Day: October 18, 2022

Application of 118511-81-2On May 23, 2013, Mattsson, Cecilia; Andreasson, Theresa; Waters, Nicholas; Sonesson, Clas published an article in Journal of Medicinal Chemistry. The article was 《Systematic in Vivo Screening of a Series of 1-Propyl-4-arylpiperidines against Dopaminergic and Serotonergic Properties in Rat Brain: A Scaffold-Jumping Approach [Erratum to document cited in CA157:687548]》. The article mentions the following:

Tables 1 through 3, Figure 2, and Figure 4 contained an incorrect structure for compound 14; the corrected structure and several related corrections to the text and Supporting Information are provided. On page 9741, lines 23-30, 31, and 34 of the right hand column contained incorrect text; the corrected text is given. The experimental part of the paper was very detailed, including the reaction process of 1-(Piperidin-4-yl)-1H-indole(cas: 118511-81-2Application of 118511-81-2)

1-(Piperidin-4-yl)-1H-indole(cas: 118511-81-2) belongs to piperidines. Piperidine derivatives are also used in solid-phase peptide synthesis (SPPS) and many degradation reactions. Application of 118511-81-2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Safety of (R)-1-tert-Butyl 3-ethyl piperidine-1,3-dicarboxylateOn September 25, 2006 ,《Asymmetric hydrogenation of pyridines: enantioselective synthesis of nipecotic acid derivatives》 was published in European Journal of Organic Chemistry. The article was written by Lei, Aiwen; Chen, Mao; He, Minsheng; Zhang, Xumu. The article contains the following contents:

An asym. hydrogenation process of 3-substituted pyridine derivatives has been developed with the use of a Rh-TangPhos complex as the catalyst. The whole process consists of an efficient partial hydrogenation of nicotinate and a subsequent highly enantioselective, Rh-catalyzed, homogeneous hydrogenation. A series of chiral nipecotic acid derivatives have been synthesized.(R)-1-tert-Butyl 3-ethyl piperidine-1,3-dicarboxylate(cas: 194726-40-4Safety of (R)-1-tert-Butyl 3-ethyl piperidine-1,3-dicarboxylate) 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 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 (R)-1-tert-Butyl 3-ethyl piperidine-1,3-dicarboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Park, Seonghun; Lee, Jieun; Kim, Bongkyum; Yuan, Daqiang; Chen, Ying-Pin; Park, Jinhee published an article in Microporous and Mesoporous Materials. The title of the article was 《Unprecedented porosity transformation of hierarchically porous TiO2 derived from Ti-Oxo clusters》.Safety of Triacetonamine The author mentioned the following in the article:

Although attaining a high porosity in TiO2 is critical to enhancing its photocatalytic and photoelec. activities, its synthesis has been challenging owing to the high reactivity of conventional Ti precursors and the laborious template removal process. Thus, we herein report a versatile method for preparing hierarchically porous organic-functionalized TiO2 (HiPOTs) using Ti-oxo clusters consisting of a rigid reactive ligand, para-aminobenzoate (p-ABA). The presence of p-ABA as a structure-directing template is crucial to obtain microporous structures with sufficiently high yields. The HiPOTs gradually transform from hierarchically micro/mesoporous structures into mesoporous structures during a sol-gel process. The Brunauer-Emmett-Teller surface areas of the HiPOTs range from 242 to 739 m2/g, which are among the highest reported for porous TiO2 materials. The presence of p-ABA on the HiPOT surface decreases the band gap of TiO2 to 2.7 eV, and prolonging the sol-gel process releases greater quantities of p-ABA, thereby increasing the band gap and the crystallinity of the anatase phase. Interestingly, unlike conventional TiO2, which experiences rapid charge recombination, the Ti3+ oxidation states of HiPOTs are successfully isolated during UV irradiation and can be applied as a proof of concept to generate reactive oxygen species such as 1O2 and •O-2. The experimental process involved the reaction of Triacetonamine(cas: 826-36-8Safety of Triacetonamine)

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.Safety of Triacetonamine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Tang, Kai; Zhao, Min; Wu, Ya-Hong; Wu, Qiong; Wang, Shu; Dong, Yu; Yu, Bin; Song, Yihui; Liu, Hong-Min published an article on February 15 ,2022. The article was titled 《Structure-based design, synthesis and biological evaluation of aminopyrazines as highly potent, selective, and cellularly active allosteric SHP2 inhibitors》, and you may find the article in European Journal of Medicinal Chemistry.Computed Properties of C6H12N2O The information in the text is summarized as follows:

Src homol.-2-containing protein tyrosine phosphatase 2 (SHP2) encoded by the proto-oncogene PTPN11 is the first identified non-receptor protein tyrosine phosphatase. SHP2 dysregulation contributes to the pathogenesis of different cancers, making SHP2 a promising therapeutic target for cancer therapy. In this article, authors report the structure-guided design based on the well-characterized SHP2 inhibitor SHP099, extensive structure-activity relationship studies (SARs) of aminopyrazines, biochem. characterization and cellular potency. These medicinal chem. efforts lead to the discovery of the lead compound TK-453 I, which potently inhibits SHP2 (SHP2WT IC50 = 0.023μM, ΔTm = 7.01°C) in a reversible and noncompetitive manner. Compound I exhibits high selectivity over SHP2PTP, SHP1 and PTP1B, and may bind at the “”tunnel”” allosteric site of SHP2 as SHP099. As the key pharmacophore, the aminopyrazine scaffold not only reorganizes the cationic-π stacking interaction with R111 via the novel hydrogen bond interaction between the S atom of thioether linker and T219, but also mediates a hydrogen bond with E250. In vitro studies indicate that I inhibits proliferation of HeLa, KYSE-70 and THP-1 cells moderately and induces apoptosis of Hela cells. Further mechanistic studies suggest that I can decrease the phosphorylation levels of AKT and Erk1/2 in HeLa and KYSE-70 cells.Piperidine-4-carboxamide(cas: 39546-32-2Computed Properties of C6H12N2O) was used in this study.

Piperidine-4-carboxamide(cas: 39546-32-2) belongs to anime. Amine, any member of a family of nitrogen-containing organic compounds that is derived, either in principle or in practice, from ammonia (NH3). Naturally occurring amines include the alkaloids, which are present in certain plants; the catecholamine neurotransmitters (i.e., dopamine, epinephrine, and norepinephrine); and a local chemical mediator, histamine, that occurs in most animal tissues.Computed Properties of C6H12N2O

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2015,Kumar, Sunil; Pathania, Anoop S.; Satti, Naresh K.; Dutt, Parbhu; Sharma, Neha; Mallik, Fayaz A.; Ali, Asif published 《Synthetic modification of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition derivatives depicting cytotoxic potential》.European Journal of Medicinal Chemistry published the findings.HPLC of Formula: 622-26-4 The information in the text is summarized as follows:

Here we report the design, synthesis and lead optimization of hydroxychavicol (I) a high yielding metabolite ubiquitously present in the Piper betel leaves with the significant cytotoxic activity. This is the first report to describe the synthetic strategies of two distinct series of hydroxychavicol by Mannich reaction and alkyne-azide cycloaddition Furthermore, all the synthesized derivatives along with parent compound were evaluated for their in-vitro cytotoxic and antiproliferative potential in several distinct cancers cell lines. Among all, the Mannich reaction derived mols., e.g., II, displayed more potent cytotoxic activities with IC50 value in a range from 3 to 9 μM, which were 7-10 fold more potent than I against five human cancer cell lines viz. HL-60, Mia PaCa-2, MCF-7, HEP G2 and SK-N-SH. Our results describe an efficient synthetic approach used to evaluate the structure activity relationship of I and its derivative in search of potential new anticancer agents. After reading the article, we found that the author used 2-(Piperidin-4-yl)ethanol(cas: 622-26-4HPLC of Formula: 622-26-4)

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.HPLC of Formula: 622-26-4

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

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

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

Liu, Wenwu; Liu, Xin; Liu, Wenjie; Gao, Yaping; Wu, Limeng; Huang, Yaoguang; Chen, Huanhua; Li, Deping; Zhou, Lijun; Wang, Nan; Xu, Zihua; Jiang, Xiaowen; Zhao, Qingchun published an article in 2022. The article was titled 《Discovery of novel β-carboline derivatives as selective AChE inhibitors with GSK-3β inhibitory property for the treatment of Alzheimer’s disease》, and you may find the article in European Journal of Medicinal Chemistry.Electric Literature of C10H20N2O2 The information in the text is summarized as follows:

The natural product harmine, a representative β-carboline alkaloid from the seeds of Peganum harmala L. (Zygophyllaceae), possesses a broad spectrum of biol. activities. In this study, a novel series of harmine derivatives containing N-benzylpiperidine moiety were identified for the treatment of Alzheimer’s disease (AD). The results showed that all the derivatives possessed significant anti-acetylcholinesterase (AChE) activity and good selectivity over butyrylcholinesterase (BChE). In particular, compound ZLWH-23 exhibited potent anti-AChE activity (IC50 = 0.27μM) and selective BChE inhibition (IC50 = 20.82μM), as well as acceptable glycogen synthase kinase-3 (GSK-3β) inhibition (IC50 = 6.78μM). Mol. docking studies and mol. dynamics simulations indicated that ZLWH-23 could form stable interaction with AChE and GSK-3β. Gratifyingly, ZLWH-23 exhibited good selectivity for GSK-3β over multi-kinases and very low cytotoxicity towards SH-SY5Y, HEK-293T, HL-7702, and HepG2 cell lines. Importantly, ZLWH-23 displayed efficient reduction against tau hyperphosphorylation on Ser-396 site in Tau (P301L) 293T cell model. Collectively, harmine-based derivatives could be considered as possible drug leads for the development of AD therapies. The results came from multiple reactions, including 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. Reduction of nitro compounds, RNO2, by hydrogen or other reducing agents produces primary amines cleanly (i.e., without a mixture of products), but the method is mostly used for aromatic amines because of the limited availability of aliphatic nitro compounds. Reduction of nitriles and oximes (R2C=NOH) also yields primary amines.Electric Literature of C10H20N2O2

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