Heterocyclic Building Blocks-piperidine

The author of 《Design, synthesis, and anticonvulsant effects evaluation of nonimidazole histamine H3 receptor antagonists/inverse agonists containing triazole moiety》 were Song, Mingxia; Yan, Rui; Zhang, Yanhui; Guo, Dongfu; Zhou, Naiming; Deng, XianQing. And the article was published in Journal of Enzyme Inhibition and Medicinal Chemistry in 2020. Category: piperidines The author mentioned the following in the article:

Histamine H3 receptors (H3R) antagonists/inverse agonists are becoming a promising therapeutic approach for epilepsy. In this article, novel nonimidazole H3R antagonists/inverse agonists have been designed and synthesized via hybriding the H3R pharmacophore (aliphatic amine with propyloxy chain) with the 1,2,4-triazole moiety as anticonvulsant drugs. The majority of antagonists/inverse agonists prepared here exerted moderate to robust activities in cAMP-response element (CRE) luciferase screening assay. 1-(3-(4-(3-Phenyl-4H-1,2,4-triazol-4-yl)phenoxy)propyl)piperidine () and 1-(3-(4-(3-(4-chlorophenyl)-4H-1,2,4-triazol-4-yl)phenoxy)propyl)piperidine displayed the highest H3R antagonistic activities, with IC50 values of 7.81 and 5.92 nM, resp. Meanwhile, the compounds with higher H3R antagonistic activities exhibited protection for mice in maximal electroshock seizure (MES)-induced convulsant model. Moreover, the protection of against the MES induced seizures was fully abrogated when mice were co-treated with RAMH, a CNS-penetrant H3R agonist, which suggested that the potential therapeutic effect of was through H3R. These results indicate that the attempt to find new anticonvulsant among H3R antagonists/inverse agonists is practicable. In addition to this study using Piperidine-4-carboxamide, there are many other studies that have used Piperidine-4-carboxamide(cas: 39546-32-2Category: piperidines) was used in this study.

Piperidine-4-carboxamide(cas: 39546-32-2) 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.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《A simple, robust and efficient structural model to predict CO2 absorption for different amine solutions: Concern to design new amine compounds》 was published in Journal of Environmental Chemical Engineering in 2020. These research results belong to Raznahan, Mohammad Moein; Riahi, Siavash; Mousavi, Seyed Hamed. Application In Synthesis of 2-(Piperidin-4-yl)ethanol The article mentions the following:

The absorption capacity (AC) and absorption rate (AR) are considered as the two main characteristics in choosing the great amine solutions for carbon dioxide absorption. However, selecting the proper amine-based solution on a vast number of exptl. procedures is unaffordable regarding cost and time. Accordingly, studying and modeling amine structures and discovering the relationship between structural parameters and the AC and AR values of amine compounds are of great necessity. The Quant. Structure-Property Relationship (QSPR) method, which is considered as an efficient procedure, is used for predicting carbon dioxide absorption by amine solutions The present study was performed on two different groups of amine solutions, including chained and non-ring-shaped structures for group 1 and major ring-shaped structures for group 2. Then, linear and nonlinear models were applied to create QSPR models, resp. The values of the square of the correlation coefficient (R2) for linear and nonlinear models were 0.753 and 0.985, as well as 0.895 and 0.954 for groups 1 and 2, resp. The results demonstrated that applying a nonlinear model is more efficient and accurate than the linear model for predicting absorption. Further, the prediction of the CO2 absorption value is achievable with high precision for groups 1 and 2 using only 1 and 2 descriptors, resp. In this paper, new amine mols. were designed based on their primary structures and the reported descriptor. Finally, the constructed compounds were found to have better AR and AC compared to initial structures. In the experimental materials used by the author, we found 2-(Piperidin-4-yl)ethanol(cas: 622-26-4Application In Synthesis 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.Application In Synthesis of 2-(Piperidin-4-yl)ethanol

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Electric Literature of C7H15NOIn 2016 ,《Library of diversely substituted 2-(quinolin-4-yl)imidazolines delivers novel non-cytotoxic antitubercular leads》 appeared in Journal of Enzyme Inhibition and Medicinal Chemistry. The author of the article were Krasavin, Mikhail; Mujumdar, Prashant; Parchinsky, Vladislav; Vinogradova, Tatiana; Manicheva, Olga; Dogonadze, Marine. The article conveys some information:

A novel library based on quinolin-4-ylimidazoline core was designed to incorporate a general quinoline antimicrobial pharmacophore. A synthesis of the well-characterized library of 36 compounds was achieved using the Pd-catalyzed Buchwald-Hartwig-type imidazoline arylation chem. developed earlier. Compounds were tested for biol. activity and were found to possess no antimalarial activity. However, the library delivered two promising antitubercular leads, which are non-cytotoxic and can be further optimized with respect to antimycobacterial potency. After reading the article, we found that the author used 2-(Piperidin-4-yl)ethanol(cas: 622-26-4Electric Literature of C7H15NO)

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 FAKElectric Literature of C7H15NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

The author of 《Hydroxyl-substituted double Schiff-base condensed 4-piperidone/cyclohexanones as potential anticancer agents with biological evaluation》 were Zhang, Lianshuang; Chen, Qin; Hou, Guige; Zhao, Wei; Hou, Yun. And the article was published in Journal of Enzyme Inhibition and Medicinal Chemistry in 2019. Reference of 1-Methyl-4-piperidone The author mentioned the following in the article:

Novel hydroxyl-substituted double Schiff-base 4-piperidone/cyclohexanone derivatives, and , were synthesized and fully characterized by 1H NMR, IR and elemental anal. The cytotoxicity against human carcinoma cell lines A549, SGC7901, HePG2, HeLa, K562, THP-1 and non-malignant LO2 cell lines were evaluated. The results showed 4-piperidinone derivatives displayed better cytotoxicity than cyclohexanone derivatives, especially for 3,4,5-trihydroxyphenyl-substituted BAP . The western blot and flow cytometry results proved can effectively promote cell apoptosis through up-regulating Bax protein and down-regulating Bcl-2 protein expression. Mol. docking modes showed that could reasonably bind to the active site of Bcl-2 protein through strong intermol. hydrogen bonds and significant hydrophobic effect. In vivo, can effectively suppress the growth of HepG2 xenografts without apparent body weight changes. This study indicates that can be a potential anticancer agent for early treatment of liver cancers. The experimental process involved the reaction of 1-Methyl-4-piperidone(cas: 1445-73-4Reference 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.Reference of 1-Methyl-4-piperidone

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Corroles and corrole/transferrin nanoconjugates as candidates for sonodynamic therapy》 was published in Chemical Communications (Cambridge, United Kingdom) in 2019. These research results belong to Sharma, Vinay Kumar; Mahammed, Atif; Soll, Matan; Tumanskii, Boris; Gross, Zeev. SDS of cas: 826-36-8 The article mentions the following:

We report the utility of water-soluble corroles and also protein-coated nanoparticles (NPs) of lipophilic corroles as potent candidates for sonodynamic therapy (SDT), through the detection and quantification of the singlet oxygen that is produced by the ultrasonic irradiation of their aqueous solutions Preliminary results on a cancer cell line provide evidence for the true utility of the NPs for SDT. In the experiment, the researchers used many compounds, for example, Triacetonamine(cas: 826-36-8SDS of cas: 826-36-8)

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.SDS of cas: 826-36-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 1974,Jerusalem Symposia on Quantum Chemistry and Biochemistry included an article by Lambrecht, G.; Mutschler, E.. COA of Formula: C8H15NO2. The article was titled 《Conformational isomerism in drug action. Does the free energy of binding induce the pharmacophoric conformation of semirigid muscarinic agonists》. The information in the text is summarized as follows:

3-Acetoxyquinuclidine (I) [827-61-2] and N-methyl-3-acetoxypiperidine [6659-33-2] had slightly greater guinea pig ileum contracting activity than acetylcholine [51-84-3]. The activity of dihydroarecoline [1690-72-8] was 513 times less than that of acetylcholine and 39 times less than quinuclidine derivatives I quaternary ammonium salt was 200 times less active than I. Methylquinuclidine-3-carboxylate [38206-86-9] was 40 times more active than its quaternary ammonium salt. On the other hand, the piperidine derivatives showed a slight increase in activity upon quaternary salt formation. The results are discussed in relation to conformational isomerism. In the part of experimental materials, we found many familiar compounds, such as Methyl 1-methylpiperidine-3-carboxylate(cas: 1690-72-8COA of Formula: C8H15NO2)

Methyl 1-methylpiperidine-3-carboxylate(cas: 1690-72-8) 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.COA of Formula: C8H15NO2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

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》.Electric Literature 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: 59234-40-1Electric Literature 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.Electric Literature of C7H11NO4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Category: piperidinesIn 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: 1445-73-4Category: 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

《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. Application 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: 1445-73-4Application 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

Quality Control 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: 826-36-8Quality Control 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.Quality Control of Triacetonamine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem