1445-73-4 | Page 2 of 9 | Heterocyclic Building Blocks-piperidine

Wu, Caijiao’s team published research in Journal of Chemical Research in 2019 | CAS: 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.COA of Formula: C6H11NO

The author of 《An improved process for the preparation of pimavanserin tartrate》 were Wu, Caijiao; Zhou, Qifan; Song, Dake; Li, Hui; Bao, Changshun; Liu, Xuelong; Bao, Xuefei; Chen, Guoliang. And the article was published in Journal of Chemical Research in 2019. COA of Formula: C6H11NO The author mentioned the following in the article:

A practical synthetic route to pimavanserin tartrate, I in which the target compound was obtained with 99.84% purity and in 46% total yield via a 5-step synthesis starting from 4-hydroxybenzaldehyde and (4-fluorophenyl)methanamine, was reported. The main advantages of the route included inexpensive starting materials, mild reaction conditions and an acceptable overall yield.1-Methyl-4-piperidone(cas: 1445-73-4COA of Formula: C6H11NO) was used in this study.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Fu, Ying’s team published research in Organic & Biomolecular Chemistry in 2019 | CAS: 1445-73-4

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.Category: piperidines

In 2019,Organic & Biomolecular Chemistry included an article by Fu, Ying; Li, Ming-Peng; Shi, Chun-Zhao; Li, Fang-Rong; Du, Zhengyin; Huo, Congde. Category: piperidines. The article was titled 《Double C-N bond cleavages of N-alkyl 4-oxopiperidinium salts: access to unsymmetrical tertiary sulfonamides》. The information in the text is summarized as follows:

In this paper, regiospecific, double intraannular C-N bond cleavages of N-alkyl 4-oxopiperidinium salts are presented. The reaction sequence involves a charge-transfer complex, in situ formed between sulfonyl chloride and N-methylmorpholine, which induces S-Cl bond homolysis of sulfonyl chloride, yielding a reactive sulfonyl radical that further induces the double C-N bond cleavages of N-alkyl 4-oxopiperidinium salt. The secondary amine thus produced was trapped by sulfonyl chloride to yield the desired sulfonamide product. The key feature of this protocol is that two intraannular C-N bonds of the 4-oxopiperidine ring are cleaved in one step under metal- and oxidant-free conditions. In the experimental materials used by the author, we found 1-Methyl-4-piperidone(cas: 1445-73-4Category: piperidines)

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Gao, Wei Ting’s team published research in Journal of Membrane Science in 2022 | CAS: 1445-73-4

In 2022,Gao, Wei Ting; Gao, Xue Lang; Gou, Wei Wei; Wang, Jia Jun; Cai, Zhi Hong; Zhang, Qiu Gen; Zhu, Ai Mei; Liu, Qing Lin published an article in Journal of Membrane Science. The title of the article was 《High-performance tetracyclic aromatic anion exchange membranes containing twisted binaphthyl for fuel cells》.Application In Synthesis of 1-Methyl-4-piperidone The author mentioned the following in the article:

The development of high-performance anion exchange membranes (AEMs) has become more urgent for fuel cells. One of the critical challenges is to prepare AEMs with sufficient ion conductivity and robust alk. endurance. In this work, bulky twisted binaphthyl units are introduced into the backbones of AEMs by a one-pot superacid-catalyzed polymerization to enhance both the conductivity and stability. The binaphthyl unit can depress the chain packing d. and enlarge the free volume of the AEMs, conducing to form well-defined microphase separation and to build well-developed ion-conductive highways. The poly(binaphthyl piperidinium)-based AEM (QABNP) shows the highest OH- conductivity of 135.25 mS cm-1 superior to the poly(quaterphenyl piperidinium)-based AEM (QAQPP) (109.12 mS cm-1). Meanwhile, the QABNP AEM exhibits about 90% conductivity retention after being tested in a harsh alk. environment (2 M NaOH at 80 °C) for 1080 h. Importantly, the QABNP based single cell possesses the highest peak power d. (PPD) of 1.16 W cm-2 at a high c.d. of 2.37 A cm-2 with a low high frequency resistance (HFR) of 0.04 Ω cm2. This study demonstrates the merits of bulky twisted binaphthyl incorporated in a polymer backbone for improving AEM performances.1-Methyl-4-piperidone(cas: 1445-73-4Application In Synthesis of 1-Methyl-4-piperidone) was used in this study.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Saccoccia, Fulvio’s team published research in ACS Infectious Diseases in 2020 | CAS: 1445-73-4

Application In Synthesis of 1-Methyl-4-piperidoneIn 2020 ,《Screening and Phenotypical Characterization of Schistosoma mansoni Histone Deacetylase 8 (SmHDAC8) Inhibitors as Multistage Antischistosomal Agents》 was published in ACS Infectious Diseases. The article was written by Saccoccia, Fulvio; Brindisi, Margherita; Gimmelli, Roberto; Relitti, Nicola; Guidi, Alessandra; Saraswati, A. Prasanth; Cavella, Caterina; Brogi, Simone; Chemi, Giulia; Butini, Stefania; Papoff, Giuliana; Senger, Johanna; Herp, Daniel; Jung, Manfred; Campiani, Giuseppe; Gemma, Sandra; Ruberti, Giovina. The article contains the following contents:

Schistosomiasis (also known as bilharzia) is a neglected tropical disease caused by platyhelminths of the genus Schistosoma. The disease is endemic in tropical and subtropical areas of the world where water is infested by the intermediate parasite host, the snail. More than 800 million people live in endemic areas and more than 200 million are infected and require treatment. Praziquantel (PZQ) is the drug of choice for schistosomiasis treatment and transmission control being safe and very effective against adult worms of all the clin. relevant Schistosoma species. Unfortunately, it is ineffective on immature, juvenile worms, therefore it does not prevent reinfection. Moreover, the risk of development and spread of drug resistance strains due to the wide use of a single drug in such a large population represents a serious threat. Therefore, research aimed to identifying novel drugs to be used alone or in combination with PZQ are needed. Histone deacetylase 8 (HDAC8) from the parasite Schistosoma mansoni is a class I zinc-dependent HDAC which is abundantly expressed in all stages of its life cycle, thus representing an interesting target for drug discovery. Through virtual screening and phenotypical characterization of selected hits, the authors discovered two main chem. classes of compounds characterized by the presence of a hydroxamate-based metal binding group coupled to a spiroindoline or a tricyclic thieno[3,2-b]indole core as capping groups. Some of the compounds of both classes were deeply investigated and showed to impair viability of larval, juvenile, and adult schistosomes, to impact egg production in vitro and/or to induce morphol. alterations of the adult schistosome reproductive systems. Noteworthy, all of them inhibit the recombinant form of SmHDAC8 enzyme in vitro. Overall, the authors identified very interesting scaffolds paving the way to the development of effective antischistosomal agents. In the experimental materials used by the author, we found 1-Methyl-4-piperidone(cas: 1445-73-4Application In Synthesis of 1-Methyl-4-piperidone)

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Huber, Imre’s team published research in Journal of Molecular Structure in 2020 | CAS: 1445-73-4

《Structure activity relationship analysis of antiproliferative cyclic C5-curcuminoids without DNA binding: Design, synthesis, lipophilicity and biological activity》 was published in Journal of Molecular Structure in 2020. These research results belong to Huber, Imre; Rozmer, Zsuzsanna; Gyongyi, Zoltan; Budan, Ferenc; Horvath, Peter; Kiss, Eszter; Perjesi, Pal. Product Details of 1445-73-4 The article mentions the following:

The chem. susceptibility of the β-diketone linker between the two aromatic rings in the structure of curcumin to hydrolysis and metabolism has made it crucial to investigate structurally modified analogs of curcumin without such shortcomings. The synthesis of twenty cyclic C5-curcuminoids, I (R = NO2, Cl, H, MeO, NMe2, X = CHMe, NH, NMe, CHOH), is described in this study in order to gain more insight into their anticancer structure-activity relationship (SAR). The design of their synthesis included four different cyclanones and five substituted aromatic aldehydes to form four, five-membered subgroups. These model compounds were evaluated in vitro for antiproliferative activity in an XTT cell viability assay against MCF-7 human non-invasive breast adenocarcinoma cancer cells and Jurkat human T lymphocyte leukemia cells in five different concentrations (10 nM, 100 nM, 1μM, 10μM and 20μM). The majority of the compounds investigated have shown remarkable cytotoxicity with IC50 values in the range of 120 nM and 2μM with very high relative toxicity values to curcumin. The SAR conclusions are drawn and summarized. A method was developed and applied in a TLC based exptl. logP measurement, which is new for such C5-curcuminoids. The logP data and structural modifications have shown a strong correlation. The correlation of these exptl. logP and the corresponding IC50 values of the model-compounds were calculated according to the Pearson and Kendall correlation coefficient and showed weak concordance. The physicochem. behaviors of the majority of these compounds are in good accordance with Lipinski’s rule. The most promising compound is I (R = NO2, X = NH), which is the most active (IC50 = 0.12-0.32μM) and most potent (80 times of curcumin) compound with the lowest lipophilicity (exptl. logP = 3.22), which is important also from a pharmacokinetic point of view. The anal. of exptl. logP and computed ClogP values have revealed good agreement. These cyclic C5-curcuminoids in contrast to curcumin do not bind to natural DNA based on their CD spectra. The results came from multiple reactions, including the reaction of 1-Methyl-4-piperidone(cas: 1445-73-4Product Details of 1445-73-4)

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Zeng, Minghao’s team published research in ACS Applied Energy Materials in 2022 | CAS: 1445-73-4

1-Methyl-4-piperidone(cas: 1445-73-4) 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.Safety of 1-Methyl-4-piperidone

In 2022,Zeng, Minghao; Liu, Wenqi; Guo, Haikun; Li, Tingting; Li, Qijia; Zhao, Chengji; Li, Xiaojin; Li, Haolong published an article in ACS Applied Energy Materials. The title of the article was 《Polyoxometalate-Cross-Linked Proton Exchange Membranes with Post-Assembled Nanostructures for High-Temperature Proton Conduction》.Safety of 1-Methyl-4-piperidone The author mentioned the following in the article:

High-temperature proton exchange membranes (HT-PEMs) are key components in high-temperature energy storage and conversion technologies, which require excellent proton conductivity and mech. strength. However, it is difficult for HT-PEMs to balance their mech. and conductive properties. Here, we present a strategy to prepare HT-PEMs based on the combination of polyoxometalate (POM)-dominated noncovalent crosslinking and H3PO4 (PA)-induced post-assembly. Hybrid membranes containing polyvinylpyrrolidone (PVP), poly(terphenyl piperidine) (PTP), and H3PW12O40 (PW) are prepared, where the polymers are electrostatically cross-linked by PW and maintain certain mobility. When the membranes adsorb PA, the polarity difference between the PVP-PW-PA moieties and the PTP-PW-PA moieties increases, causing the chains to rearrange into bicontinuous structures via a post-assembly process. The resultant membranes show a break strength over 7 MPa and a proton conductivity of ~55 mS cm-1 at 160°C. The high-temperature supercapacitors based on such membranes exhibit a specific capacitance of 145.4 F g-1 and a capacitance retention of 80% after 3000 charge-discharge cycles at 150°C. Their H2/air fuel cells display a peak power of 273.6 mW cm-2 at 160°C. This work provides a paradigm for using POMs as dynamic cross-linkers to fabricate nanostructured PEMs, which paves a feasible route to developing high-performance electrolyte materials. The experimental process involved the reaction of 1-Methyl-4-piperidone(cas: 1445-73-4Safety of 1-Methyl-4-piperidone)

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Olsson, Joel S.’s team published research in Journal of Membrane Science in 2019 | CAS: 1445-73-4

In 2019,Journal of Membrane Science included an article by Olsson, Joel S.; Pham, Thanh Huong; Jannasch, Patric. Application of 1445-73-4. The article was titled 《Tuning poly(arylene piperidinium) anion-exchange membranes by copolymerization, partial quaternization and crosslinking》. The information in the text is summarized as follows:

Ion exchange membranes with high ionic contents typically suffer from excessive water uptake and dilution effects which compromise both mech. properties and ion conductivity In the present work we develop and compare partial quaternization, copolymerization and crosslinking as three different synthetic strategies to balance the ion exchange capacity (IEC), water uptake and hydroxide conductivity of poly(arylene piperidinium)s, which belong to a new class of alkali-stable anion-exchange membrane materials. Poly(biphenyl N-methylpiperidine) (PBPip) was first produced in a polyhydroxyalkylation reaction of biphenyl and N-methyl-4-piperidone, and then partly quaternized with controlled stoichiometric shortages of alkyl halide to regulate the IEC. In the second approach, a series of copolymers with controlled IEC were prepared by introducing precise amounts of ketone co-monomers in the polyhydroxyalkylations. In the final approach, crosslinked AEMs were fabricated in a reactive casting procedure, followed by partial quaternization. The overall results of the study reveals that the copolymerization approach gives AEMs with the most attractive set of properties. Hence, at a given IEC and moderate water uptake, the copolymer AEMs reach the highest hydroxide conductivity, up to 120 mS cm-1 at 80 °C, and retain the high alk. stability of the original poly(arylene piperidinium) AEM. The study demonstrates the versatility and efficiency of these synthetic strategies to tailor and significantly improve the properties of functional high-performance AEMs for different electrochem. applications. In the part of experimental materials, we found many familiar compounds, such as 1-Methyl-4-piperidone(cas: 1445-73-4Application of 1445-73-4)

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Chen, Nanjun’s team published research in Energy & Environmental Science in 2021 | CAS: 1445-73-4

Chen, Nanjun; Paek, Sae Yane; Lee, Ju Yeon; Park, Jong Hyeong; Lee, So Young; Lee, Young Moo published their research in Energy & Environmental Science in 2021. The article was titled 《High-performance anion exchange membrane water electrolyzers with a current density of 7.68 A cm-2 and a durability of 1000 hours》.Formula: C6H11NO The article contains the following contents:

Low-cost anion exchange membrane (AEM) water electrolyzers (AEMWEs) are a new technol. for the production of high-purity hydrogen; however, their c.d. and durability are far lower than those of proton exchange membrane water electrolyzers (PEMWEs). Here, we report poly(fluorenyl-co-aryl piperidinium) (PFAP)-based anhydrous cathode AEMWEs that exceed the state-of-the-art PEMWEs with respect to c.d. In addition to a rational electrode design, PFAP-based AEMs with a high water diffusivity and ion conductivity are crucial for high-performance AEMWEs. Using platinum-group-metal (PGM) catalysts, the present AEMWEs achieved a new record c.d. of 7.68 A cm-2 at 2.0 V with a 1 M KOH anode, which surpasses that of state-of-the-art PEMWEs (6 A cm-2 at 2.0 V). PGM-free AEMWEs displayed an excellent c.d. of 1.62 A cm-2 at 2.0 V. Importantly, PGM and PGM-free AEMWEs operated stably under a 0.5 A cm-2 c.d. at 60 °C for more than 1000 h. This work sheds light on current high-performance AEMWEs. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-piperidone(cas: 1445-73-4Formula: C6H11NO)

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Nagargoje, Amol A.’s team published research in Chemistry & Biodiversity in 2020 | CAS: 1445-73-4

Product Details of 1445-73-4In 2020 ,《Quinoline Based Monocarbonyl Curcumin Analogs as Potential Antifungal and Antioxidant Agents: Synthesis, Bioevaluation and Molecular Docking Study》 appeared in Chemistry & Biodiversity. The author of the article were Nagargoje, Amol A.; Akolkar, Satish V.; Siddiqui, Madiha M.; Subhedar, Dnyaneshwar D.; Sangshetti, Jaiprakash N.; Khedkar, Vijay M.; Shingate, Bapurao B.. The article conveys some information:

In search for new fungicidal and free radical scavenging agents, we synthesized a focused library of 2-chloroquinoline based monocarbonyl analogs of curcumin (MACs). The synthesized MACs were evaluated for in vitro antifungal and antioxidant activity. The antifungal activity was evaluated against five different fungal strains such as Candida albicans, Fusarium oxysporum, Aspergillus flavus, Aspergillus niger, and Cryptococcus neoformans, resp. Most of the synthesized MACs displayed promising antifungal activity compared to the standard drug Miconazole. Furthermore, mol. docking study on a crucial fungal enzyme sterol 14α-demethylase (CYP51) could provide insight into the plausible mechanism of antifungal activity. MACs were also screened for in vitro radical scavenging activity using butylated hydroxytoluene (BHT) as a standard Almost all MACs exhibited better antioxidant activity compared to BHT. After reading the article, we found that the author used 1-Methyl-4-piperidone(cas: 1445-73-4Product Details of 1445-73-4)

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Miyazaki, Ray’s team published research in Catalysis Science & Technology in 2021 | CAS: 1445-73-4

Miyazaki, Ray; Jin, Xiongjie; Yoshii, Daichi; Yatabe, Takafumi; Yabe, Tomohiro; Mizuno, Noritaka; Yamaguchi, Kazuya; Hasegawa, Jun-ya published an article in 2021. The article was titled 《Mechanistic study of C-H bond activation by O2 on negatively charged Au clusters: α,β-dehydrogenation of 1-methyl-4-piperidone by supported Au catalysts》, and you may find the article in Catalysis Science & Technology.Application In Synthesis of 1-Methyl-4-piperidone The information in the text is summarized as follows:

Au nanoparticles supported on the manganese oxide octahedral mol. sieve OMS-2 can efficiently catalyze α,β-dehydrogenation of β-N-substituted saturated ketones using O2 as the terminal oxidant. However, despite the utility of this reaction, the active sites and the reaction mechanism remain unclear. Here, the reaction mechanism for the Au/OMS-2-catalyzed aerobic α,β-dehydrogenation of 1-methyl-4-piperidone was investigated mainly by using d. functional theory (DFT) calculations From control experiments under various reaction conditions, we found that O2 plays an important role in the α,β-dehydrogenation over Au nanoparticles. Thus, we attempted to clarify the mechanism for the α,β-dehydrogenation of 1-methyl-4-piperidone on Au nanoparticle catalysts by DFT calculations using Au cluster models. The reaction was found to cleave the C-Hα and C-Hβ bonds in that order. An O2 mol. adsorbed on the neg. charged Au cluster caused by charge transfer from OMS-2 was found to be sufficiently activated to abstract the Hα atom in the 1-methyl-4-piperidone substrate. This indirect Hα abstraction by the activated O2 was energetically more favorable than direct Hα abstraction by the Au cluster. The subsequent Hβ abstraction was found to be promoted by adsorbed oxygen species (i.e., HOO, OH, and O) formed after the Hα abstraction. The reaction mechanism proposed in this study provides general insight into the aerobic C-H bond activation by supported Au catalysts. In addition to this study using 1-Methyl-4-piperidone, there are many other studies that have used 1-Methyl-4-piperidone(cas: 1445-73-4Application In Synthesis of 1-Methyl-4-piperidone) was used in this study.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem