Tag: 100-200

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

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

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

In 2022,Liu, Binghui; Duan, Yuting; Li, Tingting; Li, Jialin; Zhang, Haiqiu; Zhao, Chengji published an article in Separation and Purification Technology. The title of the article was 《Nanostructured anion exchange membranes based on poly(arylene piperidinium) with bis-cation strings for diffusion dialysis in acid recovery》.Category: piperidines The author mentioned the following in the article:

A series of anion exchange membranes (AEMs) based on poly(arylene piperidinium) with bis-cation strings were prepared by a simple synthetic method for diffusion dialysis (DD). Through Menshutkin reaction, 1-(6-bromohexyl)-1-methylpiperidinium bromide was grafted onto the hydrophobic poly(arylene piperidine) backbone to produce side-chain-type AEMs with bis-piperidinium strings (QPBPipXAc). The self-assembled nanostructure of these AEMs was verified by SAXS and AFM images. The properties and DD performance of QPBPipXAc AEMs with different contents of bis-piperidinium ionic groups were systematically studied, including mech. properties, ionic conductivity, thermal stability. The prepared AEMs demonstrated favorable overall properties due to the formation of self-assembled nanostructured hydrophilic-hydrophobic phase separation morphol. The hydrophilic domains provide more efficient ion transport channels for high acid flux, whereas the hydrophobic domains restrict the AEMs swelling and Fe2+ ion transport. The prepared QPBPipXAc AEMs displayed high H+ dialysis coefficients (UH+, 10 x 10-3 – 65 x 10-3 m/h) and separation coefficients (S, 15.67-25.38). Compared with the com. membrane DF-120 (UH+ = 9 x 10-3 m/h, S = 18.5), the prepared AEMs have better diffusion dialysis performance, indicating that they could be the potential candidates for application for acid recovery. In the experimental materials used by the author, we found 1-Methyl-4-piperidone(cas: 1445-73-4Category: piperidines)

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.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Yan, Guoyi; Luo, Jiang; Han, Xuan; Zhang, Wenjuan; Pu, Chunlan; Zhou, Meng; Zhong, Xinxin; Hou, Xueyan; Hou, Man Zhou; Li, Rui published their research in Anti-Cancer Agents in Medicinal Chemistry in 2021. The article was titled 《Design, Synthesis and Biological Evaluation of 4, 6-Coumarin Derivatives as Anti- Cancer and Apoptosis-Inducing Agents》.Name: 2-(Piperidin-4-yl)ethanol The article contains the following contents:

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. The experimental part of the paper was very detailed, including the reaction process of 2-(Piperidin-4-yl)ethanol(cas: 622-26-4Name: 2-(Piperidin-4-yl)ethanol)

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.Name: 2-(Piperidin-4-yl)ethanol

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2017,Cheeseman, Matthew D.; Chessum, Nicola E. A.; Rye, Carl S.; Pasqua, A. Elisa; Tucker, Michael J.; Wilding, Birgit; Evans, Lindsay E.; Lepri, Susan; Richards, Meirion; Sharp, Swee Y.; Ali, Salyha; Rowlands, Martin; O’Fee, Lisa; Miah, Asadh; Hayes, Angela; Henley, Alan T.; Powers, Marissa; te Poele, Robert; De Billy, Emmanuel; Pellegrino, Loredana; Raynaud, Florence; Burke, Rosemary; van Montfort, Rob L. M.; Eccles, Suzanne A.; Workman, Paul; Jones, Keith published 《Discovery of a Chemical Probe Bisamide (CCT251236): An Orally Bioavailable Efficacious Pirin Ligand from a Heat Shock Transcription Factor 1 (HSF1) Phenotypic Screen》.Journal of Medicinal Chemistry published the findings.Computed Properties of C7H15NO The information in the text is summarized as follows:

Phenotypic screens, which focus on measuring and quantifying discrete cellular changes rather than measuring affinity for individual recombinant proteins, have recently attracted renewed interest as an efficient strategy for drug discovery. In this paper, the authors describe the discovery of a new chem. probe, bisamide I (CCT251236), identified using an unbiased phenotypic screen to detect inhibitors of the HSF1 stress pathway. The chem. probe is orally bioavailable and displays efficacy in a human ovarian carcinoma xenograft model. By developing cell-based SAR and using chem. proteomics, the authors identified pirin as a high affinity mol. target, which was confirmed by SPR and crystallog. In addition to this study using 2-(Piperidin-4-yl)ethanol, there are many other studies that have used 2-(Piperidin-4-yl)ethanol(cas: 622-26-4Computed Properties of C7H15NO) was used in this study.

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.Computed Properties of C7H15NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2016,Dai, Xi-Jie; Li, Chao-Jun published 《En Route to a Practical Primary Alcohol Deoxygenation》.Journal of the American Chemical Society published the findings.Computed Properties of C7H15NO The information in the text is summarized as follows:

A long-standing scientific challenge in the field of alc. deoxygenation has been direct catalytic sp3 C-O defunctionalization with high selectivity and efficiency, in the presence of other functionalities, such as free hydroxyl groups and amines widely present in biol. mols. Previously, the selectivity issue had been only addressed by classic multistep deoxygenation strategies with stoichiometric reagents. Herein, we propose a catalytic late-transition-metal-catalyzed redox design, on the basis of dehydrogenation/Wolff-Kishner (WK) reduction, to simultaneously tackle the challenges regarding step economy and selectivity. The early development of our hypothesis focuses on an iridium-catalyzed process efficient mainly with activated alcs., which dictates harsh reaction conditions and thus limits its synthetic utility. Later, a significant advancement has been made on aliphatic primary alc. deoxygenation by employing a ruthenium complex, with good functional group tolerance and exclusive selectivity under practical reaction conditions. Its synthetic utility is further illustrated by excellent efficiency as well as complete chemo- and regioselectivity in both simple and complex mol. settings. Mechanistic discussion is also included with exptl. supports. Overall, our current method successfully addresses the aforementioned challenges in the pertinent field, providing a practical redox-based approach to the direct sp3 C-O defunctionalization of aliphatic primary alcs.2-(Piperidin-4-yl)ethanol(cas: 622-26-4Computed Properties of C7H15NO) was used in this study.

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.Computed Properties of C7H15NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem