Tag: 100-200

In 2019,Angewandte Chemie, International Edition included an article by Chen, Tiffany Q.; MacMillan, David W. C.. SDS of cas: 2042-37-7. The article was titled 《A Metallaphotoredox Strategy for the Cross-Electrophile Coupling of α-Chloro Carbonyls with Aryl Halides》. The information in the text is summarized as follows:

Here, we demonstrate that a metallaphotoredox-catalyzed cross-electrophile coupling mechanism provides a unified method for the α-arylation of diverse activated alkyl chlorides, including α-chloroketones, α-chloroesters, α-chloroamides, α-chlorocarboxylic acids, and benzylic chlorides. This strategy, which is effective for a wide variety of aryl bromide coupling partners, is predicated upon a halogen atom abstraction/nickel radical-capture mechanism that is generically successful across an extensive range of carbonyl substrates. The construction and use of arylacetic acid products have further enabled two-step protocols for the delivery of valuable building blocks for medicinal chem., such as aryldifluoromethyl and diarylmethane motifs. In the experiment, the researchers used 2-Bromobenzonitrile(cas: 2042-37-7SDS of cas: 2042-37-7)

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.SDS of cas: 2042-37-7

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,Journal of the American Chemical Society included an article by Ghosh, Chandrani; Kim, Suyeon; Mena, Matthew R.; Kim, Jun-Hyeong; Pal, Raja; Rock, Christopher L.; Groy, Thomas L.; Baik, Mu-Hyun; Trovitch, Ryan J.. Formula: C7H4FN. The article was titled 《Efficient Cobalt Catalyst for Ambient-Temperature Nitrile Dihydroboration, the Elucidation of a Chelate-Assisted Borylation Mechanism, and a New Synthetic Route to Amides》. The information in the text is summarized as follows:

N,N-Diborylamines have emerged as promising reagents in organic synthesis; however, their efficient preparation and full synthetic utility have yet to be realized. To address both shortcomings, an effective catalyst for nitrile dihydroboration was sought. Heating CoCl2 in the presence of PyEtPDI afforded the six-coordinate Co(II) salt, [(PyEtPDI)CoCl][Cl]. Upon adding 2 equiv of NaEt3BH, hydride transfer to one chelate imine functionality was observed, giving (κ4-N,N,N,N-PyEtIPCHMeNEtPy)Co. Single-crystal x-ray diffraction and d. functional theory calculations revealed that this compound possesses a low-spin Co(II) ground state featuring antiferromagnetic coupling to a singly reduced imino(pyridine) moiety. Importantly, (κ4-N,N,N,N-PyEtIPCHMeNEtPy)Co was found to catalyze the dihydroboration of nitriles using HBPin with turnover frequencies of up to 380 h-1 at ambient temperature Stoichiometric addition experiments revealed that HBPin adds across the Co-Namide bond to generate a hydride intermediate that can react with addnl. HBPin or nitriles. Computational evaluation of the reaction coordinate revealed that the B-H addition and nitrile insertion steps occur on the antiferromagnetically coupled triplet spin manifold. Formation of the borylimine intermediate occurs following BPin transfer from the borylated chelate arm to regenerate (κ4-N,N,N,N-PyEtIPCHMeNEtPy)Co. Borylimine reduction is in turn facile and follows the same ligand-assisted borylation pathway. The independent hydroboration of alkyl and aryl imines was also demonstrated at 25°. With N,N-diborylamines in hand, their addition to carboxylic acids allowed for the direct synthesis of amides at 120°, without the need for an exogenous coupling reagent. The experimental part of the paper was very detailed, including the reaction process of 4-Fluorobenzonitrile(cas: 1194-02-1Formula: C7H4FN)

4-Fluorobenzonitrile(cas: 1194-02-1) is used as chemical intermediate, solvent for perfumes and pharmaceuticals, stabilizer for chlorinated solvents, HPLC analysis, catalyst and component of transition-metal complex catalysts.Formula: C7H4FN

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Nitrile – Wikipedia,
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In 2014,Fuchibe, Kohei; Mayumi, Yuka; Yokota, Misaki; Aihara, Hiromichi; Ichikawa, Junji published 《Indium(III)-catalyzed cationic cyclization of 1,1-difluoroallenes: regioselective synthesis of 1-fluoronaphthalenes》.Bulletin of the Chemical Society of Japan published the findings.Computed Properties of C8H6BrN The information in the text is summarized as follows:

1,1-Difluoroallenes underwent InBr3-catalyzed ring construction via in situ-generated allylic CF2 cations to give 1-fluoronaphthalenes in good yield. DFT calculations suggested that a pos. charge was localized on the CF2 carbon in the key allylic CF2 cation, which was stabilized by α-cation stabilizing effect of the fluorines and hyperconjugation with the adjuscent C-In σ bond.2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Computed Properties of 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.Computed Properties of C8H6BrN

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In 2007,Aly, Youssef L.; Pedersen, Erik B.; La Colla, Paolo; Loddo, Roberta published 《Synthesis and anti-HIV-1 activity of new MKC-442 analogues with an alkynyl-substituted 6-benzyl group》.Archiv der Pharmazie (Weinheim, Germany) published the findings.SDS of cas: 31938-07-5 The information in the text is summarized as follows:

Synthesis and antiviral activities are reported of a series of 6-(3-alkynyl benzyl)-substituted analogs of MKC-442 (6-benzyl-1-(ethoxymethyl)-5-isopropyluracil), a highly potent agent against HIV. The 3-alkynyl group is assumed to give a better stacking of the substituted benzyl group to reverse transcriptase (RT) and this was believed to improve antiviral activity against HIV-1. The bromo derivatives, 5-alkyl-6-(3-bromo-benzyl)-1-ethoxymethyl derivatives 7a, b and 5-alkyl-6-(3-bromobenzyl)-1-allyloxymethyl derivatives 9a, b, showed activity against HIV on the same level as their corresponding analogs 10a-d with a 3-trimethylsilylalkynylbenzyl substituent and their desilylated analogs 11a-d. However, they all showed activity against HIV-1 wild type in the range of more than 10fold lower than the one of MKC-442. Moderate activity against Y181C and Y181C + K103N mutated strains was also observed and, in some cases, they were marginally better than those found for MKC-442. A few amino-DABO and S-DABO analogs were also synthesized but they were found to be inactive against HIV. In the experimental materials used by the author, we found 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5SDS of cas: 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.SDS of cas: 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2004,Anders, Joachim T.; Langer, Peter published 《Domino cyclization/electrocyclization/elimination reactions of arylacetonitriles with N,N’-bis(1-naphthyl)oxaldiimidoyl dichlorides: Efficient synthesis of fluorescent 15H-benzo[h]benzo[6,7]indolo[3,2-b]quinolines》.European Journal of Organic Chemistry published the findings.Synthetic Route of C8H6BrN The information in the text is summarized as follows:

15H-Benzo[h]benzo[6,7]indolo[3,2-b]quinolines, e.g., I, were prepared by domino cyclization/electrocyclization/elimination reactions of nitriles with N,N’-bis(1-naphthyl)oxaldiimidoyl dichlorides. The products can be regarded as hexacyclic δ-carbolines and were fluorescent dyes.2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Synthetic Route of 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.Synthetic Route of C8H6BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 17201-43-3In 2021 ,《Novel quinolone-based potent and selective HDAC6 inhibitors: Synthesis, molecular modeling studies and biological investigation》 appeared in European Journal of Medicinal Chemistry. The author of the article were Relitti, Nicola; Saraswati, A. Prasanth; Chemi, Giulia; Brindisi, Margherita; Brogi, Simone; Herp, Daniel; Schmidtkunz, Karin; Saccoccia, Fulvio; Ruberti, Giovina; Ulivieri, Cristina; Vanni, Francesca; Sarno, Federica; Altucci, Lucia; Lamponi, Stefania; Jung, Manfred; Gemma, Sandra; Butini, Stefania; Campiani, Giuseppe. The article conveys some information:

The synthesis of potent and selective quinolone-based histone deacetylase 6 (HDAC6) inhibitors was reported. The quinolone moiety I and II [X= CH, N] was as an innovative bioactive cap-group for HDAC6 inhibition; its synthesis was achieved by applying a multicomponent reaction. The optimization of potency and selectivity of these products was performed by employing computational studies which leded to the discovery of the diethylaminomethyl derivatives II [X= CH, N] as the most promising hit mols. These compounds were investigated in cellular studies evaluated their anticancer effect against colon (HCT-116) and histiocytic lymphoma (U9347) cancer cells, showed good to excellent potency, leaded to tumor cell death by apoptosis induction. The small mols. I, II [X= CH, N] were able to strongly inhibit the cytoplasmic and slightly the nuclear HDAC enzymes, increased the acetylation of tubulin and of the lysine 9 and 14 of histone 3, resp. Compound II [X= CH] was also able to increase Hsp90 acetylation levels in HCT-116 cells, thus further supporting its HDAC6 inhibitory profile. Cytotoxicity and mutagenicity assays of these mols. showed a safe profile; moreover, the HPLC anal. of compound II [X= N] revealed good solubility and stability profile. The results came from multiple reactions, including the reaction of 4-Cyanobenzyl bromide(cas: 17201-43-3Application of 17201-43-3)

4-Cyanobenzyl bromide(cas: 17201-43-3) can reacts with 2H-tetrazole in the presence of KOH to yield 4-[(2H-tetra-zol-2-yl)methyl]benzonitrile. And it may be used in the synthesis of ligands containing a chelating pyrazolyl-pyridine group with a pendant aromatic nitrile.Application of 17201-43-3

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Nitrile – Wikipedia,
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In 2022,Gholinejad, Mohammad; Shojafar, Mohammad; Sansano, Jose M.; Mikhaylov, Vladimir N.; Balova, Irina A.; Khezri, Rahimeh published an article in Journal of Organometallic Chemistry. The title of the article was 《Hyperbranched polymer immobilized palladium nanoparticles as an efficient and reusable catalyst for cyanation of aryl halides and reduction of nitroarenes》.Recommanded Product: 1194-02-1 The author mentioned the following in the article:

A new nitrogen-rich hyperbranched polymer comprising imidazolium and triazole moieties was used for stabilization of Pd nanoparticles. The resulting new material, PolyTZ-IL@Pd NPs, I was characterized with different techniques including Fourier-transform IR spectroscopy (FTIR), X-ray diffraction (XRD), XPS, energy dispersive X-Ray (EDX), and transmission electron microscopy (TEM) anal. Compound I was used as an efficient catalyst in the reduction of nitroarenes to amines and cyanation of aryl bromides and iodides. The catalyst showed high stability and recyclability and recycled at least 10 times in reduction of 1-chloro-4-nitrobenzene and 5 times in cyanation of iodobenzene. The experimental part of the paper was very detailed, including the reaction process of 4-Fluorobenzonitrile(cas: 1194-02-1Recommanded Product: 1194-02-1)

4-Fluorobenzonitrile(cas: 1194-02-1) is used as chemical intermediate, solvent for perfumes and pharmaceuticals, stabilizer for chlorinated solvents, HPLC analysis, catalyst and component of transition-metal complex catalysts.Recommanded Product: 1194-02-1

Referemce:
Nitrile – Wikipedia,
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Synthetic Route of C7H4BrNIn 2022 ,《Discovery of G2019S-Selective Leucine Rich Repeat Protein Kinase 2 inhibitors with in vivo efficacy》 appeared in European Journal of Medicinal Chemistry. The author of the article were Lesniak, Robert K.; Nichols, R. Jeremy; Schonemann, Marcus; Zhao, Jing; Gajera, Chandresh R.; Fitch, William L.; Lam, Grace; Nguyen, Khanh C.; Smith, Mark; Montine, Thomas J.. The article conveys some information:

The discovery and development of compound I, an indazole-based, G2019S-selective (>2000-fold vs. WT) LRRK2 inhibitor capable of entering rodent brain (Kp = 0.5) and selectively inhibiting G2019S-LRRK2 was reported. The compounds disclosed herein present a starting point for further development of brain penetrant G2019S selective inhibitors that hopefully reduce lung phenotype side-effects and pave the way to providing a precision medicine for people with PD who carry the G2019S mutation. In the part of experimental materials, we found many familiar compounds, such as 2-Bromobenzonitrile(cas: 2042-37-7Synthetic Route of C7H4BrN)

2-Bromobenzonitrile(cas: 2042-37-7) belongs to a group of ortho-substituted bromobenzenes that have varying hepatotoxicity effects in the presence of rat liver microsomes in vitro. 2-Bromobenzonitrile is also used as a starting material to synthesize novel benzothiophene derivatives that were found to exhibit antibacterial and antifungal activity.Synthetic Route of C7H4BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Category: nitriles-buliding-blocksIn 2010 ,《New pyrazolo[1,5a]pyrimidines as orally active inhibitors of Lck》 appeared in Bioorganic & Medicinal Chemistry Letters. The author of the article were Gommermann, Nina; Buehlmayer, Peter; von Matt, Anette; Breitenstein, Werner; Masuya, Keiichi; Pirard, Bernard; Furet, Pascal; Cowan-Jacob, Sandra W.; Weckbecker, Gisbert. The article conveys some information:

A novel series of pyrazolo[1,5a]pyrimidines was optimized to target lymphocyte-specific kinase (Lck). An efficient synthetic route was developed and SAR studies toward activity and selectivity are described, leading to Lck inhibitors with enzymic, cellular, and in vivo potency. In addition to this study using 2-(3-Bromophenyl)acetonitrile, there are many other studies that have used 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Category: nitriles-buliding-blocks) was used in this study.

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.Category: nitriles-buliding-blocks

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Nitrile – Wikipedia,
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Thevenin, Marion; Chen, Gang; Kantham, Srinivas; Sun, Chunxiang; Glogauer, Michael; Young, Robert N. published their research in ACS Pharmacology & Translational Science in 2021. The article was titled 《Design, Synthesis, Pharmacokinetics, and Biodistribution of a Series of Bone-Targeting EP4 Receptor Agonist Prodrugs for Treatment of Osteoporosis and Other Bone Conditions》.Application of 17201-43-3 The article contains the following contents:

A series of bone-targeting EP4 receptor agonist conjugate prodrugs were prepared wherein a potent EP4 receptor agonist was bound to a biol. inactive, bisphosphonate-based bone-targeting moiety. Singly and doubly radiolabeled conjugates were synthesized and were shown to be stable in blood, to be rapidly eliminated from the bloodstream, and to be effectively taken up into bone in vivo after i.v. dosing. From these preliminary studies a preferred conjugate 4 (I)(also known as C3 and Mes-1007) was selected for follow up biodistribution and elimination studies. Doubly radiolabeled conjugate 4 was found to partition largely to the liver and bones, and both labels were eliminated from liver at the same rate indicating the conjugate was eliminated intact. Quantification of the labels in bones indicated that free EP4 agonist (EP4a)(2a) was released from bone-bound 4 with a half-time of about 7 days. When dosed orally, radiolabeled 4 was not absorbed and passed through the gastrointestinal tract essentially unchanged, and only traces of radiolabeled 4 were found in the liver, blood, or bones. 4 was found to bind rapidly and completely to powd. bone mineral or to various forms of calcium phosphate, forming a stable matrix suitable for implant and that could made into powders or solid forms and be sterilized without decomposition or release of 4. Basic hydrolysis released free EP4 agonist 2a (II) quant. from the material. In the experimental materials used by the author, we found 4-Cyanobenzyl bromide(cas: 17201-43-3Application of 17201-43-3)

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.Application of 17201-43-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts