Category: piperidines

Jiang, Baishan published the artcileStructure-activity relationship study of THZ531 derivatives enables the discovery of BSJ-01-175 as a dual CDK12/13 covalent inhibitor with efficacy in Ewing sarcoma, Recommanded Product: (R,E)-N-(4-(3-((5-Chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)piperidine-1-carbonyl)phenyl)-4-(dimethylamino)but-2-enamide, the publication is European Journal of Medicinal Chemistry (2021), 113481, database is CAplus and MEDLINE.

Development of inhibitors targeting CDK12/13 is of increasing interest as a potential therapy for cancers as these compounds inhibit transcription of DNA damage response (DDR) genes. We previously described THZ531, a covalent inhibitor with selectivity for CDK12/13. In order to elucidate structure-activity relationship (SAR), we have undertaken a medicinal chem. campaign and established a focused library of THZ531 analogs. Among these analogs, BSJ-01-175 demonstrates exquisite selectivity, potent inhibition of RNA polymerase II phosphorylation, and downregulation of CDK12-targeted genes in cancer cells. A 3.0 Å co-crystal structure with CDK12/CycK provides a structural rational for selective targeting of Cys1039 located in a C-terminal extension from the kinase domain. With moderate pharmacokinetic properties, BSJ-01-175 exhibits efficacy against an Ewing sarcoma tumor growth in a patient-derived xenograft (PDX) mouse model following 10 mg/kg once a day, i.p. administration. Taken together, BSJ-01-175 represents the first selective CDK12/13 covalent inhibitor with in vivo efficacy reported to date.

European Journal of Medicinal Chemistry published new progress about 1702809-17-3. 1702809-17-3 belongs to piperidines, auxiliary class Cell Cycle,CDK, name is (R,E)-N-(4-(3-((5-Chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)piperidine-1-carbonyl)phenyl)-4-(dimethylamino)but-2-enamide, and the molecular formula is C30H32ClN7O2, Recommanded Product: (R,E)-N-(4-(3-((5-Chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)piperidine-1-carbonyl)phenyl)-4-(dimethylamino)but-2-enamide.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Mao, Shuhua published the artcile(RuBpy₃)²⁺-bisterpyridinyl triangle promoted singlet oxygen (¹O₂) photosensitization for fast oxidation of sulfur mustard simulant, Quality Control of 826-36-8, the publication is Inorganic Chemistry Communications (2022), 109090, database is CAplus.

(RuBpy₃)²⁺-bisterpyridine-based metallacycle T photosensitizer was prepared by a facile single-step self-assembly process. Supramol. self-assembly strategy greatly improved metallacycle T’s photosensitized ability due to its enhanced light-harvesting capability, smaller energy gap (ΔE_ST) between lowest excited singlet state (S1) and lowest excited triplet state (T1) along with excellent solubility which exhibiting higher efficiency for singlet oxygen (¹O₂) production than the ligand L and its pendant [(RuBpy₃)²⁺·2PF₆^–]. In the practical photo-driven degradation of sulfur mustard simulant (2-chloroethyl Et sulfide, CEES), full conversion of toxic CEES to nontoxic CEESO was achieved by metallacycle T with an extremely fast lifetime of 90 s (half lifetime t_1/2 = 25 s) and 100% selectivity (without formation of highly toxic CEESO₂), while ligand L and [(RuBpy₃)²⁺·2PF₆^–] needed 130 s and 330 s, resp. This study demonstrated terpyridine-based novel supermols. can serve as efficient scaffolds for effective enhancement of photosensitization.

Inorganic Chemistry Communications published new progress about 826-36-8. 826-36-8 belongs to piperidines, auxiliary class Natural product, name is 2,2,6,6-Tetramethylpiperidin-4-one, and the molecular formula is C9H17NO, Quality Control of 826-36-8.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Xu, Rongsong published the artcileSynthesis of β-(1â†?)-oligo-D-mannuronic acid neoglycolipids, COA of Formula: C11H15NOS, the publication is Carbohydrate Research (2008), 343(1), 7-17, database is CAplus and MEDLINE.

Mammalian Toll-like receptors (TLRs) play important roles in host immune defense. The activation of TLR and down-stream signaling pathways have great impact on human physiol. Chem. diverse microbial products as well as synthetic ligands serve as agonists for these receptors. Recently, synthetic TLR ligands are being exploited as useful therapeutic agents for a variety of diseases including infections, inflammatory diseases, and cancers. Alginate polymers and oligosaccharides are strong immune stimulants mediated by TLR2/4, but synthesis of alginate oligomers is rarely studied. Reported here are the design and chem. synthesis of two β-(1â†?)-di- and β-(1â†?)-tri-D-mannuronic acid neoglycolipids I (n = 0, 1) as potential TLR ligands. By using 4,6-di-O-benzylidene-protected 1-thio mannoside as a glycosyl donor, the diastereoselective β-D-mannosylation protocol provides the β-(1â†?)-D-mannobiose and β-(1â†?)-D-mannotriose derivatives, which upon regioselective oxidation with TEMPO/[bis(acetoxy)iodo]benzene (BAIB) oxidation system yield the corresponding β-(1â†?)-D-mannuronic acid containing neoglycolipids I (n = 0, 1).

Carbohydrate Research published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C6H3ClFNO2, COA of Formula: C11H15NOS.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Ge, Teng published the artcileGiant enhanced photocatalytic H₂O₂ production over hollow hexagonal prisms carbon nitride, Category: piperidines, the publication is Journal of the Taiwan Institute of Chemical Engineers (2021), 104-111, database is CAplus.

H2O2, as a green and environmentally friendly oxidant, has been widely used in our daily life and industrial production It is of epoch-making significance to develop highly efficient photocatalysts for producing H2O2. In recent years, g-C3N4 has received much attention due to its high chem. stability, environmental friendliness and suitable energy band structure. However, some shortcomings including the fast recombination of photogenerated electron-hole pairs and small sp. surface area in traditional 2D g-C3N4 seriously impede its photocatalytic performance for the production of H2O2.1D hollow nanostructures possess intriguing physicochem. properties and are adopted to overcome the intrinsic shortcomings of g-C3N4. Herein, g-C3N4 with a hollow hexagonal prism structure (CN-HP) is prepared to produce H2O2. It is characterized by XRD, XPS, SEM, HRTEM, ESR and DRS. BET, PL spectra, photocurrent and EIS are used to explain the enhanced photocatalytic performance. Compared with traditional 2D g-C3N4, the sp. surface area of CN-HP increases to 41.513 m²/g, providing more active sites. Meanwhile, its hollow tubular structure can enhance the migration of photogenerated electrons to the catalyst surface, and electrons with a longer lifetime can participate in photocatalytic reactions to achieve high efficiency. The yield of H2O2 production can up to 4.08 μmol over CN-HP in 40 min, which is about 7 times higher than that of traditional 2D g-C3N4, and the apparent quantum efficiency (AQE) of H2O2 production at 420 nm is 2.41%. This research provides a valuable reference for the development of green materials for efficient photocatalytic production of H2O2.

Journal of the Taiwan Institute of Chemical Engineers published new progress about 826-36-8. 826-36-8 belongs to piperidines, auxiliary class Natural product, name is 2,2,6,6-Tetramethylpiperidin-4-one, and the molecular formula is C9H17NO, Category: piperidines.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Qin, Tian published the artcileVinylogous Addition of Siloxyfurans to Benzopyryliums: A Concise Approach to the Tetrahydroxanthone Natural Products, COA of Formula: C11H21BF4N2O2, the publication is Journal of the American Chemical Society (2011), 133(6), 1714-1717, database is CAplus and MEDLINE.

A concise approach to the tetrahydroxanthone natural products employing vinylogous addition of siloxyfurans to benzopyryliums and a late-stage Dieckmann cyclization was developed. With this methodol., chiral, racemic forms of the natural products blennolide B (I) and blennolide C (II) were synthesized in a maximum of four steps from a 5-hydroxychromone substrate. The regio- and diastereoselectivity of the vinylogous additions was probed using computational studies, which suggested the involvement of Diels-Alder-like transition states.

Journal of the American Chemical Society published new progress about 219543-09-6. 219543-09-6 belongs to piperidines, auxiliary class Piperidine,Fluoride,Salt,Amine,Amide, name is 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, and the molecular formula is C11H21BF4N2O2, COA of Formula: C11H21BF4N2O2.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Yu, Valentina K. published the artcileSynthesis and properties of novel alkoxy- and phenoxyalkyl ethers of secondary and tertiary ethynylpiperidin-4-ols possessing unusual analgesic, anti-bacterial, anti-spasmotic, and anti-allergic properties as well as low toxicity, HPLC of Formula: 512778-95-9, the publication is Journal of Saudi Chemical Society (2009), 13(2), 209-217, database is CAplus.

Methodol. was developed to obtain a series of unusual alkoxy- and phenoxyalkyl ethers of secondary and tertiary ethynylpiperidin-4-ols, representative examples of which were evaluated for analgesic, anti-bacterial, anti-spasmotic, and anti-allergic activity. Twenty-two new compounds were prepared and identified by elemental and spectral analyses. Etherification of 4-hydroxypiperidin-4-ols was accomplished via Williamson ether-type syntheses in dry DMF. Side reactions of the bromides used appeared to involve complex processes with DMF under a variety of conditions employed which led to modest yields of products. Since all target mols. were oils at room temperature, conversions to β-cyclodextrins were accomplished and served as vehicles for pharmacol. screening. Several ethynyl-substituted agents displayed deep analgesic activity in the tail flick model, although some alkoxy- and phenoxy ethers from secondary alcs. were less effective as analgesics. Interestingly, LD50 values for the agents exceeded that of a number of clin. agents including Dimedrole, Klemastine, Lidocaine, No-spa, Tramal, Streptomycin, and Euphilline. Three representative examples of the agents exhibited moderate anti-bacterial action against Escherichia coli, Salmonella chloerae suis, Salmonella typhimurium, and Staphylococcus aureus, but did not exceed that of Streptomycin. The absence of the ethynyl ether group resulted in no anti-bacterial activity in several ethers. A few agents possessed anti-spasmotic ability, especially the ethers of 1-(2-ethoxyethyl)-4-ethynyl-4-hydroxypiperidines in various preparations and included the systems of acetylcholine-induced spasms, the histamine-induced spasms, and the calcium chloride-induced spasms. Two examples void of the ethynyl group were not effective as anti-spasmotic compounds A small survey of five agents for anti-allergic properties revealed that two with ethynyl groups were similar in activity with Dimedrole but less than that of Klemastine in screens using acetylcholine and histamine systems. Overall, these families of piperidines possess a wide variety of important biol. properties which require further exploration.

Journal of Saudi Chemical Society published new progress about 512778-95-9. 512778-95-9 belongs to piperidines, auxiliary class Piperidine,Alcohol,Ether, name is 1-(2-Methoxyethyl)piperidin-4-ol, and the molecular formula is C11H15NO2, HPLC of Formula: 512778-95-9.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

He, Yantao published the artcileA potent and selective inhibitor for the UBLCP1 proteasome phosphatase, Computed Properties of 39546-32-2, the publication is Bioorganic & Medicinal Chemistry (2015), 23(12), 2798-2809, database is CAplus and MEDLINE.

The ubiquitin-like domain-containing C-terminal domain phosphatase 1 (UBLCP1) has been implicated as a neg. regulator of the proteasome, a key mediator in the ubiquitin-dependent protein degradation Small mol. inhibitors that block UBLCP1 activity would be valuable as research tools and potential therapeutics for human diseases caused by the cellular accumulation of misfold/damaged proteins. The authors report a salicylic acid fragment-based library approach aimed at targeting both the phosphatase active site and its adjacent binding pocket for enhanced affinity and selectivity. Screening of the focused libraries led to the identification of the first potent and selective UBLCP1 inhibitor I. Compound I exhibits an IC₅₀ of 1.0 μM for UBLCP1 and greater than 5-fold selectivity against a large panel of protein phosphatases from several distinct families. Importantly, the inhibitor possesses efficacious cellular activity and is capable of inhibiting UBLCP1 function in cells, which in turn up-regulates nuclear proteasome activity. These studies set the groundwork for further developing compound I into chem. probes or potential therapeutic agents targeting the UBLCP1 phosphatase.

Bioorganic & Medicinal Chemistry published new progress about 39546-32-2. 39546-32-2 belongs to piperidines, auxiliary class Piperidine,Amine,Amide, name is Piperidine-4-carboxamide, and the molecular formula is C6H12N2O, Computed Properties of 39546-32-2.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Shao, N. published the artcileA facile synthesis of the fucosylated N-linked glycan core and its application to solid-phase synthesis of CD52 glycopeptide, Computed Properties of 4972-31-0, the publication is Polish Journal of Chemistry (2005), 79(2), 297-307, database is CAplus.

An efficient synthesis of the fucosylated N-linked core hexasaccharide and its asparagine conjugate, as well as their applications to the solid-phase synthesis of an extensively protected glycopeptide of CD52 antigen containing the hexasaccharide, is described. The difficult β-mannosidic and α-fucosidic linkages were achieved by the Crich and in situ anomerization protocols resp., which offered excellent results. An especially acid-sensitive resin, 2-chloro-trityl resin, was used in the solid-phase synthesis, and the target glycopeptide could be released from the resin by 10% HOAc without affecting the acid-labile protecting groups and fucosidic bond.

Polish Journal of Chemistry published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C5H6N2O2, Computed Properties of 4972-31-0.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Szokan, Gy. published the artcileHPLC determination of enantiomeric purity of protected amino acid derivatives used in peptide synthesis, Recommanded Product: (R)-6-Oxopiperidine-2-carboxylic acid, the publication is Journal of Liquid Chromatography (1994), 17(13), 2759-75, database is CAplus.

An improved RP-HPLC method on ODS-Hypersil column with precolumn derivatization with Marfey’s reagent was used to monitor racemization in N-, C- and/or side-chain protected amino acid derivatives by separation of new diastereoisomeric Marfey’s compounds Chromatog. samples were obtained by partial deprotection of different starting materials. In a simple two-step procedure (deprotection and derivatization) the compounds of amino acids formed stable diastereomeric derivatives having facile resolutions

Journal of Liquid Chromatography published new progress about 72002-30-3. 72002-30-3 belongs to piperidines, auxiliary class Piperidine,Chiral,Carboxylic acid,Amide, name is (R)-6-Oxopiperidine-2-carboxylic acid, and the molecular formula is C15H16O3, Recommanded Product: (R)-6-Oxopiperidine-2-carboxylic acid.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Peter Ventura, Alejandra M. published the artcileDevelopment of Biarylalkyl Carboxylic Acid Amides with Improved Anti-schistosomal Activity, COA of Formula: C6H12N2O, the publication is ChemMedChem (2019), 14(21), 1856-1862, database is CAplus and MEDLINE.

The parasitic disease schistosomiasis is the cause of more than 200 000 human deaths per yr. Although the disease is treatable, there is one major shortcoming: praziquantel has been the only drug used to combat these parasites since 1977. The risk of the emergence of resistant schistosomes is known to be increasing, as a reduced sensitivity of these parasites toward praziquantel has been observed We developed a new class of substances, which are derived from inhibitors of human aldose reductase, and which showed promising activity against Schistosoma mansoni couples in vitro. Further optimization of the compounds led to an increase in anti-schistosomal activity with observed phenotypes such as reduced egg production, vitality, and motility as well as tegumental damage and gut dilatation. Here, we performed structure-activity relationship studies on the carboxylic acid moiety of biarylalkyl carboxylic acids. Out of 82 carboxylic acid amides, we identified 10 compounds that are active against S. mansoni at 25 μm. The best five compounds showed an anti-schistosomal activity up to 10 μm and induced severe phenotypes. Cytotoxicity tests in human cell lines showed that two derivatives had no cytotoxicity at 50 or 100 μm. These compounds are promising candidates for further optimization toward the new anti-schistosomal agents.

ChemMedChem published new progress about 39546-32-2. 39546-32-2 belongs to piperidines, auxiliary class Piperidine,Amine,Amide, name is Piperidine-4-carboxamide, and the molecular formula is C6H12N2O, COA of Formula: C6H12N2O.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem