Me piperidinium)-based anion exchange membranes devoid of benzylic sites or aryl ether bonds, that are vulnerable to degradation by hydroxide ions, are synthesized and investigated for their application as novel anion exchange membranes. The copolymers are composed of both linear para-terphenyl units and kink-structured meta-terphenyl units. The meta-connectivity in terphenyl units permits the polymer backbones to fold back, maximizing the interactions among the hydrocarbon polymer chains and enhancing the peripheral formation of ion aggregates, due to the free volume generated by the kink structure. The effects of the copolymer composition between para-terphenyl and meta-terphenyl on the morphol. and the electrochem. and physicochem. properties of the corresponding polymer membranes are investigated. In the experiment, the researchers used 1-Methyl-4-piperidone(cas: 1445-73-4Synthetic Route of C6H11NO)

1-Methyl-4-piperidone(cas: 1445-73-4) is a member of piperidine. Piperidine is a key saturated heterocyclic scaffold found in several of the top-selling small molecule pharmaceuticals and natural alkaloids, with a diverse range of biological activities. Hence, continuous efforts have been made to develop convenient methods to prepare piperidine derivatives.Synthetic Route of C6H11NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem