Category: 100-70-9

Steen, E. Johanna L. published the artcileLipophilicity and Click Reactivity Determine the Performance of Bioorthogonal Tetrazine Tools in Pretargeted In Vivo Chemistry, HPLC of Formula: 100-70-9, the main research area is lipophilicity click reactivity bioorthogonal labeled tetrazine trans cyclooctene antibody.

The development of highly selective and fast biocompatible reactions for ligation and cleavage has paved the way for new diagnostic and therapeutic applications of pretargeted in vivo chem. The concept of bioorthogonal pretargeting has attracted considerable interest, in particular for the targeted delivery of radionuclides and drugs. In nuclear medicine, pretargeting can provide increased target-to-background ratios at early time-points compared to traditional approaches. This reduces the radiation burden to healthy tissue and, depending on the selected radionuclide, enables better imaging contrast or higher therapeutic efficiency. Moreover, bioorthogonally triggered cleavage of pretargeted antibody-drug conjugates represents an emerging strategy to achieve controlled release and locally increased drug concentrations The toolbox of bioorthogonal reactions has significantly expanded in the past decade, with the tetrazine ligation being the fastest and one of the most versatile in vivo chemistries. Progress in the field, however, relies heavily on the development and evaluation of (radio)labeled compounds, preventing the use of compound libraries for systematic studies. The rational design of tetrazine probes and triggers has thus been impeded by the limited understanding of the impact of structural parameters on the in vivo ligation performance. In this work, we describe the development of a pretargeted blocking assay that allows for the investigation of the in vivo fate of a structurally diverse library of 45 unlabeled tetrazines and their capability to reach and react with pretargeted trans-cyclooctene (TCO)-modified antibodies in tumor-bearing mice. This study enabled us to assess the correlation of click reactivity and lipophilicity of tetrazines with their in vivo performance. In particular, high rate constants (>50 000 M-1 s-1) for the reaction with TCO and low calculated logD7.4 values (below -3) of the tetrazine were identified as strong indicators for successful pretargeting. Radiolabeling gave access to a set of selected 18F-labeled tetrazines, including highly reactive scaffolds, which were used in pretargeted PET imaging studies to confirm the results from the blocking study. These insights thus enable the rational design of tetrazine probes for in vivo application and will thereby assist the clin. translation of bioorthogonal pretargeting.

ACS Pharmacology & Translational Science published new progress about Azide-alkyne 1,3-dipolar cycloaddition reaction (for preparation of 18F-labeled tetrazines). 100-70-9 belongs to class nitriles-buliding-blocks, name is Picolinonitrile, and the molecular formula is C6H4N2, HPLC of Formula: 100-70-9.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Li, Hanning published the artcileTriarylamine-based porous coordination polymers performing both hydrogen atom transfer and photoredox catalysis for regioselective α-amino C(sp3)-H arylation, Computed Properties of 100-70-9, the main research area is triarylamine based porous coordination polymer photocatalyst preparation; benzylamine regioselective preparation; amine benzonitrile alpha amino CH arylation coordination polymer photocatalyst.

Herein, a heterogeneous approach to combination of hydrogen atom transfer (HAT) and photoredox catalysis for regioselective C-H arylation of benzylamines was presented. The different mol. sizes and coordination modes of ligands, tricarboxytriphenylamine (H3TCA) and tris(4-(pyridinyl)phenyl)amine (NPy3), in one coordination polymer consolidated triarylamine (Ar3N) moiety into a special structural intermediate, which enhanced chem. and thermal stability of polymers and diminished structural relaxation during catalytic process. The inherent redox potentials of Ar3N moieties prohibited in situ formed Ar3N ·+ to earn an electron from C(sp3)-H nucleophiles, but allowed abstraction of a hydrogen atom from C(sp3)-H nucleophiles, enabling formation of C(sp3) · radical and cross-coupling reaction to proceed at most electron-rich sites with excellent regioselectivity. The new heterogeneous photoredox HAT approach skipped several interactions between transient species during typical synergistic SET/HAT cycles, demonstrating a promising redox-economical and reagent-economical heterogeneous platform that had not been reported for α-amino C-H arylation to form benzylamine derivatives Control experiments based on monoligand coordination polymers suggested that mixed-ligand approach improved photochem. and photophys. properties, providing important insight into rational design and optimization of recyclable photocatalysts for rapid access to complex bioactive mols. and late-stage functionalized pharmaceuticals.

Chemical Science published new progress about Arylation catalysts (photochem., regioselective). 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

Cui, Xian-Chao published the artcileSynthesis of carbinoxamine via α-C(sp3)-H 2-pyridylation of O, S or N-containing compounds enabled by non-D-A-type super organoreductants and sulfoxide- or sulfide HAT reagents, Recommanded Product: Picolinonitrile, the main research area is alkyl oxy aryl methyl pyridine preparation; thio alkyl aryl methyl pyridine preparation; pyridine carbonitrile ether pyridylation catalyst CBZ6 benzenesulfinylbenzene; aryl alkyl pyridinyl methanamine; amine pyridine carbonitrile pyridylation catalyst CBZ6.

In this work, the discovery of a non-donor-acceptor (D-A) type organic photoreductant CBZ6 and sulfoxide/sulfide synergistically catalyzed general α-C(sp3)-H arylation of ethers, thioethers and amines to gave compounds R1R2CHXR3 [R1 = 2-pyridyl, 4-pyridyl, 3-methyl-2-pyridyl, etc.; R2 = Ph, 4-ClC6H4, 4-MeOC6H4, 2-MeC6H4, etc.; R3 = H, Bn, Me, n-Bu, etc.; X = O, S, N, NH, NCH3] was reported. By using as low as 1 mol% of CBZ6 as a recyclable organic photoreductant and sulfoxides or sulfides as a new type of HAT reagent, the 2- or 4-pyridylation of O, N, or S-containing compounds had been accomplished. This was the first base-free version of α-C-H 2-/4-pyridylation of O, N, or S-containing compounds It was the first example of sulfoxides or sulfides working as HAT reagents. It was also the first general method for photocatalytic HAT 2-pyridylation of various ethers, amines or thioethers.

Chemical Science published new progress about Arylation. 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

Chandrashekhar, Vishwas G. published the artcileNickel-catalyzed hydrogenative coupling of nitriles and amines for general amine synthesis, Name: Picolinonitrile, the main research area is amine preparation; nitrile amine hydrogenative coupling nickel catalyzed.

A homogeneous nickel catalyst for hydrogenative cross coupling of a range of aromatic, heteroaromatic, and aliphatic nitriles with primary and secondary amines or ammonia to give amines was reported. This general hydrogenation protocol was showcased by straightforward and highly selective synthesis of >230 functionalized and structurally diverse amines including pharmaceutically relevant and chiral products, as well as 15N-isotope labeling applications.

Science (Washington, DC, United States) published new progress about Coupling reaction (hydrogenative). 100-70-9 belongs to class nitriles-buliding-blocks, name is Picolinonitrile, and the molecular formula is C6H4N2, Name: Picolinonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Garcia-Vazquez, Rocio published the artcileDirect Cu-mediated aromatic 18F-labeling of highly reactive tetrazines for pretargeted bioorthogonal PET imaging, Application of Picolinonitrile, the main research area is fluoro isotope labeled aryl tetrazine preparation PET imaging.

In this work, a simple, scalable and reliable direct 18F-labeling procedure was developed. Initially the applicability of different leaving groups and labeling methods was studied to develop this procedure. The copper-mediated 18F-labeling exploiting stannane precursors showed the most promising results. This approach was then successfully applied to a set of tetrazines, including highly reactive H-tetrazines, suitable for pretargeted PET imaging. The labeling succeeded in radiochem. yields (RCYs) of up to approx. 25%. The new procedure was then applied to develop a pretargeting tetrazine-based imaging agent. The tracer was synthesized in a satisfactory RCY of ca. 10%, with a molar activity of 134 ± 22 GBq μmol-1 and a radiochem. purity of >99%. Further evaluation showed that the tracer displayed favorable characteristics (target-to-background ratios and clearance) that may qualify it for future clin. translation.

Chemical Science published new progress about Positron emission tomography. 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

Zhong, Jing published the artcileRhodium-Catalyzed Pyridine N-Oxide Assisted Suzuki-Miyaura Coupling Reaction via C(O)-C Bond Activation, Category: nitriles-buliding-blocks, the main research area is benzoylpyridine nitrogen oxide preparation rhodium catalyst; boronic acid benzoylpyridine nitrogenoxide Suzuki Miyaura carbon bond activation.

A rhodium-catalyzed Suzuki-Miyaura coupling reaction via C(O)-C bond activation to form 2-benzoylpyridine N-oxide derivatives is reported. Both the C(O)-C(sp2) and C(O)-C(sp3) bond could be activated during the reaction with yields up to 92%. The N-oxide moiety could be employed as a traceless directing group, leading to free pyridine ketones.

Organic Letters published new progress about Boronic acids Role: RCT (Reactant), RACT (Reactant or Reagent). 100-70-9 belongs to class nitriles-buliding-blocks, name is Picolinonitrile, and the molecular formula is C6H4N2, Category: nitriles-buliding-blocks.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Krasavin, Mikhail published the artcileContinued exploration of 1,2,4-oxadiazole periphery for carbonic anhydrase-targeting primary arene sulfonamides: discovery of subnanomolar inhibitors of membrane-bound hCA IX isoform that selectively kill cancer cells in hypoxic environment, COA of Formula: C6H4N2, the main research area is oxadiazole arenesulfonamide preparation antitumor carbonic anhydrase inhibitor hypoxia SAR; 1,2,4-Oxadiazole; Cancer cells; Carbonic anhydrase; Hypoxic environment; Isoform-selective inhibitors; Isosteric replacement; Periphery groups; Primary sulfonamides; Subnanomolar inhibition.

An expanded set of diversely substituted 1,2,4-oxadiazole-containing primary aromatic sulfonamides I (R1 = cyclopropyl, Ph, 2-MeOC6H4, 3-MeOC6H4, pyridin-2-yl) and II (X = m-phenylene, p-phenylene, thiophene-2,4-diyl, etc.; R2 = Me, cyclopropyl, Ph, thiophen-2-yl, etc.) was synthesized and tested for inhibition of human carbonic anhydrase I, II, IX and XII isoforms. The initial biochem. profiling revealed a significantly more potent inhibition of cancer-related, membrane-bound isoform hCA IX (reaching into submicromolar range), on top of potent inhibition of hCA XII that is another cancer target. The observed structure-activity relationships have been rationalized by mol. modeling. Comparative single-concentration profiling of the carbonic anhydrase inhibitors synthesized for antiproliferative effects against normal (ARPE-19) and cancer (PANC-1) cell lines under chem. induced hypoxia conditions revealed several candidate compounds selectively targeting cancer cells. More in-depth characterization of these leads revealed two structurally related compounds that showed promising selective cytotoxicity against pancreatic cancer (PANC-1) and melanoma (SK-MEL-2) cell lines.

European Journal of Medicinal Chemistry published new progress about Antitumor agents. 100-70-9 belongs to class nitriles-buliding-blocks, name is Picolinonitrile, and the molecular formula is C6H4N2, COA of Formula: C6H4N2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zhang, Guofu published the artcileA cascade process for directly converting nitriles (RCN) to cyanamides (RNHCN) via SO2F2-activated Tiemann rearrangement, Related Products of nitriles-buliding-blocks, the main research area is cyanamide preparation atom economy; amidoxime key intermediate preparation Tiemann rearrangement sulfonyl difluoride promoted; nitrile hydroxylamine oximation.

A simple, mild and practical process for the direct conversion of nitriles RCN (R = H, t-Bu, 2-thienyl, 4-ClC6H4, etc.) to cyanamides RNHCN was newly discovered and exhibited a wide substrate scope as well as great functional group-tolerability (36 examples). In this efficient strategy, in situ generated amidoximes R(NH2)C:NOH obtained from the reaction of nitriles with hydroxylamine subsequently underwent Tiemann rearrangement, producing corresponding cyanamides with great isolated yields under SO2F2. Addnl., the control experiments reportedly shed light on tentative mechanism involved in formation and elimination of key intermediate: a sulfonyl ester.

Organic & Biomolecular Chemistry published new progress about Atom economy. 100-70-9 belongs to class nitriles-buliding-blocks, name is Picolinonitrile, and the molecular formula is C6H4N2, Related Products of nitriles-buliding-blocks.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Long, Yang published the artcileNickel-Catalyzed Synthesis of an Aryl Nitrile via Aryl Exchange between an Aromatic Amide and a Simple Nitrile, Application of Picolinonitrile, the main research area is aromatic amide nitrile nickel catalyst cyanation; aryl nitrile preparation.

A nickel-catalyzed synthesis of an aryl nitrile via aryl exchange between an aromatic amide and a simple nitrile was developed. By using cheap, easy-to-handle, and low-toxic 4-cyanopyridine as the cyanating source, cyanation of various aromatic amides afforded an assortment of aryl nitriles including bioactive drugs and organic luminescent mols. in good yields. The reaction exhibited wide substrate scope, good functional group tolerance, and unique selectivity that were complementary to traditional methods. Moreover, two key nickel complexes formed by oxidative addition to each substrate are obtained and determined by X-ray crystallog., which gave strong support for the mechanism elucidations.

ACS Catalysis published new progress about Amino group. 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

Jiang, Chenhui published the artcileDirect Transformation of Nitrogen-Containing Methylheteroarenes to Heteroaryl Nitrile by Sodium Nitrite, Application of Picolinonitrile, the main research area is heteroaryl nitrile preparation; methylheteroarene acetyl chloride sodium nitrite cyanation.

The cyanation reaction of methylheteroarenes with acetyl chloride and sodium nitrite via the radical process in high yields is reported. According to the control experiments, the reaction mechanism underwent radical progress. It is very useful in the pharmacy industry due to its metal-free and easy treatment conditions.

Organic Letters published new progress about Benzoxazoles Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 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