Tag: M.W=200-250

Del Bubba, Massimo published the artcileEnantiomeric resolution of chiral aromatic sulfoxides on non-commercial microcrystalline cellulose triacetate and commercial cellulose acetate plates, Quality Control of 4972-31-0, the publication is Journal of Planar Chromatography–Modern TLC (2012), 25(6), 498-503, database is CAplus.

This paper reports a number of original thin-layer chromatog. enantioseparations of chiral sulfoxides that are important for their use as drugs and drug metabolites or pesticides, obtained by elution with aqueous-alc. mixtures at different ratios. Noncom. microcrystalline cellulose triacetate and com. cellulose acetate (CEL 300-10/a.c., Macherey-Nagel) plates were compared for their chiral resolution power, evidencing the much better performances of the former. The linearity of the densitometric response as a function of the amount of each enantiomer applied to the plate was studied for selected compounds Correlation coefficients higher than or equal to 0.99 were obtained in all cases, and the feasibility of the quantification of the individual enantiomers at tens to hundreds of nanograms spotted was demonstrated.

Journal of Planar Chromatography–Modern TLC 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, Quality Control of 4972-31-0.

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

Picard, Sebastien published the artcileImproved methods for the stereoselective synthesis of mannoheptosyl donors and their glycosides: toward the synthesis of the trisaccharide repeating unit of the Campylobacter jejuni RM1221 capsular polysaccharide, Application In Synthesis of 4972-31-0, the publication is Tetrahedron (2013), 69(26), 5501-5510, database is CAplus.

In view of the importance of 6-deoxymannoheptosides as structural units in the Campylobacter jejuni RM1221 capsular polysaccharide, the development of effective synthetic protocols for 4-O-6-S-α-cyanobenzylidene thio-d-mannoheptapyranoside donors carrying either 3-O-naphthylmethyl or 3-O-acetyl groups is described starting from d-mannose. In particular, tris(phenylthio)methyllithium is found to undergo highly stereoselective addition to a mannose-6-aldehyde in sharp contrast to the vinyl Grignard reagent whose reactions were essentially devoid of selectivity. A brief survey of coupling reactions with the two donors indicted the 3-O-acetyl system to be highly α-selective whereas the 3-O-naphthylmethyl congener was highly β-selective indicating that the presence of the seventh carbon atom in these donors is not detrimental to coupling selectivity in either instance.

Tetrahedron 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, Application In Synthesis of 4972-31-0.

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

Wen, Peng published the artcileAbsence of Stereodirecting Participation by 2-O-Alkoxycarbonylmethyl Ethers in 4,6-O-Benzylidene-Directed Mannosylation, Recommanded Product: 1-(Phenylsulfinyl)piperidine, the publication is Journal of Organic Chemistry (2015), 80(24), 12300-12310, database is CAplus and MEDLINE.

The preparation of a series of mannopyranosyl donors carrying 2-O-(2-oxoalkyl) ethers and their use in glycosylation reactions are described. The formation of cyclic products with the simple 2-O-phenacyl ether and with the 2-O-(t-butoxycarbonylmethyl) ether establishes the stereoelectronic feasibility of participation in such systems. The high β-selectivities observed with the bis-trifluoromethyl phenacyl ether indicate that participation can be suppressed through the introduction of electron-withdrawing substituents. The high β-selectivities and absence of cyclic products observed with the 2-O-(methoxycarbonylmethyl) ether exclude the effective participation of esters through six-membered cyclic intermediates in this series. The results are discussed in terms of the conformation of cyclic dioxenium ions (E,E-, E,Z-, or Z,Z-) and in the context of “neighboring group” participation by nonvicinal esters in glycosylation. Methods for the deprotection of the 2-O-phenacyl and 2-O-(methoxycarbonylmethyl) ethers are described.

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 C5H7NO, Recommanded Product: 1-(Phenylsulfinyl)piperidine.

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

Crich, David published the artcileInfluence of the 4,6-O-benzylidene, 4,6-O-phenylboronate, and 4,6-O-polystyrylboronate protecting groups on the stereochemical outcome of thioglycoside-based glycosylations mediated by 1-benzenesulfinyl piperidine/triflic anhydride and N-iodosuccinimide/trimethylsilyl triflate, Category: piperidines, the publication is Journal of Organic Chemistry (2003), 68(21), 8142-8148, database is CAplus and MEDLINE.

The effect of 4,6-O-benzylidene acetals, 4,6-O-phenylboronate esters, and 4,6-O-polystyrylboronate esters on the stereoselectivity of couplings to galacto-, gluco-, and mannopyranosyl thioglycosides, otherwise protected with benzyl ethers, has been investigated by the benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride (BSP), di-Ph sulfoxide/trifluoromethanesulfonic anhydride (Ph₂SO), and N-iodosuccinimide/trimethylsilyl trifluoromethanesulfonate (NIS/TMSOTf) methods. The BSP and Ph₂SO methods give comparable results in all three systems whereas the NIS method affords significantly different stereoselectivities in both the gluco and manno, but not the galacto series. The benzylidene acetal and boronate esters influence the stereochem. in a similar manner in the β-selective manno series and the α-selective galacto series but show significant differences with the glucose donors. The differences between the glucose, galactose, and mannose series reflect the established differences in reactivity and, especially for mannose, those in the anomeric effect and are best interpreted in terms of changes in the relative energetics between the α- and β-covalent triflate intermediates and the various contact ion pairs with which they are necessarily in equilibrium

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, Category: piperidines.

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

Crich, David published the artcileSynthesis of the mannosyl erythritol lipid MEL A; confirmation of the configuration of the meso-erythritol moiety, Application In Synthesis of 4972-31-0, the publication is Tetrahedron (2002), 58(1), 35-44, database is CAplus.

The total synthesis of the two possible diastereomers of mannosylerythritol lipid A, a novel biosurfactant from Candida antarctica T-34 with promising anti-proliferative properties in several cell lines, is described. By comparison with an authentic sample, the natural material is confirmed as a single diastereomer with the 4-O-(β-D-mannopyranosyl)-D-erythritol configuration.

Tetrahedron 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, Application In Synthesis of 4972-31-0.

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

Bataille, Carole J. R. published the artcileThiazolidine derivatives as potent and selective inhibitors of the PIM kinase family, Synthetic Route of 634905-21-8, the publication is Bioorganic & Medicinal Chemistry (2017), 25(9), 2657-2665, database is CAplus and MEDLINE.

The PIM family of serine/threonine kinases have become an attractive target for anti-cancer drug development, particularly for certain hematol. malignancies. Here, we describe the discovery of a series of inhibitors of the PIM kinase family using a high throughput screening strategy. Through a combination of mol. modeling and optimization studies, the intrinsic potencies and mol. properties of this series of compounds was significantly improved. An excellent pan-PIM isoform inhibition profile was observed across the series, while optimized examples show good selectivity over other kinases. Two PIM-expressing leukemic cancer cell lines, MV4-11 and K562, were employed to evaluate the in vitro anti-proliferative effects of selected inhibitors. Encouraging activities were observed for many examples, with the best example (44) giving an IC₅₀ of 0.75 μM against the K562 cell line. These data provide a promising starting point for further development of this series as a new cancer therapy through PIM kinase inhibition.

Bioorganic & Medicinal Chemistry published new progress about 634905-21-8. 634905-21-8 belongs to piperidines, auxiliary class Piperidine,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is (3-(Piperidin-1-yl)phenyl)boronic acid, and the molecular formula is C11H16BNO2, Synthetic Route of 634905-21-8.

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

Leadbetter, Elizabeth A. published the artcileNK T cells provide lipid antigen-specific cognate help for B cells, COA of Formula: C11H15NOS, the publication is Proceedings of the National Academy of Sciences of the United States of America (2008), 105(24), 8339-8344, database is CAplus and MEDLINE.

The mechanisms of T cell help for production of antilipid antibodies are largely unknown. This study shows that invariant NK T cells (iNK T cells) and B cells cooperate in a model of antilipid antigen-specific antibody responses. We use a model haptenated lipid mol., 4-hydroxy-3-nitrophenyl-αGalactosylCeramide (NP-αGalCer), to demonstrate that iNK T cells provide cognate help to lipid-antigen-presenting B cells. B cells proliferate and IgG anti-NP is produced from in vivo-immunized mice and in vitro cocultures of B and NK T cells after exposure to NP-αGalCer, but not closely related control glycolipids. This B cell response is absent in CD1d^-/- and Jα18^-/- mice but not CD4^-/- mice. The antibody response to NP-αGalCer is dominated by the IgM, IgG3, and IgG2c isotypes, and marginal zone B cells stimulate better in vitro lipid antigen-driven proliferation than follicular B cells, suggesting an important role for this B cell subset. iNK T cell help for B cells is shown to involve cognate help from CD1d-instructed lipid-specific iNK T cells, with help provided via CD40L, B7-1/B7-2, and IFN-γ, but not IL-4. This model provides evidence of iNK T cell help for antilipid antibody production, an important aspect of infections, autoimmune diseases, and vaccine development. Our findings also now allow prediction of those microbial antigens that would be expected to elicit cognate iNKT cell help for antibody production, namely those that can stimulate iNKT cells and at the same time have a polar moiety that can be recognized by antibodies.

Proceedings of the National Academy of Sciences of the United States of America 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, COA of Formula: C11H15NOS.

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

Sheppard, Daniel J. published the artcileComparison of disaccharide donors for heparan sulfate synthesis: uronic acids vs. their pyranose equivalents, HPLC of Formula: 4972-31-0, the publication is Organic & Biomolecular Chemistry (2020), 18(25), 4728-4733, database is CAplus and MEDLINE.

Late oxidation of hexose based building blocks or the use of uronic acid containing building blocks are two complementary strategies in the synthesis of glycosaminoglycans. Here we report the synthesis and evaluation of various disaccharide donors-uronic acids and their pyranose equivalent-for the synthesis of heparan sulfate, using an established protective group strategy. Hexose based “imidate” type donors perform well in the studied glycosylation, while their corresponding uronate esters fall short; a uronate ester thioglycoside performs equal to, if not better than, a hexose thioglycoside equivalent

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 C4H4N2O2, HPLC of Formula: 4972-31-0.

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

Demeter, Fruzsina published the artcileAn Efficient Synthesis of the Pentasaccharide Repeating Unit of Pseudomonas aeruginosa Psl Exopolysaccharide, Safety of 1-(Phenylsulfinyl)piperidine, the publication is Synlett (2020), 31(5), 469-474, database is CAplus.

Pseudomonas aeruginosais a biofilm-forming Gram-neg. bacterium and a leading cause of life-threatening nosocomial infections. The polysaccharide synthesis locus (Psl) exopolysaccharide of P. aeruginosais a key constituent of the defending bacterial biofilm layer and is a promising therapeutic target for resistant species. The Psl exopolysaccharide is built up from repeating pentasaccharide units which contain one α- and two β-mannosidic linkages, and one L-rhamnose and one D-glucose moieties. The preparation of this pentasaccharide was first described by Boons et al. in a 34-step synthesis. Based on their work, we have developed a new and effective pathway for the synthesis of the repeating pentasaccharide unit of the Psl exopolysaccharide. We have succeeded in simplifying the synthesis of the L-rhamnose and the α-selective D-mannose building blocks. Furthermore, taking advantage of a chemoselective pre-activation-based β-mannosylation, we directly prepare a thioglycoside disaccharide donor and use it in the next coupling reaction without further transformation. The pentasaccharide, in the form of a p-methoxyphenyl glycoside, is prepared in 26 steps, which is suitable for biol. testing.

Synlett 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.

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

Del Bubba, Massimo published the artcileEnantiomeric resolution of chiral aromatic sulfoxides on non-commercial cellulose tribenzoate plates, Quality Control of 4972-31-0, the publication is Journal of Planar Chromatography–Modern TLC (2012), 25(3), 214-219, database is CAplus.

This paper reports a number of original thin-layer chromatog. enantioseparations of chiral sulfoxides that are important for their use as drugs and drug metabolites, pesticides, or chiral auxiliaries, obtained by elution with alcs. or aqueous-alc. mixtures at different ratios on cellulose tribenzoate. Detection was performed by exposing the plates to iodine vapor, followed by densitometry at 410 nm. Under these exptl. conditions, ten of the eighteen chiral aromatic sulfoxides studied were baseline or partially resolved, thus providing useful chromatog. information for this important class of racemic compounds Data obtained with cellulose tribenzoate were compared to those achieved with microcrystalline cellulose triacetate for the same group of chiral sulfoxides, evidencing an interesting complementary behavior of the two stationary phases.

Journal of Planar Chromatography–Modern TLC 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, Quality Control of 4972-31-0.

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