Month: December 2022

Son, Sang-Hyun published the artcileStereoselective tris-glycosylation to introduce β-(1→3)-branches into gentiotetraose for the concise synthesis of phytoalexin-elicitor heptaglucoside, Application of 1-(Phenylsulfinyl)piperidine, the publication is Organic & Biomolecular Chemistry (2008), 6(8), 1441-1449, database is CAplus and MEDLINE.

Dodecyl thioglycosides (3, 4, 5) were prepared by conventional transformation of d-glucose and used as new glycosyl donors for a short-step synthesis of phytoalexin elicitor heptaglucoside. A gentio-tetraoside derivative (6) having three hydroxyl groups was synthesized by NIS-TfOH promoted glycosylate in more than 90% yield followed by selective removal of temporary protective groups. Undesired formation of α-glycosides at the introduction of β-(1→3)-branches into gentio-oligosaccharides was found to be suppressed by use of a thiophilic reagent system, BSP (1-benzenesulfinyl piperidine)-Tf₂O, giving the heptaglucoside in only four glycosylation steps.

Organic & Biomolecular 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 C28H18O4, Application of 1-(Phenylsulfinyl)piperidine.

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

Yang, Shyh-Ming published the artcile4-Bicyclic heteroaryl-piperidine derivatives as potent, orally bioavailable Stearoyl-CoA desaturase-1 (SCD1) inhibitors. Part 1: Urea-based analogs, SDS of cas: 1032229-33-6, the publication is Bioorganic & Medicinal Chemistry Letters (2013), 23(24), 6773-6776, database is CAplus and MEDLINE.

A new series of urea-based, 4-bicyclic heteroaryl-piperidine derivatives as potent SCD1 inhibitors is described. The structure-activity relationships focused on bicyclic heteroarenes and aminothiazole-urea portions are discussed. A trend of dose-dependent decrease in body weight gain in diet-induced obese (DIO) mice is also demonstrated.

Bioorganic & Medicinal Chemistry Letters published new progress about 1032229-33-6. 1032229-33-6 belongs to piperidines, auxiliary class Metabolic Enzyme,SCD, name is 4-(2-Chlorophenoxy)-N-(3-(methylcarbamoyl)phenyl)piperidine-1-carboxamide, and the molecular formula is C14H14, SDS of cas: 1032229-33-6.

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

Dai, Liang published the artcileGut Microbiota and Related Metabolites Were Disturbed in Ulcerative Colitis and Partly Restored After Mesalamine Treatment, Category: piperidines, the publication is Frontiers in Pharmacology (2020), 620724, database is CAplus and MEDLINE.

Mesalamine has been well used in the improvement of ulcerative colitis (UC) in clinics, however, the underlying mechanisms were not well illustrated. To explore its efficacy from the perspective of gut microbiota and related metabolites, we employed 16S rRNA sequencing and metabolomics approaches in stool samples across 14 normal healthy controls (NC group), 10 treatment-naïve UC patients (UC group) and 14 UC patients responded to mesalamine treatment (mesalamine group). We noted that the gut microbiota diversity and community composition were remarkably perturbed in UC group and partially restored by mesalamine treatment. The relative abundance of 192 taxa in genus level were significantly changed in UC group, and 168 genera were significantly altered after mesalamine intervention. Meanwhile, a total of 127 metabolites were significantly changed in UC group and 129 metabolites were significantly altered after mesalamine treatment. Importantly, we observed that many candidates including 49 genera (such as Escherichia-shigella, Enterococcus and Butyricicoccus) and 102 metatoblites (such as isoleucine, cholic acid and deoxycholic acid) were reversed by mesalamine. Spearman correlation anal. revealed that most of the candidates were significantly correlated with Mayo score of UC, and the relative abundance of specific genera were significant correlated with the perturbation of metabolites. Pathway anal. demonstrated that genera and metabolites candidates were enriched in many similar mol. pathways such as amino acid metabolism and secondary metabolites biosynthesis. Importantly, ROC curve anal. identified a gut microbiota signature composed of five genera including Escherichia-Shigella, Streptococcus, Megamonas, Prevotella_9 and [Eubacterium] _coprostanoligenes _group which might be used to distinguish UC group from both NC and mesalamine group. In all, our results suggested that mesalamine might exert a beneficial role in UC by modulating gut microbiota signature with correlated metabolites in different pathways, which may provide a basis for developing novel candidate biomarkers and therapeutic targets of UC.

Frontiers in Pharmacology 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

Ito, Masahiro published the artcileDiscovery of 3-Benzyl-1-(trans-4-((5-cyanopyridin-2-yl)amino)cyclohexyl)-1-arylurea Derivatives as Novel and Selective Cyclin-Dependent Kinase 12 (CDK12) Inhibitors, Safety of (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 Journal of Medicinal Chemistry (2018), 61(17), 7710-7728, database is CAplus and MEDLINE.

Cyclin-dependent kinase 12 (CDK12) plays a key role in the coordination of transcription with elongation and mRNA processing. CDK12 mutations found in tumors and CDK12 inhibition sensitize cancer cells to DNA-damaging reagents and DNA-repair inhibitors. This suggests that CDK12 inhibitors are potential therapeutics for cancer that may cause synthetic lethality. Here, we report the discovery of 3-benzyl-1-(trans-4-((5-cyanopyridin-2-yl)amino)cyclohexyl)-1-arylurea derivatives as novel and selective CDK12 inhibitors. Structure-activity relationship studies of a HTS hit, structure-based drug design, and conformation-oriented design using the Cambridge Structural Database afforded the optimized compound 2, which exhibited not only potent CDK12 (and CDK13) inhibitory activity and excellent selectivity but also good physicochem. properties. Furthermore, 2 inhibited the phosphorylation of Ser2 in the C-terminal domain of RNA polymerase II and induced growth inhibition in SK-BR-3 cells. Therefore, 2 represents an excellent chem. probe for functional studies of CDK12 and could be a promising lead compound for drug discovery.

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, Safety of (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

Yamada, Takeshi published the artcileDialkyl-phosphates as stereo-directing protecting groups in oligosaccharide synthesis, Category: piperidines, the publication is Angewandte Chemie, International Edition (2006), 45(45), 7575-7578, database is CAplus and MEDLINE.

Double duty: A phosphoric ester at the C2 position in glycosyl donors directs the glycosylation to occur selectively at the anomeric carbon atom with complete 1,2-trans selectivity. Since the phosphoric ester can be removed to give the hydroxy function, this group serves as a stereo-directing protecting group in oligosaccharide synthesis.

Angewandte Chemie, International Edition 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 C7H8BBrO3, Category: piperidines.

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

Clapham, Bruce published the artcileUse of a scintillant-containing macroporous resin in both solid phase synthesis and subsequent on-bead scintillation-based analysis, Related Products of piperidines, the publication is Tetrahedron Letters (2000), 41(13), 2257-2260, database is CAplus.

A chem.-functionalized scintillant-containing divinylbenzene-2,5-diphenyl-4-vinyloxazole-4-ethylstyrene-4-vinylbenzyl chloride copolymer macroporous resin was used successfully in a two stage solid phase organic synthesis. The second step in this synthesis involved the covalent attachment of a tritiated acetate group to the resin. The resultant radiolabeled scintillant-containing resin beads scintillate spontaneously and with high efficiency due to the close proximity of the tritium atoms to the scintillant mols. within the beads.

Tetrahedron Letters published new progress about 35661-58-6. 35661-58-6 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-((9H-Fluoren-9-yl)methyl)piperidine, and the molecular formula is C19H21N, Related Products of piperidines.

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

Crich, David published the artcileCyclofunctionalization of unsaturated alcohols, phenols, acids, and sulfonamides with 1-benzenesulfinyl piperidine and trifluoromethanesulfonic anhydride, HPLC of Formula: 4972-31-0, the publication is Heterocycles (2004), 827-830, database is CAplus.

The combination of a benzenesulfinamide, trifluoromethanesulfonic anhydride, and Huenig’s base brings about the cyclofunctionalization of unsaturated alcs., phenols, acids, and sulfonamides to give the corresponding α-phenylsulfanylmethyl cyclic ethers, lactones and sulfonamides, resp. In an unanticipated twist the products are isolated at the sulfur (II) oxidation state denoting an overall reduction in the oxidation state of the sulfur based electrophile in the course of the reaction.

Heterocycles 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 C11H15NOS, HPLC of Formula: 4972-31-0.

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

Jose, Gilish published the artcileSynthesis, molecular docking, antimycobacterial and antimicrobial evaluation of new pyrrolo[3,2-c]pyridine Mannich bases, HPLC of Formula: 39546-32-2, the publication is European Journal of Medicinal Chemistry (2017), 275-288, database is CAplus and MEDLINE.

In this report, we describe the synthesis and biol. evaluation of a new series of pyrrolo[3,2-c]pyridine Mannich bases. The Mannich bases were obtained in good yields by one-pot three component condensation of pyrrolo[3,2-c]pyridine scaffold with secondary amines and excess of formaldehyde solution in AcOH. The chem. structures of the compounds were characterized by ¹H NMR, ¹³C NMR, LC/MS and elemental anal. Single crystal X-ray diffraction has been recorded for compound I ([C₂₃H₂₉ClN₄]⁺², H₂O). The in vitro antimicrobial activities of the compounds were evaluated against various bacterial and fungal strains using Agar diffusion method and Broth micro dilution method. Compounds II (n = 1, R = 4-Me-piperazin-1-yl, N-Bn-ethanamino; n = 2, R = N-Me-2-Ph-ethanamine, piperidine-3-carboxamide, piperidine-4-carboxamide) were showed good Gram-pos. antibacterial activity against S. aureus, B. flexus, C. sporogenes and S. mutans. Furthermore, in vitro antimycobacterial activity was evaluated against Mycobacterium tuberculosis H37Rv (ATCC 27294) using MABA. Compounds II (n = 2, R = N-Me-2-Ph-ethanamine, piperidine-3-carboxamide, piperidine-4-carboxamide) were showed good antitubercular activity against Mtb (MIC ≥6.25 μg/mL). Among the tested compounds, II (n = 2, R = piperidine-3-carboxamide) was showed excellent antimycobacterial activity against Mtb (MIC <0.78 μg/mL) and low cytotoxicity against the HEK-293T cell line (SI >>25). Mol. docking of the active compounds against glutamate racemase (MurI) and Mtb glutamine synthetase were explained the structure-activity observed in vitro.

European Journal of 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, HPLC of Formula: 39546-32-2.

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

Jose, Gilish published the artcileNew polyfunctional imidazo[4,5-C]pyridine motifs: Synthesis, crystal studies, docking studies and antimicrobial evaluation, Related Products of piperidines, the publication is European Journal of Medicinal Chemistry (2014), 288-297, database is CAplus and MEDLINE.

New antimicrobial agents, imidazo[4,5-c]pyridine derivatives were synthesized. The authors have developed a new synthetic protocol for the final reaction, an efficient microwave-assisted synthesis of imidazo[4,5-c]pyridines from substituted 3,4-diaminopyridine and carboxylic acids in presence of DBU mediated by T3P. The chem. structures of the new compounds were characterized by IR, ¹H NMR, ¹³C NMR, mass spectral anal. and elemental anal. In addition, single crystal x-ray diffraction also was recorded for compound 1-(7-(3-Fluorophenyl)-2-(phenoxymethyl)-1H-imidazo[4,5c]pyridin-4-yl)piperidine-3-carbonitrile. The in vitro antimicrobial activities of the compounds were conducted against various Gram-neg., Gram-pos. bacteria and fungi. Amongst the tested, seven compounds displayed promising antimicrobial activity. The mol. docking of GlcN-6-P synthase with newly synthesized compounds was carried out.

European Journal of 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, Related Products of piperidines.

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

Wei, Juhong published the artciletert-Butyl Sulfoxide as a Starting Point for the Synthesis of Sulfinyl Containing Compounds, COA of Formula: C11H15NOS, the publication is Organic Letters (2015), 17(21), 5396-5399, database is CAplus and MEDLINE.

Sulfoxides bearing a tert-Bu group can be activated using N-bromosuccinimide (NBS) under acidic conditions and then subsequently treated with a variety of nitrogen, carbon, or oxygen nucleophiles to afford a wide range of the corresponding sulfinic acid amides, new sulfoxides, and sulfinic acid esters.

Organic Letters 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 C9H5ClO2, COA of Formula: C11H15NOS.

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