Category: piperidines

SDS of cas: 59234-40-1On September 30, 2017 ,《Stereo-selective preparation of teneraic acid, trans-(2S,6S)-piperidine-2,6-dicarboxylic acid, via anodic oxidation and cobalt-catalyzed carbonylation》 was published in Chemical & Pharmaceutical Bulletin. The article was written by Amino, Yusuke; Nishi, Seiichi; Izawa, Kunisuke. The article contains the following contents:

Teneraic acid (piperidine-2,6-dicarboxylic acid) is a naturally occurring imino acid that comprises of three stereoisomers due to its two asym. centers at C2 and C6. The configuration of natural teneraic acid is reported to correspond to trans-(2S,6S). However, a few studies are focused on the stereospecific synthesis of trans-(2S,6S)-teneraic acid. The present study investigates a convenient synthetic method that includes regiospecific anodic oxidation and stereospecific cobalt-catalyzed carbonylation to obtain trans-(2S,6S)-teneraic acid. Me (S)-N-benzoyl-α-methoxypipecolate, the key intermediate that displays a structure that corresponds to an intermediate (N-α-hydroxyalkyl amide) of intramol. amidocarbonylation, was obtained via an anodic oxidation of Me (S)-N-benzoylpipecolate. Subsequently, cobalt-catalyzed carbonylation converted the Me (S)-N-benzoyl-α-methoxypipecolate to trans-(2S,6S)-N-benzoyl-teneraic acid di-Me ester in good optical purity (>95% enantiomeric excess (ee)) and modest yield (63%). Finally, de-protection occurred via acidic hydrolysis to obtain trans-(2S,6S)-teneraic acid. The stereochem. of synthesized teneraic acid was confirmed as corresponding to trans-(2S,6S) by comparing its phys. properties with those of a cis-meso-isomer and those of a trans-(2S,6S)-isomer that were reported in previous studies. In the experiment, the researchers used Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1SDS of cas: 59234-40-1)

Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1) 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.SDS of cas: 59234-40-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Safety of Piperidine-4-carboxamideOn May 1, 2020 ,《Translation of the copper/bipyridine-promoted Petasis reaction to solid phase-coupled DNA for encoded library synthesis》 appeared in Bioorganic & Medicinal Chemistry. The author of the article were Potowski, Marco; Esken, Robin; Brunschweiger, Andreas. The article conveys some information:

The Petasis three-component reaction gives rise to diverse substituted α-aryl glycines from readily available amines, boronic acids and glyoxalic acid. Thus, this reaction is highly attractive for DNA-encoded small mol. screening library synthesis. The Petasis reaction is for instance promoted by a potentially DNA damaging copper(I)/bipyridine reagent system in dry organic solvents. We found that solid phase-coupled DNA strands tolerated this reagent system at elevated temperature allowing for synthesis of diverse substituted DNA-tagged α-aryl glycines from DNA-conjugated secondary amines. The experimental part of the paper was very detailed, including the reaction process of Piperidine-4-carboxamide(cas: 39546-32-2Safety of Piperidine-4-carboxamide)

Piperidine-4-carboxamide(cas: 39546-32-2) belongs to anime. Left-handed and right-handed forms (mirror-image configurations, known as optical isomers or enantiomers) are possible when all the substituents on the central nitrogen atom are different (i.e., the nitrogen is chiral). With amines, there is extremely rapid inversion in which the two configurations are interconverted.Safety of Piperidine-4-carboxamide

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Name: Piperidine-4-carboxamideOn March 10, 2022, Beuchel, Andreas; Robaa, Dina; Negatu, Dereje A.; Madani, Abdeldjalil; Alvarez, Nadine; Zimmerman, Matthew D.; Richter, Adrian; Mann, Lea; Hoenke, Sophie; Csuk, Rene; Dick, Thomas; Imming, Peter published an article in ACS Medicinal Chemistry Letters. The article was 《Structure-Activity Relationship of Anti-Mycobacterium abscessus Piperidine-4-carboxamides, a New Class of NBTI DNA Gyrase Inhibitors》. The article mentions the following:

Mycobacterium abscessus causes difficult-to-cure pulmonary infections. The bacterium is resistant to most anti-infective agents, including first line antituberculosis (anti-TB) drugs. MMV688844 (844) is a piperidine-4-carboxamide (P4C) with bactericidal properties against M. abscessus. We recently identified DNA gyrase as the mol. target of 844. Here, we present in silico docking and genetic evidence suggesting that P4Cs display a similar binding mode to DNA gyrase as gepotidacin. Gepotidacin is a member of the Novel Bacterial Topoisomerase Inhibitors (NBTIs), a new class of nonfluoroquinolone DNA gyrase poisons. Thus, our work suggests that P4Cs present a novel structural subclass of NBTI. We describe structure-activity relationship studies of 844 leading to analogs showing increased antibacterial activity. Selected derivatives were tested for their inhibitory activity against recombinant M. abscessus DNA gyrase. Further optimization of the lead structures led to improved stability in mouse plasma and increased oral bioavailability. The results came from multiple reactions, including the reaction of Piperidine-4-carboxamide(cas: 39546-32-2Name: Piperidine-4-carboxamide)

Piperidine-4-carboxamide(cas: 39546-32-2) belongs to anime. Acylation is one of the most important reactions of primary and secondary amines; a hydrogen atom is replaced by an acyl group (a group derived from an acid, such as RCOOH or RSO3H, by removal of ―OH, such as RC(=O)―, RS(O)2―, and so on). Reagents may be acid chlorides (RCOC1, RSO2C1), anhydrides ((RCO)2O), or even esters (RCOOR′); the products are amides of the corresponding acids.Name: Piperidine-4-carboxamide

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Synthesis and pharmacological evaluation of enantiomerically pure endo-configured KOR agonists with 2-azabicyclo[3.2.1]octane scaffold》 was published in Organic & Biomolecular Chemistry in 2021. These research results belong to Jonas, Hendrik; Aiello, Daniele; Frehland, Bastian; Lehmkuhl, Kirstin; Schepmann, Dirk; Koehler, Jens; Diana, Patrizia; Wuensch, Bernhard. Recommanded Product: (S)-1-tert-Butyl 2-ethyl 4-oxopiperidine-1,2-dicarboxylate The article mentions the following:

Conformationally restricted bicyclic KOR agonists 10 with an endo-configured amino moiety were synthesized to analyze the bioactive conformation of conformationally flexible KOR agonists such as 2-5. A seven-step synthesis starting with (S)-configured 4-oxopiperidine-2-carboxylate 13 was developed. cis- and trans-configured diesters 12 were obtained in a 3 : 1 ratio via hydrogenation of the α,β-unsaturated ester 14. After establishment of the bicyclic scaffold, a diastereoselective reductive amination of ketone 11 provided exclusively the endo-configured bicyclic amines 10a,b. The 3 : 1 mixtures of enantiomers were separated by chiral HPLC, resp., leading to enantiomerically pure KOR agonists (1S,5S,7R)-10a,b and (1R,5R,7S)-10a,b (ent-10a,b). The KOR affinity was determined in receptor binding studies with the radioligand [3H]U-69 593. The high KOR affinity of endo-configured amines 10a (Ki = 7 nM) and 10b (Ki = 13 nM) indicates that the dihedral angle of the KOR pharmacophoric element N(pyrrolidine)-C-C-N(phenylacetyl) of 42° is close to the bioactive conformation of more flexible KOR agonists. It should be noted that changing the configuration of potent and selective KOR agonists 10a and 10b led to potent and selective σ1 ligands (e.g. ent-10aKi(σ1) = 10 nM). The experimental process involved the reaction of (S)-1-tert-Butyl 2-ethyl 4-oxopiperidine-1,2-dicarboxylate(cas: 180854-44-8Recommanded Product: (S)-1-tert-Butyl 2-ethyl 4-oxopiperidine-1,2-dicarboxylate)

(S)-1-tert-Butyl 2-ethyl 4-oxopiperidine-1,2-dicarboxylate(cas: 180854-44-8) 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.Recommanded Product: (S)-1-tert-Butyl 2-ethyl 4-oxopiperidine-1,2-dicarboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Safety of Piperidine-4-carboxamideOn October 15, 2020 ,《Development of coumarine derivatives as potent anti-filovirus entry inhibitors targeting viral glycoprotein》 was published in European Journal of Medicinal Chemistry. The article was written by Gao, Yinyi; Cheng, Han; Khan, Sameer; Xiao, Gaokeng; Rong, Lijun; Bai, Chuan. The article contains the following contents:

Filoviruses, including Ebolavirus (EBOV), Marburgvirus (MARV) and Cuevavirus, cause hemorrhagic fevers in humans with up to 90% mortality rates. In the 2014-2016 West Africa Ebola epidemic, there are 15,261 laboratory confirmed cases and 11,325 total deaths. The lack of effective vaccines and medicines for the prevention and treatment of filovirus infection in humans stresses the urgency to develop antiviral therapeutics against filovirus-associated diseases. Our previous study identified a histamine receptor antagonist compound CP19 as an entry inhibitor against both EBOV and MARV. The preliminary structure-activity relationship (SAR) studies of CP19 showed that its piperidine, coumarin and linker were related with its antiviral activities. In this study, we performed detailed SAR studies on these groups with synthesized CP19 derivatives We discovered that 1) the piperidine group could be optimized with heterocycles, 2) the substitution groups of C3 and C4 of coumarin should be relatively large hydrophobic groups and 3) the linker part should be least substituted. Based on the SAR anal., we synthesized compound as a potent entry inhibitor of EBOV and MARV (IC50 = 0.5μM for EBOV and 1.5μM for MARV). The mutation studies of Ebola glycoprotein and mol. docking studies showed that the coumarin and its substituted groups of compound 32 bind to the pocket of Ebola glycoprotein in a similar way to the published entry inhibitor compound 118a. However, the carboxamide group of compound 32 does not have strong interaction with N61 as compound 118a does. The coumarin skeleton structure and the binding model of compound 32 elucidated by this study could be utilized to guide further design and optimization of entry inhibitors targeting the filovirus glycoproteins. In addition to this study using Piperidine-4-carboxamide, there are many other studies that have used Piperidine-4-carboxamide(cas: 39546-32-2Safety of Piperidine-4-carboxamide) was used in this study.

Piperidine-4-carboxamide(cas: 39546-32-2) belongs to anime. Amines have a free lone pair with which they can coordinate to metal centers. Amine–metal bonds are weaker because amines are incapable of backbonding, but they are still important for sensing applications.While stronger than hydrogen bonds, amine–metal bonds are still weaker than both covalent and ionic bonds.Safety of Piperidine-4-carboxamide

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Application of 126832-81-3On March 1, 2008, Imaeda, Yasuhiro; Miyawaki, Toshio; Sakamoto, Hiroki; Itoh, Fumio; Konishi, Noriko; Hiroe, Katsuhiko; Kawamura, Masaki; Tanaka, Toshimasa; Kubo, Keiji published an article in Bioorganic & Medicinal Chemistry. The article was 《Discovery of sulfonylalkylamides: A new class of orally active factor Xa inhibitors》. The article mentions the following:

Factor Xa (FXa) is a trypsin-like serine protease involved in the coagulation cascade and has received great interest as a potential target for the development of new antithrombotic agents. Most of amidine-type FXa inhibitors reported have been found to show extremely poor oral bioavailability. I is one of the first reported non-amidine type FXa inhibitors. To discover novel and orally active FXa inhibitors, we investigated flexible linear linkers between the 6-chloronaphthalene ring and the 1-(pyridin-4-yl)piperidine moiety of I and found an orally active sulfonylalkylamide with an FXa IC50 of 0.05 μM, comparable with that of I. Further modification to reduce the CYP3A4 inhibitory activity of the sulfonylalkylamide resulted in a potent, selective, and orally active 2-methylpyridine analog (FXa IC50 of 0.061 μM), for which the liability of CYP3A4 inhibition was significantly weakened compared to the sulfonylalkylamide. the 2-methylpyridine sulfonylalkylamide analog also showed long lasting anticoagulant activity in cynomolgus monkeys. The experimental part of the paper was very detailed, including the reaction process of 1-Pyridin-4-ylpiperidin-4-one(cas: 126832-81-3Application of 126832-81-3)

1-Pyridin-4-ylpiperidin-4-one(cas: 126832-81-3) belongs to piperidines. Piperidine derivatives are also used in solid-phase peptide synthesis (SPPS) and many degradation reactions. Application of 126832-81-3

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Studies on synthesis and anticancer activity of selected N-(2-fluoroethyl)-N-nitrosoureas》 was published in Journal of Medicinal Chemistry in 1984. These research results belong to Johnston, Thomas P.; Kussner, Conrad L.; Carter, Ronald L.; Frye, Jerry L.; Lomax, Nancita R.; Plowman, Jacqueline; Narayanan, V. L.. Recommanded Product: Benzyl (2,6-dioxopiperidin-3-yl)carbamate The article mentions the following:

Aminolysis of FCH2CH2N(NO)CO2C6H4NO2-2 with H2NCH2CH2OH, 1α,2β,3α-2-amino-1,3-cyclohexanediol, cis-1,2-aminocyclohexanol, and 2-amino-2-deoxy-D-glucose gave the corresponding H2O-sol ureas, e.g., I. The H2O-insoluble glutarimide analog II was prepared by nitrosation of the corresponding urea. In trials with B16 melanoma and Lewis lung carcinoma the compounds were comparable to their Cl analogs as inhibitors; I seemed to be the most effective. In the experimental materials used by the author, we found Benzyl (2,6-dioxopiperidin-3-yl)carbamate(cas: 24666-55-5Recommanded Product: Benzyl (2,6-dioxopiperidin-3-yl)carbamate)

Benzyl (2,6-dioxopiperidin-3-yl)carbamate(cas: 24666-55-5) belongs to anime. In organic chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (NH3), wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines).Recommanded Product: Benzyl (2,6-dioxopiperidin-3-yl)carbamate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Quality Control of tert-Butyl 4-hydroxypiperidine-1-carboxylateIn 2020 ,《Structure-Activity Relationship for the Oxadiazole Class of Antibacterials》 was published in ACS Medicinal Chemistry Letters. The article was written by Boudreau, Marc A.; Ding, Derong; Meisel, Jayda E.; Janardhanan, Jeshina; Spink, Edward; Peng, Zhihong; Qian, Yuanyuan; Yamaguchi, Takao; Testero, Sebastian A.; O’Daniel, Peter I.; Leemans, Erika; Lastochkin, Elena; Song, Wei; Schroeder, Valerie A.; Wolter, William R.; Suckow, Mark A.; Mobashery, Shahriar; Chang, Mayland. The article contains the following contents:

A structure-activity relationship (SAR) for the oxadiazole class of antibacterials was evaluated by syntheses of 72 analogs and determination of the minimal-inhibitory concentrations (MICs) against the ESKAPE panel of bacteria. Selected compounds were further evaluated for in vitro toxicity, plasma protein binding, pharmacokinetics (PK), and a mouse model of methicillin-resistant Staphylococcus aureus (MRSA) infection. Oxadiazole 72c shows potent in vitro antibacterial activity, exhibits low clearance, a high volume of distribution, and 41% oral bioavailability, and shows efficacy in mouse models of MRSA infection. In the experiment, the researchers used tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas: 109384-19-2Quality Control 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.Quality Control of tert-Butyl 4-hydroxypiperidine-1-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Application In Synthesis of tert-Butyl 4-aminopiperidine-1-carboxylateIn 2019 ,《Design, synthesis, cytotoxicity and 3D-QSAR analysis of new 3,6-disubstituted-1,2,4,5-tetrazine derivatives as potential antitumor agents》 appeared in Arabian Journal of Chemistry. The author of the article were Canete-Molina, Alvaro; Espinosa-Bustos, Christian; Gonzalez-Castro, Marcos; Faundez, Mario; Mella, Jaime; Tapia, Ricardo A.; Cabrera, Alan R.; Brito, Ivan; Aguirre, Adam; Salas, Cristian O.. The article conveys some information:

Two new series of 3-substituted-6-(2,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazines I [Ar = Ph, 3,5-dimethylphenyl, 2-naphthyl, etc.] and II [R = Ph, 4-NO2-C6H4, 2-pyridyl, etc.], and analyzed them for a potential role as antitumor agents were reported. Twenty-two compounds were obtained, and four mol. structures were determined by X-ray diffraction anal. Using flow cytometry and MTT assay, potential action on cell toxicity was determined for each of the compounds for four cancer cell lines. The potency and selectivity demonstrated by these compounds were dependent on the cancer cell line, where the following compounds were found the most promising agents against certain cell lines: compounds I [Ar = 2-naphthyl, 3-chlorophenyl] for HL-60 cells, and I [Ar = Ph, 3,5-dimethylphenyl] on HCT116 cells, I [Ar = 4-CN-C6H4] on Hela cells and II [R = 2-(3-trifluoromethyl)pyridyl] on H1975 cells. The action exerted by these compounds was comparable to the well-known cancer treatment drug etoposide and higher than vatalanib. To arrive at the structural requirements for activity on each cell line, a SAR and 3D-QSAR anal. was carried out. From the 3D-QSAR models, steric and electronic features were identified in the aromatic centers, and were key components for cytotoxic activity on HL-60 cell lines. The cytometry results suggested that some tetrazine derivatives induced apoptosis on HCT116 cells. In addition to this study using tert-Butyl 4-aminopiperidine-1-carboxylate, there are many other studies that have used tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7Application In Synthesis of tert-Butyl 4-aminopiperidine-1-carboxylate) was used in this study.

tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7) belongs to anime. Primary amines having a tertiary alkyl group (R3CNH2) are difficult to prepare with most methods but are made industrially by the Ritter reaction. In this method a tertiary alcohol reacts with hydrogen cyanide (HCN) in the presence of a concentrated strong acid; a formamide, RNH―CHO, is formed first, which then undergoes hydrolysis.Application In Synthesis of tert-Butyl 4-aminopiperidine-1-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2022,Wu, Xingyu; Chen, Nanjun; Klok, Harm-Anton; Lee, Young Moo; Hu, Xile published an article in Angewandte Chemie, International Edition. The title of the article was 《Branched Poly(Aryl Piperidinium) Membranes for Anion-Exchange Membrane Fuel Cells》.HPLC of Formula: 1445-73-4 The author mentioned the following in the article:

Anion-exchange membrane fuel cells (AEMFCs) are a promising, next-generation fuel cell technol. AEMFCs require highly conductive and robust anion-exchange membranes (AEMs), which are challenging to develop due to the tradeoff between conductivity and water uptake. Here we report a method to prepare high-mol.-weight branched poly(aryl piperidinium) AEMs. We show that branching reduces water uptake, leading to improved dimensional stability. The optimized membrane, b-PTP-2.5, exhibits simultaneously high OH- conductivity (>145 mS cm-1 at 80 °C), high mech. strength and dimensional stability, good processability, and excellent alk. stability (>1500 h) in 1 M KOH at 80 °C. AEMFCs based on b-PTP-2.5 reached peak power densities of 2.3 W cm-2 in H2-O2 and 1.3 W cm-2 in H2-air at 80 °C. The AEMFCs can run stably under a constant current of 0.2 A cm-2 over 500 h, during which the b-PTP-2.5 membrane remains stable. In the experiment, the researchers used 1-Methyl-4-piperidone(cas: 1445-73-4HPLC of Formula: 1445-73-4)

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.HPLC of Formula: 1445-73-4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem