Month: November 2022

Ye, Jian published the artcileInvestigation of catalytic self-cleaning process of multiple active species decorated macroporous PVDF membranes through peroxymonosulfate activation, Computed Properties of 826-36-8, the publication is Journal of Colloid and Interface Science (2021), 178-189, database is CAplus and MEDLINE.

Currently, carbon-based catalysts integrated with macroporous catalytic membrane have aroused considerable attention for environmental remediation because of its practicability and high efficiency. Herein, nitrogen doped carbon nanotube hybrids (Fe-Co@NC-CNTs) decorated with multiple active species (Fe₃Co₇/CoFe₂O₄@Fe/Co-N-C) were designed through N-mol. assisted pyrolysis of bimetallic (Fe/Co) metal-organic frameworks, and then immobilized on poly(vinylidene fluoride) (PVDF) membrane to construct macroporous Fe-Co@NC-CNTs/PVDF catalytic membrane via directional freezing technique, where active sites were efficiently exposed for oxidants and target pollutants. As expected, Fe-Co@NC-CNTs/PVDF membrane successfully achieved almost 100% bisphenol A (BPA) degradation after 40 min via PMS activation, which was significantly overperformed the majority of conventional carbon-based catalysts. Besides, we found that Fe-Co@NC-CNTs/PVDF membrane not only exhibited ideal catalytic and self-cleaning property in humic acid (HA)-BPA coexistence system, but also maintained the excellent reusability and ultrahigh water flux (10464.45 L m^-2 h^-1) even after 5 cycles. Notably, in EPR anal. and quenching experiments, it was found that sulfate radicals (SO₄·^– and ·OH) and singlet oxygen (¹O₂) participated the degradation process while ¹O₂ made a major contribution. More significantly, this study is very meaningful for the development of novel catalytic self-cleaning membranes with PMS activation.

Journal of Colloid and Interface Science 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 C10H16Br3N, Computed Properties of 826-36-8.

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

Rubach, Jon K. published the artcileThe Amino-Acid Substituents of Dipeptide Substrates of Cathepsin C Can Determine the Rate-Limiting Steps of Catalysis, Safety of 1-((9H-Fluoren-9-yl)methyl)piperidine, the publication is Biochemistry (2012), 51(38), 7551-7568, database is CAplus and MEDLINE.

We examined the cathepsin C-catalyzed hydrolysis of dipeptide substrates of the form Yaa-Xaa-AMC, using steady-state and pre-steady-state kinetic methods. The substrates group into three kinetic profiles based upon the broad range observed for k_cat/K_a and k_cat values, pre-steady-state time courses, and solvent kinetic isotope effects (sKIEs). The dipeptide substrate Gly-Arg-AMC displayed large values for k_cat/K_a (1.6±0.09 μM^-1 s^-1) and k_cat (255±6 s^-1), an inverse sKIE on k_cat/K_a (^D(k_cat/K_a) = 0.6±0.15), a modest, normal sKIE on k_cat (^Dk_cat = 1.6±0.2), and immeasurable pre-steady-state kinetics, indicating an extremely fast pre-steady-state rate (>400 s^-1). (Errors on fitted values are omitted in the text for clarity but may be found in Table 2.). These results conformed to a kinetic model where the acylation (k_ac) and deacylation (k_dac) half-reactions are very fast and similar in value. The second substrate type, Gly-Tyr-AMC and Ser-Tyr-AMC, the latter the subject of a comprehensive kinetic study (Schneck et al. (2008) Biochem. 47, 8697-8710), were found to be less active substrates compared to Gly-Arg-AMC, with resp. k_cat/K_a values of 0.49±0.07 μM^-1 s^-1 and 5.3±0.5 μM^-1 s^-1, and k_cat values of 28±1 s^-1 and 25±0.5 s^-1. Solvent kinetic isotope effects for Ser-Tyr-AMC were found to be inverse for k_cat/K_a (^D(k_cat/K_a) = 0.74±0.05) and normal for k_cat (^Dk_cat = 2.3±0.1) but unlike Gly-Arg-AMC, pre-steady-state kinetics of Gly-Tyr-AMC and Ser-Tyr-AMC were measurable and characterized by a single-exponential burst, with fast transient rates (490 s^-1 and 390 s^-1, resp.), from which it was determined that k_ac ≫ k_dac ∼ k_cat. The third substrate type, Gly-Ile-AMC, gave very low values of k_cat/K_a (0.0015±0.0001 μM^-1 s^-1) and k_cat (0.33±0.02 s^-1), no sKIEs, (^D(k_cat/K_a) = 1.05±0.5 and ^Dk_cat = 1.06±0.4), and pre-steady-state kinetics exhibited a discernible, but negligible, transient phase. For this third class of substrate, kinetic modeling was consistent with a mechanism in which k_dac > k_ac ∼ k_cat, and for which an isotope-insensitive step in the acylation half-reaction is the slowest. The combined results of these studies suggested that the identity of the amino acid at the P₁ position of the substrate is the main determinant of catalysis. On the basis of these kinetic data, together with crystallog. studies of substrate analogs and mol. dynamics anal. with models of acyl-enzyme intermediates, we present a catalytic model derived from the relative rates of the acylation vs. deacylation half-reactions of cathepsin C. The chem. steps of catalysis are proposed to be dependent upon the conformational freedom of the amino acid substituents for optimal alignment for thiolation (acylation) or hydrolysis (deacylation). These studies suggest ideas for inhibitor design for papain-family cysteine proteases and strategies to progress drug discovery for other classes of disease-relevant cysteine proteases.

Biochemistry 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, Safety of 1-((9H-Fluoren-9-yl)methyl)piperidine.

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

Mallinger, Aurelie published the artcileDiscovery of Potent, Orally Bioavailable, Small-Molecule Inhibitors of WNT Signaling from a Cell-Based Pathway Screen, Product Details of C6H12N2O, the publication is Journal of Medicinal Chemistry (2015), 58(4), 1717-1735, database is CAplus and MEDLINE.

WNT signaling is frequently deregulated in malignancy, particularly in colon cancer, and plays a key role in the generation and maintenance of cancer stem cells. The authors report the discovery and optimization of a 3,4,5-trisubstituted pyridine, 1-(3,5-Dichloropyridin-4-yl)piperidine-4-carboxamide (9), using a high-throughput cell-based reporter assay of WNT pathway activity. The authors demonstrate a twisted conformation about the pyridine-piperidine bond of (9) by small-mol. x-ray crystallog. Medicinal chem. optimization to maintain this twisted conformation, cognisant of physicochem. properties likely to maintain good cell permeability, led to 8-[3-Chloro-5-[4-(1-methyl-1H-pyrazol-4-yl)phenyl]pyridin-4-yl]-2,8-diazaspiro[4,5]decan-1-one (74) (CCT251545), a potent small-mol. inhibitor of WNT signaling with good oral pharmacokinetics. The authors demonstrate inhibition of WNT pathway activity in a solid human tumor xenograft model with evidence for tumor growth inhibition following oral dosing. This work provides a successful example of hypothesis-driven medicinal chem. optimization from a singleton hit against a cell-based pathway assay without knowledge of the biochem. target.

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, Product Details of C6H12N2O.

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

Brenna, Elisabetta published the artcileChemo-Enzymatic Oxidative Rearrangement of Tertiary Allylic Alcohols: Synthetic Application and Integration into a Cascade Process, Category: piperidines, the publication is Advanced Synthesis & Catalysis (2018), 360(19), 3677-3686, database is CAplus.

A chemo-enzymic catalytic system, comprised of Bobbitt’s salt and laccase from Trametes versicolor, allowed the [1,3]-oxidative rearrangement of endocyclic allylic tertiary alcs. into the corresponding enones under an Oxygen atm. in aqueous media. The yields were in most cases quant., especially for the cyclopent-2-en-1-ol or the cyclohex-2-en-1-ol substrates without an electron withdrawing group (EWG) on the side chain. Transpositions of macrocyclic alkenols or tertiary alcs. bearing an EWG on the side chain were instead carried out in acetonitrile by using an immobilized laccase preparation Dehydro-Jasmone, dehydro-Hedione, dehydro-Muscone and other fragrance precursors were directly prepared with this procedure, while a synthetic route was developed to easily transform a cyclopentenone derivative into trans-Magnolione and dehydro-Magnolione_. The rearrangement of exocyclic allylic alcs. was tested as well, and a dynamic kinetic resolution was observed: α,β-unsaturated ketones with (E)-configuration and a high diastereomeric excess were synthesized. Finally, the 2,2,6,6-tetramethyl-1-piperidinium tetrafluoroborate (TEMPO⁺BF₄^–)/laccase catalyzed oxidative rearrangement was combined with the ene-reductase/alc. dehydrogenase cascade process in a one-pot three-step synthesis of cis or trans 3-methylcyclohexan-1-ol, in both cases with a high optical purity.

Advanced Synthesis & Catalysis 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, Category: piperidines.

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

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

Martinez Porcel, Joaquin E. published the artcilePlasmonic silica-gold core-shell nanoparticles: Interaction with organic dyes for light-induced applications, Application of 2,2,6,6-Tetramethylpiperidin-4-one, the publication is Journal of Photochemistry and Photobiology, A: Chemistry (2022), 114016, database is CAplus.

The interaction of plasmonic nanoparticles with ground- and excited states of dyes can strongly affect the fluorescence of the organic mols., as well as the generation of reactive oxygen species (ROS). This interaction can be exploited in bioimaging and photodynamic therapy (PDT) of tumors. In this line, we prepare here gold-decorated silica nanoparticles (SiO₂@Au NPs) via a novel method, which combines the synthesis of gold nuclei through reduction of a Au³⁺ salt, with a photochem. route driving the growth of the metallic nuclei. In this hybrid nanomaterial, the surface groups of the silica particle can potentially act as adsorption sites for the dyes in a range close to the gold nanoparticles, favoring the interaction. The ability of SiO₂@Au NPs to enhance fluorescence and generation of ROS upon irradiation of riboflavin and Rose Bengal is evaluated. SiO₂@Au enhance the fluorescence emission of both dyes, although through different mechanisms. The excitation of the flavin is enhanced, whereas for Rose Bengal the radiative decay rate is increased by the nanoparticles. For neither of the two dyes, SiO₂@Au affect ROS generation as measured by ESR (EPR) spectroscopy. However, the increase in fluorescence emission observed for both dyes demonstrates the potential application of SiO₂@Au in fluorescence-sensing methods and bioimaging.

Journal of Photochemistry and Photobiology, A: Chemistry 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, Application of 2,2,6,6-Tetramethylpiperidin-4-one.

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

Kim, Hyojin published the artcileSynthesis and biological evaluation of thiazole derivatives as GPR119 agonists, Category: piperidines, the publication is Bioorganic & Medicinal Chemistry Letters (2017), 27(23), 5213-5220, database is CAplus and MEDLINE.

A series of 4-(phenoxymethyl)thiazole derivatives was synthesized and evaluated for their GPR119 agonistic effect. Several 4-(phenoxymethyl)thiazoles with pyrrolidine-2,5-dione moieties showed potent GPR119 agonistic activities. Among them, compound I (R = F, Me) showed good in vitro activity with an EC₅₀ value of 49 nM and 18 nM, resp. with improved human and rat liver microsomal stability compare with MBX-2982. Compound I (R = F, Me) did not exhibit significant CYP inhibition, hERG binding, and cytotoxicity. Moreover, these compounds lowered the glucose excursion in mice in an oral glucose-tolerance test.

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, Category: piperidines.

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

Chen, Lixue published the artcileThe synthesis of 4-arylamido-2-arylaminoprimidines as potent EGFR T790M/L858R inhibitors for NSCLC, Application In Synthesis of 39546-32-2, the publication is Bioorganic & Medicinal Chemistry (2018), 26(23-24), 6087-6095, database is CAplus and MEDLINE.

A series of 4-arylamido-2-arylaminoprimidines bearing acrylamide pharmacophore were synthesized as potent EGFR^T790M/L858R inhibitors among which I [R¹ = H, NR²R³ = N(CH₂CH₂)₂CHCONH₂] (IC₅₀ = 0.5872 nM), I [R¹ = H, NR²R³ = NMe₂] (IC₅₀ = 2.213 nM), or I [R¹ = 3,4-(MeO)₂, NR²R³ = N(CH₂CH₂)₂NMe] (II) (IC₅₀ = 12.57 nM) showed more potent anti-EGFR^T790M/L858R activity compared with AZD-9291 (IC₅₀ = 20.80 nM) and possessed high SI displaying 307.6, 56.5, or 12.5 for EGFR^T790M/L858R over the wild-type resp. II also showed pretty good activity against H 1975 cells with an IC₅₀ of 1.664 μM and exhibited low toxicity against the normal HBE cells (IC₅₀ > 20 μM). II had moderate selectivity for H 1975 over A 431 (SI = 7.0) and the other selected cell lines. Morphol. staining results further indicated that II could promote apoptosis. Hence, II was a promising compound for further investigation as a potential EGFR^T790M/L858R inhibitor for the treatment of NSCLC.

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, Application In Synthesis of 39546-32-2.

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

Gao, Yinyi published the artcileDevelopment of coumarine derivatives as potent anti-filovirus entry inhibitors targeting viral glycoprotein, Quality Control of 39546-32-2, the publication is European Journal of Medicinal Chemistry (2020), 112595, database is CAplus and MEDLINE.

Filoviruses, including Ebolavirus (EBOV), Marburgvirus (MARV) and Cuevavirus, cause hemorrhagic fevers in humans with up to 90% mortality rates. In the 2014-2016 West Africa Ebola epidemic, there are 15,261 laboratory confirmed cases and 11,325 total deaths. The lack of effective vaccines and medicines for the prevention and treatment of filovirus infection in humans stresses the urgency to develop antiviral therapeutics against filovirus-associated diseases. Our previous study identified a histamine receptor antagonist compound CP19 as an entry inhibitor against both EBOV and MARV. The preliminary structure-activity relationship (SAR) studies of CP19 showed that its piperidine, coumarin and linker were related with its antiviral activities. In this study, we performed detailed SAR studies on these groups with synthesized CP19 derivatives We discovered that 1) the piperidine group could be optimized with heterocycles, 2) the substitution groups of C3 and C4 of coumarin should be relatively large hydrophobic groups and 3) the linker part should be least substituted. Based on the SAR anal., we synthesized compound as a potent entry inhibitor of EBOV and MARV (IC₅₀ = 0.5μM for EBOV and 1.5μM for MARV). The mutation studies of Ebola glycoprotein and mol. docking studies showed that the coumarin and its substituted groups of compound 32 bind to the pocket of Ebola glycoprotein in a similar way to the published entry inhibitor compound 118a. However, the carboxamide group of compound 32 does not have strong interaction with N61 as compound 118a does. The coumarin skeleton structure and the binding model of compound 32 elucidated by this study could be utilized to guide further design and optimization of entry inhibitors targeting the filovirus glycoproteins.

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, Quality Control of 39546-32-2.

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