Month: November 2022

Carpino, Louis A. published the artcile9-Fluorenylmethoxycarbonyl amino-protecting group, COA of Formula: C19H21N, the publication is Journal of Organic Chemistry (1972), 37(22), 3404-9, database is CAplus.

The 9-fluorenylmethoxycarbonyl group (FMOC) is a new amino-protecting group, which is stable toward acids and catalytic hydrogenation but readily cleaved under mildly basic, non-hydrolytic conditions. The FMOC group may be introduced by reaction of the amine with 9-fluorenylmethyl chloroformate. A number of protected amino acid derivatives were coupled with other amino acids or esters by use of the corresponding N-hydroxypiperidine esters. Deblocking of the FMOC group was carried out with liquid NH3 or at room temperature with piperidine, morpholine, ethanolamine. etc.

Journal of Organic Chemistry 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, COA of Formula: C19H21N.

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

Angles d’Ortoli, Thibault published the artcileStructure-Reactivity Relationships of Conformationally Armed Disaccharide Donors and Their Use in the Synthesis of a Hexasaccharide Related to the Capsular Polysaccharide from Streptococcus pneumoniae Type 37, Product Details of C11H15NOS, the publication is Journal of Organic Chemistry (2017), 82(15), 8123-8140, database is CAplus and MEDLINE.

To advance the field of glycobiol., efficient synthesis methods of oligosaccharides and glycoconjugates are a requisite. In glycosylation reactions using super-armed donors, both selectivity and reactivity issues must be considered, and we herein investigate these aspects for differently protected β-linked 2-O-glycosylated glucosyl donors carrying bulky tert-butyldimethylsilyl groups to different extents. The acceptors in reactions being secondary alcs. presents a challenging situation with respect to steric crowding. Conformational pyranose ring equilibrium of the super-armed disaccharide donors with axial-rich substituents contained skew and boat conformations, and three-state models were generally assumed. With NIS/TfOH as the promotor, 2,6-di-tert-butyl-4-methylpyridine as the base, and a dichloromethane/toluene solvent mixture, Et 1-thio-β-D-glucosyl disaccharide donors having 6-O-benzyl group(s) besides tert-butyldimethylsilyl groups were efficiently coupled at -40 °C to the hydroxyl group at position 3 of glucopyranosyl acceptors to form β-(1â†?),β-(1â†?)-linked trisaccharides, isolated in excellent 95% yield. The more axial-rich donors in skew and boat conformations are thus pre-organized closer to the assumed transition state in these glycosylation reactions. The developed methodol. was subsequently applied in the synthesis of a multi-branched hexasaccharide related to the capsular polysaccharide from Streptococcus pneumoniae type 37, which consists of a β-(1â†?)-linked backbone and a β-(1â†?)-linked side chain of D-glucosyl residues in disaccharide repeating units.

Journal of Organic 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 C11H15NOS, Product Details of C11H15NOS.

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

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

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

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

Meng, Genyi published the artcileModular click chemistry libraries for functional screens using a diazotizing reagent, Safety of (1-Methylpiperidin-3-yl)methanamine, the publication is Nature (London, United Kingdom) (2019), 574(7776), 86-89, database is CAplus and MEDLINE.

Alkyl and aryl azides were prepared from the corresponding primary alkyl and aryl amines by reaction with fluorosulfonyl azide generated in situ from a fluorosulfonylimidazolium triflate and sodium azide, expanding access to azides and both to the 1,2,3-triazoles derived from them and to functional screens employing them. The method allowed the preparation of a library of >1000 azides from the corresponding amines; the azide library underwent copper-catalyzed azide-alkyne cycloaddition reactions to yield a library of >1000 1,2,3-triazoles.

Nature (London, United Kingdom) published new progress about 14613-37-7. 14613-37-7 belongs to piperidines, auxiliary class Piperidine,Amine, name is (1-Methylpiperidin-3-yl)methanamine, and the molecular formula is C7H16N2, Safety of (1-Methylpiperidin-3-yl)methanamine.

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

Wu, Ting-Ting published the artcileDesign, synthesis and bioevaluation of novel substituted triazines as potential dual PI3K/mTOR inhibitors, Application In Synthesis of 39546-32-2, the publication is European Journal of Medicinal Chemistry (2020), 112637, database is CAplus and MEDLINE.

A series of novel substituted triazines bearing a benzimidazole scaffold I [R = morpholino, 4-methylpiperazin-1-yl, ((1S)-2-amino-1-methyl-2-oxo-ethyl)amino, etc.] were designed and synthesized based on the structures of known anti-cancer agents, namely gedatolisib and alpelisib. All the target compounds were screened for inhibitory activity against PI3Kα and mTOR kinases. Notably, most analogs exhibited IC₅₀ in the nanomolar range. Investigation of the isoenzyme selectivity indicated that the compounds exhibited remarkable inhibitory activity against PI3Kδ, especially compound I [R = 4-carbamoyl-1-piperidyl] showed an IC₅₀ value of 2.3 nM for PI3Kδ and moderate δ-isoenzyme selectivity over other class I PI3K isoforms and mTOR (with IC₅₀ values of 14.6, 34.0, 849.0 and 15.4 nM for PI3Kα, β, γ and mTOR, resp.). An in vitro MTT assay was conducted to assess the antiproliferative and cytotoxic effects of the prepared analogs. It was revealed that the compounds displayed significant inhibitory activities against the HCT116 human colon cancer cell line. Compound I [R = morpholino] showed 4.7-fold higher potency than the pos. control gedatolisib (0.3 vs. 1.4μM, IC₅₀ values). Phosphoblot studies demonstrated that I [R = morpholino, (2R)-2-carbamoylpyrrolidin-1-yl] could significantly suppress the PI3K/Akt/mTOR signaling pathway at 10μM. Moreover, analogs I [R = morpholino, (2S)-2-carbamoylpyrrolidin-1-yl, (2R)-2-carbamoylpyrrolidin-1-yl] displayed better stability in artificial gastric fluids than gedatolisib, while I [R = morpholino] was indicated not very stable in rat liver microsomes, and may occur phase I metabolic transformations.

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 C9H8BrNO4, Application In Synthesis of 39546-32-2.

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

Han, Si-yin published the artcileMaillard reaction of sisal hemp juice hydrolysate and its volatile composition, Recommanded Product: 1-Ethylpiperidin-3-ol, the publication is Shipin Gongye (Shanghai, China) (2014), 35(3), 14-17, database is CAplus.

Sisal hemp juice was hydrolyzed by muriatic acid, hydrolyzate obtained from that would have Maillard reaction, and volatile components of the Maillard reaction products were detected. A hydrolysis of sisal hemp juice by muriatic acid 6 mol/L, volume ratio of muriatic acid and sisal juice 4:1 and hydrolysis in 100 °C for 14 h leaded to a degree hydrolysis of 16.8%. The highest browning degree was measured in the hydrolyzate at pH 7 after incubation in 100 °C for 30 min. Under this condition the volatile components of these Maillard reaction products mainly included 8 categories via the detection of GC-MS, which were alc., aldehyde, ketone, acid, ester, phenol, alkene and furan, and it can be developed as a natural fumette for tobacco.

Shipin Gongye (Shanghai, China) published new progress about 13444-24-1. 13444-24-1 belongs to piperidines, auxiliary class Piperidine,Alcohol, name is 1-Ethylpiperidin-3-ol, and the molecular formula is C7H15NO, Recommanded Product: 1-Ethylpiperidin-3-ol.

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

Kozikowski, Alan P. published the artcileIdentification of a Glycogen Synthase Kinase-3β Inhibitor that Attenuates Hyperactivity in CLOCK Mutant Mice, HPLC of Formula: 170364-89-3, the publication is ChemMedChem (2011), 6(9), 1593-1602, database is CAplus and MEDLINE.

Bipolar disorder is characterized by a cycle of mania and depression, which affects approx. 5 million people in the United States. Current treatment regimes include the so-called “mood-stabilizing drugs”, such as lithium and valproate that are relatively dated drugs with various known side effects. Glycogen synthase kinase-3β (GSK-3β) plays a central role in regulating circadian rhythms, and lithium is known to be a direct inhibitor of GSK-3β. We designed a series of second generation benzofuran-3-yl-(indol-3-yl)maleimides containing a piperidine ring that possess IC₅₀ values in the range of 4 to 680 nM against human GSK-3β. Compound 3a (I) exhibits reasonable kinase selectivity and promising preliminary absorption, distribution, metabolism, and excretion (ADME) data. The administration of this compound at doses of 10 to 25 mg kg^-1 resulted in the attenuation of hyperactivity in amphetamine/chlordiazepoxide-induced manic-like mice together with enhancement of prepulse inhibition, similar to the effects found for valproate (400 mg kg^-1) and the antipsychotic haloperidol (1 mg kg^-1). We also tested this compound in mice carrying a mutation in the central transcriptional activator of mol. rhythms, the CLOCK gene, and found that the same compound attenuates locomotor hyperactivity in response to novelty. This study further demonstrates the use of inhibitors of GSK-3β in the treatment of manic episodes of bipolar/mood disorders, thus further validating GSK-3β as a relevant therapeutic target in the identification of new therapies for bipolar patients.

ChemMedChem published new progress about 170364-89-3. 170364-89-3 belongs to piperidines, auxiliary class Indole,Piperidine,Amide, name is tert-Butyl 4-(1H-indol-1-yl)piperidine-1-carboxylate, and the molecular formula is C18H24N2O2, HPLC of Formula: 170364-89-3.

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