Day: December 1, 2022

Sun, Jian published the artcileModulated construction of Fe-based MOF via formic acid modulator for enhanced degradation of sulfamethoxazole:Design, degradation pathways, and mechanism, Safety of 2,2,6,6-Tetramethylpiperidin-4-one, the publication is Journal of Hazardous Materials (2022), 128299, database is CAplus and MEDLINE.

Metal-organic frameworks (MOFs) have attracted more attention because of their excellent environmental catalytic capabilities. Modulation approach as an advanced assistant strategy is vital essential to enhancing the performance of MOFs. In this study, the modulated method was used to successfully synthesize a group of Fe-based MOFs, with formic acid as the modulator on the synthesis mixture The most modulated sample Fe-MOFs-2 exhibit high sp. surface areas and higher catalytic activity, which could effectively degrade SMX via PS activation, with almost 95% removal efficiency within 120 min. The results revealed that the % RSE of modulated Fe-MOFs-2 increased from 2.31 to 3.27 when compared with the origin Fe-MOFs. This may be due to the addition of formic acid induces the formation of more coordinatively unsaturated metal sites in the catalyst, resulting in structural defects. In addition, the quenching experiment and EPR anal. verified SO^–₄·and·OH as the major active free radicals in the degradation process. Modulated Fe-MOFs-2 demonstrated good reusability and stability under fifth cycles. Finally, four possible degradation pathways and catalytic mechanism of Fe-MOFs-2 was tentatively proposed. Our work provides insights into the rational design of modulated Fe-MOFs as promising heterogeneous catalysts for advanced wastewater treatment.

Journal of Hazardous Materials 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 C15H23BO2, Safety of 2,2,6,6-Tetramethylpiperidin-4-one.

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

Ringheim, Garth E. published the artcileBruton′s tyrosine kinase (BTK) inhibitors and autoimmune diseases: making sense of BTK inhibitor specificity profiles and recent clinical trial successes and failures, COA of Formula: C26H25N5O3, the publication is Frontiers in Immunology (2021), 662223, database is CAplus and MEDLINE.

Clin. development of BTK kinase inhibitors for treating autoimmune diseases has lagged behind development of these drugs for treating cancers, due in part from concerns over the lack of selectivity and associated toxicity profiles of first generation drug candidates when used in the long term treatment of immune mediated diseases. Second generation BTK inhibitors have made great strides in limiting off-target activities for distantly related kinases, though they have had variable success at limiting cross-reactivity within the more closely related TEC family of kinases. We investigated the BTK specificity and toxicity profiles, drug properties, disease associated signaling pathways, clin. indications, and trial successes and failures for the 13 BTK inhibitor drug candidates tested in phase 2 or higher clin. trials representing 7 autoimmune and 2 inflammatory immune-mediated diseases. We focused on rheumatoid arthritis (RA), multiple sclerosis (MS), and systemic lupus erythematosus (SLE) where the majority of BTK nonclin. and clin. studies have been reported, with addnl. information for pemphigus vulgaris (PV), Sjogren′s disease (SJ), chronic spontaneous urticaria (CSU), graft vs. host disease (GVHD), and asthma included where available. While improved BTK selectivity vs. kinases outside the TEC family improved clin. toxicity profiles, less profile distinction was evident within the TEC family. Anal. of genetic associations of RA, MS, and SLE biomarkers with TEC family members revealed that BTK and TEC family members may not be drivers of disease. They are, however, mediators of signaling pathways associated with the pathophysiol. of autoimmune diseases. BTK in particular may be associated with B cell and myeloid differentiation as well as autoantibody development implicated in immune mediated diseases. Successes in the clinic for treating RA, MS, PV, ITP, and GVHD, but not for SLE and SJ support the concept that BTK plays an important role in mediating pathogenic processes amenable to therapeutic intervention, depending on the disease. Based on the data collected in this study, we propose that current compound characteristics of BTK inhibitor drug candidates for the treatment of autoimmune diseases have achieved the selectivity, safety, and coverage requirements necessary to deliver therapeutic benefit.

Frontiers in Immunology published new progress about 1971920-73-6. 1971920-73-6 belongs to piperidines, auxiliary class Other Aliphatic Heterocyclic,Piperidine,Alkenyl,Amine,Benzene,Ether,Inhibitor,Inhibitor, name is (R)-1-(1-Acryloylpiperidin-3-yl)-4-amino-3-(4-phenoxyphenyl)-1H-imidazo[4,5-c]pyridin-2(3H)-one, and the molecular formula is C26H25N5O3, COA of Formula: C26H25N5O3.

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

Frihed, Tobias Gylling published the artcileInfluence of O6 in Mannosylations Using Benzylidene Protected Donors: Stereoelectronic or Conformational Effects?, Formula: C11H15NOS, the publication is Journal of Organic Chemistry (2013), 78(6), 2191-2205, database is CAplus and MEDLINE.

The stereoselective synthesis of β-mannosides and the underlying reaction mechanism have been thoroughly studied, and especially the benzylidene-protected mannosides have gained a lot of attention since the corresponding mannosyl triflates often give excellent selectivity. The hypothesis for the enhanced stereoselectivity has been that the benzylidene locks the mol. in a less reactive conformation with the O6 trans to the ring oxygen (O5), which would stabilize the formed α-triflate and subsequent give β-selectivity. In this work, the hypothesis is challenged by using the carbon analog (C7) of the benzylidene-protected mannosyl donor, which is investigated in terms of diastereoselectivity and reactivity and by low-temperature NMR. In terms of diastereoselectivity, the C-7-analog behaves similarly to the benzylidene-protected donor, but its low-temperature NMR reveals the formation of several reactive intermediate. One of the intermediates was found to be the β-oxosulfonium ion. The reactivity of the donor was found to be in between that of the “torsional” disarmed and an armed donor.

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, Formula: C11H15NOS.

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

Wierzbicka, Magdalena published the artcileOne-pot cyclization and cleavage of peptides with N-terminal cysteine via the N,S-acyl shift of the N-2-[thioethyl]glycine residue, Related Products of piperidines, the publication is Journal of Organic Chemistry (2021), 86(17), 12292-12299, database is CAplus and MEDLINE.

We developed a one-pot method for peptide cleavage from a solid support via the N,S-acyl shift of N-2-[thioethyl]glycine and transthioesterification using external thiols to produce cyclic peptides through native chem. self-ligation with the N-terminal cysteine. The feasibility of this methodol. is validated by the syntheses of model short peptides, including a tetrapeptide, the bicyclic sunflower trypsin inhibitor SFTI-1, and rhesus Θ-defensin RTD-1. Synthesis of the whole peptide precursor can be fully automated and proceeds without epimerization or dimerization.

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 C8H19NO2, Related Products of piperidines.

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

Mikhlina, E. E. published the artcileSynthesis of 3- and 4-hydroxypiperidine derivatives, Related Products of piperidines, the publication is Zhurnal Obshchei Khimii (1960), 1885-93, database is CAplus.

cf. CA 54, 22632h. Refluxing 1-ethyl-3-hydroxypiperidine with p-ClC₆H₄COCl in C₆H₆ gave 62.5% 1-ethyl-3-(p-chlorobenzoxy)piperidine-HCl, m. 185-7°. Similarly were prepared 68-93% yields of HCl salts of the corresponding: acetate, m. 179-81°; propionate, m. 174-5°; p-nitrobenzoate, m. 175-7°; phenoxyacetate, m. 160-2°; and cinnamate, m. 164-6°. 4-Piperidone-HCl with NaBH₄ in EtOH with ice cooling gave in 20 h. 61% 4-hydroxypiperidine, b₁₃ 106°. Similarly was prepared 83.5% 1-methyl-4-hydroxypiperidine, b₁₂ 94°, and 84.5% 1-ethyl-4-hydroxypiperidine, b₅ 91°. 1-Ethyl-3-hydroxypiperidine with CH₂:CHCN in dioxane-MeOH in the presence of 30% KOH in MeOH gave in 4 h. at 65° 80.2% 1-ethyl-3-(2-cyanoethoxy)piperidine (I), b₃ 125-6°. Similarly were prepared 80% 1-methyl-4-(2-cyanoethoxy)piperidine, b₇ 125-6°, n¹⁷_D 1.4668, and 1-Et analog, b₄ 122°. I and dry HCl in refluxing EtOH 4 h. gave 66.6% 1-ethyl-3-(2-carbethoxyethoxy)piperidine (II), b₃ 120-1°, n¹⁷_D 1.4589, also formed by the use of EtOH-H₂SO₄ in 18 h. at reflux. Similarly were prepared 48% 1-methyl-4-(2-carbethoxyethoxy)piperidine, b₂ 102°, n¹⁸_D 1.4558, and 66% 1-ethyl-4-(2-carbethoxyethoxy)piperidine, b₄ 113°. II with LiAlH₄ in Et₂O gave 86.8% 1-ethyl-3-(γ-hydroxypropoxy)piperidine (III), b₃ 116-18°, n¹⁷_D 1.4749. Similarly were prepared 76.3% 1-methyl-4-(γ-hydroxypropyl)piperidine, b₄ 114-16°, n¹⁷_D 1.4741, and 88% 1-Et analog, b₅ 125°, n²⁴_D 1.4713. III treated with EtOH-HCl, evaporated, and treated with SOCl₂ in MePh gave after aqueous treatment 1-ethyl-3-(γ-chloropropoxy)piperidine, which refluxed 6 h. with thiourea in N HCl then heated with aqueous NaOH 0.5 h. gave 71.4% 1-ethyl-3-(γ-mercaptopropoxy)piperidine, b₈ 132-3°. Similarly was prepared 71% 1-methyl-4-(γ-mercaptopropoxy)piperidine (IV), b_0.7 100°, and 57.2% 1-ethyl-4-(γ-mercaptopropoxy)piperidine, b₁ 110°. III treated with SOCl₂ in hot C₆H₆ 3 h. at 65°, evaporated, and made alk. with K₂CO₃ gave crude 1-ethyl-3-(γ-chloropropoxy)piperidine, which treated with thiourea in aqueous EtOH 6 h. gave 43.2% bis[γ-(1-ethyl-3-piperidyloxy)propyl] sulfide, b_0.5 202-7°. Heating 1-methyl-4-(γ-hydroxypropoxy)piperidine with AcCl in C₆H₆ 6 h. gave 94% 1-methyl-4-(γ-acetoxypropoxy)piperidine, b₃ 111°; methiodide m. 77-9°. IV with BzCl in Et₂O gave 91% 1-methyl-4-(γ-benzoylthiopropoxy)piperidine-HCl, m. 129.5-30°. Similarly were prepared the following 1-ethyl-3-(γ-acyloxypropoxy)piperidines (acyl group shown): propionate, b₁ 125-7°; benzoate, b₁ 190-2°; p-nitrobenzoate, b₁ 201-3°; and pyridylcarbonyl, b_0.6 177-8°. Also reported was 1-ethyl-3-(γ-acetylthiopropoxy)piperidine, b_0.75 135°. The following 1-alkyl-4-[γ-acyloxy(or acylthio)propoxy] piperidines were reported (alkyl and acyl groups shown, resp.): Me, benzoxy, b₃ 170-1° (HCl salt m. 120°); Me, p-nitrobenzoylthio (HCl salt m. 127-8°); Me, p-chlorobenzoylthio (HCl salt m. 127-31°; Me, acetylthio, b_0.5 107-10°; Me, diphenylacetylthio (HCl salt m. 57-7.5°); Et, acetoxy, b_0.5 97°; Et, benzoxy, b_0.5 155-61°; Et, diphenylacetoxy, b_0.7 203-5°; Et, acetylthio (HCl salt m. 68°); Et, benzoylthio (HCl salt m. 124-5°); Et, phenylacetylthio (HCl salt m. 95-7°); Et, diphenylacetylthio (HCl salt m. 103-7°); Bu, benzoylthio (HCl salt m. 115-18°); Bu, acetylthio (HCl salt m. 102-3°). Acrylonitrile with 4-hydroxypiperidine in the presence of KOH in MeOH-dioxane gave 74.5% 4-(2-cyanoethoxy)piperidine, b₂ 135°, n¹⁴_D 1.4630, which with HCl-EtOH at reflux gave 65.5% 4-(2-carbethoxyethoxy)piperidine, b₄ 122°. This in pyridine treated with PrCOCl 4 h. at 65°, the crude product after aqueous treatment neutralized with K₂CO₃, extracted with C₆H₆, and reduced with LiAlH₄ gave 56% 1-butyl-4-(γ-hydroxypropoxy)piperidine, b_0.5 130-2°.

Zhurnal Obshchei Khimii 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, Related Products of piperidines.

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

Crich, David published the artcileSynthesis and Glycosylation of a Series of 6-Mono-, Di-, and Trifluoro S-Phenyl 2,3,4-Tri-O-benzyl-thiorhamnopyranosides. Effect of the Fluorine Substituents on Glycosylation Stereoselectivity, SDS of cas: 4972-31-0, the publication is Journal of the American Chemical Society (2007), 129(38), 11756-11765, database is CAplus and MEDLINE.

A series of 6-mono-, di-, and trifluoro analogs of S-Ph 2,3,4-tri-O-benzyl-D– or L-thiorhamnopyranoside has been synthesized and used as donors in glycosylation reactions, with activation by the 1-benzene-sulfinyl piperidine/triflic anhydride system. The stereochem. outcome of the glycosylation reactions was found to depend on the electron-withdrawing capability of the disarming substituent at the 6-position, i.e., on the number of fluorine atoms present. The results are explained with regard to the increased stability of the glycosyl triflates, shown to be intermediates in the reaction by low-temperature ¹H NMR experiments, with increased fluorine content.

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, SDS of cas: 4972-31-0.

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

Crich, David published the artcileThe 3,4-O-Carbonate Protecting Group as a β-Directing Group in Rhamnopyranosylation in Both Homogeneous and Heterogeneous Glycosylations As Compared to the Chameleon-like 2,3-O-Carbonates, SDS of cas: 4972-31-0, the publication is Journal of Organic Chemistry (2003), 68(22), 8453-8458, database is CAplus and MEDLINE.

It is demonstrated that the β-selectivity observed in the insoluble silver salt mediated couplings of 2,3-O-carbonate-protected rhamnosyl bromides is uniquely due to the heterogeneous nature of the reaction. In homogeneous solution these same donors are α-selective, a fact that is attributed to the half-chair conformation of these substances which reduces the energy barrier to oxacarbenium ion formation. It is suggested that the 2,3-O-carbonate group be dubbed torsionally arming in the manno- and rhamnopyranose series. When the carbonate group is removed to the 3,4-O-position a β-selective system is formed, in both homogeneous and heterogeneous conditions, and it is demonstrated that this selectivity arises from the combination of the electron-withdrawing nature of the carbonate and its inability to take part in neighboring participation.

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, SDS of cas: 4972-31-0.

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

Bartmann, K. published the artcileCan the experimental guinea-pig tuberculosis be influenced by a Azorhodanid H depot treatment?, Safety of 1-Ethylpiperidin-3-ol, the publication is Beitraege zur Klinik der Tuberkulose und Spezifischen Tuberkulose-Forschung (1955), 75-8, database is CAplus.

Azorhodanid H in the dose used (weekly 30 mg. as suspension subcutaneously) barely influences the course of guinea-pig tuberculosis, while a lower but still optimal isoniazid treatment of the animals (5 mg./kg. for 4 weeks and further for 9.5 weeks twice weekly) practically completely prevented lymphogenous and hematogenous spread.

Beitraege zur Klinik der Tuberkulose und Spezifischen Tuberkulose-Forschung 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, Safety of 1-Ethylpiperidin-3-ol.

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

Pettenuzzo, Andrea published the artcileDesign, physico-chemical characterization and in vitro biological activity of organogold(III) glycoconjugates, SDS of cas: 39546-32-2, the publication is Dalton Transactions (2021), 50(25), 8963-8979, database is CAplus and MEDLINE.

To develop new metal-based glycoconjugates as potential anticancer agents, four organometallic Au(III)-dithiocarbamato glycoconjugates [Au(III)(2-Bnpy)(SSC-Inp-GlcN)](PF₆) (2-Bnpy: 2-benzylpyridine; Inp: isonipecotic moiety; GlcN: amino-glucose scaffold; Au3-Au6) and the corresponding model nonglycosylated counterparts [Au(III)(2-Bnpy)(SSC-Inp-R)](PF₆) (R: OEt (Au1), NH₂ (Au2)) were generated and characterized by several anal. techniques (elemental anal., FTIR, ¹H-/¹³C-NMR, ESI-MS, UV-visible, x-ray crystallog.). Their stability under physiol.-relevant conditions (PBS solution) and n-octanol/PBS distribution coefficient (D_7.4) also were evaluated. Au(III) glycoconjugates showed an antiproliferative effect against ovarian carcinoma A2780 cells, with GI₅₀ values in the low micromolar range. Remarkably, their cell growth inhibitory effect increases upon the addition of a glucose transporter 1 (GLUT1) inhibitor, thus ruling out the involvement of GLUT1 in their transport inside the cell. Addnl. mechanistic studies were carried out in A2780 cells, supporting the hypothesis of a facilitated diffusion mechanism (possibly mediated by glucose transporters other than GLUT1), and revealing their capability to act as topoisomerase I and II inhibitors and to disrupt mitochondrial membrane integrity, giving ROS, thus resulting in the promotion of oxidative stress and, eventually, cell death.

Dalton Transactions 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, SDS of cas: 39546-32-2.

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

Giannini, Giuseppe published the artcileST7612AA1, a Thioacetate-ω(γ-lactam carboxamide) Derivative Selected from a Novel Generation of Oral HDAC Inhibitors, Quality Control of 72002-30-3, the publication is Journal of Medicinal Chemistry (2014), 57(20), 8358-8377, database is CAplus and MEDLINE.

A systematic study of medicinal chem. aimed at identifying a new generation of HDAC inhibitors, through the introduction of a thiol zinc-binding group and of an amide-lactam in the ω-position of the polyethylene chain of the vorinostat scaffold, allowed the selection of a new class of potent pan-HDAC inhibitors (pan-HDACis). Simple, highly versatile, and efficient synthetic approaches were used to synthesize a library of these new derivatives, which were then submitted to a screening for HDAC inhibition as well as to a preliminary in vitro assessment of their antiproliferative activity. Mol. docking into HDAC crystal structures suggested a binding mode for these thiol derivatives consistent with the stereoselectivity observed upon insertion of amide-lactam substituents in the ω-position. ST7612AA1 I, selected as a drug candidate for further development, showed an in vitro activity in the nanomolar range associated with a remarkable in vivo antitumor activity, highly competitive with the most potent HDAC inhibitors, currently under clin. trials. A preliminary study of PK and metabolism is also illustrated.

Journal of Medicinal Chemistry 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 C6H9NO3, Quality Control of 72002-30-3.

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