Category: piperidines

《Amides of pyrrole- and thiophene-fused anthraquinone derivatives: a role of the heterocyclic core in antitumor properties》 was written by Tikhomirov, Alexander S.; Litvinova, Valeria A.; Andreeva, Daria V.; Tsvetkov, Vladimir B.; Dezhenkova, Lyubov G.; Volodina, Yulia L.; Kaluzhny, Dmitry N.; Treshalin, Ivan D.; Schols, Dominique; Ramonova, Alla A.; Moisenovich, Mikhail M.; Shtil, Alexander A.; Shchekotikhin, Andrey E.. Quality Control of tert-Butyl 4-aminopiperidine-1-carboxylate And the article was included in European Journal of Medicinal Chemistry in 2020. The article conveys some information:

A new series of naphtho[2,3-f]indole-3-carboxamides I [R1 = Me; R2 = (3S)-3-aminopyrrolidin-1-yl, ((3S)-pyrrolidin-3-yl)amino, 4-amino-1-piperidyl, etc.; X = NH, NMe, NBn, etc.;] and anthra[2,3-b]thiophene-3-carboxamides I [R1 = H, X = S] was synthesized via coupling the resp. acids with cyclic diamines and dissected the role of the heterocyclic core in antitumor properties. New compounds demonstrated a submicromolar antiproliferative potency close to doxorubicin (Dox) against five tumor cell lines of various tissue origin. In contrast to Dox, the new compounds were similarly cytotoxic for HCT116 colon carcinoma cells (wild type p53) and their isogenic p53 knockout counterparts. Compound I [R1 = Me; R2 = (3S)-3-aminopyrrolidin-1-yl; X = NH] formed more affine complexes with DNA duplex than furan and thiophene analogs, a property that could be translated into a stronger inhibition of topoisomerase 1 mediated DNA unwinding. At tolerable doses the water soluble derivative I [R1 = Me; R2 = (3S)-3-aminopyrrolidin-1-yl; X = NH] significantly inhibited tumor growth (up to 79%) and increased the lifespan (153%) of mice bearing P388 lymphoma transplants. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7Quality Control of tert-Butyl 4-aminopiperidine-1-carboxylate)

tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7) belongs to anime. In organic chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (NH3), wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines).Quality Control of tert-Butyl 4-aminopiperidine-1-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Recommanded Product: 826-36-8On March 1, 2019, Gao, Panpan; Tian, Xike; Nie, Yulun; Yang, Chao; Zhou, Zhaoxin; Wang, Yanxin published an article in Chemical Engineering Journal (Amsterdam, Netherlands). The article was 《Promoted peroxymonosulfate activation into singlet oxygen over perovskite for ofloxacin degradation by controlling the oxygen defect concentration》. The article mentions the following:

Recently, perovskite is becoming a promising alternative as peroxymonosulfate (PMS) activator for the remediation of organic pollutants in water. But the factor determining PMS activation efficiency of perovskite and the evolution of reactive oxygen species (ROS) remain equivocal and elusive. In this study, we proposed an oxygen defect dependent PMS activation mechanism over perovskite with the singlet oxygen (1O2) as the dominant ROS. Among the tested four perovskites, ofloxacin (OFX) degradation efficiency increased with the following order: LaFeO3 < LaZnO3 < LaMnO3 < LaNiO3, which agreed well with their oxygen defect amounts based on XPS and ESR (EPR) anal. The results clearly demonstrated a good relationship among oxygen defects in LaBO3, OFX degradation efficiency and 1O2 concentration Moreover, 1O2 evolution mechanism over perovskite by decreasing the activation energy of PMS self-decomposition was proposed. The 1O2 mediated OFX degradation pathway was further studied by HPLC-MS technique and three-dimensional excitation-emission matrix fluorescence spectroscopy (3D EEMs). This work provides a new insight into PMS activation by perovskites and favors its application in actual water treatment. In the experiment, the researchers used many compounds, for example, Triacetonamine(cas: 826-36-8Recommanded Product: 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.Recommanded Product: 826-36-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Application of 126832-81-3On October 31, 1994 ,《Synthesis of 3,5-lutidine by catalytic transfer hydrogenation via 1,2,5,6-tetrahydropyridine》 was published in Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry. The article was written by Sathe, Dhananjay G.; Kulkarni, Vithal M.. The article contains the following contents:

Substituted pyridines, e.g. 3,5-lutidine, have been prepared from the corresponding N-benzyl-1,2,5,6-tetrahydropyridines by catalytic transfer hydrogenation in one stage. A mechanism for such a catalytic transfer hydrogenation (CTH) has been proposed. In the experiment, the researchers used 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

Mohd Sarofil, Anith Dzhanxinah; Devina, Winda; Albertina, Ingrid; Chandra, Christian; Kim, Jaehoon published an article on February 25 ,2022. The article was titled 《Toad egg-like bismuth nanoparticles encapsulated in an N-doped carbon microrod via supercritical acetone as anodes in lithium-ion batteries》, and you may find the article in Journal of Industrial and Engineering Chemistry (Amsterdam, Netherlands).Application of 826-36-8 The information in the text is summarized as follows:

A toad egg-inspired structure comprising bismuth (Bi) nanoparticles (NPs) contained in a carbon microrod shell (Bi@C) was synthesized via the one-pot supercritical acetone (scAct) route and subsequent carbonization. During the formation of Bi NPs in scAct in the presence of nitric acid, a few decomposed acetone mols. acted as carbon sources, which generated an albumen-like N-doped carbon microrod with an average shell thickness of 38 nm and were embedded with yolk-like Bi NPs having size in the range of 30-200 nm. The densely packed Bi NPs inside the carbon micron shell resulted in a high Bi loading of 78 wt%. When utilized for Li storage, the Bi@C delivered a high reversible capacity of 337 mAh g-1 after 70 cycles at 0.05 A g-1, long-term cyclability of 0.04 decay per cycle for 1000 cycles at 1 A g-1, and high volumetric energy d. of 870 mAh cm-3. The use of a mixed ether- and ester-based electrolyte in the Bi@C cell reduced the resistivity and increased the capacitive contribution, thereby resulting in a better high-rate performance and long-term stability than those obtained using conventional ester-based electrolytes. The experimental part of the paper was very detailed, including the reaction process of Triacetonamine(cas: 826-36-8Application of 826-36-8)

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.Application of 826-36-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Recommanded Product: 1445-73-4In 2021 ,《Design, synthesis of novel pyrazolopyridine derivatives and CREBBP bromodomain inhibitors docking and molecular dynamics》 appeared in Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry. The author of the article were Saamanthi, M.; Aruna, S.; Girija, R.; Vinod, D.. The article conveys some information:

A sequence of novel compounds pyrazolopyridines I [R = Ph, 2-phenylethenyl, 3-(trifluoromethyl)phenyl, 2,4-dimethylphenyl, etc.; X = O, S] have been prepared by a general synthetic method. Due to high efficiency and selectivity, anticancer agents consisting of combined mols. have gained great interests. The IC50 values have been determined against cell line U937, and the results obtained indicate the potential effects against cancer cell line. The cell potency of cell line is best for compounds I [R = 4-(trifluoromethyl)phenyl; X = O] IC50 = 62.5μM, I (R = Ph; X = S) IC50 = 62.5μM, I (R = Ph; X = O) IC50 = 31.2μM, I [R = 3-(trifluoromethyl)phenyl; X = O] IC50 = 31.2μM, selectivity and in vivo. Further, the mol. docking studies indicate that substituted pyrazolo[4,3-c]pyridine derivatives I show good anticancer activity in the medicinal field. The ease of synthesis and the significant biol. activities make these compounds I potential new frameworks for progress of cancer therapeutics. Compound I (R = 2,4-dimethylphenyl; X = O) shows anticancer effect in cancer cell lines and in vivo that corresponds with antitumor activity in an AML cancer type. For the mol. docking with the ligands, the RMSD value has been calculated, and the protein with the least RMSD is found to be 5KTU screening with 20 small mols. The experimental process involved the reaction of 1-Methyl-4-piperidone(cas: 1445-73-4Recommanded Product: 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.Recommanded Product: 1445-73-4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Turk, Benjamin E.; Jiang, Hongsi; Liu, Jun O. published an article in Proceedings of the National Academy of Sciences of the United States of America. The title of the article was 《Binding of thalidomide to α1-acid glycoprotein may be involved in its inhibition of tumor necrosis factor α production》.Recommanded Product: Benzyl (2,6-dioxopiperidin-3-yl)carbamate The author mentioned the following in the article:

In addition to its well known sedative and teratogenic effects, thalidomide also possesses potent immunomodulatory and antiinflammatory activities, being most effective against leprosy and chronic graft-vs.-host disease. The immunomodulatory activity of thalidomide has been ascribed to the selective inhibition of tumor necrosis factor α from monocytes. The mol. mechanism for the immunomodulatory effect of thalidomide remains unknown. To elucidate this mechanism, we synthesized an active photoaffinity label of thalidomide as a probe to identify the mol. target of the drug. Using the probe, we specifically labeled a pair of proteins of 43-45 kDa with high acidity from bovine thymus extract Purification of these proteins and partial peptide sequence determination revealed them to be α1-acid glycoprotein (AGP). We show that the binding of thalidomide photoaffinity label to authentic human AGP is competed with both thalidomide and the nonradioactive photoaffinity label at concentrations comparable to those required for inhibition of production of tumor necrosis factor α from human monocytes, suggesting that AGP may be involved in the immunomodulatory activity of thalidomide. The experimental process involved the reaction of Benzyl (2,6-dioxopiperidin-3-yl)carbamate(cas: 24666-55-5Recommanded Product: Benzyl (2,6-dioxopiperidin-3-yl)carbamate)

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

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2019,Proceedings of the National Academy of Sciences of the United States of America included an article by Hong, W. David; Benayoud, Farid; Nixon, Gemma L.; Ford, Louise; Johnston, Kelly L.; Clare, Rachel H.; Cassidy, Andrew; Cook, Darren A. N.; Siu, Amy; Shiotani, Motohiro; Webborn, Peter J. H.; Kavanagh, Stefan; Aljayyoussi, Ghaith; Murphy, Emma; Steven, Andrew; Archer, John; Struever, Dominique; Frohberger, Stefan J.; Ehrens, Alexandra; Hubner, Marc P.; Hoerauf, Achim; Roberts, Adam P.; Hubbard, Alasdair T. M.; Tate, Edward W.; Serwa, Remigiusz A.; Leung, Suet C.; Qie, Li; Berry, Neil G.; Gusovsky, Fabian; Hemingway, Janet; Turner, Joseph D.; Taylor, Mark J.; Ward, Stephen A.; O’Neill, Paul M.. Safety of 2-(Piperidin-4-yl)ethanol. The article was titled 《AWZ1066S, a highly specific anti-Wolbachia drug candidate for a short-course treatment of filariasis》. The information in the text is summarized as follows:

Onchocerciasis and lymphatic filariasis are two neglected tropical diseases that together affect ∼ 157 million people and inflict severe disability. Both diseases are caused by parasitic filarial nematodes with elimination efforts constrained by the lack of a safe drug that can kill the adult filaria (macrofilaricide). Previous proof-of-concept human trials have demonstrated that depleting > 90% of the essential nematode endosymbiont bacterium, Wolbachia, using antibiotics, can lead to permanent sterilization of adult female parasites and a safe macrofilaricidal outcome. AWZ1066S is a highly specific anti-Wolbachia candidate selected through a lead optimization program focused on balancing efficacy, safety and drug metabolism/pharmacokinetic (DMPK) features of a thienopyrimidine/quinazoline scaffold derived from phenotypic screening. AWZ1066S shows superior efficacy to existing anti-Wolbachia therapies in validated preclin. models of infection and has DMPK characteristics that are compatible with a short therapeutic regimen of 7 days or less. This candidate mol. is well-positioned for onward development and has the potential to make a significant impact on communities affected by filariasis. The experimental process involved the reaction of 2-(Piperidin-4-yl)ethanol(cas: 622-26-4Safety of 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.Safety of 2-(Piperidin-4-yl)ethanol

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Pei, Dan-Ni; Liu, Chang; Zhang, Ai-Yong; Pan, Xiao-Qiang; Yu, Han-Qing published their research in Proceedings of the National Academy of Sciences of the United States of America on December 8 ,2020. The article was titled 《In situ organic Fenton-like catalysis triggered by anodic polymeric intermediates for electrochemical water purification》.Application of 826-36-8 The article contains the following contents:

Organic Fenton-like catalysis was recently developed for water purification, but redox-active compounds have to be ex situ added as oxidant activators, causing secondary pollution problem. Electrochem. oxidation is widely used for pollutant degradation, but suffers from severe electrode fouling caused by high-resistance polymeric intermediates. Herein, the authors develop an in situ organic Fenton-like catalysis by using the redox-active polymeric intermediates, e.g., benzoquinone, hydroquinone, and quinhydrone, generated in electrochem. pollutant oxidation as H2O2 activators. By taking phenol as a target pollutant, the in situ organic Fenton-like catalysis not only improves pollutant degradation, but also refreshes working electrode with a better catalytic stability. Both 1O2 nonradical and A·OH radical are generated in the anodic phenol conversion in the in situ organic Fenton-like catalysis. The authors’ findings might provide a new opportunity to develop a simple, efficient, and cost-effective strategy for electrochem. water purification In the part of experimental materials, we found many familiar compounds, such as Triacetonamine(cas: 826-36-8Application of 826-36-8)

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.Application of 826-36-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Zhang, Jianjun; Zhang, Kaiyu; Liang, Xian; Yu, Weisheng; Ge, Xiaolin; Shehzad, Muhammad A.; Ge, Zijuan; Yang, Zhengjin; Wu, Liang; Xu, Tongwen published an article in 2021. The article was titled 《Self-aggregating cationic-chains enable alkaline stable ion-conducting channels for anion-exchange membrane fuel cells》, and you may find the article in Journal of Materials Chemistry A: Materials for Energy and Sustainability.Application of 1445-73-4 The information in the text is summarized as follows:

Precise manipulation of the polyelectrolyte self-assembly process, to form the desired microstructure with ion-conducting channels, is of fundamental and technol. importance to many fields, such as fuel cells, flow batteries and electrodialysis. To fabricate anion exchange membranes (AEMs) with highly conductive and alk. stable ion-conducting channels, we hereby report a strategy for designing self-aggregating side chains with optimized alk. stability, by inserting dipolar ethylene oxide (EO) spacers in the cationic side chain. Simulation and nano-scale microscopy analyses verify the self-assembly process of the flexible side chain with cation-dipole interaction to construct interconnected ionic highways for fast water and ion transportation. The resulting O-PDQA AEM exhibits higher hydroxide conductivity (106 mS cm-1 at 80 °C) and a competitive peak power d. (1.18 W cm-2 at 70 °C) in alk. H2/O2 single-cell fuel cells. Moreover, O-PDQA shows excellent alk. stability with over 96% conductivity retention after storage in 2 M NaOH solution at 80 °C for 1080 h. This new concept of introducing dipolar moieties in the cationic side chain can accelerate the development of technologies that involve polyelectrolytes. The experimental part of the paper was very detailed, including the reaction process of 1-Methyl-4-piperidone(cas: 1445-73-4Application 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.Application of 1445-73-4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Electric Literature of C6H12N2OOn March 31, 2021, Xin, Chao; Cheng, Cuilin; Hou, Kexin; Bao, Meili; Zhang, Hua; Wang, Zhenyu published an article in Materials Science & Engineering, C: Materials for Biological Applications. The article was 《A novel melanin complex displayed the affinity to HepG2 cell membrane and nucleus》. The article mentions the following:

Chitosan-melanin complex from Catharsius molossus L. has proven to possess superior pharmaceutical excipient performance and may be the new source of water-soluble protein-free natural melanin. Herein, it was enzymically hydrolyzed into the chitooligosaccharide-melanin complex (CMC) whose main chem. units were composed of eumelanin and chitooligosaccharides and showed three-layer structures. Addnl., this biomacromol. could self-assemble into 40 nm nanoparticles (CMC Nps) in a weakly acidic aqueous solution Interestingly, CMC displayed strong affinity for cell membrane by binding the phosphatidylserine, glycoprotein, glycolipids and glycosaminoglycans accumulated on the surface of tumor cells, notably, CMC Nps could enter cells and mainly target the nucleus by interacting with DNA and/or RNA substrates located around the nucleus to disrupt the proliferation and apoptosis processes. The findings suggest CMC may be the novel material for subcellular organelle targeting of cancer cells.Piperidine-4-carboxamide(cas: 39546-32-2Electric Literature of C6H12N2O) 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.Electric Literature of C6H12N2O

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem