Day: November 21, 2022

Hammer, C. F. published the artcileReactions of β-substituted amines. II. Nucleophilic displacement reactions on 3-chloro-1-ethylpiperidine, Quality Control of 13444-24-1, the publication is Tetrahedron (1972), 28(2), 239-53, database is CAplus.

Synthetic, kinetic, and optical activity studies established that 3-chloro-1-ethylpiperidine undergoes nucleophilic displacement reactions in solution by a 2-step, neighboring group participation mechanism. N displaces chloride internally, to give an ambident bicyclic aziridinium ion, which then reacts with nucleophiles to give pyrrolidine and piperidine isomers. The aziridinium ion, 1-ethyl-1-azoniabicyclo[3.1.0]hexane perchlorate, was synthesized sep.

Tetrahedron 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, Quality Control of 13444-24-1.

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

Abdel-Rahman, M. O. published the artcileHeterocyclic aminoacrylate esters of potential biological activity, Product Details of C7H15NO, the publication is Qatar University Science Bulletin (1985), 63-9, database is CAplus.

Acrylate esters I and II (X = O, S; R = N-methyl-4-piperidyl, N-ethyl-4-piperidyl, N-methyl-3-piperidyl, N-ethyl-4-piperidyl, 3-quinuclidinyl, CH₂CH₂NMe₂, CH₂CH₂NEt₂) were prepared from the corresponding acids or acid chlorides and aminoalcs.

Qatar University Science Bulletin 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, Product Details of C7H15NO.

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

Neel, Andrew J. published the artcileAsymmetric Cross-Dehydrogenative Coupling Enabled by the Design and Application of Chiral Triazole-Containing Phosphoric Acids, Formula: C11H21BF4N2O2, the publication is Journal of the American Chemical Society (2013), 135(38), 14044-14047, database is CAplus and MEDLINE.

Nonracemic triazolylbinaphthylphosphoric acids I [R = PhCH₂, Ph₂CH, bis(1-naphthyl)methyl, 1-naphthyl, 9-anthracenyl, 1-pyrenyl, 2,4,6-Me₃C₆H₂, 2,4,6-i-Pr₃C₆H₂, 2,4,6-(c-C₆H₁₁)₃C₆H₂, 4-t-BuC₆H₄, 3,5-t-Bu₂C₆H₃, 1-adamantyl] were prepared using azide-alkyne cycloadditions of a protected diethynylbinaphthol with azides RN₃ [R = PhCH₂, Ph₂CH, bis(1-naphthyl)methyl, 1-naphthyl, 9-anthracenyl, 1-pyrenyl, 2,4,6-Me₃C₆H₂, 2,4,6-i-Pr₃C₆H₂, 2,4,6-(c-C₆H₁₁)₃C₆H₂, 4-t-BuC₆H₄, 3,5-t-Bu₂C₆H₃, 1-adamantyl]; in the presence of I, an acetamidopiperidineoxoammonium salt, and trisodium phosphate in p-xylene, tetrahydroisoquinolinylbenzamides II [R¹ = PhCH₂, 4-MeC₆H₄CH₂, 4-MeOC₆H₄CH₂, 4-O₂NC₆H₄CH₂, 2-MeOC₆H₄CH₂, Ph, 3-MeC₆H₄, 2-MeC₆H₄, 1-naphthyl, 2-ClC₆H₄, 2-HOC₆H₄, t-Bu, cyclohexyl, (R)-MeO₂CCH(i-Pr), (S)-MeO₂CCH(i-Pr); R² = H, Me, Br, F₃C] underwent enantioselective cross-dehydrogenative coupling reactions to give tetrahydroisoquinolinoquinazolinones III [R¹ = PhCH₂, 4-MeC₆H₄CH₂, 4-MeOC₆H₄CH₂, 4-O₂NC₆H₄CH₂, 2-MeOC₆H₄CH₂, Ph, 3-MeC₆H₄, 2-MeC₆H₄, 1-naphthyl, 2-ClC₆H₄, 2-HOC₆H₄, t-Bu, cyclohexyl, (R)-MeO₂CCH(i-Pr), (S)-MeO₂CCH(i-Pr); R² = H, Me, Br, F₃C] in 38-93% yields and in 73-93% ee or in 3:1-7:1 dr. I were designed to use attractive hydrogen-bonding interactions with substrates rather than catalyst steric bulk to improve the stereoselectivity of the coupling reaction. The azides used in the preparation of I are potentially explosive and should be handled and reacted using appropriate precautions.

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, Formula: C11H21BF4N2O2.

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

Mueller, Stephan G. published the artcileDesign, synthesis and evaluation of MCH receptor 1 antagonists-Part I: Optimization of HTS hits towards an in vivo efficacious tool compound BI 414, HPLC of Formula: 39546-32-2, the publication is Bioorganic & Medicinal Chemistry Letters (2015), 25(16), 3264-3269, database is CAplus and MEDLINE.

Despite recent approvals of antiobesity drugs there is still a high therapeutic need for alternative options with higher efficacy in humans. As part of the MCH-R1 antagonist program for the treatment of obesity, a series of biphenylacetamide HTS hits was evaluated. Several issues of the initial lead structures had to be resolved, such as potency, selectivity over related GPCRs and P-gp efflux limiting brain exposure in this series. The authors could demonstrate that all parameters can be significantly improved by structural modifications resulting in I as a potent and orally available MCH-R1 antagonist tool compound with acceptable in vivo efficacy in an animal model of obesity.

Bioorganic & Medicinal Chemistry Letters 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

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