M.W=200-250 | Page 10 of 35 | Heterocyclic Building Blocks-piperidine

Lachkar, David’s team published research in Canadian Journal of Chemistry in 90 | CAS: 4972-31-0

Canadian 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 C11H15NOS, Related Products of piperidines.

Lachkar, David published the artcile2-(Selenocyanatomethyl)-2-propenol – A convenient synthon for ligation via the deselenative allylic rearrangement of allyl selenosulfides: preparation, functional group compatibility, and application, Related Products of piperidines, the publication is Canadian Journal of Chemistry (2012), 90(11), 944-953, database is CAplus.

The preparation and reactions of 2-(selenocyanatomethyl)-2-propenol are described and reveal the compatibility of the allylic selenocyanate group with a range of mild oxidizing and Lewis acidic conditions. 2-(Selenocyanatomethyl)-2-propenol and its derivatives are employed in the functionalization of simple and amino acid derived thiols in methanolicsoln. at room temperature to give 2-(hydroxymethyl)allyl sulfides in good to excellent yield.

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

Ball, Matthew’s team published research in Organic Process Research & Development in 20 | CAS: 1416134-49-0

Organic Process Research & Development published new progress about 1416134-49-0. 1416134-49-0 belongs to piperidines, auxiliary class Piperidine,Chiral,Amine,Benzene,Amide, name is (2S,5R)-5-((Benzyloxy)amino)piperidine-2-carboxamide, and the molecular formula is C13H19N3O2, Quality Control of 1416134-49-0.

Ball, Matthew published the artcileDevelopment of a Manufacturing Route to Avibactam, a β-Lactamase Inhibitor, Quality Control of 1416134-49-0, the publication is Organic Process Research & Development (2016), 20(10), 1799-1805, database is CAplus.

Process development work to provide an efficient, robust, and cost-effective manufacturing route to avibactam, a β-lactamase inhibitor is presented herewith. Aspects of this optimization work include the counterintuitive introduction of a protecting group to effect a difficult urea formation and the use of controlled feed hydrogenation conditions to facilitate an elegant one pot debenzylation and sulfation reaction. Overall, the com. process delivers avibactam in much improved yield with significant reduction in the environmental footprint.

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

Ekholm, Filip S.’s team published research in Chemistry – A European Journal in 18 | CAS: 4972-31-0

Chemistry – A European Journal 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.

Ekholm, Filip S. published the artcileStudies Related to Norway Spruce Galactoglucomannans: Chemical Synthesis, Conformation Analysis, NMR Spectroscopic Characterization, and Molecular Recognition of Model Compounds, Product Details of C11H15NOS, the publication is Chemistry – A European Journal (2012), 18(45), 14392-14405, database is CAplus and MEDLINE.

Galactoglucomannan (GGM) is a polysaccharide mainly consisting of mannose, glucose, and galactose. GGM is the most abundant hemicellulose in the Norway spruce (Picea abies), but is also found in the cell wall of flax seeds, tobacco plants, and kiwi fruit. Although several applications for GGM polysaccharides have been developed in pulp and paper manufacturing and the food and medical industries, attempts to synthesize and study distinct fragments of this polysaccharide have not been reported previously. Herein, the synthesis of one of the core trisaccharide units of GGM together with a less-abundant tetrasaccharide fragment is described. In addition, detailed NMR spectroscopic characterization of the model compounds, comparison of the spectral data with natural GGM, investigation of the acetyl-group migration phenomena that takes place in the polysaccharide by using small model compounds, and a binding study between the tetrasaccharide model fragment and a galactose-binding protein (the toxin viscumin) are reported.

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

Crich, David’s team published research in Journal of the American Chemical Society in 126 | CAS: 4972-31-0

Journal of the American Chemical Society 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, Safety of 1-(Phenylsulfinyl)piperidine.

Crich, David published the artcileDirect Chemical Synthesis of the β-D-Mannans: The β-(1→2) and β-(1→4) Series, Safety of 1-(Phenylsulfinyl)piperidine, the publication is Journal of the American Chemical Society (2004), 126(45), 14930-14934, database is CAplus and MEDLINE.

The direct syntheses of a β-(1→2)-mannooctaose and of a β-(1→4)-mannohexaose are reported by means of 4,6-O-benzylidene-protected β-mannosyl donors. The synthesis of the (1→2)-mannan was achieved by means of the sulfoxide coupling protocol, whereas the (1→4)-mannan was prepared using the analogous thioglycoside/sulfinamide methodol. In the synthesis of the (1→4)-mannan, the glycosylation yields and stereoselectivities remain approx. constant with increasing chain length, whereas those for the (1→2)-mannan consist of two groups with the formation of the tetra- and higher saccharides giving yields and selectivities consistently lower than those of the lower homologs. The decrease in yield after the trisaccharide in the (1→2)-mannan synthesis is attributed to steric interference by the n-3 residue and is consistent with the collapsed, disordered structure predicted by early computational work. The consistently high yields and selectivities seen in the synthesis of the (1→4)-mannan are congruent with the more open, ordered structure originally predicted for this polymer. The lack of order in the structure of the (1→2)-mannan, as compared to the high degree of order in the (1→4)-mannan, is also evident from a comparison of the NMR spectra of the two polymers and even from their phys. nature: the (1→2)-mannan is a gum and the (1→4)-mannan is a high melting solid.

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

Crich, David’s team published research in Journal of Carbohydrate Chemistry in 24 | CAS: 4972-31-0

Journal of Carbohydrate 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, Related Products of piperidines.

Crich, David published the artcileImproved synthesis of 1-benzenesulfinyl piperidine and analogs for the activation of thioglycosides in conjunction with trifluoromethanesulfonic anhydride, Related Products of piperidines, the publication is Journal of Carbohydrate Chemistry (2005), 24(4-6), 415-424, database is CAplus and MEDLINE.

An improved protocol for the large-scale production of 1-benzenesulfinyl piperidine and other sulfinamides is described. It is demonstrated that 1-benzenesulfinyl pyrrolidine and N,N-di-Et benzenesulfinamide function analogously to 1-benzenesulfinyl piperidine in the trifluoromethanesulfonic anhydride-mediated activation of thioglycosides, and that their less crystalline nature enables them to be used at -78°C as opposed to the -60°C required to keep 1-benzenesulfinyl piperidine in solution N,N-Dicyclohexyl benzenesulfinamide does not activate thioglycosides in combination with trifluoromethanesulfonic anhydride, which is attributed to its greater steric bulk.

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

Fan, Ren-Hua’s team published research in Organic Letters in 7 | CAS: 4972-31-0

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 C11H15NOS, Computed Properties of 4972-31-0.

Fan, Ren-Hua published the artcileOrthogonal Sulfation Strategy for Synthetic Heparan Sulfate Ligands, Computed Properties of 4972-31-0, the publication is Organic Letters (2005), 7(22), 5095-5098, database is CAplus and MEDLINE.

An orthogonal sulfation strategy involving six different protecting groups has been developed for generating sulfated carbohydrate libraries based on heparan. Chemoselective cleavage conditions (optimized for a heparan disaccharide) can be performed in the presence of sulfate esters as well as the remaining protecting groups.

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

Lin, Hong-Jyune’s team published research in Chemistry – A European Journal in 19 | CAS: 4972-31-0

Lin, Hong-Jyune published the artcileTotal Synthesis of an Immunomodulatory Glycophospholipid from Thermophilic Bacteria, Application of 1-(Phenylsulfinyl)piperidine, the publication is Chemistry – A European Journal (2013), 19(24), 7989-7998, database is CAplus and MEDLINE.

A method for the stereocontrolled synthesis of a bacterial glycophospholipid (PGL1) isolated from Thermophilic bacteria is described. The key features of the synthesis include a highly α-selective glycosylation reaction between a trichloroacetimidate donor and a D-lyxose-derived primary alc. acceptor and the late-stage incorporation of the phospholipid.

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

Maricich, Tom J.’s team published research in Journal of Organic Chemistry in 49 | CAS: 4972-31-0

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, Recommanded Product: 1-(Phenylsulfinyl)piperidine.

Maricich, Tom J. published the artcileReaction of benzenesulfinyl azide with thiols and amines. Preparation of thiosulfinates and sulfinamides, Recommanded Product: 1-(Phenylsulfinyl)piperidine, the publication is Journal of Organic Chemistry (1984), 49(11), 1931-4, database is CAplus.

Treating PhS(O)N₃ with RSH (R = Ph, PhCH₂, Pr, Me₂CH, Me₃C, HOCH₂CH₂, Me₃CCH₂) at -20° gave PhS(O)SR and HN₃. A similar reaction using R¹NHR² [R¹ = Ph, Bu, HOCH₂CH₂, R² = H; R¹R² = (CH₂)₅] gave PhS(O)NR¹R² and HN₃. Thiosulfinates and sulfinamides containing a free OH group could be prepared Yields ranged from 41 to 93%.

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

Giancola, JoLynn B.’s team published research in European Journal of Medicinal Chemistry in 2020-12-15 | CAS: 73874-95-0

European Journal of Medicinal Chemistry published new progress about Alkylation. 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Synthetic Route of 73874-95-0.

Giancola, JoLynn B. published the artcileStructure-activity relationships for a series of (Bis(4-fluorophenyl)methyl)sulfinylethyl-aminopiperidines and -piperidine amines at the dopamine transporter: Bioisosteric replacement of the piperazine improves metabolic stability, Synthetic Route of 73874-95-0, the main research area is aminopiperidine piperidine amine preparation dopamine transporter SAR; Atypical dopamine uptake inhibitors; Cocaine; DAT; Modafinil; NET; Psychostimulant use disorders; SERT; Sigma receptors.

The bioisosteric substitutions of the piperazine ring were explored with a series of aminopiperidines and piperidine amines wherein compounds with either a terminal tertiary amine or amide were synthesized. Several lead compounds showed high to moderate DAT affinities and metabolic stability in rat liver microsomes. N-(2-((bis(4-fluorophenyl)methyl)sulfinyl)ethyl)-1-(4-fluorobenzyl)piperidin-4-amine (DAT Ki = 50.6 nM), I [R= F] (DAT Ki = 77.2 nM) and II [X1=X2= F] (DAT Ki = 30.0 nM) produced only minimal stimulation of ambulatory activity in mice, compared to cocaine, suggesting an atypical DAT inhibitor profile.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Bae, Jinsu’s team published research in Molecules in 2022 | CAS: 73874-95-0

Molecules published new progress about Analgesics. 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Computed Properties of 73874-95-0.

Bae, Jinsu published the artcileSynthesis and Structure-Activity Relationship Studies of Benzimidazole-4,7-dione-Based P2X3 Receptor Antagonists as Novel Anti-Nociceptive Agents, Computed Properties of 73874-95-0, the main research area is neuropathic pain antinociceptive structure activity relationship; P2X3 receptor; adenosine 5′-triphosphate; antagonist; anti-nociceptive agents; neuropathic pain; structure−activity relationship study.

P2X3 receptors (P2X3R) are ATP-gated ion channels predominantly expressed in C- and Aδ-fiber primary afferent neurons and have been introduced as a novel therapeutic target for neurol. disorders, including neuropathic pain and chronic cough. Because of its localized distribution, antagonism of P2X3R has been thoroughly considered, and the avoidance of issues related to CNS side effects has been proven in clin. trials. In this article, benzimidazole-4,7-dione-based derivatives were introduced as a new chem. entity for the development of P2X3R antagonists. Starting from the discovery of a hit compound from the screening of 8364 random library compounds in the Korea Chem. Bank, which had an IC50 value of 1030 nM, studies of structure-activity and structure-property relationships enabled further optimization toward improving the antagonistic activities as well as the drug′s physicochem. properties, including metabolic stability. As for the results, the final optimized compound 14h was developed with an IC50 value of 375 nM at P2X3R with more than 23-fold selectivity vs. P2X2/3R, along with properties of metabolic stability and improved solubility In neuropathic pain animal models evoked by either nerve ligation or chemotherapeutics in male Sprague-Dawley rats, compound 14h showed anti-nociceptive effects through an increase in the mech. withdrawal threshold as measured by von Frey filament following i.v. administration.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem