Tag: 100-200

In 2008,Jautze, Sascha; Peters, Rene published 《Enantioselective bimetallic catalysis of Michael additions forming quaternary stereocenters》.Angewandte Chemie, International Edition published the findings.Product Details of 31938-07-5 The information in the text is summarized as follows:

Low catalyst loadings of a planar-chiral ferrocenyl bispalladacycle are sufficient to catalyze the Michael addition of trisubstituted α-cyanoacetates to enones with excellent yields (TONs up to 2450) and high enantioselectivity. The reaction proceeds by a cooperative bimetallic mechanism and is superior to previous methods relying on soft Lewis acid catalysts.2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Product Details of 31938-07-5) was used in this study.

2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) has been used in the synthesis of 2-(1-cyano-1-(3-bromophenyl))methylidene-3-phenylthiazolidine-4,5-dione or a series of aminoethylbiphenyls, novel 5-HT7 receptor ligands.Product Details of 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ali, Abdelselam; Bliese, Marianne; Rasmussen, Jo-Anne M.; Sargent, Roger M.; Saubern, Simon; Sawutz, David G.; Wilkie, John S.; Winkler, David A.; Winzenberg, Kevin N.; Woodgate, Ruth C. J. published an article on February 15 ,2007. The article was titled 《Discovery of (Z)-2-phenyl-3-(1H-pyrrol-2-yl)acrylonitrile derivatives active against Haemonchus contortus and Ctenocephalides felis (cat flea)》, and you may find the article in Bioorganic & Medicinal Chemistry Letters.Application In Synthesis of 3-Chloro-4-fluorophenylacetonitrile The information in the text is summarized as follows:

A series of 2-phenyl-3-(1H-pyrrol-2-yl)acrylonitrile derivatives, e.g., I, were synthesized and evaluated for in vitro activity against the endoparasite Haemonchus contortus and the ectoparasite Ctenocephalides felis. Some compounds had significant in vitro activity against these parasites. The experimental process involved the reaction of 3-Chloro-4-fluorophenylacetonitrile(cas: 658-98-0Application In Synthesis of 3-Chloro-4-fluorophenylacetonitrile)

3-Chloro-4-fluorophenylacetonitrile(cas: 658-98-0) belongs to nitriles. Nitriles are found in many useful compounds. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons.Application In Synthesis of 3-Chloro-4-fluorophenylacetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 3-Oxo-3-phenylpropanenitrileIn 2022 ,《Synthesis and in vitro antiproliferative activity of certain novel pyrazolo[3,4-b]pyridines with potential p38α MAPK-inhibitory activity》 appeared in Archiv der Pharmazie (Weinheim, Germany). The author of the article were Farahat, Aya A.; Samir, Eman M.; Zaki, Mayssoune Y.; Serya, Rabah A. T.; Abdel-Aziz, Hatem A.. The article conveys some information:

Novel series of pyrazolo[3,4-b]pyridines 9a-j and 14a-f were prepared via a one-pot three-component reaction. Compounds 9a-j were synthesized by the reaction of 3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-5-amine (4) with benzoyl acetonitriles 3a,b and aldehydes 5a-e, whereas the spiro derivatives 14a-f were synthesized by the reaction of pyrazole derivative 4 with 3a-c and indoline-2,3-diones 10a,b. Screening of the antiproliferative activity of 9a-j and 14a-f revealed that 14a and 14d were the most potent analogs against HepG2 and HeLa cells, with IC50 = 4.2 and 5.9 μM, resp. Moreover, compounds 9c and 14a could promote cell cycle disturbance and apoptosis in HepG2 cells, as evidenced by DNA flow cytometry and Annexin V-FITC/PI assays. Cell cycle anal. of 9c and 14a indicated a reduction in HepG2 cells in the G1 phase, with arrest in the S phase and the G2/M phase, resp. Also, 9c and 14a are good apoptotic inducers in the HepG2 cell line. Furthermore, compounds 9h and 14d stood out as the most efficient antiproliferative agents in the NCI 60-cell line panel screening, with mean GI % equal to 60.3% and 55.4%, resp. Addnl., 9c, 9h, 14a, and 14d showed good inhibitory action against the cellular pathway regulator p38α kinase, with IC50 = 0.42, 0.41, 0.13, and 0.64 μM, resp. A docking study was carried out on the p38α kinase active site, showing a binding mode comparable to that of reported p38 mitogen-activated protein kinase inhibitors. These newly discovered pyrazolo[3,4-b]pyridines could be considered as potential candidates for the development of newly targeted anticancer agents. In the experiment, the researchers used 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Reference of 3-Oxo-3-phenylpropanenitrile)

3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used in the synthesis of substituted naphtho[1,8-bc]pyrans. It was also used as building block in the preparation of 4H-pyrans, 2-pyridones, furans and carbocyclics.Reference of 3-Oxo-3-phenylpropanenitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Huang, Weichen; Keess, Sebastian; Molander, Gary A. published an article in Journal of the American Chemical Society. The title of the article was 《Dicarbofunctionalization of [1.1.1]Propellane Enabled by Nickel/Photoredox Dual Catalysis: One-Step Multicomponent Strategy for the Synthesis of BCP-Aryl Derivatives》.Reference of 2-Bromobenzonitrile The author mentioned the following in the article:

Bicyclo[1.1.1]pentane (BCP) motifs as para-disubstituted aryl bioisosteres are playing an emerging role in pharmaceutical, agrochem., and materials chem. The vast majority of these structures are obtained from a BCP electrophile or nucleophile, which are themselves derived from [1.1.1]propellane via cleavage of the internal C-C bond through the addition of either radicals or metal-based nucleophiles. Compared with the current stepwise approaches, a multicomponent reaction that provides direct access to complex and diverse disubstituted BCP products would be more attractive. Herein, authors report a single-step, multicomponent approach to synthetically versatile arylated BCP products via nickel/photoredox catalysis. Importantly, this three-component process allows two C-C bonds to be formed in a single step and sets three quaternary centers, unprecedented in any previously reported methods. The method has been demonstrated to allow access to complex BCP architectures from aryl halide and radical precursor substrates. In the experimental materials used by the author, we found 2-Bromobenzonitrile(cas: 2042-37-7Reference of 2-Bromobenzonitrile)

2-Bromobenzonitrile(cas: 2042-37-7) is a precursor to the quinazolinones, a class of drugs used to treat autoimmune diseases and coronary heart disease. This substrate molecule undergoes a palladium-catalyzed coupling reaction to form an aromatic ring. The light emission from this reaction can be seen in the reaction solution.Reference of 2-Bromobenzonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Yamada, Shigeyuki; Yoshida, Keigo; Sakurai, Tsuneaki; Hara, Mitsuo; Konno, Tustome published an article in Molecular Systems Design & Engineering. The title of the article was 《Effect of fluorine atoms in flexible chains on the phase transitions and photophysical behavior of D-π-A-type 4-alkoxy-4′-cyanodiphenylacetylene》.Application of 623-00-7 The author mentioned the following in the article:

D-π-A-type 4-alkoxy-4′-cyanodiphenylacetylenes bearing a decyloxy chain show a nematic liquid crystalline (LC) phase, whereas the incorporation of a semifluoroalkyl fragment results in a switch to the smectic A phase. The D-π-A-type π-conjugated mesogen exhibits photoluminescence, not only in solution and in the crystalline phase, but also in the mol. aggregated structure of the LC phase. In the experiment, the researchers used 4-Bromobenzonitrile(cas: 623-00-7Application of 623-00-7)

4-Bromobenzonitrile(cas: 623-00-7) is classified as organic nitriles, which are commonly use solvents and are reacted further for various applications such as manufacture of polymers and intermediates for pharmaceuticals and other organic chemicals,Application of 623-00-7 It can also be used as an aryl halide test compound in developing greener reaction conditions for Suzuki cross-coupling between aryl halides and phenyl boronic acid.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Tauber, Carolin; Wamser, Rebekka; Arkona, Christoph; Tuegend, Marisa; Abdul Aziz, Umer Bin; Pach, Szymon; Schulz, Robert; Jochmans, Dirk; Wolber, Gerhard; Neyts, Johan; Rademann, Joerg published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《Chemical Evolution of Antivirals Against Enterovirus D68 through Protein-Templated Knoevenagel Reactions》.Name: 3-Oxo-3-phenylpropanenitrile The article contains the following contents:

The generation of bioactive mols. from inactive precursors is a crucial step in the chem. evolution of life, however, mechanistic insights into this aspect of abiogenesis are scarce. Here, we investigate the protein-catalyzed formation of antivirals by the 3C-protease of enterovirus D68. The enzyme induces aldol condensations yielding inhibitors with antiviral activity in cells. Kinetic and thermodn. analyses reveal that the bioactivity emerges from a dynamic reaction system including inhibitor formation, alkylation of the protein target by the inhibitors, and competitive addition of non-protein nucleophiles to the inhibitors. The most active antivirals are slowly reversible inhibitors with elongated target residence times. The study reveals first examples for the chem. evolution of bio-actives through protein-catalyzed, non-enzymic C-C couplings. The discovered mechanism works under physiol. conditions and might constitute a native process of drug development. In the experiment, the researchers used many compounds, for example, 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Name: 3-Oxo-3-phenylpropanenitrile)

3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used to produce 2-benzoyl-3-furan-2-yl-acrylonitrile. It is an active methylene compound, useful in heterocyclic synthesis, e.g. polyfunctional pyridines and pyrimidines.Name: 3-Oxo-3-phenylpropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,Journal of Asian Natural Products Research included an article by Zhang, Juan; Li, Jia-Cheng; Song, Jia-Li; Cheng, Zhi-Qiang; Sun, Ji-Zheng; Jiang, Cheng-Shi. COA of Formula: C8H6BrN. The article was titled 《Synthesis and evaluation of coumarin/1,2,4-oxadiazole hybrids as selective BChE inhibitors with neuroprotective activity》. The information in the text is summarized as follows:

A series of new coumarin/1,2,4-oxadiazole hybrids were synthesized and evaluated for cholinesterase inhibitory and neuroprotective activities. Among them, enantiomers and showed potent hBChE inhibitory activity with IC50 values of 8.17 and 9.56 μM, resp., and also exhibited good selectivity for hBChE over hAChE by 9.49- and 7.58-fold, resp. In addition, both compounds could protect SH-SY5Y cells against Aβ25-35-induced neurotoxicity. The preliminary bioassay results provided a new chemotype for multifunctional anti-Alzheimer′s disease agents and continuing investigation into compounds and is warranted. In the experiment, the researchers used 4-Cyanobenzyl bromide(cas: 17201-43-3COA of Formula: C8H6BrN)

4-Cyanobenzyl bromide(cas: 17201-43-3) is used in the synthesis of ligands containing a chelating pyrazolyl-pyridine group with a pendant aromatic nitrile. It is also useful in the preparation of 4-[(2H-tetra-zol-2-yl)methyl]benzonitrile by reaction with 2H-tetrazole in the presence of potassium hydroxide.COA of Formula: C8H6BrN

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2008,Norris, Timothy; Leeman, Kyle published 《Development of a New Variant of the Migita Reaction for Carbon-Sulfur Bond Formation Used in the Manufacture of Tetrahydro-4-[3-[4-(2-methyl-1H-imidazol-1-yl)phenyl]thio]phenyl-2H-pyran-4-carboxamide》.Organic Process Research & Development published the findings.HPLC of Formula: 31938-07-5 The information in the text is summarized as follows:

Palladium-catalyzed carbon-sulfur bond formation using modified Migita reaction conditions was explored and applied to the synthesis of a former antiasthma drug candidate, tetrahydro-4-[3-[4-(2-methyl-1H-imidazol-1-yl)phenyl]thio]phenyl-2H-pyran-4-carboxamide (1). The reaction was developed into a general method for thioaryl halide cross-coupling, and a specific example of its use to synthesize a key intermediate, tetrahydro-4-[3-(4-fluorophenyl)thio]phenyl-2H-pyran-4-carboxamide was demonstrated at large scale to provide phase II clin. supplies of 1. Comparison of the multistep phase I process and the two-step phase II process showed an overall yield advantage over the bond-forming steps from common starting material to active pharmaceutical ingredient API 1 of 40%. The ligand effect in the modified Migita reaction is described in detail. The second step of the scale-up process illustrated formation of carbon-nitrogen bonds without use of palladium catalysis, providing a contrast to the first reaction; both reactions were developed into efficient single-vessel direct isolation processes. The experimental process involved the reaction of 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5HPLC of Formula: 31938-07-5)

2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) has been used in the synthesis of a series of aminoethylbiphenyls, novel 5-HT7 receptor ligands or 2-(1-cyano-1-(3-bromophenyl))methylidene-3-phenylthiazolidine-4,5-dione.HPLC of Formula: 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Wu, Wenliang; Su, Weiping published their research in Journal of the American Chemical Society on August 10 ,2011. The article was titled 《Mild and Selective Ru-Catalyzed Formylation and Fe-Catalyzed Acylation of Free (N-H) Indoles Using Anilines as the Carbonyl Source》.Electric Literature of C10H6N2O The article contains the following contents:

Indoles undergo regioselective formylation and acylation reactions with N-methylaniline or N-benzylanilines in the presence of either ruthenium(III) or iron(II) chlorides using tert-Bu hydroperoxide as the oxidant to give 3-formyl or 3-benzoylindoles in 34-86% yields. The processes are operationally simple and compatible with a variety of functional groups. Reaction of indole with N-(13C-methyl)aniline yields 3-(13C-formyl)indole in 70% yield, unambiguously establishing that the carbonyl carbon in the formylation products originates from the Me group of N-Me aniline. In the experiment, the researchers used 3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9Electric Literature of C10H6N2O)

3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Electric Literature of C10H6N2O

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Kunj M. Trivedi; Patel, Unnati P.; Dabhi, Ranjit C.; Maru, Jayesh J. published an article in Russian Journal of Bioorganic Chemistry. The title of the article was 《Synthesis, Computational Insights and Anticancer Activity of Novel Indole-Schiff Base Derivatives》.Name: 4-Cyanobenzyl bromide The author mentioned the following in the article:

This paper described computational insights and synthesis of novel indole clubbed Schiff base derivatives I [R = Ph, 3-pyridyl, 4-MeC6H4, etc.] with improved biol. profile. The prepared derivatives I were evaluated for their in vitro anticancer activity against A549 cell line using MTT assay. Results revealed significant potential of the synthesized compounds, especially I [R = 2-furyl] which exhibited high anticancer activity. The experimental part of the paper was very detailed, including the reaction process of 4-Cyanobenzyl bromide(cas: 17201-43-3Name: 4-Cyanobenzyl bromide)

4-Cyanobenzyl bromide(cas: 17201-43-3) is a white solid. Its melting point is 113-117°C, and flash point is 125.1°C. It is insoluble in water at 20°C. It is stable under normal temperatures and pressures. It should be stored at 0-5°C.Name: 4-Cyanobenzyl bromide

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts