Category: piperidines

In 2019,ACS Applied Materials & Interfaces included an article by Yan, Xiaoming; Zhang, Huaqing; Hu, Zhongyue; Li, Lv; Hu, Lei; Li, Zhi’ang; Gao, Li; Dai, Yan; Jian, Xigao; He, Gaohong. Application In Synthesis of 1-Methyl-4-piperidone. The article was titled 《Amphoteric-Side-Chain-Functionalized “”Ether-Free”” Poly(arylene piperidinium) Membrane for Advanced Redox Flow Battery》. The information in the text is summarized as follows:

To solve the stability issue of cost-effective non-fluorinated membranes, a ether-free poly(arylene piperidinium) (PBPip) based membrane is 1st applied in redox flow batteries (RFBs). For improved efficiencies of RFB, amphoteric side chains are introduced onto the PBPip. Without ether bond in the polymer backbone, the membrane shows a good stability in the strong oxidation environment. The FTIR spectra exhibit no obvious changes for 30 days of oxidation test. Different from traditional blended amphoteric membranes, the amphoteric side chain allows that cation and anion exchange capacities both increase with grafting degree, which leads to a very high total IEC (4.19 mmol/g). Outstanding ion conduction ability (area resistance: 0.22 Ω cm2) comparable to Nafion 212 (0.24 Ω cm2) is consequently achieved. Ionic crosslinking structure between cationic and anionic groups results in low swelling rate (13.9%). Combining with repelling effect of pos. charged piperidinium, a low VO2+ permeability (1.31×10-8 cm2/s) is accomplished. From these good properties, the membrane exhibits excellent vanadium battery performances, especially at high current densities. The WE and EE both exceeds 80% even at 200 mA/cm2. The battery performances have no obvious reductions after 500 cycles. This work provides a new orientation to design the membrane for RFB. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-piperidone(cas: 1445-73-4Application In Synthesis of 1-Methyl-4-piperidone)

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.Application In Synthesis of 1-Methyl-4-piperidone

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2014,Rzasa, Robert M.; Frohn, Michael J.; Andrews, Kristin L.; Chmait, Samer; Chen, Ning; Clarine, Jeffrey G.; Davis, Carl; Eastwood, Heather A.; Horne, Daniel B.; Hu, Essa; Jones, Adrie D.; Kaller, Matthew R.; Kunz, Roxanne K.; Miller, Silke; Monenschein, Holger; Nguyen, Thomas; Pickrell, Alexander J.; Porter, Amy; Reichelt, Andreas; Zhao, Xiaoning; Treanor, James J. S.; Allen, Jennifer R. published 《Synthesis and preliminary biological evaluation of potent and selective 2-(3-alkoxy-1-azetidinyl) quinolines as novel PDE10A inhibitors with improved solubility》.Bioorganic & Medicinal Chemistry published the findings.Formula: C7H15NO The information in the text is summarized as follows:

We report the discovery of a novel series of 2-(3-alkoxy-1-azetidinyl) quinolines as potent and selective PDE10A inhibitors. Structure-activity studies improved the solubility (pH 7.4) and maintained high PDE10A activity compared to initial lead compound 3, with select compounds demonstrating good oral bioavailability. X-ray crystallog. studies revealed two distinct binding modes to the catalytic site of the PDE10A enzyme. An ex vivo receptor occupancy assay in rats demonstrated that this series of compounds covered the target within the striatum. The experimental part of the paper was very detailed, including the reaction process of 2-(Piperidin-4-yl)ethanol(cas: 622-26-4Formula: C7H15NO)

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.Formula: C7H15NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Witt, Anette; Gustavsson, Annika; Bergman, Jan published their research in Journal of Heterocyclic Chemistry on February 28 ,2003. The article was titled 《Studies towards the synthesis of the benzodiazepine alkaloid auranthine. Synthesis of an acetylated derivative》.Category: piperidines The article contains the following contents:

Different approaches towards the synthesis of auranthine have been investigated. A completed synthesis of 3-[2-(4-oxo-3,4-dihydro-quinazolin-2-yl)-ethyl]-3,4-dihydro-1H-benzo[e][1,4]-diazepine-2,5-dione I, an auranthine precursor, which after dehydration with 50% propylphosphonic acid anhydride solution in Et acetate and DMA gave a C-acetyl derivative of auranthine. Addnl. studies towards the synthesis of fused quinazolinones yielded the C-acetylated pyrido[2,1-b]quinazolinones or butyric acid derivatives In the part of experimental materials, we found many familiar compounds, such as Benzyl (2,6-dioxopiperidin-3-yl)carbamate(cas: 24666-55-5Category: piperidines)

Benzyl (2,6-dioxopiperidin-3-yl)carbamate(cas: 24666-55-5) 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.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Peng, Yanhua; Xie, Guansheng; Shao, Penghui; Ren, Wei; Li, Mengling; Hu, Yufeng; Yang, Liming; Shi, Hui; Luo, Xubiao published their research in Applied Catalysis, B: Environmental on August 5 ,2022. The article was titled 《A comparison of SMX degradation by persulfate activated with different nanocarbons: Kinetics, transformation pathways, and toxicity》.Safety of Triacetonamine The article contains the following contents:

Nanocarbon-based advanced oxidation processes (AOPs) are widely used in wastewater purification However, the properties of different carbon catalysts lead to differences in the organic degradation mechanism and toxicity of wastewater treatment. Herein, this study provides insight into the differences between the oxidation of sulfamethoxazole (SMX) by carbon nanotube (CNT)/peroxymonosulfate (PMS), nanodiamond (ND)/PMS and PMS-alone systems. The pseudo-first-order reaction constant of the reaction of the SO4·–dominated CNT/PMS system with SMX is 19-fold and 30-fold higher than those of the 1O2-dominated ND/PMS system and PMS direct oxidation system at pH= 7, resp. In addition, d. functional theory (DFT) calculations and product anal. show that SO4·- mainly attacks the aniline and sulfonyl groups, while oxidation of the aniline group is the dominant mode of PMS direct oxidation and 1O2 reactivity. The formation of nitro and nitroso byproducts after SMX degradation determines the toxicity difference, and the CNT/PMS system is even more advantageous. In the experiment, the researchers used Triacetonamine(cas: 826-36-8Safety of Triacetonamine)

Triacetonamine(cas: 826-36-8) 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.Safety of Triacetonamine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

COA of Formula: C10H20N2O2In 2022 ,《Design and synthesis of dual inhibitors targeting snail and histone deacetylase for the treatment of solid tumor cancer》 appeared in European Journal of Medicinal Chemistry. The author of the article were Cui, Hao; Huang, Jingkun; Lei, Yan; Chen, Quanwei; Hu, Zan; Niu, Jiaqi; Wei, Ran; Yang, Kang; Li, Hongmei; Lu, Tao; Zhu, Yong; Huang, Yatian. The article conveys some information:

In this work, a series of Snail/HDAC dual inhibitors I (R = H, F; R1 = (1H-pyrazol-3-yl)aminyl, [1-[(tert-butoxy)carbonyl]piperidin-4-yl]aminyl, morpholin-4-yl, [(4-fluorophenyl)methyl]aminyl, etc.) were synthesized. Compound I (R = F; R1 = (5-methyl-1H-pyrazol-3-yl)aminyl) displayed the most potent inhibitory activity against HDAC1 with an IC50 of 0.405μM, potent inhibition against Snail with a Kd of 0.180μM, and antiproliferative activity in HCT-116 cell lines with an IC50 of 0.0751μM. Compound I (R = F; R1 = (5-methyl-1H-pyrazol-3-yl)aminyl) showed a good inhibitory effect on NCI-H522 (GI50 = 0.0488μM), MDA-MB-435 (GI50 = 0.0361μM), and MCF7 (GI50 = 0.0518μM). Docking studies showed that compound I (R = F; R1 = (5-methyl-1H-pyrazol-3-yl)aminyl) can be well docked into the active binding sites of Snail and HDAC. Further studies showed that compound I (R = F; R1 = (5-methyl-1H-pyrazol-3-yl)aminyl) increased histone H4 acetylation in HCT-116 cells and decreased the expression of Snail protein to induce cell apoptosis. These findings highlight the potential for the development of Snail/HDAC dual inhibitors as anti-solid tumor cancer drugs. In the experiment, the researchers used tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7COA of Formula: C10H20N2O2)

tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7) belongs to anime. Examples of direct uses of amines and their salts are as corrosion inhibitors in boilers and in lubricating oils (morpholine), as antioxidants for rubber and roofing asphalt (diarylamines), as stabilizers for cellulose nitrate explosives (diphenylamine), as protectants against damage from gamma radiation (diarylamines), as developers in photography (aromatic diamines), as flotation agents in mining, as anticling and waterproofing agents for textiles, as fabric softeners, in paper coating, and for solubilizing herbicides.COA of Formula: C10H20N2O2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2022,Nagarale, Rajaram. K.; Bavdane, Priyanka P.; Sreenath, Sooraj; Pawar, Chetan M.; Dave, Vidhiben; Satpati, A. K. published an article in Journal of Polymer Research. The title of the article was 《Polyaniline derivatized anion exchange membrane for acid recovery》.Related Products of 1445-73-4 The author mentioned the following in the article:

Herein we are demonstrating the utility of an aniline derivatized anion exchange membrane for acid recovery by diffusion dialysis. The membrane was synthesized by oxidative polymerization of N-Methyl-4-piperidone derivative and confirmed by detailed spectroscopic characterisations. Free-standing membranes M1 and M2 was obtained by addition of different amount of PVA. For the comparison purpose, PVA blend with neat polyaniline was synthesized. Excellent physicochem. properties coupled with outstanding chem. stability in bentonite mine effluent with total acid concentration of ∼ 8 M, drawn interest to use in acid recovery by diffusion dialysis. In a simulated solution containing 6% iron and 3.5 M HCl, calculated proton dialysis coefficient (UH+) was 31 x 10-3 m h-1 and iron dialysis coefficient (UFe2+) was 3 x 10-4 m h-1 for the best membrane M2. It corresponded to separation factor (S) of 103 units, which was comparable with literature known best membranes like Neosepta. For effluent solution obtained from a local bentonite mine, membrane M2 showed UH+ value of 37 x 10-3 m h-1 and UFe2+ value of 6 x 10-4 m h-1 suggesting its best utility in acid recovery. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-piperidone(cas: 1445-73-4Related Products of 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.Related Products of 1445-73-4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Yang, Xiao-Guang; Du, Feng-Huan; Li, Jun-Jie; Zhang, Chi published an article in 2022. The article was titled 《Late-Stage Dehydroxyazidation of Alcohols Promoted by Trifunctional Hypervalent Azido-Iodine(III) Reagents》, and you may find the article in Chemistry – A European Journal.Related Products of 109384-19-2 The information in the text is summarized as follows:

A practical method for dehydroxyazidation of alcs. via an SN2 pathway involving PPh3 and trifunctional benziodazolone-based hypervalent azido-iodine(III) reagents, which function as an electrophilic center, an azido source and a base was reported. This mild, chemoselective method was used for late-stage azidation of structurally complex alcs., as well as for a new synthetic route to the antiepileptic drug rufinamide. The reaction mechanism was also investigated both exptl. and computationally. The experimental process involved the reaction of tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas: 109384-19-2Related Products 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.Related Products of 109384-19-2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Srivastava, Vikash; Singh, Surya Pal published an article in 2021. The article was titled 《A facile and regioselective synthesis of t-butyl 4-(5-amino-6-methoxy-2H-indazol-2-yl)piperidine-1-carboxylates and their antiprotozoal activity》, and you may find the article in Chemistry & Biology Interface.Electric Literature of C10H20N2O2 The information in the text is summarized as follows:

Herein, a series of tert-Bu 4-(5-amino-6-methoxy-2H-indazol-2-yl)piperidine-1-carboxylate derivatives were synthesized and evaluated for antiprotozoal activity. Metronidazole and Albendazole were used as reference drugs and compounds I, II and III were found antagonistic to the three protozoa. Nevertheless, all the tested compounds exhibited potency as antiprotozoal agents, with metronidazole being superior to the drug of choice in almost all cases. The experimental part of the paper was very detailed, including the reaction process 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. 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.Electric Literature of C10H20N2O2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Hammock, Bruce D.; McReynolds, Cindy B.; Wagner, Karen; Buckpitt, Alan; Cortes-Puch, Irene; Croston, Glenn; Lee, Kin Sing Stephen; Yang, Jun; Schmidt, William K.; Hwang, Sung Hee published an article in 2021. The article was titled 《Movement to the Clinic of Soluble Epoxide Hydrolase Inhibitor EC5026 as an Analgesic for Neuropathic Pain and for Use as a Nonaddictive Opioid Alternative》, and you may find the article in Journal of Medicinal Chemistry.Reference of tert-Butyl 4-aminopiperidine-1-carboxylate The information in the text is summarized as follows:

This report describes the development of an orally active analgesic that resolves inflammation and neuropathic pain without the addictive potential of opioids. EC5026 (I) acts on the cytochrome P 450 branch of the arachidonate cascade to stabilize epoxides of polyunsaturated fatty acids (EpFA), which are natural mediators that reduce pain, resolve inflammation, and maintain normal blood pressure. EC5026 is a slow-tight binding transition-state mimic that inhibits the soluble epoxide hydrolase (sEH) at picomolar concentrations The sEH rapidly degrades EpFA; thus, inhibiting sEH increases EpFA in vivo and confers beneficial effects. This mechanism addresses disease states by shifting endoplasmic reticulum stress from promoting cellular senescence and inflammation toward cell survival and homeostasis. We describe the synthesis and optimization of EC5026 and its development through human Phase 1a trials with no drug-related adverse events. Addnl., we outline fundamental work leading to discovery of the analgesic and inflammation-resolving CYP450 branch of the arachidonate cascade. 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: 87120-72-7Reference 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. 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.Reference of tert-Butyl 4-aminopiperidine-1-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Design, synthesis and biological activities of novel pleuromutilin derivatives with a substituted triazole moiety as potent antibacterial agents》 was written by Zhang, Zhe; Li, Kang; Zhang, Guang-Yu; Tang, You-Zhi; Jin, Zhen. Safety of 2-(Piperidin-4-yl)ethanol And the article was included in European Journal of Medicinal Chemistry in 2020. The article conveys some information:

A series of novel pleuromutilin derivatives possessing 1,2,3-triazole moieties, I (R1 = NEt2, 4-hydroxypiperidin-1-yl, pyrrolidin-1-yl, etc.) and II (R2 = Me, Ph, 2-ClC6H4, 3-FC6H4, etc.), were synthesized via click reactions under mild conditions. The in vitro antibacterial activities of these derivatives against four strains of S. aureus (MRSA ATCC 43300, ATCC 29213, AD 3, and 144) and one strain of E. coli (ATCC 25922) were tested by the broth dilution method. The majority of the synthesized derivatives displayed potent antibacterial activities against MRSA (MIC = 0.125-2μg/mL). It was also found that most compounds had no significant inhibitory effect on the proliferation of RAW264.7 cells at the concentration of 8μg/mL. Among these derivatives, compound I (R1 = NMe2) (III) (∼1.71 log10 CFU/g) containing dimethylamine group side chain displayed more effective activity than tiamulin (∼0.77 log10 CFU/g) at a dose of 20 mg/kg in reducing MRSA load in thigh infected mice. Addnl., compound III (survival rate was 50%) also displayed superior in vivo efficacy to that of tiamulin (survival rate was 20%) in the mouse systemic model. Structure-activity relationship (SAR) studies resulted in compound III with the most potent in vitro and in vivo antibacterial activity among the series. Moreover, compound III was evaluated in CYP450 inhibition assay and showed moderate in vitro inhibition of CYP3A4 (IC50 = 6.148μM).2-(Piperidin-4-yl)ethanol(cas: 622-26-4Safety of 2-(Piperidin-4-yl)ethanol) was used in this study.

2-(Piperidin-4-yl)ethanol(cas: 622-26-4) have been used as an intermediate in the synthetic preparation of cellular-active allosteric inhibitors of FAKSafety of 2-(Piperidin-4-yl)ethanol

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem