Tag: 100-200

In 2014,Liu, Yang; Meng, Ge; Zheng, Aqun; Chen, Fener; Chen, Wenxue; Clercq, Erik De; Pannecouque, Christophe; Balzarini, Jan published 《Design and synthesis of a new series of cyclopropylamino-linking diarylpyrimidines as HIV non-nucleoside reverse transcriptase inhibitors》.European Journal of Pharmaceutical Sciences published the findings.Recommanded Product: 31938-07-5 The information in the text is summarized as follows:

A new series of 29 diarylpyrimidine analogs featuring a cyclopropylamino group between the pyrimidine scaffold and the aryl wing have been synthesized. All of the new compounds have been characterized by spectra anal. The target mols. were evaluated for their in vitro anti-HIV activity with FDA-approved drugs as references Some of the compounds exhibited moderate to potent activities against wild-type HIV-1. The compound 4-((4-((cyclopropylamino)(2,5-difluorophenyl)methyl)pyrimidin-2-yl)amino)benzonitrile (1e) displayed potent anti-HIV-1 activity against WT HIV-1 with an IC50 of 0.099 μM and a selectivity index of 2302. The preliminary structure-activity relationship (SAR) of this new series of compounds was also investigated. The experimental part of the paper was very detailed, including the reaction process of 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Recommanded Product: 31938-07-5)

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.Recommanded Product: 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2013,Guin, Joyram; Varseev, Georgy; List, Benjamin published 《Catalytic Asymmetric Protonation of Silyl Ketene Imines》.Journal of the American Chemical Society published the findings.COA of Formula: C8H6BrN The information in the text is summarized as follows:

An efficient catalytic and highly enantioselective protonation of silyl ketene imines is described. The reaction is catalyzed by the chiral phosphoric acids TRIP or STRIP (I and II, resp.) in the presence of a stoichiometric amount of methanol as the proton source and silyl acceptor. A variety of substituted racemic silyl ketene imines have been transformed into highly enantioenriched nitriles [e.g., (±)-(4-MeOC6H4)MeC:C:NTBS → (S)-(4-MeOC6H4)CHMeCN].2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5COA of Formula: C8H6BrN) 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.COA of Formula: C8H6BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Luo, Ling; Liu, Dan; Lan, Shichao; Gan, Xiuhai published an article in Frontiers in Chemistry (Lausanne, Switzerland). The title of the article was 《Design, synthesis and biological activity of novel chalcone derivatives containing an 1,2,4-oxadiazole moiety》.Category: nitriles-buliding-blocks The author mentioned the following in the article:

To discover a lead compound for agricultural use, 34 novel chalcone derivatives I [R1 = H, 4-MeO, 2,4-di-Cl, etc; R2 = H, 4-Me, 4-F, 4-Cl] and II [R1 = H, 4-Me, 4-MeO, 2-Cl, 2,4-di-Cl; R2 = H, 4-Me, 4-F, 4-Cl] containing an 1,2,4-oxadiazole moiety were designed and synthesized. Their nematocidal activities against Bursaphelenchus xylophilus, Aphelenchoides besseyi and Ditylenchus dipsaci and their antiviral activities against tobacco mosaic virus (TMV), pepper mild mottle virus (PMMoV) and tomato spotted wilt virus (TSWV) were evaluated. Biol. assay results indicated that compounds I [R1 = 3-MeO, 4-MeO, R2 = H] showed good nematocidal activities against B. xylophilus, A. besseyi and D. dipsaci, with LC50 values of 35.5, 44.7 and 30.2μg/mL and 31.8, 47.4 and 36.5μg/mL, resp., which are better than tioxazafen, fosthiazate and abamectin. Furthermore, compound I [R1 = 2-MeO, R2 = H] demonstrated excellent protective activity against TMV, PMMoV and TSWV, with EC50 values of 210.4, 156.2 and 178.2μg/mL, resp., which are superior to ningnanmycin (242.6, 218.4 and 180.5μg/mL). In the experimental materials used by the author, we found 4-Fluorobenzonitrile(cas: 1194-02-1Category: nitriles-buliding-blocks)

4-Fluorobenzonitrile(cas: 1194-02-1) is used in the synthesis of flurenones, pharmaceutical prerequisites, as well as opiod receptor antagonists.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Lan, Chunling Blue; Auclair, Karine published their research in European Journal of Organic Chemistry in 2021. The article was titled 《Ammonium Chloride-Promoted Rapid Synthesis of Monosubstituted Ureas under Microwave Irradiation》.Application of 1194-02-1 The article contains the following contents:

Ammonium chloride promoted the reaction between amines and potassium cyanate to generate monosubstituted ureas in water. This method proceeded rapidly under microwave irradiation and tolerates a broad range of functional groups. Unlike previous strategies, it was compatible with other nucleophiles, acid-labile moieties and most of the common protecting groups. The products precipitate out of solution, allowing facile isolation without column chromatog. In addition to this study using 4-Fluorobenzonitrile, there are many other studies that have used 4-Fluorobenzonitrile(cas: 1194-02-1Application of 1194-02-1) was used in this study.

4-Fluorobenzonitrile(cas: 1194-02-1) is used in the synthesis of flurenones, pharmaceutical prerequisites, as well as opiod receptor antagonists.Application of 1194-02-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,Organic Process Research & Development included an article by Perkins, Robert J.; Hughes, Alexander J.; Weix, Daniel J.; Hansen, Eric C.. Reference of 4-Bromobenzonitrile. The article was titled 《Metal-Reductant-Free Electrochemical Nickel-Catalyzed Couplings of Aryl and Alkyl Bromides in Acetonitrile》. The information in the text is summarized as follows:

While reductive cross-electrochem. coupling is an attractive approach for the synthesis of complex mols. at both small and large scale, two barriers for large-scale applications have remained: the use of stoichiometric metal reductants and a need for amide solvents. In this communication, new conditions that address these challenges are reported. The nickel-catalyzed reductive cross-coupling of aryl bromides with alkyl bromides can be conducted in a divided electrochem. cell using acetonitrile as the solvent and diisopropylamine as the sacrificial reductant to afford coupling products in synthetically useful yields (22-80%). Addnl., the use of a combination of the ligands 4,4′,4”-tri-tert-butyl-2,2′:6′,2′-terpyridine and 4,4′-di-tert-butyl-2,2′-bipyridine is essential to achieve high yields. In the experiment, the researchers used many compounds, for example, 4-Bromobenzonitrile(cas: 623-00-7Reference of 4-Bromobenzonitrile)

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,Reference of 4-Bromobenzonitrile 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

In 2013,Vogt, Matthias; Nerush, Alexander; Iron, Mark A.; Leitus, Gregory; Diskin-Posner, Yael; Shimon, Linda J. W.; Ben-David, Yehoshoa; Milstein, David published 《Activation of Nitriles by Metal Ligand Cooperation. Reversible Formation of Ketimido- and Enamido-Rhenium PNP Pincer Complexes and Relevance to Catalytic Design》.Journal of the American Chemical Society published the findings.Reference of 2-(3-Bromophenyl)acetonitrile The information in the text is summarized as follows:

The dearomatized complex cis-[Re-(PNPtBu*)-(CO)2] (4) undergoes cooperative activation of CN triple bonds of nitriles via [1,3]-addition Reversible C-C and Re-N bond formation in 4 was investigated in a combined exptl. and computational study. The reversible formation of the ketimido complexes (5-7) was observed When nitriles bearing an alpha methylene group are used, reversible formation of the enamido complexes (8 and 9) takes place. The reversibility of the activation of the nitriles in the resulting ketimido compounds was demonstrated by the displacement of p-CF3-benzonitrile from cis-[Re-(PNPtBu-N=CPhpCF3)-(CO)2] (6) upon addition of an excess of benzonitrile and by the temperature-dependent [1,3]-addition of pivalonitrile to complex 4. The reversible binding of the nitrile in the enamido compound cis-[Re-(PNPtBu-HNC=CHPh)-(CO)2] (9) was demonstrated via the displacement of benzyl cyanide from 9 by CO. Computational studies suggest a stepwise activation of the nitriles by 4, with remarkably low activation barriers, involving precoordination of the nitrile group to the Re-(I) center. The enamido complex 9 reacts via β-carbon methylation to give the primary imino complex cis-[Re-(PNPtBu-HN=CC-(Me)-Ph)-(CO)2]-OTf 11. Upon deprotonation of 11 and subsequent addition of benzyl cyanide, complex 9 is regenerated and the monomethylation product 2-phenylpropanenitrile is released. Complexes 4 and 9 were found to catalyze the Michael addition of benzyl cyanide derivatives to α,β-unsaturated esters and carbonyls. In addition to this study using 2-(3-Bromophenyl)acetonitrile, there are many other studies that have used 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Reference of 2-(3-Bromophenyl)acetonitrile) was used in this study.

According to other reports, 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) is used in the preparation of diarylpyrimidines (DAPYs) as HIV-1 non-nucleoside reverse transcriptase inhibitors.Reference of 2-(3-Bromophenyl)acetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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

Referemce:
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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts