Heterocyclic Building Blocks-piperidine

Ohtani, Bunsho; Kusakabe, Satoshi; Okada, Katsumi; Tsuru, Shigeto; Nishimoto, Sei-ichi; Amino, Yusuke; Izawa, Kunisuke; Nakato, Yoshihiro; Matsumura, Michio; Nakaoka, Yasuhiro; Nosaka, Yoshio published their research in Journal of the Chemical Society, Perkin Transactions 2 on February 28 ,2001. The article was titled 《Photocatalytic stereoselective N-cyclization of 2,6-diaminopimelic acid into piperidine-2,6-dicarboxylic acid by an aqueous suspension of activated cadmium(II) sulfide particles》.Computed Properties of C7H11NO4 The article contains the following contents:

Photoirradiation at a wavelength of >300 nm of a deaerated suspension of cadmium(II) sulfide (CdS) particles in an aqueous solution of a mixture of stereoisomers of 2,6-diaminopimelic acid [DAP; (S,S):(R,S):(R,R) = 1:2:1] produced piperidine-2,6-dicarboxylic acid (PDC) via a redox-combined mechanism including oxidation and reduction by pos. holes and photoexcited electrons, resp. Both the yield and trans:cis ratio of PDC markedly depended on the kinds of CdS photocatalysts, their pre-treatment, and the loading of fine platinum (or its oxide) particles. A CdS photocatalyst prepared by heat treatment of a com. powder in hexagonal (wurtzite) structure at 1023 K in the presence of a small amount of air gave the highest yield and trans:cis ratio. Analyses of the activated CdS powder by powder x-ray diffraction (XRD), photoluminescence (PL), XPS, ESR, and BET surface area measurements revealed the formation of sulfur vacancies due to heat treatment, which promote the photoinduced cadmium metal (Cd0) deposition. The Cd0, deposited in situ on the CdS surface and detected by reduction of methylviologen, may act as a reduction site for photoexcited electrons toward a cyclic Schiff base intermediate produced by oxidation of DAP with pos. holes followed by deamination and intramol. condensation. Optically pure (R,R)- or (S,S)-PDCs were prepared successfully by photocatalytic reaction with the activated CdS particles using (R,R)- or (S,S)-DAPs, indicating that stereoselective conversion of organic compounds can be achieved via photocatalytic reaction under controlled conditions. The results came from multiple reactions, including the reaction of Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1Computed Properties of C7H11NO4)

Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1) 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.Computed Properties of C7H11NO4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Computed Properties of C6H11NOIn 2021 ,《Determination of phenolics and flavonoids of some useful medicinal plants and bioassay-guided fractionation substances of Sclerocarya birrea (A. Rich) Hochst stem (bark) extract and their efficacy against Salmonella typhi》 was published in Frontiers in Chemistry (Lausanne, Switzerland). The article was written by Abdallah, Muhammad Salihu; Mustafa, Muskhazli; Nallappan, Meenakshii A. P.; Choi, Sangho; Paik, Jin-Hyub; Rusea, Go. The article contains the following contents:

Gallic acid and catechin are the most abundant phenolic and flavonoid contents found in all plant extracts The contents and the bioassay-guided fractionating substances of the Sclerocarya birrea (A. Rich) Hochst (Anacardiaceae) fraction played vital roles. The goals of the study were to determine the contents of some useful medicinal plants and the bioassay guided fractionation substances of S. birrea fraction compounds capable of acting against Salmonella isolate using LC-MS/LC-HRMS (Dionex ultimate 3000 RS UPLC with Thermo Scientific Q Exactive Orbitrap Hybrid Tandem Mass Spectrometer). The Folin-Ciocalteu reagent procedure and flavonoid content determination were conducted spectrophotometrically. Bioassay-guided fractionation, chronol. partitioning, and screening of the antibacterial action against Salmonella typhi were performed. The Et acetate fraction extracts of S. birrea stem (bark) extract were analyzed using LC-MS/LCHRMS. The gallic acid content increased tremendously in Vachellia nilotica (L.) P.J.H. Hurter and Mabb (Fabaceae) pod extracts with curve fitting (R2 = 0.9958). Catechin content increase was significantly increased in S. birrea stem (bark) extracts followed by that of V. nilotica pod extracts with curve fitting (R2 = 0.9993); they were all significantly different in the Guiera senegalensis J.F. Gmel. and the Leptadenia lanceolata (Poir.) Goyder leaves extracts at p value <0.0001. Subsequently, 10 mg/mL of S. birrea stem (bark) Et acetate fraction extract was the MIC, where no MBC was recorded and susceptible to the pos. control with the highest inhibition zone, followed by the Et acetate fraction extract at 10 mg/mL (9.7 ± 0.0) at Turkey's p < 0.0001. Vidarabine is one of the novel compounds, specifically having antimicrobial actions, found in the S. birrea stem (bark). Reasonable amounts of phenolic and flavonoid contents determined the actions of the individual plant extract The experimental part of the paper was very detailed, including the reaction process of 1-Methyl-4-piperidone(cas: 1445-73-4Computed Properties of C6H11NO)

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.Computed Properties of C6H11NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《HDAC6 inhibitor accelerates wound healing by inhibiting tubulin mediated IL-1β secretion in diabetic mice》 was written by Karnam, Kalyani; Sedmaki, Kavitha; Sharma, Pravesh; Routholla, Ganesh; Goli, Sriharshini; Ghosh, Balaram; Venuganti, Venkata Vamsi Krishna; Kulkarni, Onkar Prakash. Related Products of 1445-73-4 And the article was included in Biochimica et Biophysica Acta, Molecular Basis of Disease in 2020. The article conveys some information:

Delayed wound healing in diabetes is characterized by sustained activation of inflammasome and increased expression of IL-1β in macrophages. Identification and validation of novel pathways to regulate IL-1β expression will provide therapeutic targets for diabetic wounds. Here we report sustained over-expression of histone deacetylase 6 (HDAC6) in wounds of diabetic mice and its role in delayed wound healing. Topical application of HDAC6 inhibitor; Tubastatin A (TSA) gel promoted the wound healing in diabetic mice. TSA hydrogel reduced the infiltration of neutrophils, T-cells and macrophages in the early phase of wound healing. TSA treatment promoted the wound healing by inducing collagen deposition, angiogenesis (CD31) and fibrotic factors (TGF-β1) in the late phase of healing. Protein anal. of the diabetic wounds treated with TSA showed increased acetylated α-tubulin and decreased levels of mature IL-1β with no significant effect on the expression of pro-IL-1β, pro-caspase-1 and active caspase-1. In in vitro assays, macrophages exhibited upregulation of HDAC6, IL-1β and downregulation of IL-10 upon stimulation with high glucose and LPS. TSA inhibited the IL-1β secretion and promoted IL-10 in stimulated macrophages with high glucose and LPS. Further investigations showed that TSA inhibits IL-1β release by inhibiting tubulin dependent lysosomal exocytosis without affecting its transcription and maturation. Nocodazole (known acetylation inhibitor) pre-treatment inhibited TSA effect on IL-1β secretion in high glucose stimulated macrophages. Overall, our findings indicate that sustained HDAC6 expression in diabetic wounds contributes to impaired healing responses and HDAC6 may represent a new therapeutic target for diabetic wounds. In the experimental materials used by the author, we found 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

Safety of TriacetonamineOn March 20, 2022, Wu, Xuan; Sun, Dedong; Ma, Hongchao; Ma, Chun; Zhang, Xinxin; Hao, Jun published an article in Colloids and Surfaces, A: Physicochemical and Engineering Aspects. The article was 《Activation of peroxymonosulfate by magnetic CuFe2O4@ZIF-67 composite catalyst for the study on the degradation of methylene blue》. The article mentions the following:

In this research, a novel magnetically recoverable composite catalyst, CuFe2O4 @ZIF-67, was synthesized. CuFe2O4@ZIF-67 composite catalyst was applied to degrade methylene blue (MB) in water by activating peroxymonosulfate (PMS). The results showed that the degradation rate of MB (20 mg/L) reached 98.9% in 30 min in the 0.2-CuFe2O4@ZIF-67 (75 mg/L) + PMS (125 mg/L) system. Both ESR (EPR) studies and radical quenching experiments revealed that SO-4•, •OH, 1O2 and •O-2 were involved in the degradation of MB. We proposed a catalytic mechanism of PMS activation by CuFe2O4@ZIF-67. With the synergistic effect of Co3+/Co2+, Fe3+/Fe2+ and Cu2+/Cu+ redox cycles, it can keep its outstanding catalytic activity. Recycling tests showed that the removal rate of MB can still be maintained above 85%, indicating that CuFe2O4@ZIF-67 has good reusability. In general, owing to its reusability and excellent catalytic activity, the CuFe2O4@ZIF-67 composite catalyst has a good application prospect in water pollution control.Triacetonamine(cas: 826-36-8Safety of Triacetonamine) was used in this study.

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

In 1957,Recueil des Travaux Chimiques des Pays-Bas et de la Belgique included an article by Beyerman, H. C.; Eenshuistra, J.; Eveleens, W.. Formula: C7H14ClNO2. The article was titled 《Absolute configuration of sedamine and sedridine》. The information in the text is summarized as follows:

Synthetic 1-phenyl-2-(2-N-methylpiperidyl)ethanol (I) was previously separated into its 2-diastereoisomeric pairs, (±)-sedamine (Ia) and (±)-allosedamine (Ib) (cf. B. and Enthoven, C.A. 50, 13005i). By using Dg-(+)-dibenzoyltartaric acid, Ia, m. 89-90°, gave (+)-sedamine Dg-bis(dibenzoyltartrate) monohydrate, m. 133-4°, [α]D18 87.5 ± 1.7° (c 3.00, alc.), converted to (+)-sedamine, m. 61-2°, [α]D18 91.5 ± 1° (c 3.29, alc.) (not previously isolated from Sedum acre L.). Similar resolution of Ib through (-)-allosedamine Lg-bis(dibenzoyltartrate) monohydrate, m. 110-11°, [α]D18 -82.5 ± 1° (c 2.01, alc.) and (+)-allosedamine Dg-bis(dibenzoyltartrate) monohydrate, m. 112-13°, [α]D19 83.2 ± 1° (c 1.74, alc.) yielded (+)-allosedamine (Ic), m. 79-80°, [α]D20 18.6 ± 0.4° (c 2.42, alc.), and (-)-allosedamine (Id), m. 79-80°, [α]D21 -18.9 ± 0.9° (c 2.06, alc.); chloroaurate, m. 182-3°. Ic or Id is probably identical with the alkaloid, C14H21NO, of Wieland, et al. (C.A. 34, 1088). Ic and (-)-sedamine (II) refluxed 1 hr. with CrO3 in 4NH2SO4 gave (+)-N-methylpipecolic acid HCl salt, m. 211-12°, [α]D20 47.2 ± 0.8° (c 2.42, H2O), and (-)-N-methylpipecolic acid HCl salt, m. 211-12° [α]D20 47.2 ± 0.8° (c 2.42, H2O), identical with the HCl salts originating from the N-methylation of (-)- or (+)-pipecolic acid (III) with HCHO. III is related via the alkaloid baikiaine with L-aspartic acid (cf. King, et al., C.A. 45, 7083b) and accordingly, in II and Id, the arrangement of the bonds around the piperidine ring asym. C atom corresponds to the Ls configuration. The absolute configuration of the piperidine part of natural (+)-sedridine (IV), m. 83-4°, [α]D22 26° (c 1.28, alc.), [α]D20 286 ± 0.9° (c 2.28, alc.), may be deduced from the literature data and it would seem that the asym. center in the piperidine ring of IV also has the Ls configuration. These stereochem. findings are consistent with the conception of the origin of the piperidine portion of II and IV from L-amino acids. The experimental part of the paper was very detailed, including the reaction process of 1-Methylpiperidine-2-carboxylic acid hydrochloride(cas: 25271-35-6Formula: C7H14ClNO2)

1-Methylpiperidine-2-carboxylic acid hydrochloride(cas: 25271-35-6) 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.Formula: C7H14ClNO2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Product Details of 1445-73-4In 2020 ,《Construction and bioimaging application of novel indole heptamethine cyanines containing functionalized tetrahydropyridine rings》 appeared in Journal of Materials Chemistry B: Materials for Biology and Medicine. The author of the article were Ma, Xiaoxie; Zhang, Chen; Feng, Lan; Liu, Sheng Hua; Tan, Ying; Yin, Jun. The article conveys some information:

IR780 as a com. available dye with near-IR emission has been extensively applied in fluorescent probes and bioimaging. In this work, to further intensify the optical behavior, a tetrahydropyridine ring was used to replace the cyclohexene ring at the center of IR780, forming a cyanine dye Cy-NH with near-IR emission. Photophys. properties demonstrated that Cy-NH exhibits good optical performance. In particular, Cy-NH contains two functional reaction sites (e.g. Cl and NH sites on the tetrahydropyridine ring) and can be used to construct functional cyanine dyes. Investigation on imaging showed that these cyanines can be used as near-IR fluorescent imaging agents in living cells and in vivo. In addition to this study using 1-Methyl-4-piperidone, there are many other studies that have used 1-Methyl-4-piperidone(cas: 1445-73-4Product Details of 1445-73-4) was used in this study.

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.Product Details of 1445-73-4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Recommanded Product: 59234-40-1On October 31, 1982 ,《The excitatory actions of a series of piperidine dicarboxylates on central neurons of the rat, snail, leech, and horseshoe crab and on crab neuromuscular junction》 was published in Comparative Biochemistry and Physiology, C: Comparative Pharmacology. The article was written by King, D. J.; McBain, Anne E.; Jais, M. Mat; Roberts, C. Jane; Collins, J. F.; Wheal, H. V.; Walker, R. J.. The article contains the following contents:

The 2,3- [46026-75-9], 2,4- [84211-45-0], 2,5- [84619-48-7], and 2,6-piperidine dicarboxylates [59234-40-1] were devoid of direct or indirect effects of the Helix neuron; the 2,5-analog mimicked the actions of L-glutamate (I) [56-86-0] on Limulus neurons, and these were inhibited by I. All 4 piperidines mimicked the actions of I on Hirudo and rat neurons and Eupagurus muscle. All were weak agonists on rat neurons, whereas on Hirudo neurons the 2,5-analog was the most potent; on the Eupagurus muscle the 2,3- and 2,6-analogs were the most potent. All 4 piperidines potentiated the action of I on rat and Hirudo neurons and on Eupagurus leg muscle and of muscle excitatory junction potentials. Thus, there are probably differences between I receptors used in the study, and the preferred conformation for I on crab leg muscle may be the partially folded one and that for Hirudo neurons is more extended. The experimental part of the paper was very detailed, including the reaction process of Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1Recommanded Product: 59234-40-1)

Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1) 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.Recommanded Product: 59234-40-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Safety of TriacetonamineOn October 1, 2022 ,《Plasmonic silica-gold core-shell nanoparticles: Interaction with organic dyes for light-induced applications》 was published in Journal of Photochemistry and Photobiology, A: Chemistry. The article was written by Martinez Porcel, Joaquin E.; Churio, Maria S.; Moya, Sergio E.; Arce, Valeria B.; Martire, Daniel O.. The article contains the following contents:

The interaction of plasmonic nanoparticles with ground- and excited states of dyes can strongly affect the fluorescence of the organic mols., as well as the generation of reactive oxygen species (ROS). This interaction can be exploited in bioimaging and photodynamic therapy (PDT) of tumors. In this line, we prepare here gold-decorated silica nanoparticles (SiO2@Au NPs) via a novel method, which combines the synthesis of gold nuclei through reduction of a Au3+ salt, with a photochem. route driving the growth of the metallic nuclei. In this hybrid nanomaterial, the surface groups of the silica particle can potentially act as adsorption sites for the dyes in a range close to the gold nanoparticles, favoring the interaction. The ability of SiO2@Au NPs to enhance fluorescence and generation of ROS upon irradiation of riboflavin and Rose Bengal is evaluated. SiO2@Au enhance the fluorescence emission of both dyes, although through different mechanisms. The excitation of the flavin is enhanced, whereas for Rose Bengal the radiative decay rate is increased by the nanoparticles. For neither of the two dyes, SiO2@Au affect ROS generation as measured by ESR (EPR) spectroscopy. However, the increase in fluorescence emission observed for both dyes demonstrates the potential application of SiO2@Au in fluorescence-sensing methods and bioimaging. After reading the article, we found that the author 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

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

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