Day: November 29, 2022

Yadav, Nisha published the artcileTricyclic dihydrobenzoxazepine and tetracyclic indole derivatives can specifically target bacterial DNA ligases and can distinguish them from human DNA ligase I, Name: Piperidine-4-carboxamide, the publication is Organic & Biomolecular Chemistry (2015), 13(19), 5475-5487, database is CAplus and MEDLINE.

DNA ligases are critical components for DNA metabolism in all organisms. NAD⁺-dependent DNA ligases (LigA) found exclusively in bacteria and certain entomopoxviruses are drawing increasing attention as therapeutic targets as they differ in their cofactor requirement from ATP-dependent eukaryotic homologs. Due to the similarities in the cofactor binding sites of the two classes of DNA ligases, it is necessary to find determinants that can distinguish between them for the exploitation of LigA as an anti-bacterial target. In the present endeavor, we have synthesized and evaluated a series of tricyclic dihydrobenzoxazepine and tetracyclic indole derivatives, e.g. I [X = S, O, CH₂; R = 1-piperidinyl,, 4-hydroxy-1-piperidinyl, 1-pyrrolidinyl, etc.], for their ability to distinguish between bacterial and human DNA ligases. The in vivo inhibition assays that employed LigA deficient E. coli GR501 and S. typhimurium LT2 bacterial strains, rescued by ATP-dependent T4 DNA ligase or Mycobacterium tuberculosis NAD⁺-dependent DNA ligase (Mtb LigA), resp., showed that the compounds can specifically inhibit bacterial LigA. The in vitro enzyme inhibition assays using purified MtbLigA, human DNA ligase I & T4 DNA ligase showed specific inhibition of MtbLigA at low micromolar range. Our results demonstrate that tricyclic dihydrobenzoxazepine and tetracyclic indole derivatives can distinguish between bacterial and human DNA ligases by ∼5-folds. In silico docking and enzyme inhibition assays identified that the compounds bind to the cofactor binding site and compete with the cofactor. Ethidium bromide displacement and gel-shift assays showed that the inhibitors do not exhibit any unwanted general interactions with the substrate DNA. These results set the stage for the detailed exploration of this compound class for development as antibacterials.

Organic & Biomolecular 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 C10H14O2, Name: Piperidine-4-carboxamide.

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

Wei, Peng published the artcileFactors Affecting Stereocontrol during Glycosidation of 2,3-Oxazolidinone-Protected 1-Tolylthio-N-acetyl-D-glucosamine, Product Details of C11H15NOS, the publication is Journal of Organic Chemistry (2005), 70(10), 4195-4198, database is CAplus and MEDLINE.

It is demonstrated that a ring-fused 2,3-oxazolidinone-protected derivative of 1-tolylthio-N-acetyl-D-glucosamine, e.g. β-I (R = SPhMe), undergoes high-yield stereoselective glycosidation under mild donor activation conditions to give the corresponding glycosides, e.g. I (R = OBn). Stereoselective formation of α-linked or β-linked glycosides is dependent on reactivity of acceptor alcs., where rate of glycosidation correlates to stereochem. outcome. Evidence for the role of glycosyl triflate intermediates and the N-acetyl substituent of the 2N,3O-oxazolidinone ring in stereochem. control is presented.

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 C8H15NO, Product Details of C11H15NOS.

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

Ovian, John M. published the artcileAccessing N-Acyl Azoles via Oxoammonium Salt-Mediated Oxidative Amidation, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Organic Letters (2017), 19(6), 1286-1289, database is CAplus and MEDLINE.

An operationally simple, robust, metal-free approach to the synthesis of N-acyl azoles from both alcs. and aldehydes is described. Oxidative amidation is facilitated by a com. available organic oxidant (4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) and proceeds under very mild conditions for an array of structurally diverse substrates. Tandem reactions of these activated amides, such as transamidation and esterification, enable further elaboration. Also, the spent oxidant can be recovered and used to regenerate the oxoammonium salt.

Organic Letters 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, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate.

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

Mercadante, Michael A. published the artcile1,3-γ-Silyl-elimination in electron-deficient cationic systems, Related Products of piperidines, the publication is Chemical Science (2014), 5(10), 3983-3994, database is CAplus.

Placement of an electron-withdrawing trifluoromethyl group (-CF₃) at a putative cationic center enhanced γ-silyl neighboring-group participation (NGP). In stark contrast to previously studied γ-silyl-substituted systems, the preferred reaction pathway was 1,3-γ-silyl elimination, giving ring closure over solvent substitution or alkene formation. The scope of this cyclopropanation reaction was explored for numerous cyclic and acyclic examples, proving this method to be a viable approach for preparing CF₃-substituted cyclopropanes and bicyclic systems, both containing quaternary centers. Rate-constants, kinetic isotope effects, and quantum mech. calculations provided evidence for this enhancement and further elaborated the disparity in the reaction outcome between these systems and previously studied γ-silyl systems.

Chemical Science 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, Related Products of piperidines.

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

Mercadante, Michael A. published the artcileSynthesis of 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxammonium tetrafluoroborate and 4-acetamido-(2,2,6,6-tetramethyl-1-piperidinyl)oxyl and their use in oxidative reactions, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Nature Protocols (2013), 8(4), 666-676, database is CAplus and MEDLINE.

E authors describe the synthesis of a lesser-known stoichiometric oxidation reagent 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxammonium tetrafluoroborate [Bobbitt’s salt, 4-(acetylamino)-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate(1-)] (I) and 4-acetamido-(2,2,6,6-tetramethyl-piperidin-1-yl)oxyl (AcNH-TEMPO) (II). Several representative oxidation reactions are also presented to demonstrate the oxidative capability of Bobbitt’s salt. Bobbitt’s salt I has a range of applications, from the oxidation of various alcs. to their corresponding carbonyl derivatives to the oxidative cleavage of benzyl ethers, whereas II has been shown to serve as a catalytic or stoichiometric oxidant. The oxyl radical can be obtained in 85% yield over two steps on a one mol scale from com. available 4-amino-2,2,6,6-tetramethylpiperidine and is far more cost-effective to prepare inhouse than purchase com. An addnl. step converts the oxyl radical into the oxammonium salt (Bobbitt’s salt) I in 88% yield with an overall yield of 75%. The synthesis of the salt takes ∼5 d to complete. Oxammonium salts are metal-free, nontoxic and environmentally friendly oxidants (green chem. method). Preparation of I is also inherently a green process, as water can be used as a solvent and the use of environmentally unfriendly materials is minimized. Moreover, after it has been used, the spent oxidant can be recovered and used to regenerate I, thereby making the process recyclable. The synthesis of the target compound I was achieved by a reaction of 4-(Acetylamino)-2,2,6,6-tetramethyl-1-piperidinyloxy [(acetylamino)TEMPO]. Oxidation of 3-(4-methylphenyl)-2-propyn-1-ol provided 3-(4-methylphenyl)-2-propynoic acid. Oxidation of 1-decanol gave decanal.

Nature Protocols 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, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate.

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

Lambert, Kyle M. published the artcileA Practical Oxidation Experiment for Undergraduate Students: Bobbitt′s Salt as a “Green” Alternative, Synthetic Route of 219543-09-6, the publication is Journal of Chemical Education, database is CAplus.

Oxidation reactions are critical components of the synthetic toolbox taught to undergraduate students during introductory organic chem. courses. However, the oxidation reactions discussed in the undergraduate curriculum are often outdated as many organic chem. textbooks emphasize chromium-based oxidants that are no longer in regular use by practitioners, which may limit an instructor′s time to allocate to discussion of other oxidants. Further, laboratory courses have since either removed oxidation experiments or replaced them with oxidative processes not discussed in lectures, thus leading to a disconnect between the two learning settings. As part of an effort to bridge this divide and modernize the oxidation reactions discussed in our curricula, we have developed a new laboratory experiment that uses a com. available oxoammonium salt (Bobbitt′s salt) to cleanly oxidize cinnamyl alc. to cinnamaldehyde. In addition to being a safe, convenient, colorimetric and “green oxidant” suitable for use in the undergraduate teaching laboratory, the hydride-transfer mechanism allows for overlap with key course concepts presented in both introductory and advanced lecture courses. The procedure is well-suited for small and large organic I, II or advanced laboratory sections alike, and can be completed within a standard 3-4 h laboratory period. Aside from exposing students to a modern green oxidation protocol, the experiment contains expanded opportunities for interpretation of ¹H NMR, ¹³C NMR, and IR spectra. An optional addendum for advanced students involving Hammett correlations was also developed.

Journal of Chemical Education 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, Synthetic Route of 219543-09-6.

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

Hamlin, Trevor A. published the artcileToward a Unified Mechanism for Oxoammonium Salt-Mediated Oxidation Reactions: A Theoretical and Experimental Study Using a Hydride Transfer Model, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Journal of Organic Chemistry (2015), 80(16), 8150-8167, database is CAplus and MEDLINE.

A range of oxoammonium salt-based oxidation reactions have been explored computationally using d. functional theory (DFT), and the results have been correlated with exptl. derived trends in reactivity. Mechanistically, most reactions involve a formal hydride transfer from an activated C-H bond to the oxygen atom of the oxoammonium cation. Several new potential modes of reactivity have been uncovered and validated exptl.

Journal of Organic Chemistry 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, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate.

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

Hamlin, Trevor A. published the artcileDehydrogenation of Perfluoroalkyl Ketones by Using a Recyclable Oxoammonium Salt, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is European Journal of Organic Chemistry (2013), 2013(18), 3658-3661, database is CAplus.

A novel dehydrogenation reaction of perfluoroalkyl ketones by the oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (4-NHAc-TEMPO⁺ BF₄^–, Bobbitt’s salt) is described. The reaction proceeds under mildly basic conditions and appears to be unique to perfluoroalkyl ketones. E.g., in presence of Bobbitt’s salt and 2,6-lutidine in refluxing CH₂Cl₂, dehydrogenation of PhCH₂CH₂COCF₃ gave 65% (E)-I. A proposed mechanism for this unusual transformation is given. The byproduct of the reaction, 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinyloxy, can easily be recovered and used to regenerate the oxoammonium salt.

European Journal of Organic Chemistry 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, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate.

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

Eddy, Nicholas A. published the artcileAccess to Dienophilic Ene-Triketone Synthons by Oxidation of Diketones with an Oxoammonium Salt, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, the publication is Organic Letters (2012), 14(2), 498-501, database is CAplus and MEDLINE.

The oxidation of 1,3-cycloalkanediones with 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (Bobbitt’s salt) to generate 5-ene-1,2,4-triones in moderate-to-good (40-80%) yields was reported. This inexpensive oxidant facilitated an unprecedented cascade of oxidation and elimination to yield novel ene-triketones. The reactivity of these products was explored in the Diels-Alder reaction and provided moderate-to-good yields of cycloaddition products. The products described in this study represent unique, densely functionalized, and versatile building blocks for the synthesis of more complex mols.

Organic Letters 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, Application of 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate.

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

Patel, Gautam published the artcileKinase Scaffold Repurposing for Neglected Disease Drug Discovery: Discovery of an Efficacious, Lapatanib-Derived Lead Compound for Trypanosomiasis, Name: 1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine, the publication is Journal of Medicinal Chemistry (2013), 56(10), 3820-3832, database is CAplus and MEDLINE.

Lapatinib analogs such as I (X = O, CH₂) were prepared as trypanocidal agents for use as lead compounds in the development of treatments for human African trypanosomiasis which do not require i.v. administration. Lapatinib was previously shown to kill T. brucei with low micromolar EC₅₀ values; analogs replacing the methylfurylquinazoline moiety with a heteroarylsulfonylphenylquinazolinyl moiety were prepared and tested against both T. brucei and human hepatocarcinoma cells. 4-Anilinoquinazolines, particularly I (X = O) (NEU617), were found to be highly potent and orally bioavailable inhibitors of trypanosome replication. I (X = O) blocks duplication of the kinetoplast and arrests cytokinesis in T. brucei, which may make it useful as a chem. tool for studying regulation of the trypanosome cell cycle.

Journal of Medicinal Chemistry published new progress about 859833-21-9. 859833-21-9 belongs to piperidines, auxiliary class Piperidine,Boronic acid and ester,Benzene,Boronic Acids,Boronate Esters, name is 1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine, and the molecular formula is C18H28BNO2, Name: 1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine.

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