Category: piperidines

Name: Piperidine-4-carboxamideOn October 15, 2020 ,《Design, synthesis and bioevaluation of novel substituted triazines as potential dual PI3K/mTOR inhibitors》 was published in European Journal of Medicinal Chemistry. The article was written by Wu, Ting-Ting; Guo, Qing-Qing; Chen, Zi-Li; Wang, Li-Li; Du, Yao; Chen, Rui; Mao, Yuan-Hu; Yang, Sheng-Gang; Huang, Jing; Wang, Jian-Ta; Wang, Ling; Tang, Lei; Zhang, Ji-Quan. The article contains the following contents:

A series of novel substituted triazines bearing a benzimidazole scaffold I [R = morpholino, 4-methylpiperazin-1-yl, ((1S)-2-amino-1-methyl-2-oxo-ethyl)amino, etc.] were designed and synthesized based on the structures of known anti-cancer agents, namely gedatolisib and alpelisib. All the target compounds were screened for inhibitory activity against PI3Kα and mTOR kinases. Notably, most analogs exhibited IC50 in the nanomolar range. Investigation of the isoenzyme selectivity indicated that the compounds exhibited remarkable inhibitory activity against PI3Kδ, especially compound I [R = 4-carbamoyl-1-piperidyl] showed an IC50 value of 2.3 nM for PI3Kδ and moderate δ-isoenzyme selectivity over other class I PI3K isoforms and mTOR (with IC50 values of 14.6, 34.0, 849.0 and 15.4 nM for PI3Kα, β, γ and mTOR, resp.). An in vitro MTT assay was conducted to assess the antiproliferative and cytotoxic effects of the prepared analogs. It was revealed that the compounds displayed significant inhibitory activities against the HCT116 human colon cancer cell line. Compound I [R = morpholino] showed 4.7-fold higher potency than the pos. control gedatolisib (0.3 vs. 1.4μM, IC50 values). Phosphoblot studies demonstrated that I [R = morpholino, (2R)-2-carbamoylpyrrolidin-1-yl] could significantly suppress the PI3K/Akt/mTOR signaling pathway at 10μM. Moreover, analogs I [R = morpholino, (2S)-2-carbamoylpyrrolidin-1-yl, (2R)-2-carbamoylpyrrolidin-1-yl] displayed better stability in artificial gastric fluids than gedatolisib, while I [R = morpholino] was indicated not very stable in rat liver microsomes, and may occur phase I metabolic transformations. After reading the article, we found that the author used Piperidine-4-carboxamide(cas: 39546-32-2Name: Piperidine-4-carboxamide)

Piperidine-4-carboxamide(cas: 39546-32-2) belongs to anime. Hydrogen peroxide (H2O2) and peroxy acids generally add an oxygen atom to the nitrogen of amines. With primary amines, this step is normally followed by further oxidation, leading to nitroso compounds, RNO, or nitro compounds, RNO2. Secondary amines are converted to hydroxylamines, R2NOH, and tertiary amines to amine oxides, R3NO.Name: Piperidine-4-carboxamide

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Reference of Piperidine-4-carboxamideOn March 15, 2019, de Andrade, Peterson; Mantoani, Susimaire P.; Goncalves Nunes, Paulo Sergio; Magadan, Carlos Roca; Perez, Concepcion; Xavier, Danilo Jordao; Hojo, Elza Tiemi Sakamoto; Campillo, Nuria E.; Martinez, Ana; Carvalho, Ivone published an article in Bioorganic & Medicinal Chemistry. The article was 《Highly potent and selective aryl-1,2,3-triazolyl benzylpiperidine inhibitors toward butyrylcholinesterase in Alzheimer’s disease》. The article mentions the following:

Acetylcholinesterase (AChE) is the key enzyme targeted in Alzheimer’s disease (AD) therapy, nevertheless butyrylcholinesterase (BuChE) has been drawing attention due to its role in the disease progression. Thus, we aimed to synthesize novel cholinesterases inhibitors considering structural differences in their peripheral site, exploiting a moiety replacement approach based on the potent and selective hAChE drug donepezil. Hence, two small series of N-benzylpiperidine based compounds have successfully been synthesized as novel potent and selective hBuChE inhibitors. The most promising compounds (9(I) and 11(II)) were not cytotoxic and their kinetic study accounted for dual binding site mode of interaction, which is in agreement with further docking and mol. dynamics studies. Therefore, this study demonstrates how our strategy enabled the discovery of novel promising and privileged structures. Remarkably, II proved to be one of the most potent (0.17 nM) and selective (>58,000-fold) hBuChE inhibitor ever reported. In the experiment, the researchers used many compounds, for example, Piperidine-4-carboxamide(cas: 39546-32-2Reference of Piperidine-4-carboxamide)

Piperidine-4-carboxamide(cas: 39546-32-2) belongs to anime. Amines characteristically form salts with acids; a hydrogen ion, H+, adds to the nitrogen. With the strong mineral acids (e.g., H2SO4, HNO3, and HCl), the reaction is vigorous. Salt formation is instantly reversed by strong bases such as NaOH. Neutral electrophiles (compounds attracted to regions of negative charge) also react with amines; alkyl halides (R′X) and analogous alkylating agents are important examples of electrophilic reagents.Reference of Piperidine-4-carboxamide

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Safety of Piperidine-4-carboxamideOn October 19, 2020 ,《Biocarbon Supported Nanoscale Ruthenium Oxide-Based Catalyst for Clean Hydrogenation of Arenes and Heteroarenes》 was published in ACS Sustainable Chemistry & Engineering. The article was written by Kumar, Adarsh; Goyal, Vishakha; Sarki, Naina; Singh, Baint; Ray, Anjan; Bhaskar, Thallada; Bordoloi, Ankur; Narani, Anand; Natte, Kishore. The article contains the following contents:

Despite considerable achievements in the hydrogenation of aromatic hydrocarbons over the past few years, the ability to hydrogenate arene or heteroarene rings in a highly selective manner in the presence of other reducible sites or without harming the remaining mol. structure has long been a major challenge. Such chemoselectivity and functional group tolerance is highly desirable for enabling direct access to key building blocks of polymers and pharmaceutical agents. For achieving such high selectivity, the development of suitable catalysts is of central importance. Herein, we report a convenient method for the scalable preparation of ruthenium oxide (RuO2) nanoparticles supported on pine needle char (PNC) by simple impregnation of ruthenium salt on unactivated PNC, a solid byproduct (biochar) obtained in the slow pyrolysis of biomass pine needles. The resulting RuO2-based nanocatalyst (RuO2@PNC) exhibited remarkable activity and high selectivity for the hydrogenation of more than 50 challenging arenes and heteroarenes, including biomass-derived aromatic compounds (e.g., 4-n-propylphenol, furfuryl alc., and 2-Me furan). The synthetic value of this transformation is showcased for the hydrogenation of arene mixture present in petroleum refineries or coal tars as well as biomass-derived oils (bio-oils) with enriched furfural, ether, and phenol derivatives Under optimized conditions, the performance of this new catalyst was compared with state-of-the-art com. catalysts such as Ru/C, Pd/C, and Raney nickel and found that RuO2@PNC is more superior and selective. Furthermore, the catalyst is easily recovered and reused up to four cycles. Biocarbon supported RuO2-based catalyst exhibited remarkable activity and selectivity for clean hydrogenation of arenes and heteroarenes. After reading the article, we found that the author used Piperidine-4-carboxamide(cas: 39546-32-2Safety of Piperidine-4-carboxamide)

Piperidine-4-carboxamide(cas: 39546-32-2) belongs to anime. Hydrogen peroxide (H2O2) and peroxy acids generally add an oxygen atom to the nitrogen of amines. With primary amines, this step is normally followed by further oxidation, leading to nitroso compounds, RNO, or nitro compounds, RNO2. Secondary amines are converted to hydroxylamines, R2NOH, and tertiary amines to amine oxides, R3NO.Safety of Piperidine-4-carboxamide

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

COA of Formula: C13H23NO4On May 15, 2009 ,《4-Piperidines and 3-pyrrolidines as dual serotonin and noradrenaline reuptake inhibitors: Design, synthesis and structure-activity relationships》 appeared in Bioorganic & Medicinal Chemistry Letters. The author of the article were Fish, Paul V.; Andrews, Mark D.; Jonathan Fray, M.; Stobie, Alan; Wakenhut, Florian; Whitlock, Gavin A.. The article conveys some information:

A variety of [(aryloxy)(pyridinyl)methyl]piperidine and pyrrolidine derivatives are inhibitors of monoamine reuptake. Structure-activity relationships established that monoamine reuptake inhibition is a function of amine, pyridine isomer, aryloxy ring substitution and stereochem. Consequently, selective NRIs, selective SRIs, dual SNRIs and triple SNDRIs were all identified. Dual SNRIs I and II were evaluated in addnl. pharmacol. and pharmacokinetic studies as representative examples from this series. In addition to this study using (R)-1-tert-Butyl 3-ethyl piperidine-1,3-dicarboxylate, there are many other studies that have used (R)-1-tert-Butyl 3-ethyl piperidine-1,3-dicarboxylate(cas: 194726-40-4COA of Formula: C13H23NO4) was used in this study.

(R)-1-tert-Butyl 3-ethyl piperidine-1,3-dicarboxylate(cas: 194726-40-4) 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.COA of Formula: C13H23NO4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Synthesis of Temperature-Responsive Polymers Containing Piperidine Carboxamide and N,N-diethylcarbamoly Piperidine Moiety via RAFT Polymerization》 was written by Akiyama, Yoshikatsu. Quality Control of Piperidine-4-carboxamide And the article was included in Macromolecular Rapid Communications on August 31 ,2021. The article conveys some information:

In this study, poly(N-acryloylnipecotamide) (PNANAm), poly(N-acryloylisonipecotamide) (PNAiNAm), and poly(N-acryloyl-N,N-diethylnipecotamide) (PNADNAm) are synthesized as temperature-responsive polymers using reversible addition-fragmentation chain-transfer polymerization Aqueous solutions of the three polymers are examined via temperature-dependent optical transmittance measurements. The PNANAm sample with a hydrophilic terminal group shows an upper critical solution temperature (UCST) in phosphate-buffered saline (PBS) when its mol. weight (Mn) is ≥ 7600, whereas PNANAm (Mn < 7600) is soluble The UCST is influenced by mol. weight and polymer concentration In contrast, PNANAm sample with nonionic terminal group shows UCST, when Mn is < 7600, suggesting that the terminal nonionic group possibly increases UCST of PNANAm. The urea addition experiment suggests that the driving force for expression of UCST of PNANAm is the formation of inter- and intramol. hydrogen bonds among the polymer chains. PNAiNAm is soluble in PBS but exhibits an UCST in an appropriate concentration of ammonium sulfate. In contrast, PNADNAm exhibits a lower critical solution temperature Comparing the chem. structure of these polymers and their phase transition behaviors suggests that the carboxamide group position in the piperidine ring could determine the UCST expression. The results could help design temperature-responsive polymers with a desired cloud point temperaturePiperidine-4-carboxamide(cas: 39546-32-2Quality Control of Piperidine-4-carboxamide) was used in this study.

Piperidine-4-carboxamide(cas: 39546-32-2) belongs to anime. The methylamines occur in small amounts in some plants. Many polyfunctional amines (i.e., those having other functional groups in the molecule) occur as alkaloids in plants—for example, mescaline, 2-(3,4,5-trimethoxyphenyl)ethylamine; the cyclic amines nicotine, atropine, morphine, and cocaine; and the quaternary salt choline, N-(2-hydroxyethyl)trimethylammonium chloride, which is present in nerve synapses and in plant and animal cells.Quality Control of Piperidine-4-carboxamide

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Structure-activity relations of arecaidine derivatives on the guinea pig isolated atria》 was published in European Journal of Pharmacology in 1967. These research results belong to Christiansen, Anneliese; Lullmann, Heinz; Mutschler, Ernst. Application of 1690-72-8 The article mentions the following:

The influence of arecaidine esters, arecaidine methiodide esters, dihydroarecaidine esters, and dihydroarecaidine methiodide esters was tested on the amplitude of contraction of elec. stimulated isolated atria from the guinea pig. The amplitude of contraction was reduced by all arecaidine esters. This effect was abolished by atropine. Arecaidine Et ester possessed the highest activity and arecaidine iso-Pr ester was the least active. Like arecaidine Me ester, arecaidine methiodide Me ester showed muscarine-like properties. Quaternary esters with a longer chain showed nicotine-like action or acted as inhibitors. Dihydroarecaidine esters and dihydroarecaidine methiodide esters were antagonists; only dihydroarecaidine Me ester and dihydroarecaidine methiodide Me ester showed muscarine-like action. The experimental process involved the reaction of Methyl 1-methylpiperidine-3-carboxylate(cas: 1690-72-8Application of 1690-72-8)

Methyl 1-methylpiperidine-3-carboxylate(cas: 1690-72-8) 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.Application of 1690-72-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

SDS of cas: 87120-72-7In 2022 ,《Investigation of Janus Kinase (JAK) Inhibitors for Lung Delivery and the Importance of Aldehyde Oxidase Metabolism》 appeared in Journal of Medicinal Chemistry. The author of the article were Wellaway, Christopher R.; Baldwin, Ian R.; Bamborough, Paul; Barker, Daniel; Bartholomew, Michelle A.; Chung, Chun-wa; Dumpelfeld, Birgit; Evans, John P.; Fazakerley, Neal J.; Homes, Paul; Keeling, Steven P.; Lewell, Xiao Q.; McNab, Finlay W.; Morley, Joanne; Needham, Deborah; Neu, Margarete; van Oosterhout, Antoon J. M.; Pal, Anshu; Reinhard, Friedrich B. M.; Rianjongdee, Francesco; Robertson, Craig M.; Rowland, Paul; Shah, Rishi R.; Sherriff, Emma B.; Sloan, Lisa A.; Teague, Simon; Thomas, Daniel A.; Wellaway, Natalie; Wojno-Picon, Justyna; Woolven, James M.; Coe, Diane M.. The article conveys some information:

The Janus family of tyrosine kinases (JAK1, JAK2, JAK3, and TYK2) play an essential role in the receptor signaling of cytokines that have been implicated in the pathogenesis of severe asthma, and there is emerging interest in the development of small-mol.-inhaled JAK inhibitors as treatments. Here, we describe the optimization of a quinazoline series of JAK inhibitors and the results of mouse lung pharmacokinetic (PK) studies where only low concentrations of parent compound were observed Subsequent investigations revealed that the low exposure was due to metabolism by aldehyde oxidase (AO), so we sought to identify quinazolines that were not metabolized by AO. We found that specific substituents at the quinazoline 2-position prevented AO metabolism and this was rationalized through computational docking studies in the AO binding site, but they compromised kinome selectivity. Results presented here highlight that AO metabolism is a potential issue in the lung. The experimental part of the paper was very detailed, including the reaction process of tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7SDS of cas: 87120-72-7)

tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7) belongs to anime. Milder oxidation, using reagents such as NaOCl, can remove four hydrogen atoms from primary amines of the type RCH2NH2 to form nitriles (R―C≡N), and oxidation with reagents such as MnO2 can remove two hydrogen atoms from secondary amines (R2CH―NHR′) to form imines (R2C=NR′). Tertiary amines can be oxidized to enamines (R2C=CHNR2) by a variety of reagents.SDS of cas: 87120-72-7

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Jiang, Donghao; Zhang, Jian; He, Hongfu; Li, Jiao; Hu, Deyu; Song, Baoan published an article in 2021. The article was titled 《Discovery of novel chromone derivatives containing a sulfonamide moiety as potential anti-TSWV agents》, and you may find the article in Bioorganic & Medicinal Chemistry Letters.Recommanded Product: 87120-72-7 The information in the text is summarized as follows:

A number of chromone derivatives containing sulfonamide structure were designed and synthesized. Firstly, the target compounds were evaluated for anti-TSWV activities in vivo by the half-leaf method. We found that most of the compounds had good anti-TSWV activities. Among them, compound 12B had excellent anti-TSWV inactivating activity with an EC50 of 80.5 μg/mL, which was significantly better than xiangcaoliusuobingmi (765.7 μg/mL). Secondly, TSWV nucleocapsid protein (N) was expressed and purified, and the affinity between the compounds and TSWV N was tested by microscale thermophoresis (MST). Compound 12B had a good affinity for TSWV N with a Kd value of 5.02 μM, which was superior to xiangcaoliusuobingmi (29.83 μM). Finally, in order to study the mode of interaction between the compound 12B and TSWV N, we carried out mol. docking. The results indicated that compound 12B might inactivate the virus by destroying the TSWV N oligomer structure. These results lay a solid foundation for the further discovery of chromone derivatives containing sulfonamide structure with high anti-TSWV activities. In the experiment, the researchers used tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7Recommanded Product: 87120-72-7)

tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7) belongs to anime. Large quantities of aliphatic amines are made synthetically. The most widely used industrial method is the reaction of alcohols with ammonia at a high temperature, catalyzed by metals or metal oxide catalysts (e.g., nickel or copper). Mixtures of primary, secondary, and tertiary amines are thereby produced.Recommanded Product: 87120-72-7

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Antien, Kevin; Geraci, Andrea; Parmentier, Michael; Baudoin, Olivier published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《A New Dioxazolone for the Synthesis of 1,2-Aminoalcohols via Iridium(III)-Catalyzed C(sp3)-H Amidation》.Product Details of 109384-19-2 The article contains the following contents:

Vicinal aminoalcs. are widespread structural motifs in bioactive mols. The development of a new dioxazolone reagent containing a p-nitrophenyldifluoromethyl group, which 1. displays a good safety profile; 2. shows a remarkably high reactivity in the oxime-directed iridium(III)-catalyzed amidation of unactivated C(sp3)-H bonds; 3. leads to amide products which can be hydrolyzed under mild conditions has been reported. The amidation reaction is mild, general and compatible with both primary C-H bonds of tertiary and secondary alcs., as well as secondary C-H bonds of cyclic secondary alcs. This method provides an easy access to free 1,2-aminoalcs. after efficient and mild cleavage of the oxime directing group and activated amide. In the part of experimental materials, we found many familiar compounds, such as tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas: 109384-19-2Product Details 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.Product Details of 109384-19-2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Yan, Jiangkun; Gu, Yanting; Sun, Yixiang; Zhang, Ziheng; Zhang, Xiangyu; Wang, Xinran; Wu, Tianxiao; Zhao, Dongmei; Cheng, Maosheng published their research in Archiv der Pharmazie (Weinheim, Germany) in 2021. The article was titled 《Design, synthesis, and biological evaluation of 5-aminotetrahydroquinoline-based LSD1 inhibitors acting on Asp375》.Recommanded Product: 109384-19-2 The article contains the following contents:

The abnormal expression of lysine-specific histone demethylase 1 (LSD1) is associated with different cancer types, and LSD1 inhibitory activity seems to have high therapeutic potential in cancer treatment. Here, we report the design, synthesis, and biochem. evaluation of novel 5-aminotetrahydroquinoline-based LSD1 inhibitors such as I. Among them, eight of the compounds showed preferable inhibitory effects on LSD1, with IC50 = 0.19-0.82μM. Several potent compounds were selected to evaluate their antiproliferative activity on A549 cells and MCF-7 cells with a high expression of LSD1. The potential binding modes of the compounds were revealed through mol. docking to rationalize the potency of compounds toward LSD1. Our data recognized that the 5-aminotetrahydroquinoline scaffold may serve as a starting point for developing potent LSD1 inhibitors for cancer therapy. In the experiment, the researchers used tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas: 109384-19-2Recommanded Product: 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.Recommanded Product: 109384-19-2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem