Month: October 2022

Pan, Zhangjin; Li, Wenbo; Zhu, Shuai; Liu, Feng; Wu, Hai-Hong; Zhang, Junliang published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《Palladium/TY-Phos-Catalyzed Asymmetric Intermolecular α-Arylation of Aldehydes with Aryl Bromides》.Computed Properties of C7H3BrFN The article contains the following contents:

Herein, an efficient Pd-catalyzed asym. intermol. α-arylation reaction of α-alkyl-α-aryl disubstituted aldehydes with aryl bromides, which provided a rapid access to chiral aldehydes bearing an α-all-carbon quaternary stereocenter in moderate to good yields with good er in most cases was reported. In addition, a pair of enantiomers could be easily prepared with the use of the same ligand by exchanging the aryl groups of aldehyde and aryl bromide.4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Computed Properties of C7H3BrFN) was used in this study.

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Computed Properties of C7H3BrFN 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

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

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 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

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

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

Staron, Jakub; Pietrus, Wojciech; Bugno, Ryszard; Kurczab, Rafal; Satala, Grzegorz; Warszycki, Dawid; Lenda, Tomasz; Wantuch, Anna; Hogendorf, Adam S.; Hogendorf, Agata; Duszynska, Beata; Bojarski, Andrzej J. published an article in 2021. The article was titled 《Tuning the activity of known drugs via the introduction of halogen atoms, a case study of SERT ligands – Fluoxetine and fluvoxamine》, and you may find the article in European Journal of Medicinal Chemistry.Electric Literature of C7H3BrFN The information in the text is summarized as follows:

To elucidate the role of halogen atoms in the binding of SSRIs to SERT, a series of 22 fluoxetine and fluvoxamine analogs substituted with fluorine, chlorine, bromine, and iodine atoms, differently arranged on the Ph ring was designed. The obtained biol. activity data, supported by a thorough in silico binding mode anal., allowed the identification of two partners for halogen bond interactions: the backbone carbonyl oxygen atoms of E493 and T497. Addnl., compounds with heavier halogen atoms were found to bind with the SERT via a distinctly different binding mode, a result not presented elsewhere. The subsequent anal. of the prepared XSAR sets showed that E493 and T497 participated in the largest number of formed halogen bonds. The XSAR library anal. led to the synthesis of two of the most active compounds (3,4-diCl-fluoxetine, SERT Ki = 5 nM and 3,4-diCl-fluvoxamine, SERT Ki = 9 nM, fluoxetine SERT Ki = 31 nM, fluvoxamine SERT Ki = 458 nM). An example of the successful use of a rational methodol. was presented to analyze binding and design more active compounds by halogen atom introduction. ‘XSAR library anal.’, a new tool in medicinal chem., was instrumental in identifying optimal halogen atom substitution. The results came from multiple reactions, including the reaction of 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Electric Literature of C7H3BrFN)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Electric Literature of C7H3BrFN 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
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

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