Category: piperidines

Treatment of glioblastoma with re-purposed renin-angiotensin system modulators: Results of a phase I clinical trial was written by O’Rawe, Michael;Wickremesekera, Agadha C.;Pandey, Ramesh;Young, David;Sim, Dalice;FitzJohn, Trevor;Burgess, Carl;Kaye, Andrew H.;Tan, Swee T.. And the article was included in Journal of Clinical Neuroscience in 2022.Safety of (2E,4E)-5-(Benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one This article mentions the following:

Glioblastoma is the most common and most aggressive primary brain cancer in adults. Standard treatment of glioblastoma consisting of maximal safe resection, adjuvant radiotherapy and chemotherapy with temozolomide, results in an overall median survival of 14.6 mo. The aggressive nature of glioblastoma has been attributed to the presence of glioblastoma stem cells which express components of the renin-angiotensin system (RAS). This phase I clin. trial investigated the tolerability and efficacy of a treatment targeting the RAS and its converging pathways in patients with glioblastoma. Patients who had relapsed following standard treatment of glioblastoma who met the trial criteria were commenced on dose-escalated oral RAS modulators (propranolol, aliskiren, cilazapril, celecoxib, curcumin with piperine, aspirin, and metformin). Of the 17 patients who were enrolled, ten completed full dose-escalation of the treatment. The overall median survival was 19.9 (95% CI:14.1-25.7) months. Serial FET-PET/CTs showed a reduction in both tumor volume and uptake in one patient, an increase in tumor uptake in nine patients with decreased (n = 1), unchanged (n = 1) and increased (n = 7) tumor volume, in the ten patients who had completed full dose-escalation of the treatment. Two patients experienced mild side effects and all patients had preservation of quality of life and performance status during the treatment. There is a trend towards increased survival by 5.3 mo although it was not statistically significant. These encouraging results warrant further clin. trials on this potential novel, well-tolerated and cost-effective therapeutic option for patients with glioblastoma. In the experiment, the researchers used many compounds, for example, (2E,4E)-5-(Benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one (cas: 94-62-2Safety of (2E,4E)-5-(Benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one).

(2E,4E)-5-(Benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one (cas: 94-62-2) belongs to piperidine derivatives. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Safety of (2E,4E)-5-(Benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Stereogenic (chiral) methyl groups: determination of configuration by direct tritium NMR spectroscopy was written by Anet, Frank A. L.;O’Leary, Daniel J.;Beale, John M.;Floss, Heinz G.. And the article was included in Journal of the American Chemical Society in 1989.Application In Synthesis of (R)-2-Methylpiperidine This article mentions the following:

The configuration of CHDTX, where X is a leaving group, can be determined by direct tritium NMR of the product obtained by methylation of resolved 2-methylpiperidine with CHDTX and this provides a new and highly accurate determination of enantiomeric purity in CHDTX. The two diastereomers of [7-²H₁,³H]-1,2-dimethylpiperidine differ in chem. shifts by 4.4 Hz (0.014 ppm), with the tritium more shielded in the (2R,7S) than in the (2S,7S) diastereomer, in agreement with predictions based on the proton NMR of the racemate of 1,2-dimethylpiperidine monodeuterated on the N-Me group. In the experiment, the researchers used many compounds, for example, (R)-2-Methylpiperidine (cas: 1722-95-8Application In Synthesis of (R)-2-Methylpiperidine).

(R)-2-Methylpiperidine (cas: 1722-95-8) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst. Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol.Application In Synthesis of (R)-2-Methylpiperidine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Orally active and potent inhibitors of 纬-aminobutyric acid uptake was written by Ali, Fadia E.;Bondinell, William E.;Dandridge, Penelope A.;Frazee, James S.;Garvey, Eleanor;Girard, Gerald R.;Kaiser, Carl;Ku, Thomas W.;Lafferty, John J.. And the article was included in Journal of Medicinal Chemistry in 1985.Formula: C22H26ClNO2 This article mentions the following:

GABA聽聽[56-12-2]-uptake inhibitors that are more potent, more lipophilic, and in limited testing, at least as selective as the parent amino acids were obtained by alkylation of the appropriate butyric-, cyclohexane- and piperidinecarboxylic and pyrrolinidineacetic acids. The ability of these alkylated amino acids to inhibit Na-dependent, high-affinity GABA uptake was measured after preincubation for 15 min with rat brain synaptosomes. N-(4,4-Diphenyl-3-butenyl)-3-piperidinecarboxylic聽acid (I) [85375-85-5] is a specific GABA-uptake inhibitor more potent, more lipophilic and, as selective as the nonalkylated parent; I and its analogs also exhibited anticovulsant activity in rodents. Structure-activity relations are discussed. In the experiment, the researchers used many compounds, for example, SKF-89976A Hydrochloride (cas: 85375-15-1Formula: C22H26ClNO2).

SKF-89976A Hydrochloride (cas: 85375-15-1) belongs to piperidine derivatives. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst. Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol.Formula: C22H26ClNO2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Adsorption liquid chromatography on silica for the chiral separation of amino acids and asymmetric amines derivatized with optically active N-伪-9-fluorenylmethyloxycarbonyl-amino acid-N-carboxyanhydrides was written by Pugniere, Martine;Mattras, Helene;Castro, Bertrand;Previero, Aldo. And the article was included in Journal of Chromatography A in 1997.Reference of 1722-95-8 This article mentions the following:

Optically pure N-伪-Fmoc-amino acid-N-carboxyanhydrides (Fmoc-AA-NCAs, Fmoc = 9-fluorenylmethyloxycarbonyl) are proposed as precolumn reagents for the chiral anal. of asym. amines, including 伪-amino acid alkyl esters. Separation of diastereomers arising from racemic amines was better achieved by liquid-solid adsorption chromatog. on silica than by reversed-phase techniques. Sample preparation is easily performed, and the properties of the Fmoc group allows high sensitivity by fluorescent detection. In this mode, picomolar limits of enantiomeric excess were detected. In the experiment, the researchers used many compounds, for example, (R)-2-Methylpiperidine (cas: 1722-95-8Reference of 1722-95-8).

(R)-2-Methylpiperidine (cas: 1722-95-8) belongs to piperidine derivatives.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. Piperidine derivatives bearing a masked aldehyde function in the 蔚-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Reference of 1722-95-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Study of organoboron oligomers as UV stabilizers for glass fiber-reinforced plastics was written by Ozhogin, A. V.;Lenskii, M. A.;Korabel’nikov, D. V.;Novitskii, A. N.. And the article was included in Plasticheskie Massy in 2018.Name: Bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate This article mentions the following:

The results of the investigation of the resistance to UV radiation of glass fiber-reinforced plastics modified by additives of polymethylene ethers of phenols and boric acid, pigments and stabilizers based on benzophenone, benzotriazole, and sebacate are represented in article. The dependence of changes in tensile strength of the glass fiber-reinforced plastics from the accelerated aging is shown. In the experiment, the researchers used many compounds, for example, Bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate (cas: 41556-26-7Name: Bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate).

Bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate (cas: 41556-26-7) belongs to piperidine derivatives. Piperidine has a role as a reagent, a protic solvent, a base, a catalyst, a plant metabolite, a human metabolite and a non-polar solvent. Several piperidine alkaloids isolated from natural herbs, were found to exhibit antiproliferation and antimetastatic effects on various types of cancers both in vitro and in vivo for example Piperine, Evodiamine, Matrine, Berberine and Tetrandine.Name: Bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Electrochemical Acceptorless Dehydrogenation of N-Heterocycles Utilizing TEMPO as Organo-Electrocatalyst was written by Wu, Yong;Yi, Hong;Lei, Aiwen. And the article was included in ACS Catalysis in 2018.Formula: C11H21N2O2 This article mentions the following:

Catalytic acceptorless dehydrogenation (CAD) was a basically important organic transformation to ubiquitous unsaturated compounds without the usage of a sacrificial H acceptor. The authors successfully developed the 1st electrochem. acceptorless dehydrogenation (ECAD) of N-heterocycles using TEMPO as the organo-electrocatalyst. The authors have achieved the catalytic dehydrogenation of N-heterocycles in an anode and the release of H₂ in a cathode using an undivided-cell system. A variety of six-membered and five-membered N-heteroarenes can be synthesized in good yields in this system. This protocol can also be used in the application of important mol. synthesis. The authors’ electrochem. strategy provides a mild and metal-free route for (hetero)aromatic compounds synthesis via the CAD strategy. In the experiment, the researchers used many compounds, for example, 4-Acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl (cas: 14691-89-5Formula: C11H21N2O2).

4-Acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl (cas: 14691-89-5) belongs to piperidine derivatives. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. Piperidine derivatives are being utilized in different ways as anticancer, antiviral, antimalarial, antimicrobial, antifungal, antihypertension, analgesic, anti-inflammatory, anti-Alzheimer, antipsychotic and/or anticoagulant agents.Formula: C11H21N2O2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

1-Benzyl-4-methylpiperidinyl moiety in donepezil: The priority ticket across the blood-brain-barrier in rats was written by Zdarova Karasova, Jana;Sestak, Vit;Korabecny, Jan;Mezeiova, Eva;Palicka, Vladimir;Kuca, Kamil;Mzik, Martin. And the article was included in Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences in 2018.Electric Literature of C17H23NO3 This article mentions the following:

The main aim of the authors’ study was to clarify which part of the donepezil mol. determines its ability to cross the blood-brain barrier (BBB). The authors developed and fully validated a rapid, selective and sensitive method to quantify donepezil and its three fragments in rat plasma and brain homogenate, employing ultra-HPLC with high resolution mass spectrometry (Orbitrap, Q-Exactive Focus), and used it to assess the pharmacokinetics after concomitant administration of donepezil and its three fragments. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxy-2-(piperidin-4-ylmethyl)-2,3-dihydro-1H-inden-1-one (cas: 120014-30-4Electric Literature of C17H23NO3).

5,6-Dimethoxy-2-(piperidin-4-ylmethyl)-2,3-dihydro-1H-inden-1-one (cas: 120014-30-4) belongs to piperidine derivatives. The piperidine ring can be found not only in more than half of the currently known structures of alkaloids, but also in many natural or synthetic compounds with interesting biological activities. Piperidine prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N鈥揌 bond in an axial position, and the other in an equatorial position.Electric Literature of C17H23NO3

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

SAR exploration of the non-imidazole histamine H₃ receptor ligand ZEL-H16 reveals potent inverse agonism was written by Wagner, Gabor;Mocking, Tamara A. M.;Ma, Xiaoyuan;Slynko, Inna;Da Costa Pereira, Daniel;Breeuwer, Robin;Rood, Niek J. N.;van der Horst, Cas;Vischer, Henry F.;de Graaf, Chris;de Esch, Iwan J. P.;Wijtmans, Maikel;Leurs, Rob. And the article was included in Archiv der Pharmazie (Weinheim, Germany).Name: 1-(3-Chloropropyl)piperidine hydrochloride This article mentions the following:

Histamine H3 receptor (H3R) agonists without an imidazole moiety remain very scarce. Of these, ZEL-H16 (1) has been reported previously as a high-affinity non-imidazole H3R (partial) agonist. Our structure-activity relationship anal. using derivatives of 1 identified both basic moieties as key interaction motifs and the distance of these from the central core as a determinant for H3R affinity. However, in spite of the reported H3R (partial) agonism, in our hands, 1 acts as an inverse agonist for G伪i signaling in a CRE-luciferase reporter gene assay and using an H3R conformational sensor. Inverse agonism was also observed for all of the synthesized derivatives of 1. Docking studies and mol. dynamics simulations suggest ionic interactions/hydrogen bonds to H3R residues D1143.32 and E2065.46 as essential interaction points. In the experiment, the researchers used many compounds, for example, 1-(3-Chloropropyl)piperidine hydrochloride (cas: 5472-49-1Name: 1-(3-Chloropropyl)piperidine hydrochloride).

1-(3-Chloropropyl)piperidine hydrochloride (cas: 5472-49-1) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Name: 1-(3-Chloropropyl)piperidine hydrochloride

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Light-fast performance of coated handmade papers was written by Wang, Kuo-Tsai;Wang, Eugene I-Chen;Perng, Yuan-Shing. And the article was included in Taiwan Linye Kexue in 2008.Reference of 41556-26-7 This article mentions the following:

The purpose of the study was to prepare Fenglachien papers, a kind of high-caliber coated paper mostly for Chinese calligraphic use made of coated handmade paper. The parameters studied for the coating and color formulations included the base papers, white complex pigments, various hued pigments and their concentrations, binders, and additives such as a wax emulsion, an insolubilizer, and a photostabilizer. All coated papers were evaluated for their light-fastness through UV irradiation, as this is one of the most important preservation characteristics for colored Fenglachien paper. We also tested the light-fastness of glossy golden- and silver-colored pearlite pigments used for color-painting and pattern-printing on the coated papers. The results indicated that the 2 kinds of base papers performed differently in terms of the white and colored pigments. The colored pigments interacted with the binders in complicated ways, and there appeared to be no rule for the changes observed For the same colors, a more-saturated hue had better light-fastness than a paler hue. Among the white pigments, precipitated silica had the best light-fastness performance, while titanium dioxide fared the worst. The wax emulsion and insolubilizer contributed pos. to the light-fastness of the Fenglachien paper. The tested photostabilizer, however, did not appear to have the anticipated efficacy. Certain synthetic golden pigments showed good light-fastness that allowed for the substitution for actual gold foil flakes for pattern-printing of Fenglachien graphic designs. In the experiment, the researchers used many compounds, for example, Bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate (cas: 41556-26-7Reference of 41556-26-7).

Bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate (cas: 41556-26-7) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising 伪-glucosidase inhibitors. The former are analogs of DNJ with an improved 伪-glucosidase inhibitory profile than that of DNJ. Boisson et al.Reference of 41556-26-7

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Identification of phenylcarbamoylazinane-1,3,4-oxadiazole amides as lipoxygenase inhibitors with expression analysis and in silico studies was written by Bashir, Bushra;Shahid, Wardah;Ashraf, Muhammad;Saleem, Muhammad;Aziz-ur-Rehman;Muzaffar, Saima;Imran, Muhammad;Amjad, Hira;Bhattarai, Keshab;Riaz, Naheed. And the article was included in Bioorganic Chemistry in 2021.Application of 1126-09-6 This article mentions the following:

In search for new anti-inflammatory agents that inhibit the enzymes of arachidonic acid pathway as the drug targets, the present article describes the screening of 1,3,4-oxadiazole analogs against lipoxygenase (LOX) enzyme. The work is based on the synthesis of new N-alkyl/aralky/aryl derivatives (6a-o) of 2-(4-phenyl-5-(1-phenylcarbamoylpiperidine)-4H-1,3,4-oxadiazol-3-ylthio)acetamide which were obtained by the reaction of 1,3,4-oxadiazole (3) with various electrophiles (5a-o), in KOH. The synthesized analogs showed potent to moderate inhibitory activity against the soybean 15-LOX enzyme; especially 6g, 6b, 6a and 6l displayed the potent inhibitory potential with IC₅₀ values 7.15 卤 0.26, 9.32 卤 0.42, 15.83 卤 0.45 & 18.37 卤 0.53渭M, resp., while excellent to moderate inhibitory profiles with IC₅₀ values in the range of 26.13-98.21渭M were observed from the compounds 6k, 6m, 6j, 6o, 6h, 6f, 6n and 6c. Most of the active compounds exhibited considerable cell viability against blood mononuclear cells (MNCs) at 0.25 mM by MTT assay except 6f, 6h, 6k and 6m which showed around 50% cell viability. Flow cytometry studies of the selected compounds 6a, 6j and 6n revealed that these caused 79.5-88.51% early apoptotic changes in MNCs compared with 4.26% for control quercetin at their resp. IC₅₀ values. The relative expression of 5-LOX gene was monitored in MNCs after treatment with these three mols. and all down-regulated the enzyme activity. In silico ADME and mol. docking studies further supported these studies of oxadiazole derivatives and considered it as potential ‘lead’ compounds in drug discovery and development. In the experiment, the researchers used many compounds, for example, Ethyl piperidine-4-carboxylate (cas: 1126-09-6Application of 1126-09-6).

Ethyl piperidine-4-carboxylate (cas: 1126-09-6) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst. Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol.Application of 1126-09-6

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem