Category: piperidines

Crystal Structures of Three Organically Modified Metal Halides was written by Zhao, Jin-Jing;Wang, Yan-Ning;Jia, Hong-Li;Yu, Jie-Hui;Xu, Ji-Qing. And the article was included in Journal of Cluster Science in 2014.SDS of cas: 15336-72-8 This article mentions the following:

Under the hydro(solvo)thermal conditions, the reactions of metal halides with organic N-heterocyclic mols. produced three new organically modified metal halides [tmbp][Cu₂Br₄] (1) (tmbp²⁺ = N,N,N’,N’-tetramethyl-4,4′-bipiperidinium), [H₂(dmbpp)][Pb₂I₆] (2) (dmbpp = dimethyl-1,3-bis(4-piperidyl)propane) and [PbI₂(bpp)] (3) (bpp = 1,3-bis(4-pyridyl)propane). It is noteworthy that tmbp²⁺ in compound 1 originated from the in situ alkylation of 4,4′-bipiperidine with CH₃OH. The mechanism study indicates that H⁺ and Br^– play a key role in the alkylation reaction. X-ray single-crystal diffraction anal. revealed that (i) compounds 1 and 2 are the organically templated halometallates. Both possess the 1D chain structures. The 1D chain of compound 1 can be regarded as a linear arrangement of CuBr₄ tetrahedra by sharing the edges, whereas that of compound 2 can be considered as an endless extension of PbI₆ octahedra by sharing the faces; (ii) compound 3 is the 1:1 adduct of PbI₂ and bpp. The PbI₂ chain shows a linear shape. Bpp serves as the connector, propagating the PbI₂ chains into a 2D layer network of compound 3. In the experiment, the researchers used many compounds, for example, 4,4′-Bipiperidine (cas: 15336-72-8SDS of cas: 15336-72-8).

4,4′-Bipiperidine (cas: 15336-72-8) 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. 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.SDS of cas: 15336-72-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

(Indolylalkyl)piperidine carbamates as inhibitors of fatty acid amide hydrolase (FAAH) was written by Dahlhaus, Helmut;Hanekamp, Walburga;Lehr, Matthias. And the article was included in MedChemComm in 2017.Safety of 4-(1-Boc-4-piperidyl)-1-butanol This article mentions the following:

A series of Ph 4-[(indol-1-yl)alkyl]piperidine carbamates was synthesized and tested for inhibition of the endocannabinoid degrading enzyme fatty acid amide hydrolase (FAAH) and for metabolic stability in rat liver S9 fractions and porcine blood plasma. Structure-activity relationship studies revealed that variation of the length of the alkyl spacer connecting the indole and the piperidine heterocycle, introduction of substituents into the indole ring, replacement of the piperidine by a piperazine scaffold as well as opening of the piperidine ring system affect activity significantly. The metabolic stability of this compound class proved to be significantly higher than that of corresponding Ph N-(indol-1-ylalkyl)carbamates. In the experiment, the researchers used many compounds, for example, 4-(1-Boc-4-piperidyl)-1-butanol (cas: 142355-83-7Safety of 4-(1-Boc-4-piperidyl)-1-butanol).

4-(1-Boc-4-piperidyl)-1-butanol (cas: 142355-83-7) 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. Fluorinated piperidines are also the subject of continued interest in medicinal chemistry, for example in the synthesis of selective dipeptidyl peptidase II (DPP II) inhibitors. Piperidine derivatives are also used in solid-phase peptide synthesis (SPPS) and many degradation reactions.Safety of 4-(1-Boc-4-piperidyl)-1-butanol

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Design and Synthesis of High Affinity Inhibitors of Plasmodium falciparum and Plasmodium vivax N-Myristoyltransferases Directed by Ligand Efficiency Dependent Lipophilicity (LELP) was written by Rackham, Mark D.;Brannigan, James A.;Rangachari, Kaveri;Meister, Stephan;Wilkinson, Anthony J.;Holder, Anthony A.;Leatherbarrow, Robin J.;Tate, Edward W.. And the article was included in Journal of Medicinal Chemistry in 2014.Computed Properties of C10H21N This article mentions the following:

N-Myristoyltransferase (NMT) is an essential eukaryotic enzyme and an attractive drug target in parasitic infections such as malaria. We have previously reported that 2-(3-(piperidin-4-yloxy)benzo[b]thiophen-2-yl)-5-((1,3,5-trimethyl-1H-pyrazol-4-yl)methyl)-1,3,4-oxadiazole (34c) is a high affinity inhibitor of both Plasmodium falciparum and P. vivax NMT and displays activity in vivo against a rodent malaria model. Here we describe the discovery of 34c through optimization of a previously described series. Development, guided by targeting a ligand efficiency dependent lipophilicity (LELP) score of less than 10, yielded a 100-fold increase in enzyme affinity and a 100-fold drop in lipophilicity with the addition of only two heavy atoms. 34c was found to be equipotent on chloroquine-sensitive and -resistant cell lines and on both blood and liver stage forms of the parasite. These data further validate NMT as an exciting drug target in malaria and support 34c as an attractive tool for further optimization. In the experiment, the researchers used many compounds, for example, 1,2,2,6,6-Pentamethylpiperidine (cas: 79-55-0Computed Properties of C10H21N).

1,2,2,6,6-Pentamethylpiperidine (cas: 79-55-0) 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.Computed Properties of C10H21N

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Diphenidol-related diamines as novel muscarinic M₄ receptor antagonists was written by Varoli, Lucilla;Andreani, Aldo;Burnelli, Silvia;Granaiola, Massimiliano;Leoni, Alberto;Locatelli, Alessandra;Morigi, Rita;Rambaldi, Mirella;Bedini, Andrea;Fazio, Nicola;Spampinato, Santi. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2008.COA of Formula: C10H20N2 This article mentions the following:

A series of hydrochloride derivatives and quaternary ammonium derivatives of diphenidol have been synthesized and characterized in receptor binding and cellular functional assays vs. human muscarinic M₁-M₅ receptors expressed in CHO cells. A methiodide derivative (I) with a bipiperidinyl moiety and a second diphenidol framework, showed a potent and selective M₄ activity as competitive antagonist. Moreover I, acting as an allosteric modulator, was able to retard the dissociation rate of [³H]-N-methylscopolamine from CHO-M₄ cell membranes exposed to atropine. Taken together, these data suggest that I might open new avenues to the discovery of novel multivalent antagonists for the muscarinic receptors. In the experiment, the researchers used many compounds, for example, 4,4′-Bipiperidine (cas: 15336-72-8COA of Formula: C10H20N2).

4,4′-Bipiperidine (cas: 15336-72-8) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. 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.COA of Formula: C10H20N2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Structure activity relationships leading to the identification of the indirect activator of AMPK, R419 was written by Shaw, Simon J.;Goff, Dane A.;Carroll, David C.;Singh, Rajinder;Sweeny, David J.;Park, Gary;Jenkins, Yonchu;Markovtsov, Vadim;Sun, Tian-Qiang;Issakani, Sarkiz D.;Hitoshi, Yasumichi;Payan, Donald G.. And the article was included in Bioorganic & Medicinal Chemistry in 2022.Safety of tert-Butyl 4-(4-fluorobenzoyl)piperidine-1-carboxylate This article mentions the following:

Using an in-cell AMPK activation assay, we have developed structure-activity relationships around a hit pyridine dicarboxamide 5 that resulted in 40 (R419). A particular focus was to retain the on-target potency while also improving microsomal stability and reducing off-target activities, including hERG inhibition. We were able to show that removing a tertiary amino group from the piperazine unit of hit compound 5 improved microsomal stability while hERG inhibition was improved by modifying the substitution of the central core pyridine ring. The SAR resulted in 40, which continues to maintain on-target potency. Compound 40 was able to activate AMPK in vivo after oral administration and showed efficacy in animal models investigating activation of AMPK as a therapy for glucose control (both db/db and DIO mouse models). In the experiment, the researchers used many compounds, for example, tert-Butyl 4-(4-fluorobenzoyl)piperidine-1-carboxylate (cas: 160296-40-2Safety of tert-Butyl 4-(4-fluorobenzoyl)piperidine-1-carboxylate).

tert-Butyl 4-(4-fluorobenzoyl)piperidine-1-carboxylate (cas: 160296-40-2) 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.Safety of tert-Butyl 4-(4-fluorobenzoyl)piperidine-1-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis and SAR evaluation of novel thioridazine derivatives active against drug-resistant tuberculosis was written by Scalacci, Nicolo;Brown, Alistair K.;Pavan, Fernando R.;Ribeiro, Camila M.;Manetti, Fabrizio;Bhakta, Sanjib;Maitra, Arundhati;Smith, Darren L.;Petricci, Elena;Castagnolo, Daniele. And the article was included in European Journal of Medicinal Chemistry in 2017.Category: piperidines This article mentions the following:

The neuroleptic drug thioridazine was recently repositioned as possible anti-tubercular drug. Thioridazine showed anti-tubercular activity against drug resistant mycobacteria but it is endowed with adverse side effects. A small library of thioridazine derivatives was designed through the replacement of the piperidine and phenothiazine moieties, with the aim to improve the anti-tubercular activity and to reduce the cytotoxic effects. Among the resulting compounds, the indole derivative 1-(2-(piperidin-2-yl)ethyl)-1H-indole showed an antimycobacterial activity significantly better than thioridazine and a cytotoxicity 15-fold lower. In the experiment, the researchers used many compounds, for example, tert-Butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate (cas: 118811-03-3Category: piperidines).

tert-Butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate (cas: 118811-03-3) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. 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.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Stability indicating RP-HPLC method for determination of glasdegib in bulk and pharmaceutical dosage form was written by Rao, P. Venkateswara;Meghana, P.;Bhavana, J.;Lakshmi, K. Bhagya;Ramya, K.. And the article was included in International Journal of Research in Pharmacy and Chemistry in 2020.Product Details of 1095173-27-5 This article mentions the following:

A simple, rapid, precise, sensitive and reproducible reverse phase high performance liquid chromatog. (RP-HPLC) method has been developed for the quant. anal. of Glasdegib in pharmaceutical dosage form. Chromatog. separation of Glasdegib was achieved on Waters Alliance-e2695, by using Waters Symmetry C18, 150×4.6mm, 3.5渭m column and the mobile phase containing 0.1% TEA adjusting pH=2.5 with OPA & Acetonitrile in the ratio of 90:10% volume/volume The flow rate was 0.5 mL/min; detection was carried out by absorption at 268nm using a photodiode array detector at ambient temperature The number of theor. plates and tailing factor for Glasdegib is NLT 2000 and should not more than 2 resp.% Relative standard deviation of peak areas of all measurements always less than 2.0. The proposed method was validated according to ICH guidelines. The method was found to be simple, economical, suitable, precise, accurate & robust method for quant. anal. of Glasdegib. In the experiment, the researchers used many compounds, for example, 1-((2R,4R)-2-(1H-Benzo[d]imidazol-2-yl)-1-methylpiperidin-4-yl)-3-(4-cyanophenyl)urea (cas: 1095173-27-5Product Details of 1095173-27-5).

1-((2R,4R)-2-(1H-Benzo[d]imidazol-2-yl)-1-methylpiperidin-4-yl)-3-(4-cyanophenyl)urea (cas: 1095173-27-5) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. 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.Product Details of 1095173-27-5

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of GABA_A Receptor Agonists and Evaluation of their 伪-Subunit Selectivity and Orientation in the GABA Binding Site was written by Jansen, Michaela;Rabe, Holger;Strehless, Axelle;Dieler, Sandra;Debus, Fabian;Dannhardt, Gerd;Akabas, Myles H.;Lueddens, Hartmut. And the article was included in Journal of Medicinal Chemistry in 2008.Product Details of 280110-69-2 This article mentions the following:

Drugs used to treat various disorders target GABA_A receptors. To develop 伪 subunit selective compounds, we synthesized 5-(4-piperidyl)-3-isoxazolol (4-PIOL) derivatives The 3-isoxazolol moiety was substituted by 1,3,4-oxadiazol-2-one , 1,3,4-oxadiazol-2-thione, and substituted 1,2,4-triazol-3-one heterocycles, e.g. I (R = 4-piperidyl, 2-pyrrolidinyl, H₂NCH₂CH₂, etc., X = O, S, Y = O; R = 4-piperidinyl, H₂NCH₂, X = O, S, Y = PhCH₂N), with modifications to the basic piperidine substituent as well as substituents without basic nitrogen. Compounds were screened by [³H]muscimol binding and in patch-clamp experiments with heterologously expressed GABA_A 伪_i尾₃纬₂ receptors (i = 1-6). The effects of 5-aminomethyl-3H-[1,3,4]oxadiazol-2-one were comparable to GABA for all 伪 subunit isoforms. 5-Piperidin-4-yl-3H-[1,3,4]oxadiazol-2-one and 5-piperidin-4-yl-3H-[1,3,4]oxadiazol-2-thione (II) were weak agonists at 伪₂-, 伪₃-, and 伪₅-containing receptors. When coapplied with GABA, they were antagonistic in 伪₂-, 伪₄-, and 伪₆-containing receptors and potentiated 伪₃-containing receptors. II protected GABA binding site cysteine-substitution mutants 伪₁F64C and 伪₁S68C from reacting with methanethiosulfonate-ethylsulfonate. II specifically covalently modified the 伪₁R66C thiol, in the GABA binding site, through its oxadiazolthione sulfur. These results demonstrate the feasibility of synthesizing 伪 subtype selective GABA mimetic drugs. In the experiment, the researchers used many compounds, for example, 1-Boc-4-(5-Methyl-1,3,4-oxadiazol-2-yl)piperidine (cas: 280110-69-2Product Details of 280110-69-2).

1-Boc-4-(5-Methyl-1,3,4-oxadiazol-2-yl)piperidine (cas: 280110-69-2) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. 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.Product Details of 280110-69-2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Combining structure- and property-based optimization to identify selective FLT3-ITD inhibitors with good antitumor efficacy in AML cell inoculated mouse xenograft model was written by Heng, Hao;Wang, Zhijie;Li, Hongmei;Huang, Yatian;Lan, Qingyuan;Guo, Xiaoxing;Zhang, Liang;Zhi, Yanle;Cai, Jiongheng;Qin, Tianren;Xiang, Li;Wang, Shuxian;Chen, Yadong;Lu, Tao;Lu, Shuai. And the article was included in European Journal of Medicinal Chemistry in 2019.Synthetic Route of C6H14N2 This article mentions the following:

FLT3 mutation is among the most common genetic mutations in acute myeloid leukemia (AML), which is also related with poor overall survival and refractory in AML patients. Recently, FLT3 inhibitors have been approved for AML therapy. Herein, a series of new compounds with pyrazole amine scaffold was discovered, which showed potent inhibitory activity against FLT3-ITD and significant selectivity against both FLT3-ITD and AML cells expressing FLT3-ITD. Compound 46, possessing the most promising cellular activity, blocked the autophosphorylation of FLT3 pathway in MV4-11 cell line. Furthermore, the apoptosis and down regulation of P-STAT5 were also observed in tumor cells extracted from the MV4-11 cell xenografts model upon compound 46 treatment. Compound 46 was also metabolically stable in vitro and suppressed tumor growth significantly in MV4-11 xenografts model in vivo. Compound 46 showed no toxicity to the viscera of mice and caused no decrease in body weight of mice. In conclusion, the results of this study could provide valuable insights into discovery of new FLT3 inhibitors, and compound 46 was worthy of further development as potential drug candidate to treat AML. In the experiment, the researchers used many compounds, for example, 4-Amino-1-methylpiperidine (cas: 41838-46-4Synthetic Route of C6H14N2).

4-Amino-1-methylpiperidine (cas: 41838-46-4) 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. 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.Synthetic Route of C6H14N2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Design, synthesis and structure of new dendritic melamines. First use of a tandem C-2-substituted serinol-O,O-masked 4-piperidone as a peripheral unit in iterative synthesis was written by Popa, Flavia;Lameiras, Pedro;Moldovan, Oana;Tomoaia-Cotisel, Maria;Henon, Eric;Martinez, Agathe;Sacalis, Carmen;Mocanu, Aurora;Ramondenc, Yvan;Darabantu, Mircea. And the article was included in Tetrahedron in 2012.Application In Synthesis of 4,4′-Bipiperidine This article mentions the following:

The iterative chemoselective amination of cyanuric chloride to dimers of new G-2 dendritic N-substituted-2,4,6-triamino-s-triazines (melamines) having C-2-substituted 2-aminopropane-1,3-diols (‘serinols’) in tandem with the ethylene ketal of 4-piperidone as peripheral units is reported. The structure as a function of increasing mol. size was studied by NMR spectroscopy, DFT calculation and AFM imaging. A concise nomenclature defining the restricted rotational phenomena about the newly created C(s-triazine)-N(exocyclic) partial double bonds, seen as axes of (pro)diastereomerism, is used. We propose a new form of frontier rotamerism for the dendrimer surface, which operates over a long range. In the experiment, the researchers used many compounds, for example, 4,4′-Bipiperidine (cas: 15336-72-8Application In Synthesis of 4,4′-Bipiperidine).

4,4′-Bipiperidine (cas: 15336-72-8) 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. 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.Application In Synthesis of 4,4′-Bipiperidine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem