Heterocyclic Building Blocks-piperidine

On May 31, 2017, Dalwadi, Dhwanil A.; Kim, Seongcheol; Schetz, John A. published an article.Name: 4-(4-Chlorophenyl)piperidin-4-ol The title of the article was Activation of the sigma-1 receptor by haloperidol metabolites facilitates brain-derived neurotrophic factor secretion from human astroglia. And the article contained the following:

Glial cells play a critical role in neuronal support which includes the production and release of the neurotrophin brain-derived neurotrophic factor (BDNF). Activation of the sigma-1 receptor (S1R) has been shown to attenuate inflammatory stress-mediated brain injuries, and there is emerging evidence that this may involve a BDNF-dependent mechanism. In this report we studied S1R-mediated BDNF release from human astrocytic glial cells. Astrocytes express the S1R, which mediates BDNF release when stimulated with the prototypical S1R agonists 4-PPBP and (+)-SKF10047. This effect could be antagonized by a selective concentration of the S1R antagonist BD1063. Haloperidol is known to have high affinity interactions with the S1R, yet it was unable to facilitate BDNF release. Remarkably, however, two metabolites of haloperidol, haloperidol I and haloperidol II (reduced haloperidol), were discovered to facilitate BDNF secretion and this effect was antagonized by BD1063. Neither 4-PPBP, nor either of the haloperidol metabolites affected the level of BDNF mRNA as assessed by qPCR. These results demonstrate for the first time that haloperidol metabolites I and II facilitate the secretion of BDNF from astrocytes by acting as functionally selective S1R agonists. The experimental process involved the reaction of 4-(4-Chlorophenyl)piperidin-4-ol(cas: 39512-49-7).Name: 4-(4-Chlorophenyl)piperidin-4-ol

The Article related to human astroglia haloperidol metabolite brain neurotrophic factor sigma receptor, (+)-skf10047, 4-ppbp, astrocytes, bd1063, bdnf, haloperidol (pubchem cid: 3559), haloperidol metabolite i, haloperidol metabolite iii, in situ elisa, ne-100, neurotrophin, pf-04418948, pge2, reduced haloperidol, sigma receptor and other aspects.Name: 4-(4-Chlorophenyl)piperidin-4-ol

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

On May 7, 2020, Hehn, Joerg P.; Blum, Andreas; Hucke, Oliver; Peters, Stefan published a patent.Recommanded Product: 1251006-64-0 The title of the patent was Preparation of pyridine-3-sulfonamide derivatives as amine oxidase copper containing 3 (AOC3) inhibitors and pharmaceutical compositions and uses thereof. And the patent contained the following:

The invention relates to new pyridinyl sulfonamide derivatives of the formula I [ring A = azetidin-1-yl, pyrrolidin-1-yl, 3-azabicyclo[3.1.0]hexan-3-yl, or piperidin-4-yl; R1 = H, F, Ci, Br, cyano, OH, or each (un)substituted C1-4-alkyl, C1-4-alkyloxy, (CH2)m-CO2H, (CH2)m-C(O)O-(C1-4-alkyl), (CH2)m-C(O)-heterocyclyl, (CH2)m-C(O)NH2, (CH2)m-C(O)NH-(C1-4-alkyl), (CH2)m-C(O)-N-(C1-4-alkyl)2, C(O)-NH-C3-6-cycloalkyl, C(O)-NH-heterocyclyl, (CH2)m-NH-C(O)(C1-3-alkyl), N-(C1-3-alkyl)-C(O)-(C1-4-alkyl), N-(C1-3-alkyl)-C(O)NH2, NH-C(O)NH-(C1-4-alkyl), heterocyclyl, or Ph; wherein multiple R1 may be identical or different, if n = 2; n = 1 or 2; m = 0, 1, or 2] or salts thereof. The compounds I or salts thereof are selective inhibitors of AOC3 (amine oxidase, copper containing 3; vascular adhesion protein 1) and are useful for the treatment of cancer, NASH (non-alc. steatohepatitis), pulmonary fibrosis, retinopathy, nephropathy, or stroke. Thus, a solution of 0.19 mmol 1-[1-(6-chloropyridine-3-sulfonyl)piperidin-4-yl]-3-methylimidazolidin-2-one in NMP and Et3N was cooled in an ice bath, treated with a solution of 0.19 mmol tert-butyl-N-[2-(fluoromethylidene)-3-hydroxypropyl]carbamate in 0.5 mL THF and 390μL 2 M sodium tert-butoxide/THF, and stirred at room temperature for 2 h to give 1-[1-[6-((Z)-2-(tert-butoxycarbonylamino)methyl-3-fluoroallyloxy)pyridine-3-sulfonyl]piperidin-4-yl]-3-methylimidazolidin-2-one (isolated as trifluoroacetate salt) which was stirred with CF3CO2H in CH2Cl2 at room temperature for 2 h to give 1-[1-[6-((Z)-2-aminomethyl-3-fluoroallyloxy)pyridine-3-sulfonyl]piperidin-4-yl]-3-methylimidazolidin-2-one trifluoroacetate (II). II showed IC50 of 7, 120, 15,265 nM, and >50.0μM against AOC3, AOC2, AOC1, and monoamine oxidase-A (MAO-A), resp. The experimental process involved the reaction of tert-Butyl 3-(piperidin-4-yl)azetidine-1-carboxylate(cas: 1251006-64-0).Recommanded Product: 1251006-64-0

The Article related to pyridinesulfonamide preparation aoc3 inhibitor, amine oxidase copper containing 3 aoc3 inhibitor, vascular adhesion protein 1 inhibitor, azetidinylsulfonylpyridine pyrrolidinylsulfonylpyridine preparation aoc3 inhibitor, azabicyclohexanylsulfonylpyridine piperidinylsulfonylpyridine preparation aoc3 inhibitor and other aspects.Recommanded Product: 1251006-64-0

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

On May 7, 2020, Hehn, Joerg P.; Blum, Andreas; Hucke, Oliver; Peters, Stefan published a patent.Name: tert-Butyl 3-(piperidin-4-yl)azetidine-1-carboxylate The title of the patent was Preparation of pyridine-3-sulfonamide derivatives as amine oxidase copper containing 3 (AOC3) inhibitors and pharmaceutical compositions and uses thereof. And the patent contained the following:

The invention relates to new pyridinyl sulfonamide derivatives of the formula I [ring A = azetidin-1-yl, pyrrolidin-1-yl, 3-azabicyclo[3.1.0]hexan-3-yl, or piperidin-4-yl; R1 = H, F, Ci, Br, cyano, OH, or each (un)substituted C1-4-alkyl, C1-4-alkyloxy, (CH2)m-CO2H, (CH2)m-C(O)O-(C1-4-alkyl), (CH2)m-C(O)-heterocyclyl, (CH2)m-C(O)NH2, (CH2)m-C(O)NH-(C1-4-alkyl), (CH2)m-C(O)-N-(C1-4-alkyl)2, C(O)-NH-C3-6-cycloalkyl, C(O)-NH-heterocyclyl, (CH2)m-NH-C(O)(C1-3-alkyl), N-(C1-3-alkyl)-C(O)-(C1-4-alkyl), N-(C1-3-alkyl)-C(O)NH2, NH-C(O)NH-(C1-4-alkyl), heterocyclyl, or Ph; wherein multiple R1 may be identical or different, if n = 2; n = 1 or 2; m = 0, 1, or 2] or salts thereof. The compounds I or salts thereof are selective inhibitors of AOC3 (amine oxidase, copper containing 3; vascular adhesion protein 1) and are useful for the treatment of cancer, NASH (non-alc. steatohepatitis), pulmonary fibrosis, retinopathy, nephropathy, or stroke. Thus, 326 mg trans-3-[(6-chloropyridin-3-yl)sulfonyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid methylamide and 216 mg tert-Bu N-[2-(fluoromethylidene)-3-hydroxypropyl]carbamate were dissolved in 1 mL THF and 1 mL DMSO, cooled to 0°, treated with 0.53 mL 2 M sodium tert-butoxide/THF solution, and to give stirred at 0° for 5 min and at room temperature for 35 min to give trans-3-[6-[[2-[[(tert-butoxycarbonyl)amino]methyl]-3-fluoroallyl]oxy]pyridine-3-sulfonyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid methylamide trifluoroacetate. The latter precursor (410 mg) was dissolved in 15 mL CH2Cl2, treated with 266μL CF3CO2H, and stirred at room temperature for 2.5 h to give 38% trans-3-[6-[((E)-2-aminomethyl-3-fluoroallyl)oxy]pyridine-3-sulfonyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid methylamide trifluoroacetate (II). II showed IC50 of 12, 162, 43,370 nM against AOC3, AOC2, and AOC1, resp. The experimental process involved the reaction of tert-Butyl 3-(piperidin-4-yl)azetidine-1-carboxylate(cas: 1251006-64-0).Name: tert-Butyl 3-(piperidin-4-yl)azetidine-1-carboxylate

The Article related to pyridinesulfonamide preparation aoc3 inhibitor, amine oxidase copper containing 3 aoc3 inhibitor, vascular adhesion protein 1 inhibitor, azetidinylsulfonylpyridine pyrrolidinylsulfonylpyridine preparation aoc3 inhibitor, azabicyclohexanylsulfonylpyridine piperidinylsulfonylpyridine preparation aoc3 inhibitor and other aspects.Name: tert-Butyl 3-(piperidin-4-yl)azetidine-1-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

On October 18, 2019, Lin, Zhiyang; Lan, Yun; Wang, Chuan published an article.Formula: C11H14ClNO The title of the article was Reductive Allylic Defluorinative Cross-Coupling Enabled by Ni/Ti Cooperative Catalysis. And the article contained the following:

Tertiary alkyl chlorides, secondary alkyl chlorides and bromides, and primary alkyl bromides underwent chemoselective defluorinative cross-coupling reactions with α-trifluoromethyl aryl alkenes in the presence of (indenyl)TiCl3, NiBr2, and 3,4,7,8-tetramethyl-1,10-phenanthroline to yield α-substituted aryl difluoroalkenes such as 4-MeOC6H4C(:CF2)CH2R (R = t-Bu, cyclohexyl, n-octyl). Unfunctionalized and ester-functionalized alkyl halides underwent cross-coupling under the reaction conditions, while a variety of functionalized aryl alkenes underwent cross-coupling. Using this method, gem-difluoroalkene analogs of azaperone, haloperidol, and benperidol were prepared The experimental process involved the reaction of 4-(4-Chlorophenyl)piperidin-4-ol(cas: 39512-49-7).Formula: C11H14ClNO

The Article related to alkyl aryl difluoroalkene chemoselective preparation, nickel titanium catalyst reductive defluorinative coupling trifluoromethylalkene chloroalkane bromoalkane, tertiary secondary chloroalkane reductive defluorinative coupling trifluoromethyl aryl alkene, secondary primary bromoalkane reductive defluorinative coupling trifluoromethyl aryl alkene and other aspects.Formula: C11H14ClNO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Design, physico-chemical characterization and in vitro biological activity of organogold(III) glycoconjugates》 was published in Dalton Transactions in 2021. These research results belong to Pettenuzzo, Andrea; Vezzu, Keti; Di Paolo, Maria Luisa; Fotopoulou, Eirini; Marchio, Luciano; Via, Lisa Dalla; Ronconi, Luca. Safety of Piperidine-4-carboxamide The article mentions the following:

To develop new metal-based glycoconjugates as potential anticancer agents, four organometallic Au(III)-dithiocarbamato glycoconjugates [Au(III)(2-Bnpy)(SSC-Inp-GlcN)](PF6) (2-Bnpy: 2-benzylpyridine; Inp: isonipecotic moiety; GlcN: amino-glucose scaffold; Au3-Au6) and the corresponding model nonglycosylated counterparts [Au(III)(2-Bnpy)(SSC-Inp-R)](PF6) (R: OEt (Au1), NH2 (Au2)) were generated and characterized by several anal. techniques (elemental anal., FTIR, 1H-/13C-NMR, ESI-MS, UV-visible, x-ray crystallog.). Their stability under physiol.-relevant conditions (PBS solution) and n-octanol/PBS distribution coefficient (D7.4) also were evaluated. Au(III) glycoconjugates showed an antiproliferative effect against ovarian carcinoma A2780 cells, with GI50 values in the low micromolar range. Remarkably, their cell growth inhibitory effect increases upon the addition of a glucose transporter 1 (GLUT1) inhibitor, thus ruling out the involvement of GLUT1 in their transport inside the cell. Addnl. mechanistic studies were carried out in A2780 cells, supporting the hypothesis of a facilitated diffusion mechanism (possibly mediated by glucose transporters other than GLUT1), and revealing their capability to act as topoisomerase I and II inhibitors and to disrupt mitochondrial membrane integrity, giving ROS, thus resulting in the promotion of oxidative stress and, eventually, cell death. 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. 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.Safety of Piperidine-4-carboxamide

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Category: piperidinesOn May 5, 2022 ,《Monodispersed CuO nanoparticles supported on mineral substrates for groundwater remediation via a nonradical pathway》 appeared in Journal of Hazardous Materials. The author of the article were Wang, Gen; Zhang, Yue; Ge, Lei; Liu, Zhuoyue; Zhu, Xiurong; Yang, Shengjiong; Jin, Pengkang; Zeng, Xiangkang; Zhang, Xiwang. The article conveys some information:

Nonradical oxidation based on singlet oxygen (1O2) has attracted great interest in groundwater remediation due to the selective oxidation property and good resistance to background constituents. Herein, recoverable CuO nanoparticles (NPs) supported on mineral substrates (SiO2) were prepared by calcination of surface-coated metal-plant phenolic networks and explored for peroxymonosulfate (PMS) activation to generate 1O2 for degrading organic pollutants in groundwater. CuO NPs with a close particle size (40 nm) were spatially monodispersed on SiO2 substrates, allowing highly exposure of active sites and consequently leading to outstanding catalytic performance. Efficient removal of various organic pollutants was obtained by the supported CuO NPs/PMS system under wide operation conditions, e.g., working pH, background anions and natural organic matters. Chem. scavenging experiments, ESR tests, furfuryl alc. decay and solvent dependency experiments confirmed the formation of 1O2 and its dominant role in pollutants removal. In situ characterization with ATR-FTIR and Raman spectroscopy and computational calculation revealed that a redox cycle of surface Cu(II)-Cu(III)-Cu(II) was responsible for the generation of 1O2. The feasibility of the supported CuO NPs/PMS for actual groundwater remediation was evaluated via a flow-through test in a fixed-bed column, which manifested long-term durability, high mineralization ratio and low metal ion leaching. The experimental part of the paper was very detailed, including the reaction process of Triacetonamine(cas: 826-36-8Category: piperidines)

Triacetonamine(cas: 826-36-8) 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.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

SDS of cas: 826-36-8On May 5, 2022 ,《Modulated construction of Fe-based MOF via formic acid modulator for enhanced degradation of sulfamethoxazole:Design, degradation pathways, and mechanism》 appeared in Journal of Hazardous Materials. The author of the article were Sun, Jian; Wan, Jinquan; Wang, Yan; Yan, Zhicheng; Ma, Yongwen; Ding, Su; Tang, Min; Xie, Yongchang. The article conveys some information:

Metal-organic frameworks (MOFs) have attracted more attention because of their excellent environmental catalytic capabilities. Modulation approach as an advanced assistant strategy is vital essential to enhancing the performance of MOFs. In this study, the modulated method was used to successfully synthesize a group of Fe-based MOFs, with formic acid as the modulator on the synthesis mixture The most modulated sample Fe-MOFs-2 exhibit high sp. surface areas and higher catalytic activity, which could effectively degrade SMX via PS activation, with almost 95% removal efficiency within 120 min. The results revealed that the % RSE of modulated Fe-MOFs-2 increased from 2.31 to 3.27 when compared with the origin Fe-MOFs. This may be due to the addition of formic acid induces the formation of more coordinatively unsaturated metal sites in the catalyst, resulting in structural defects. In addition, the quenching experiment and EPR anal. verified SO-4·and·OH as the major active free radicals in the degradation process. Modulated Fe-MOFs-2 demonstrated good reusability and stability under fifth cycles. Finally, four possible degradation pathways and catalytic mechanism of Fe-MOFs-2 was tentatively proposed. Our work provides insights into the rational design of modulated Fe-MOFs as promising heterogeneous catalysts for advanced wastewater treatment. The experimental part of the paper was very detailed, including the reaction process of Triacetonamine(cas: 826-36-8SDS of cas: 826-36-8)

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.SDS of cas: 826-36-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2019,Organic Chemistry Frontiers included an article by Xu, Yuliang; Xu, Ze-Jun; Liu, Zhao-Peng; Lou, Hongxiang. Formula: C10H20N2O2. The article was titled 《Visible-light-mediated de-aminative alkylation of N-arylamines with alkyl Katritzky salts》. The information in the text is summarized as follows:

A visible-light-mediated de-aminative alkylation of N-arylamines was developed, providing direct access to α-amino C-H functionalization of N-arylamines from readily available Katritzky salts under mild conditions to get tetrahydroisoquinolines, e.g., I, and alkyl-N-aryl-aminoesters, e.g., II. In some cases, this operationally simple protocol could be performed in the absence of a photocatalyst. A wide range of substrates and functional groups were tolerated. The utility of this approach was highlighted by its application to the late-state modification of drug mols., natural products and peptides. The experimental part of the paper was very detailed, including the reaction process of tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7Formula: C10H20N2O2)

tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7) 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.Formula: C10H20N2O2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

The author of 《Robust poly(aryl piperidinium)/N-spirocyclic poly(2,6-dimethyl-1,4-phenyl) for hydroxide-exchange membranes》 were Chen, Nanjun; Lu, Chuanrui; Li, Yunxi; Long, Chuan; Zhu, Hong. And the article was published in Journal of Membrane Science in 2019. Recommanded Product: 1-Methyl-4-piperidone The author mentioned the following in the article:

Herein, for realizing the high efficiency and long lifetime of hydroxide exchange membranes (HEMs) for alk. membrane fuel cell (AMFC) applications, a series of robust poly(biphenyl piperidinium) (PBP)/6-azaspiro[5.5] undecane (ASU)-functionalized polyphenyl ether (ASU-PPO) membranes were prepared by a crosslinked strategy. Crosslinked PBP-ASU-PPO membrane combines the advantage of PBP and ASU-PPO membranes as well as addresses the problem of high water uptake of PBP and the insufficient film-forming property of ASU-PPO. As expected, these crosslinked PBP-ASU-PPO membranes exhibit commendably comprehensive performances, such as good ion conductivity, durability, and mech. properties. The crosslinked PBP-ASU-PPO membrane reaches a maximum OH- conductivity of 128 mS/cm at 80 °C, accompanying with a 15.7% membrane swelling. Besides, only 13.6% degradation in Cl- conductivity was observed in PBP-ASU-PPO after alk. treatment in 1 M NaOH at 80 °C for 2000 h. Besides, the selected PBP-ASU-PPO membrane achieves a maximum power d. of 324 mW/cm2 at c.d. of 750 mA/cm2. The results came from multiple reactions, including the reaction of 1-Methyl-4-piperidone(cas: 1445-73-4Recommanded Product: 1-Methyl-4-piperidone)

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.Recommanded Product: 1-Methyl-4-piperidone

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

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.

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

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem