Category: 100-70-9

Frejat, Firas Obaid Arhema published the artcileNovel 1,2,4-oxadiazole/pyrrolidine hybrids as DNA gyrase and topoisomerase IV inhibitors with potential antibacterial activity, Application In Synthesis of 100-70-9, the main research area is DNA gyrase topoisomerase IV inhibitor antibacterial oxadiazole pyrrolidine hybrids.

DNA gyrase is a promising target for antibacterial agents. Several classes of small-mol. inhibitors have been discovered in recent decades, but none of these have reached the market. We have designed a small library of 1,2,4-oxadiazole/pyrrolidine hybrids with mid nanomolar inhibitory and potent antibacterial activities against DNA gyrase and topoisomerase IV. Compounds 9, 15, 16, 19, and 21 inhibited Escherichia coli DNA gyrase to a similar extent as the reference compound, novobiocin, with inhibitory values ranging from 120 nM to 270 nM. Compound 16 was one of the most potent compounds in the series, with an IC50 value of 120 nM against E. coli gyrase, which is lower than the IC50 value of novobiocin (170 nM). Compound 16 had the highest inhibitory activity, with min. inhibitory concentrations (MIC) of 24 and 62 ng/mL against Staphylococcus aureus and E. coli, resp., which compared favorably with ciprofloxacin (30 and 60 ng/mL, resp.). Compounds 9, 15, 19, and 21 were similar to novobiocin in terms of their activity against E. coli and S. aureus topoisomerase IV, while compound 16 was more potent than novobiocin.

Arabian Journal of Chemistry published new progress about Antibacterial agents. 100-70-9 belongs to class nitriles-buliding-blocks, name is Picolinonitrile, and the molecular formula is C6H4N2, Application In Synthesis of 100-70-9.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Frejat, Firas O. A. published the artcileNew 1,2,4-oxadiazole/pyrrolidine hybrids as topoisomerase IV and DNA gyrase inhibitors with promising antibacterial activity, Product Details of C6H4N2, the main research area is pyrrolidine oxadiazole moiety DNA gyrase topoisomerase antibacterial activity; DNA; bacterial resistance; cell viability; gyrase; topoisomerase.

A series of hybridized pyrrolidine compounds with a 1,2,4-oxadiazole moiety were synthesized to develop effective mols. against the enzymes DNA gyrase and topoisomerase IV (Topo IV). Compounds 8-20 were developed based on a previously disclosed series of compounds from our lab, but with small structural modifications in the hopes of increasing the compounds′ biol. activity. In comparison to novobiocin, with IC50 = 170 nM, the findings of the DNA gyrase inhibitory assay revealed that compounds 16 and 17 were the most potent of all synthesized derivatives, with IC50 values of 180 and 210 nM, resp. Compound 17 had the strongest inhibitory effect against Escherichia coli Topo IV of all the synthesized compounds, with an IC50 value of 13 μM, which was comparable to novobiocin (IC50 = 11 μM). Therefore, hybrids 16 and 17 appeared to be potential dual-target inhibitors. In the minimal inhibitory concentration (MIC) assays, compound 17 outperformed ciprofloxacin against E. coli, with an MIC of 55 ng/mL, compared to 60 ng/mL for ciprofloxacin. Finally, the docking study, along with the in vitro experiments, supports our promising approach to effectively develop potent leads for further optimization as dual DNA gyrase and Topo IV inhibitors.

Archiv der Pharmazie (Weinheim, Germany) published new progress about Antibacterial agents. 100-70-9 belongs to class nitriles-buliding-blocks, name is Picolinonitrile, and the molecular formula is C6H4N2, Product Details of C6H4N2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ilin, Mikhail V. published the artcileAminonitrones as highly reactive bifunctional synthons. An expedient one-pot route to 5-amino-1,2,4-triazoles and 5-amino-1,2,4-oxadiazoles – potential antimicrobials targeting multi-drug resistant bacteria, Computed Properties of 100-70-9, the main research area is aminonitrone synthon triazole oxadiazole preparation antibacterial multidrug agent.

The developed one-pot protocol to 5-amino-1,2,4-triazoles or 5-amino-1,2,4-oxadiazoles includes an interplay between aminonitrones R1C(NH2)N+(Me)O- (R1 = Alk, Ar, Het), isocyanides R2NC (R2 = Alk, Ar), Br2, and hydrazines (for the triazoles) or hydroxylamine (for the oxadiazoles). This formally four-component reaction, involving aminonitrones, isocyanides, bromine, and N-nucleophiles, proceeds very rapidly under mild conditions (10 min, 20-25°), and is insensitive to moisture and air (in undried CHCl3-MeOH, in air) and it gives the heterocyclic systems in good yields (up to 86%; 26 examples). The reaction scope includes aromatic-, heteroaromatic-, and aliphatic aminonitrones and also aliphatic- and aromatic isocyanides. Results of DFT calculations (M06-2X/6-311+G(d,p) level of theory) indicate that the O-nucleophilic center of bifunctional aminonitrones is more reactive than the N center; it first reacts with in situ generated R2NCBr2 to grant 2-methyl-1,2,4-oxadiazolium salts, which are then converted to the target heterocyclic systems upon treatment with hydrazines or hydroxylamine. The nature and strength of the intramol. hydrogen bonds N-H···N and O-H···N, which significantly contribute to the total energies of different transition states and products of the nucleophilic substitution, were studied theor. using the topol. anal. of the electron d. distribution within the framework of Bader’s theory (QTAIM method). Several new 5-amino-3-aryl-1,2,4-triazoles and -1,2,4-oxadiazoles exhibit high antibacterial activity against multidrug-resistant bacteria strains such as Staphylococcus aureus and Klebsiella pneumoniae (MIC = 8 mg L-1).

New Journal of Chemistry published new progress about Antibacterial agents. 100-70-9 belongs to class nitriles-buliding-blocks, name is Picolinonitrile, and the molecular formula is C6H4N2, Computed Properties of 100-70-9.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Davies, Sarah published the artcileDevelopment of a self-immolative linker for tetrazine-triggered release of alcohols in cells, Quality Control of 100-70-9, the main research area is antibacterial drug triclosan prodrug preparation cycloocten tetrazine bond cleavage.

Bioorthogonal decaging reactions are a promising strategy for prodrug activation because they involve bond cleavage to release a mol. of interest. The trans-cyclooctene (TCO)-tetrazine inverse electron-demand Diels-Alder reaction has been widely applied in vivo for decaging of amine prodrugs, however, the release of alc.-containing bioactive compounds has been less well studied. Here, we report a TCO-carbamate benzyl ether self-immolative linker for the release of OH-mols. upon reaction with a tetrazine trigger. The benzyl ether linker proved to be highly stable and can rapidly liberate alcs. under physiol. conditions upon reaction with tetrazines. The mechanism and decaging yield were systematically examined by fluorescence and HPLC anal. by using a fluorogenic TCO-benzyl ether-coumarin probe and different 3,6-substituted tetrazine derivatives This study revealed that decaging occurs rapidly (t1/2 = 27 min) and the cycloaddition step happens within seconds (t1/2 = 7 s) with reaction rates of ≈100 M-1s-1. Importantly, the reaction is compatible with living organisms as demonstrated by the decaging of a prodrug of the antibacterial compound triclosan in the presence of live E. coli, that resulted in complete cell killing by action of the released “”OH-active drug””. Overall, this work describes a new linker for masking alc. functionality that can be rapidly reinstated through tetrazine-triggered decaging.

Organic & Biomolecular Chemistry published new progress about Antibacterial agents. 100-70-9 belongs to class nitriles-buliding-blocks, name is Picolinonitrile, and the molecular formula is C6H4N2, Quality Control of 100-70-9.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Shekhovtsov, Nikita A. published the artcileA 1-Hydroxy-1H-imidazole ESIPT Emitter Demonstrating anti-Kasha Fluorescence and Direct Excitation of a Tautomeric Form, Safety of Picolinonitrile, the main research area is hydroxy imidazole preparation fluorescence crystal structure ESIPT; computational chemistry; heterocycles; hydrogen bonds; photochemistry; tautomerism.

The ability of 1-hydroxy-1H-imidazoles to exist in the form of two prototropic tautomers, the N-hydroxy and the N-oxide forms, can be utilized in the design of new types of ESIPT-fluorophores (ESIPT=excited state intramol. proton transfer). Here we report the first example of 1-hydroxy-1H-imidazole-based ESIPT-fluorophores, 1-hydroxy-5-methyl-2,4-di(pyridin-2-yl)-1H-imidazole (HL), featuring a short intramol. hydrogen bond O-H···N (O···N 2.56 Å) as a pre-requisite for ESIPT. The emission of HL originates from the anti-Kasha S2→S0 fluorescence in the N-oxide form as a result of a large S2-S1 energy gap slowing down the S2→S1 internal conversion. Due to an energy barrier between the N-hydroxy and N-oxide forms in the ground state, the HL mols. can be trapped and photoexcited in the N-oxide form leading to the Stokes shift of ca. 60 nm which is the smallest among known ESIPT-fluorophores.

ChemPlusChem published new progress about Conical intersection. 100-70-9 belongs to class nitriles-buliding-blocks, name is Picolinonitrile, and the molecular formula is C6H4N2, Safety of Picolinonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Lee, Jaewoon published the artcileOne-pot bifunctionalization of silica nanoparticles conjugated with bioorthogonal linkers: application in dual-modal imaging, Computed Properties of 100-70-9, the main research area is nanosilica bioorthogonal linker fluorescence tomog imaging.

Covalent surface modification of silica nanoparticles (SNPs) offers great potential for the development of multimodal nanomaterials for biomedical applications. Herein, we report the synthesis of covalently conjugated bifunctional SNPs and their application to in vivo multimodal imaging. Bis(methallyl)silane 15 with cyclopropene and maleimide, designed as a stable bifunctional linker, was efficiently synthesized by traceless Staudiger ligation, and subsequently introduced onto the surface of monodispersed SNPs via Sc(OTf)3-catalyzed siloxane formation. The bifunctional linker-grafted SNP 20 underwent both thiol-conjugated addition and tetrazine cycloaddition in one pot. Finally, positron emission tomog./computed tomog. and fluorescence imaging study of dual functional SNP [125I]28 labeled with NIR dye and 125I isotope showed a prolonged circulation in mice, which is conducive to the systemic delivery of therapeutics.

Biomaterials Science published new progress about Fluorescence imaging. 100-70-9 belongs to class nitriles-buliding-blocks, name is Picolinonitrile, and the molecular formula is C6H4N2, Computed Properties of 100-70-9.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zhou, Xukai published the artcileOlefination via Cu-Mediated Dehydroacylation of Unstrained Ketones, Recommanded Product: Picolinonitrile, the main research area is olefin preparation; unstrained ketone dehydroacylation copper mediated.

The dehydroacylation of ketones to olefins was realized under mild conditions, which exhibited a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N’-methylpicolinohydrazonamide (MPHA) reagent was key to enable efficient cleavage of ketone C-C bonds at room temperature Diverse alkyl- and aryl-substituted olefins, dienes and special alkenes were generated with broad functional group tolerance. Strategic applications of this method were also demonstrated.

Journal of the American Chemical Society published new progress about Acylation (dehydro). 100-70-9 belongs to class nitriles-buliding-blocks, name is Picolinonitrile, and the molecular formula is C6H4N2, Recommanded Product: Picolinonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Arunachalam, Rajendran published the artcileCatalytic Conversion of Carbon Dioxide Using Binuclear Double-Stranded Helicates: Cyclic Carbonate from Epoxides and Diol, Application of Picolinonitrile, the main research area is transition metal Schiff pyridylaldehyde malonohydrazide succinohydrazide glutarohydrazide complex preparation; carbonation catalyst transition metal Schiff pyridylaldehyde malonohydrazide succinohydrazide glutarohydrazide; crystal structure transition metal Schiff pyridylaldehyde malonohydrazide succinohydrazide glutarohydrazide.

The construction of sophisticated mol. architectures from chem. subunits requires careful selection of the spacers, precise synthetic strategies, and substantial efforts. The authors report a series of binuclear double-stranded helicates synthesized from different combinations of pyridyl hydrazone-based multidentate ligands (H2L1, H2L2, H2L3) by increasing the methylene spacer and transition metals (Co, Ni, and Zn). The ligands H2L1 (N’1,N’3-bis((E)-pyridin-2-ylmethylene)malonohydrazide), H2L2 (N’1,N’4-bis((E)-pyridin-2-ylmethylene)succinohydrazide), and H2L3 (N’1,N’5-bis((E)-pyridin-2-ylmethylene)glutarohydrazide) and their resp. complexes with Co, Ni, and Zn were obtained. Single-crystal X-ray diffraction studies of these binuclear metallohelicates confirm the double-stranded helical structure of the complexes derived from H2L2. The set of helicates Co-1, Co-2, and Co-3; Ni-1, Ni-2, and Ni-3; and Zn-1, Zn-2, and Zn-3 were investigated for its catalytic activity in the cyclic carbonate formation reaction. Intriguingly, among the synthesized catalyst, Co-1 was found to be better in terms of conversions with the calculated TOF (turnover frequency) of 128/h. The catalytic performance was significantly improved by adding 0.2 mmol of tetrabutylammonium bromide by achieving 76% conversion in 30 min, with the observed TOF of 15,934 h-1/mol. and 7967 h-1/Co center. The results obtained herein show that the double-stranded helicates are effective catalysts for converting both terminal and non-terminal epoxides into their corresponding cyclic carbonates. The striking feature of this catalytic protocol lies in demonstrating the catalytic activity for the conversion of diol to cyclic carbonate, and the detailed kinetic experiments tempted us to propose a tentative reaction mechanism for this conversion.

ACS Omega published new progress about Carbonation catalysts. 100-70-9 belongs to class nitriles-buliding-blocks, name is Picolinonitrile, and the molecular formula is C6H4N2, Application of Picolinonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ohno, Hajime published the artcileDirect dimethyl carbonate synthesis from CO2 and methanol catalyzed by CeO2 and assisted by 2-cyanopyridine: a cradle-to-gate greenhouse gas emission study, Application In Synthesis of 100-70-9, the main research area is dimethyl carbonate carbon dioxide methanol CeO2 cyanopyridine greenhouse gas.

The direct synthesis of di-Me carbonate (DMC) from CO2 and methanol is an attractive alternative route utilizing CO2 instead of toxic phosgene as a carbonate source. The route is thermodynamically difficult because of the equilibrium limitation of the reaction 2CH3OH + CO2 → (CH3O)2O + H2O. In addition, the azeotrope formed by DMC and methanol makes the separation of DMC from unreacted methanol complex and energy intensive. The use of CeO2 and 2-cyanopyridine as a catalyst and dehydration agent solved both the equilibrium constraint and the separation challenge. In this study, the direct DMC synthesis from CO2 and methanol over CeO2 with 2-cyanopyridine was evaluated in terms of greenhouse gas (GHG) emission with the aid of process simulation. It was validated that the cradle-to-gate greenhouse gas emission attributed to the product of this system (0.39 kg-CO2-eq per kg-DMC) becomes much lower than that in conventional commercialized processes. The heat exchange in the process reduced the emission further to 0.34 kg-CO2-eq per kg-DMC. Among the items associated with emissions, methanol consumption shared the largest part (0.63 kg-CO2-eq per kg-DMC), while the converted CO2 was regarded as an important offset (-0.49 kg-CO2-eq per kg-DMC). It is due to the use of the typical methanol production from natural gas (0.88 kg-CO2-eq per kg-methanol). It suggests that if the methanol production with its associated GHG emission accounting for less than 0.41 or 0.34 kg-CO2-eq per kg-methanol is applicable for with or without heat-exchanging cases, the presented process achieves neg. emission. Furthermore, based on the results, the requirements for the practical process implementation are discussed by comparing the lifecycle GHG emission results with other DMC synthesis routes.

Green Chemistry published new progress about Dehydration catalysts. 100-70-9 belongs to class nitriles-buliding-blocks, name is Picolinonitrile, and the molecular formula is C6H4N2, Application In Synthesis of 100-70-9.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Qian, Deyun published the artcileLigand-Controlled Regiodivergent Hydroalkylation of Pyrrolines, Computed Properties of 100-70-9, the main research area is pyridine oxazoline ligand preparation; alkyalated pyrrolidine preparation regioselective; pyrroline halide hydroalkylation pyridine oxazoline ligand nickel catalyst; alkenes; heterocycles; hydroalkylation; nickel; reaction mechanisms.

Two series of C-alkylated pyrrolidines I [R = Boc, Cbz; R1 = i-Pr, cyclopentyl, indol-1-yl, etc.] and II [R2 = CO2Ph, Boc, Cbz; R3 = cyclohexyl, (CH2)3Ph, 2-thienyl, etc.] were synthesized via ligand controlled nickel-catalyzed regiodivergent hydroalkylation of 3-pyrrolines with alkyl/aryl halides. This method demonstrated broad scope and high functional-group tolerance and could be applied in late-stage functionalizations.

Angewandte Chemie, International Edition published new progress about Alkylation catalysts. 100-70-9 belongs to class nitriles-buliding-blocks, name is Picolinonitrile, and the molecular formula is C6H4N2, Computed Properties of 100-70-9.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts