October 2022 | Page 67 of 68 | Heterocyclic Building Blocks-piperidine

Turk, Benjamin E.’s team published research in Proceedings of the National Academy of Sciences of the United States of America in 1996 | CAS: 24666-55-5

Benzyl (2,6-dioxopiperidin-3-yl)carbamate(cas: 24666-55-5) belongs to anime. Left-handed and right-handed forms (mirror-image configurations, known as optical isomers or enantiomers) are possible when all the substituents on the central nitrogen atom are different (i.e., the nitrogen is chiral). With amines, there is extremely rapid inversion in which the two configurations are interconverted.Recommanded Product: Benzyl (2,6-dioxopiperidin-3-yl)carbamate

Turk, Benjamin E.; Jiang, Hongsi; Liu, Jun O. published an article in Proceedings of the National Academy of Sciences of the United States of America. The title of the article was 《Binding of thalidomide to α1-acid glycoprotein may be involved in its inhibition of tumor necrosis factor α production》.Recommanded Product: Benzyl (2,6-dioxopiperidin-3-yl)carbamate The author mentioned the following in the article:

In addition to its well known sedative and teratogenic effects, thalidomide also possesses potent immunomodulatory and antiinflammatory activities, being most effective against leprosy and chronic graft-vs.-host disease. The immunomodulatory activity of thalidomide has been ascribed to the selective inhibition of tumor necrosis factor α from monocytes. The mol. mechanism for the immunomodulatory effect of thalidomide remains unknown. To elucidate this mechanism, we synthesized an active photoaffinity label of thalidomide as a probe to identify the mol. target of the drug. Using the probe, we specifically labeled a pair of proteins of 43-45 kDa with high acidity from bovine thymus extract Purification of these proteins and partial peptide sequence determination revealed them to be α1-acid glycoprotein (AGP). We show that the binding of thalidomide photoaffinity label to authentic human AGP is competed with both thalidomide and the nonradioactive photoaffinity label at concentrations comparable to those required for inhibition of production of tumor necrosis factor α from human monocytes, suggesting that AGP may be involved in the immunomodulatory activity of thalidomide. The experimental process involved the reaction of Benzyl (2,6-dioxopiperidin-3-yl)carbamate(cas: 24666-55-5Recommanded Product: Benzyl (2,6-dioxopiperidin-3-yl)carbamate)

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Saamanthi, M.’s team published research in Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry in 2021 | CAS: 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.Recommanded Product: 1445-73-4

Recommanded Product: 1445-73-4In 2021 ,《Design, synthesis of novel pyrazolopyridine derivatives and CREBBP bromodomain inhibitors docking and molecular dynamics》 appeared in Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry. The author of the article were Saamanthi, M.; Aruna, S.; Girija, R.; Vinod, D.. The article conveys some information:

A sequence of novel compounds pyrazolopyridines I [R = Ph, 2-phenylethenyl, 3-(trifluoromethyl)phenyl, 2,4-dimethylphenyl, etc.; X = O, S] have been prepared by a general synthetic method. Due to high efficiency and selectivity, anticancer agents consisting of combined mols. have gained great interests. The IC50 values have been determined against cell line U937, and the results obtained indicate the potential effects against cancer cell line. The cell potency of cell line is best for compounds I [R = 4-(trifluoromethyl)phenyl; X = O] IC50 = 62.5μM, I (R = Ph; X = S) IC50 = 62.5μM, I (R = Ph; X = O) IC50 = 31.2μM, I [R = 3-(trifluoromethyl)phenyl; X = O] IC50 = 31.2μM, selectivity and in vivo. Further, the mol. docking studies indicate that substituted pyrazolo[4,3-c]pyridine derivatives I show good anticancer activity in the medicinal field. The ease of synthesis and the significant biol. activities make these compounds I potential new frameworks for progress of cancer therapeutics. Compound I (R = 2,4-dimethylphenyl; X = O) shows anticancer effect in cancer cell lines and in vivo that corresponds with antitumor activity in an AML cancer type. For the mol. docking with the ligands, the RMSD value has been calculated, and the protein with the least RMSD is found to be 5KTU screening with 20 small mols. The experimental process involved the reaction of 1-Methyl-4-piperidone(cas: 1445-73-4Recommanded Product: 1445-73-4)

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Mohd Sarofil, Anith Dzhanxinah’s team published research in Journal of Industrial and Engineering Chemistry (Amsterdam, Netherlands) in 2022 | CAS: 826-36-8

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.Application of 826-36-8

Mohd Sarofil, Anith Dzhanxinah; Devina, Winda; Albertina, Ingrid; Chandra, Christian; Kim, Jaehoon published an article on February 25 ,2022. The article was titled 《Toad egg-like bismuth nanoparticles encapsulated in an N-doped carbon microrod via supercritical acetone as anodes in lithium-ion batteries》, and you may find the article in Journal of Industrial and Engineering Chemistry (Amsterdam, Netherlands).Application of 826-36-8 The information in the text is summarized as follows:

A toad egg-inspired structure comprising bismuth (Bi) nanoparticles (NPs) contained in a carbon microrod shell (Bi@C) was synthesized via the one-pot supercritical acetone (scAct) route and subsequent carbonization. During the formation of Bi NPs in scAct in the presence of nitric acid, a few decomposed acetone mols. acted as carbon sources, which generated an albumen-like N-doped carbon microrod with an average shell thickness of 38 nm and were embedded with yolk-like Bi NPs having size in the range of 30-200 nm. The densely packed Bi NPs inside the carbon micron shell resulted in a high Bi loading of 78 wt%. When utilized for Li storage, the Bi@C delivered a high reversible capacity of 337 mAh g-1 after 70 cycles at 0.05 A g-1, long-term cyclability of 0.04 decay per cycle for 1000 cycles at 1 A g-1, and high volumetric energy d. of 870 mAh cm-3. The use of a mixed ether- and ester-based electrolyte in the Bi@C cell reduced the resistivity and increased the capacitive contribution, thereby resulting in a better high-rate performance and long-term stability than those obtained using conventional ester-based electrolytes. The experimental part of the paper was very detailed, including the reaction process of Triacetonamine(cas: 826-36-8Application of 826-36-8)

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Sathe, Dhananjay G.’s team published research in Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry in 1994 | CAS: 126832-81-3

1-Pyridin-4-ylpiperidin-4-one(cas: 126832-81-3) belongs to piperidines. Piperidine derivatives are also used in solid-phase peptide synthesis (SPPS) and many degradation reactions. Application of 126832-81-3

Application of 126832-81-3On October 31, 1994 ,《Synthesis of 3,5-lutidine by catalytic transfer hydrogenation via 1,2,5,6-tetrahydropyridine》 was published in Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry. The article was written by Sathe, Dhananjay G.; Kulkarni, Vithal M.. The article contains the following contents:

Substituted pyridines, e.g. 3,5-lutidine, have been prepared from the corresponding N-benzyl-1,2,5,6-tetrahydropyridines by catalytic transfer hydrogenation in one stage. A mechanism for such a catalytic transfer hydrogenation (CTH) has been proposed. In the experiment, the researchers used 1-Pyridin-4-ylpiperidin-4-one(cas: 126832-81-3Application of 126832-81-3)

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Yu, Tao’s team published research in ACS Medicinal Chemistry Letters in 2010-08-31 | 91419-53-3

ACS Medicinal Chemistry Letters published new progress about Antitumor agents. 91419-53-3 belongs to class piperidines, and the molecular formula is C11H18N2O2, Product Details of C11H18N2O2.

Yu, Tao; Tagat, Jayaram R.; Kerekes, Angela D.; Doll, Ronald J.; Zhang, Yonglian; Xiao, Yushi; Esposite, Sara; Belanger, David B.; Curran, Patrick J.; Mandal, Amit K.; Siddiqui, M. Arshad; Shih, Neng-Yang; Basso, Andrea D.; Liu, Ming; Gray, Kimberly; Tevar, Seema; Jones, Jennifer; Lee, Suining; Liang, Lianzhu; Ponery, Samad; Smith, Elizabeth B.; Hruza, Alan; Voigt, Johannes; Ramanathan, Lata; Prosise, Winifred; Hu, Mengwei published the artcile< Discovery of a Potent, Injectable Inhibitor of Aurora Kinases Based on the Imidazo-[1,2-a]-Pyrazine Core>, Product Details of C11H18N2O2, the main research area is imidazopyrazine pyrazolyl isothiazolylamino derivative preparation aurora kinase inhibition activity; pyrazolyl isothiazolylamino imidazopyrazine solubility antitumor activity; Aurora kinase inhibitors; SCH 1473759; aqueous solubility; cell potency; imidazo-[1,2-a]-pyrazine; tumor xenograft model.

The imidazo-[1,2-a]-pyrazine I is a dual inhibitor of Aurora kinases A and B with modest cell potency (IC50 = 250 nM) and low solubility (5 μM). Lead optimization guided by the binding mode led to the acyclic amino alc. II (SCH 1473759), which is a picomolar inhibitor of Aurora kinases (TdF Kd Aur A = 0.02 nM and Aur B = 0.03 nM) with improved cell potency (phos-HH3 inhibition IC50 = 25 nM) and intrinsic aqueous solubility (11.4 mM). It also demonstrated efficacy and target engagement in human tumor xenograft mouse models.

ACS Medicinal Chemistry Letters published new progress about Antitumor agents. 91419-53-3 belongs to class piperidines, and the molecular formula is C11H18N2O2, Product Details of C11H18N2O2.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Chen, Yilin’s team published research in Chem in 2020-01-09 | 25504-47-6

Chem published new progress about Bond cleavage catalysts (C-C, regioselective). 25504-47-6 belongs to class piperidines, and the molecular formula is C7H11NO3, Synthetic Route of 25504-47-6.

Chen, Yilin; Du, Jianbo; Zuo, Zhiwei published the artcile< Selective C-C Bond Scission of Ketones via Visible-Light-Mediated Cerium Catalysis>, Synthetic Route of 25504-47-6, the main research area is hydrazine regioselective preparation photochem; ketone DIAD photochem carbon bond cleavage cerium catalyst.

A general catalytic manifold for selective C-C bond scission of ketones via exploitation of ligand-to-metal charge transfer (LMCT) excitation mode was reported. Through a cooperative utilization of Lewis acid catalysis and LMCT catalysis, the C-C bond of ketones could be selectively and effectively cleaved, enabling installation of different functionalities at each carbon of cleaved C-C bond through a sequential and orthogonal manner. This reaction manifold served as a photocatalytic alternative to Norrish type I reaction with combination of visible light and inexpensive cerium salts. Under operationally simple conditions, a wide range of acyclic and cyclic ketones, from simple strained cyclobutanones to complex androsterone with less strained cyclopentanone moiety, could be successfully transformed into versatile chem. building blocks.

Chem published new progress about Bond cleavage catalysts (C-C, regioselective). 25504-47-6 belongs to class piperidines, and the molecular formula is C7H11NO3, Synthetic Route of 25504-47-6.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Blahun, Oleksandr P’s team published research in European Journal of Organic Chemistry in 2020-06-01 | 91419-53-3

European Journal of Organic Chemistry published new progress about Carboxylation. 91419-53-3 belongs to class piperidines, and the molecular formula is C11H18N2O2, Recommanded Product: tert-Butyl 3-cyanopiperidine-1-carboxylate.

Blahun, Oleksandr P.; Melnychenko, Heorhii; Kuchkovska, Yuliya O.; Zhersh, Serhii; Tolmachev, Andrey A.; Grygorenko, Oleksandr O. published the artcile< Synthesis of Functionalized Bridged Bicyclic Sulfonamides with a Bridgehead Nitrogen Atom>, Recommanded Product: tert-Butyl 3-cyanopiperidine-1-carboxylate, the main research area is dioxothiazabicycloalkanecarboxylate bridged sultam preparation.

Sultams with bridgehead nitrogen atoms such as I and II were prepared Dioxothiazabicycloalkanecarboxylic acids such as I with carboxylic acid-substituted bridgehead atoms were prepared in seven steps from Boc-protected azaheterocyclylcarbonitriles such as tert-Bu 3-cyano-1-pyrrolidinecarboxylate by chloromethylation, substitution with a thiolate, oxidative chlorination, substitution of the sulfonyl chloride with fluoride, Boc deprotection, base-mediated cyclization, and nitrile hydrolysis. Dioxothiazabicycloalkanecarboxylic acids such as I with carboxylic acid-substituted bridging atoms were prepared by carboxylation of bridged sultams [prepared in six steps by literature procedures from Boc-protected (hydroxymethyl)azacycles]. Two approaches to the synthesis of functionalized bridged bicyclic sulfonamides with a bridgehead nitrogen atom were developed. Both types of bridged sultams were prepared on > 1g scales.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Zacharie, Boulos’s team published research in European Journal of Organic Chemistry in 2018 | 25504-47-6

European Journal of Organic Chemistry published new progress about Amino acids Role: SPN (Synthetic Preparation), PREP (Preparation). 25504-47-6 belongs to class piperidines, and the molecular formula is C7H11NO3, SDS of cas: 25504-47-6.

Zacharie, Boulos; Abbott, Shaun D.; Baigent, Christopher B.; Doyle, Christopher; Yalagala, Ravi Shekar published the artcile< An Efficient Two-Step Preparation of α-, β-, γ- or δ-Amino Acids from 2-Pyrazinones, 2-Hydroxypyrimidines or 2-Pyridones Respectively>, SDS of cas: 25504-47-6, the main research area is amino acid alpha beta gamma preparation pyrazinone hydroxypyrimidine pyridone.

A practical and efficient two-step procedure is reported for the preparation of a variety of α-, β-, γ- and δ-amino acids from 2-pyridone, 2-pyrazinone or 2-hydroxypyrimidine and derivatives The procedure is amenable to scale-up and in most cases no chromatog. purification of the product is required. This approach is useful, especially in the synthesis of amino acids or deuterated amino acids that are not obtained by other methods.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Kalliokoski, Tuomo’s team published research in Bioorganic & Medicinal Chemistry Letters in 2020-04-15 | 91419-53-3

Bioorganic & Medicinal Chemistry Letters published new progress about Bipolar disorder. 91419-53-3 belongs to class piperidines, and the molecular formula is C11H18N2O2, Application In Synthesis of 91419-53-3.

Kalliokoski, Tuomo; Rummakko, Petteri; Rantanen, Marja; Blaesse, Michael; Augustin, Martin; Ummenthala, Goverdhan Reddy; Choudhary, Sapan; Venalainen, Jarkko published the artcile< Discovery of sulfonamides and 9-oxo-2,8-diazaspiro[5,5]undecane-2-carboxamides as human kynurenine aminotransferase 2 (KAT2) inhibitors>, Application In Synthesis of 91419-53-3, the main research area is human kynurenine aminotransferase 2 KAT2 reversible inhibitor virtual screening; Human kynurenine aminotransferase 2; KAT2; Reversible inhibitor; Virtual screening.

Human kynurenine aminotransferase 2 (KAT2) inhibitors could be potentially used to treat the cognitive deficits associated with bipolar disease and schizophrenia. Although, there has been active drug research activity by several industrial and academic groups in developing KAT2 inhibitors over the years, no such compound has proceeded to the clinics. Here, we report two different chem. series of reversible KAT2 inhibitors with sub-micromolar activities. The first series was identified by a high-throughput screening of a diverse random library and the second one by structure-based virtual screening. Two novel crystal structures of KAT2 complexed with different reversible inhibitors were also deposited to the Protein databank which could be useful for future drug discovery efforts.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Wagener, Tobias’s team published research in Angewandte Chemie, International Edition in 2021-03-22 | 25504-47-6

Angewandte Chemie, International Edition published new progress about Hydrogenation. 25504-47-6 belongs to class piperidines, and the molecular formula is C7H11NO3, COA of Formula: C7H11NO3.

Wagener, Tobias; Lueckemeier, Lukas; Daniliuc, Constantin G.; Glorius, Frank published the artcile< Interrupted pyridine hydrogenation: Asymmetric synthesis of δ-lactams>, COA of Formula: C7H11NO3, the main research area is delta lactam preparation oxazolidinone substituted pyridine interrupted hydrogenation; asymmetric catalysis; heterogeneous catalysis; hydrogenation; lactams; nitrogen heterocycles.

Metal-catalyzed hydrogenation is an effective method to transform readily available arenes into saturated motifs, however, current hydrogenation strategies are limited to the formation of C-H and N-H bonds. The stepwise addition of hydrogen yields reactive unsaturated intermediates that are rapidly reduced. In contrast, the interruption of complete hydrogenation by further functionalization of unsaturated intermediates offers great potential for increasing chem. complexity in a single reaction step. Overcoming the tenet of full reduction in arene hydrogenation has been seldom demonstrated. In this work the authors report the synthesis of sought-after, enantioenriched δ-lactams from oxazolidinone-substituted pyridines and water by an interrupted hydrogenation mechanism.

Angewandte Chemie, International Edition published new progress about Hydrogenation. 25504-47-6 belongs to class piperidines, and the molecular formula is C7H11NO3, COA of Formula: C7H11NO3.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem