Day: February 22, 2023

Synthesis of N-substituted aminoalkyl derivatives of some epoxyisoindoles as potential pharmacological agents was written by Kossakowski, Jerzy;Raszkiewicz, Aldona. And the article was included in Acta Poloniae Pharmaceutica in 2005.Application of 5472-49-1 This article mentions the following:

Title compounds I and II (n = 2, R = NMe₂, NEt₂, piperidino, morpholino; n = 3, R = NMe₂, piperidino) were prepared by aminoalkylation of the N-unsubstituted epoxyisoindolediones with Cl(CH₂)_nR. I and II (n = 2, 3; R = NMe₂) showed no activity against 3 cancer cell lines; 8 of the products were tested for anti-HIV activity but showed none. In the experiment, the researchers used many compounds, for example, 1-(3-Chloropropyl)piperidine hydrochloride (cas: 5472-49-1Application of 5472-49-1).

1-(3-Chloropropyl)piperidine hydrochloride (cas: 5472-49-1) 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. 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 of 5472-49-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of apixaban was written by He, Chao;Hou, Yunlei;Zhu, Yan;Ma, Longsheng;Zhao, Yanfang. And the article was included in Zhongguo Yiyao Gongye Zazhi in 2014.Quality Control of 1-(4-Nitrophenyl)piperidin-2-one This article mentions the following:

The key intermediate 3-(4-morpholinyl)-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one (5) was obtained via amidation, cyclization, dichlorination and elimination with 4-nitroaniline as the starting material. While another intermediate Et 2-chloro-2-[2-(4-methoxyphenyl)hydrazono]acetate (6) was prepared from 4-anisidine by diazotization and Japp-Klingemann reaction with Et 2-chloro-3-oxobutanoate. Apixaban, a factor Xa direct inhibitor, was synthesized from 5 and 6 by 1,3-dipolar cycloaddition, olefination, reduction, amidation, cyclization and aminolysis with an overall yield of 25% (based on 4-nitroaniline) and a HPLC purity of 99%. The improved process had several advantages over those reported procedures, such as mild conditions and simple operations, which is more suitable for industrial production In the experiment, the researchers used many compounds, for example, 1-(4-Nitrophenyl)piperidin-2-one (cas: 38560-30-4Quality Control of 1-(4-Nitrophenyl)piperidin-2-one).

1-(4-Nitrophenyl)piperidin-2-one (cas: 38560-30-4) 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. 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.Quality Control of 1-(4-Nitrophenyl)piperidin-2-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Structure-biodegradability correlations among xenobiotic industrial amines was written by Rothkopf, G. S.;Bartha, R.. And the article was included in JAOCS, J. Am. Oil Chem. Soc. in 1984.Application In Synthesis of 3-(2-Methylpiperidin-1-yl)propan-1-amine This article mentions the following:

Using acclimated sewage sludge enrichment cultures, 60 amines with potential uses in industrial processes were evaluated for their biodegradability. Biodegradation was measured as cell protein yield with 0.05% amine serving as the sole source of C, N, and energy in a mineral solution Inhibitory properties of the amines, measured by their ability to decrease protein yield on a glucose medium, were unrelated to biodegradability. Under the specified test conditions, all amines that contained tertiary C atoms were recalcitrant. Ring N-substituted heterocyclics were readily degraded, but ring C-substituted piperidines, with the exception of pipecolinic聽acid聽聽[535-75-1] were not. When amines lacked other functional groups, tertiary amino groups hindered degradation Amines with alkyldiamine moieties shorter than Pr did not serve as growth substrates. Predictive generalizations of this type about biodegradability serve as an aid in selecting environmentally safe compounds for industrial processes. In the experiment, the researchers used many compounds, for example, 3-(2-Methylpiperidin-1-yl)propan-1-amine (cas: 25560-00-3Application In Synthesis of 3-(2-Methylpiperidin-1-yl)propan-1-amine).

3-(2-Methylpiperidin-1-yl)propan-1-amine (cas: 25560-00-3) 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 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.Application In Synthesis of 3-(2-Methylpiperidin-1-yl)propan-1-amine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Research on enhancing of the regioselective oxidation of cellulose from bagasse pith by ultrasonic pretreatments was written by Gao, Xin;Zhang, Heng;Chen, Keli;Liu, Qixing;Zhu, Zhengliang. And the article was included in Cailiao Daobao in 2014.Application of 14691-89-5 This article mentions the following:

Cellulose from bagasse pith was pretreated by ultrasonic wave. The influence of ultrasound treatment on regioselective oxidation by 4-acetamide-2,2,6,6-tetramethylpiperidine-1-oxyl (4-AcNH-TEMPO)/NaClO/NaClO₂ systems was discussed. The results were shown that the regioselective oxidation reactivity of cellulose was significantly improved by the ultrasound treatment. And the ultrasound power and time were the most important factors on the properties of oxidized cellulose. Furthermore, the oxidized products obtained from this reactive system were comprised of water-soluble and insoluble samples. The structure and morphol. of native cellulose, pretreated samples and the two kinds of oxidized products were characterized by means of FT-IR, SEM and XRD. In the experiment, the researchers used many compounds, for example, 4-Acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl (cas: 14691-89-5Application of 14691-89-5).

4-Acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl (cas: 14691-89-5) 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 14691-89-5

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

3-(4-Fluoropiperidin-3-yl)-2-phenylindoles as high affinity, selective, and orally bioavailable h5-HT_2A receptor antagonists was written by Rowley, Michael;Hallett, David J.;Goodacre, Simon;Moyes, Christopher;Crawforth, James;Sparey, Timothy J.;Patel, Smita;Marwood, Rose;Patel, Shil;Thomas, Steven;Hitzel, Laure;O’Connor, Desmond;Szeto, Nicola;Castro, Jose L.;Hutson, Peter H.;MacLeod, Angus M.. And the article was included in Journal of Medicinal Chemistry in 2001.Recommanded Product: 1-Benzylpiperidin-3-one hydrochloride This article mentions the following:

The development of very high affinity, selective, and bioavailable h5-HT_2A receptor antagonists is described. By investigation of the optimal position for the basic nitrogen in a series of 2-phenyl-3-piperidylindoles, it was found that with the basic nitrogen at the 3-position of the piperidine it was not necessary to further substitute the piperidine in order to obtain good binding at h5-HT_2A receptors. This meant the compounds no longer had high affinity at the IKr potassium channel, an issue with previous series of 2-aryl-3-(4-piperidyl)indoles. Improvements could be made to oral bioavailability in this series by reduction of the pK_a of the basic nitrogen, by adding a fluorine atom to the piperidine ring, leading to 3-(4-fluoropiperidin-3-yl)-2-phenyl-1H-indole (17). Metabolic studies with this compound identified oxidation at the 6-position of the indole as a major route in vitro and in vivo in rats. Blocking this position with a fluorine atom led to 6-fluoro-3-(4-fluoropiperidin-3-yl)-2-phenyl-1H-indole (22), an antagonist with 0.06 nM affinity for h5-HT_2A receptors, with bioavailability of 80% and half-life of 12 h in rats. In the experiment, the researchers used many compounds, for example, 1-Benzylpiperidin-3-one hydrochloride (cas: 50606-58-1Recommanded Product: 1-Benzylpiperidin-3-one hydrochloride).

1-Benzylpiperidin-3-one hydrochloride (cas: 50606-58-1) 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. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Recommanded Product: 1-Benzylpiperidin-3-one hydrochloride

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Evaluation of Piperine as Natural Coformer for Eutectics Preparation of Drugs Used in the Treatment of Cardiovascular Diseases was written by Wilhelm-Romero, Krissia;Quiros-Fallas, Maria Isabel;Vega-Baudrit, Jose Roberto;Guillen-Giron, Teodolito;Vargas-Huertas, Felipe;Navarro-Hoyos, Mirtha;Araya-Sibaja, Andrea Mariela. And the article was included in AAPS PharmSciTech in 2022.SDS of cas: 94-62-2 This article mentions the following:

Piperine (PIP) was evaluated as a natural coformer in the preparation of multicomponent organic materials for enhancing solubility and dissolution rate of the poorly water-soluble drugs: curcumin (CUR), lovastatin (LOV), and irbesartan (IBS). A screening based on liquid assisted grinding technique was performed using 1:1 drug-PIP molar ratio mixtures, followed by differential scanning calorimetry (DSC) and powder X-ray diffraction (PXRD) anal. Three eutectic mixtures (EMs) composed of CUR-PIP, LOV-PIP, and IBS-PIP were obtained. Therefore, binary phase and Tamman鈥瞫 diagrams were constructed for each system to obtain the exact eutectic composition, which was 0.41:0.59, 0.29:0.71, and 0.31:0.69 for CUR-PIP, LOV-PIP, and IBS-PIP, resp. Further, bulk materials of each system were prepared to characterize them through DSC, PXRD fully, Fourier transform IR spectroscopy (FT-IR), and solution-state NMR (NMR) spectroscopy. In addition, the contact angle, solubility, and dissolution rate of each system were evaluated. The preserved characteristic in the PXRD patterns and FT-IR spectra of the bulk material of each system confirmed the formation of EM mixture without mol. interaction in solid-state. The formation of EM resulted in improved aqueous solubility and dissolution rate associated with the increased wettability observed by the decrease in contact angle. In addition, solution NMR analyses of CUR-PIP, LOV-PIP, and IBS-PIP suggested no significant intermol. interactions in solution between the components of the EM. Hence, this study concludes that PIP could be an effective coformer to improve the solubility and dissolution rate of CUR, LOV, and IBS. 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: 94-62-2SDS of cas: 94-62-2).

(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.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. 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.SDS of cas: 94-62-2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Highly Efficient Synthesis of a Staphylococcus aureus Targeting Payload to Enable the First Antibody-Antibiotic Conjugate was written by Linghu, Xin;Segraves, Nathaniel L.;Abramovich, Ifat;Wong, Nicholas;Mueller, Barbara;Neubauer, Nadja;Fantasia, Serena;Rieth, Sebastian;Bachmann, Stephan;Jansen, Michael;Sowell, C. Gregory;Askin, David;Koenig, Stefan G.;Gosselin, Francis. And the article was included in Chemistry – A European Journal in 2018.Application In Synthesis of N,N-Dimethylpiperidin-4-amine This article mentions the following:

A practical synthesis of the complex payload for an anti-Staphylococcus aureus THIOMAB^TM antibody-antibiotic conjugate (TAC) is described. The route takes advantage of a delicate oxidative condensation, achieved using a semi-continuous flow procedure. It allows for the generation of kilogram quantities of a key intermediate to enable a mild nucleophilic aromatic substitution to the tertiary amine free drug. The linker component is introduced as a benzylic chloride, which allows formation of the quaternary ammonium salt linker-drug. This chem. process surmounts numerous synthetic challenges and navigates deeply colored and unstable compounds to support clin. studies to counter S. aureus bacterial infections. In the experiment, the researchers used many compounds, for example, N,N-Dimethylpiperidin-4-amine (cas: 50533-97-6Application In Synthesis of N,N-Dimethylpiperidin-4-amine).

N,N-Dimethylpiperidin-4-amine (cas: 50533-97-6) 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 bearing a masked aldehyde function in the 蔚-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Application In Synthesis of N,N-Dimethylpiperidin-4-amine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Development of selective small molecule MDM2 degraders based on nutlin was written by Wang, Bo;Wu, Suzhen;Liu, Jin;Yang, Ka;Xie, Haibo;Tang, Weiping. And the article was included in European Journal of Medicinal Chemistry in 2019.Safety of 3-(4-Bromo-1-oxoisoindolin-2-yl)piperidine-2,6-dione This article mentions the following:

Tumor suppressor protein p53 is important to the regulation of many cellular processes and the prevention of cancer development. In some cancer cells, the function of p53 is inhibited by murine double minute 2 protein (MDM2). To restore the function of p53, the inhibition or depletion of MDM2 has become a potential therapeutic treatment. We have successfully developed a series of small mol. MDM2 degraders that can promote the proteolysis of MDM2 oncoprotein, thus reactivating tumor suppressor p53. The superior degrader features a nutlin-based MDM2 ligand and a lenalidomide-based cereblon E3 ubiquitin ligase ligand with a short linker between the two ligands. At low nanomolar concentrations in RS4; 11 leukemia cells, this degrader promotes efficient degradation of MDM2. It also inhibits the proliferation of leukemia cells with an IC₅₀ value of 3.2 nM and induces apoptosis effectively. All of these data indicate that MDM2 degraders are promising therapeutics for the treatment of cancers, such as leukemia. In the experiment, the researchers used many compounds, for example, 3-(4-Bromo-1-oxoisoindolin-2-yl)piperidine-2,6-dione (cas: 2093387-36-9Safety of 3-(4-Bromo-1-oxoisoindolin-2-yl)piperidine-2,6-dione).

3-(4-Bromo-1-oxoisoindolin-2-yl)piperidine-2,6-dione (cas: 2093387-36-9) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. 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.Safety of 3-(4-Bromo-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Sensitive enantiomeric separation of aliphatic and aromatic amines using aromatic anhydrides as non-chiral derivatizing agents was written by Pawlowska, Maria;Zukowski, Janusz;Armstrong, Daniel W.. And the article was included in Journal of Chromatography A in 1994.SDS of cas: 1722-95-8 This article mentions the following:

New pre-column derivatizing reagents: phthalic anhydride, 3-nitrophthalic anhydride, diphenic anhydride, 1,8-naphthalic anhydride and diphenylmaleic anhydride have been developed for resolving chiral compounds having amine groups. Although all of these agents produce derivatives with high molar absorptivities, the later two also fluoresce. Upon derivatization, aromatic analytes containing free carboxylic groups are produced. Both of these moieties enhance chiral recognition on cyclodextrin-based columns. The derivatization reaction is carried out at room temperature by shaking a buffered aqueous solution of a sample with an acetonitrile solution of the reagent. The reaction is fast and proceeds without any detectable racemization. The labeled compounds have favorable chromatog. properties which are demonstrated by resolution of a number of chiral compounds on cyclodextrin-bonded phases operated with non-aqueous polar organic eluents. The selectivity and good efficiency of this system contributes to its high sensitivity and in its applicability for detecting low levels of enantiomeric impurities. The detection limit is in the picomole range and less than 0.1% enantiomeric impurities can be determined in some cases. In the experiment, the researchers used many compounds, for example, (R)-2-Methylpiperidine (cas: 1722-95-8SDS of cas: 1722-95-8).

(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. 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.SDS of cas: 1722-95-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Administration of Memantine During Withdrawal Mitigates Overactivity and Spatial Learning Impairments Associated with Neonatal Alcohol Exposure in Rats was written by Idrus, Nirelia M.;McGough, Nancy N. H.;Riley, Edward P.;Thomas, Jennifer D.. And the article was included in Alcoholism: Clinical & Experimental Research in 2014.Safety of 1-(4-Chlorophenyl)-2-(4-(4-fluorobenzyl)piperidin-1-yl)ethan-1-ol This article mentions the following:

Background : Prenatal alc. exposure can disrupt central nervous system development, manifesting as behavioral deficits that include motor, emotional, and cognitive dysfunction. Both clin. and animal studies have reported binge drinking during development to be highly correlated with an increased risk of fetal alc. spectrum disorders (FASD). We hypothesized that binge drinking may be especially damaging because it is associated with episodes of alc. withdrawal. Specifically, we have been investigating the possibility that NMDA receptor-mediated excitotoxicity occurs during alc. withdrawal and contributes to developmental alc.-related neuropathol. Consistent with this hypothesis, administration of the NMDA receptor antagonists MK-801 or eliprodil during withdrawal attenuates behavioral alterations associated with early alc. exposure. In this study, we investigated the effects of memantine, a clin. used NMDA receptor antagonist, on minimizing ethanol-induced overactivity and spatial learning deficits. Methods : Sprague-Dawley pups were exposed to 6.0 g/kg ethanol via intubation on postnatal day (PD) 6, a period of brain development that models late gestation in humans. Controls were intubated with a calorically matched maltose solution During withdrawal, 24 and 36 h after ethanol exposure, subjects were injected with a total of either 0, 20, or 30 mg/kg memantine. The subjects’ locomotor levels were recorded in open field activity monitors on PDs 18 to 21 and on a serial spatial discrimination reversal learning task on PDs 40 to 43. Results : Alc. exposure induced overactivity and impaired performance in spatial learning. Memantine administration significantly attenuated the ethanol-associated behavioral alterations in a dose-dependent manner. Thus, memantine may be neuroprotective when administered during ethanol withdrawal. Conclusions : These data have important implications for the treatment of EtOH’s neurotoxic effects and provide further support that ethanol withdrawal significantly contributes to FASD. In the experiment, the researchers used many compounds, for example, 1-(4-Chlorophenyl)-2-(4-(4-fluorobenzyl)piperidin-1-yl)ethan-1-ol (cas: 119431-25-3Safety of 1-(4-Chlorophenyl)-2-(4-(4-fluorobenzyl)piperidin-1-yl)ethan-1-ol).

1-(4-Chlorophenyl)-2-(4-(4-fluorobenzyl)piperidin-1-yl)ethan-1-ol (cas: 119431-25-3) 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. 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 1-(4-Chlorophenyl)-2-(4-(4-fluorobenzyl)piperidin-1-yl)ethan-1-ol

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem