Month: October 2022

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Mechanistic Analysis of Metallaphotoredox C-N Coupling: Photocatalysis Initiates and Perpetuates Ni(I)/Ni(III) Coupling Activity》 was written by Till, Nicholas A.; Tian, Lei; Dong, Zhe; Scholes, Gregory D.; MacMillan, David W. C.. Electric Literature of C7H4BrN And the article was included in Journal of the American Chemical Society in 2020. The article conveys some information:

The combined use of reaction kinetic anal., ultrafast spectroscopy, and stoichiometric organometallic studies has enabled the elucidation of the mechanistic underpinnings to a photocatalytic C-N cross-coupling reaction. Steady-state and ultrafast spectroscopic techniques were used to track the excited-state evolution of the employed iridium photocatalyst, determine the resting states of both iridium and nickel catalysts, and uncover the photochem. mechanism for reductive activation of the nickel cocatalyst. Stoichiometric organometallic studies along with a comprehensive kinetic study of the reaction, including rate-driving force anal., unveiled the crucial role of photocatalysis in both initiating and sustaining a Ni(I)/Ni(III) cross-coupling mechanism. The insights gleaned from this study further enabled the discovery of a new photocatalyst providing a >30-fold rate increase. The results came from multiple reactions, including the reaction of 4-Bromobenzonitrile(cas: 623-00-7Electric Literature of C7H4BrN)

4-Bromobenzonitrile(cas: 623-00-7) has been used in the synthesis of 4-iodobenzonitrile via photo-induced aromatic Finkelstein iodination reaction.Electric Literature of C7H4BrN 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

El-serwy, Walaa s.; El-serwy, Weam s.; Mohamed, Neama a.; Kassem, Emad m. m.; Mostafa, Rasha e.; Mohamed, Hanaa s. published their research in Russian Journal of Bioorganic Chemistry in 2021. The article was titled 《Synthesis, Biological Evaluation, Molecular Docking, ADME Predictions and QSAR Studies of Novel 1,2-Diazet and Pyrrole Derivatives as Anti-Inflammatory Agents》.Category: nitriles-buliding-blocks The article contains the following contents:

Here we synthesized novel 1, 2-diazet and pyrrole derivatives and screened for their anti-inflammatory activity. In vivo anti-inflammatory evaluation results revealed that compounds (XVI), (XIV) and (XI) exhibited the highest anti-inflammatory potencies all over the 4 h, while compounds (VII), (V) and (XV) exhibited the lowest potencies when compared to indomethacin group. Mol. docking study was used to predict the binding mode towards c-Jun N-Terminal Kinase. In addition, ADME (absorption, distribution, metabolism, and excretion) prediction and QSAR (quant. structure-activity relationship) study of compounds was carried out resp. The experimental process involved the reaction of 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Category: nitriles-buliding-blocks)

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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Sathiyan, Govindasamy; Mathivanan, Dhamodiran; Bhuvaneshwari, Balasubramaniam; Garg, Ashish; Gupta, Raju Kumar; Singh, Anand published an article in 2021. The article was titled 《Olefin-linked conjugated fluorescent oligomer: Design, synthesis, photophysical studies and detection of nitroaromatic compounds (NACs) in aqueous media》, and you may find the article in Sensors and Actuators, A: Physical.Safety of 4-Cyanobenzyl bromide The information in the text is summarized as follows:

The development of novel fluorescent polymers has attracted significant attention owing to their potential applications in energy and environmental sciences. This study reports novel oligomer (TRZBT) synthesis via Wittig-Horner reaction using bithiophene aldehyde and triazine tri-Et phosphite. The resulting oligomer possesses large porous morphol., which was confirmed using SEM anal. Further, the chem. structure of TRZBT was confirmed by FT-IR, NMR, and GPC studies. The triazine acceptor (A) unit linked with bithiophene donor (D) unit through olefin π-conjugation resulted in a Donor-π-Acceptor (D-π-A) type oligomer. Detailed studies of the solvent-dependent photophys. properties of TRZBT were performed. Due to the alternate D-A structure of oligomer, enhanced intramol. charge transfer (ICT) properties between D and A moiety was observed Further, TRZBT in THF and THF: H2O (10:90) system effectively detected nitro-explosives in aqueous media, which exhibited high sensitivity, selectivity, and quick response via fluorescence quenching. TRZBT showed a higher quenching constant (Ksv) value of 4.91 x 105 M-1 towards picric acid as compared with other nitroaroms. Significantly, the detection limit of 1.58 nM in a 100% aqueous medium confirms that the synthesized material can detect even trace levels of the analyte. The experimental part of the paper was very detailed, including the reaction process of 4-Cyanobenzyl bromide(cas: 17201-43-3Safety of 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.Safety of 4-Cyanobenzyl bromide

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Dreas, Agnieszka; Kucwaj-Brysz, Katarzyna; Pyziak, Karolina; Kulesza, Urszula; Wincza, Ewelina; Fabritius, Charles-Henry; Michalik, Kinga; Gabor-Worwa, Ewelina; Golas, Aniela; Milik, Mariusz; Masiejczyk, Magdalena; Majewska, Eliza; Pysniak, Kazimiera; Wojcik-Trechcinska, Urszula; Sandowska-Markiewicz, Zuzanna; Brzozka, Krzysztof; Ostrowski, Jerzy; Rzymski, Tomasz; Mikula, Michal published an article in 2021. The article was titled 《Discovery of indazole-pyridinone derivatives as a novel class of potent and selective MNK1/2 kinase inhibitors that protecting against endotoxin-induced septic shock》, and you may find the article in European Journal of Medicinal Chemistry.Formula: C8H6BrN The information in the text is summarized as follows:

The mitogen-activated protein kinase (MAPK)-interacting kinases 1 and 2 (MNKs 1/2) and their downstream target eIF4E, play a role in oncogenic transformation, progression and metastasis. These results provided rationale for development of first MNKs inhibitors, currently in clin. trials for cancer treatment. Inhibitors of the MNKs/eIF4E pathway are also proposed as treatment strategy for inflammatory conditions. Here we present results of optimization of indazole-pyridinone derived MNK1/2 inhibitors among which compounds I and II, selective and metabolically stable derivatives Both compounds decreased levels of eIF4E Ser206 phosphorylation (pSer209-eIF4E) in MOLM16 cell line. When administered in mice compounds I and II significantly improved survival rates of animals in the endotoxin LD challenge model, with concomitant reduction of proinflammatory cytokine levels – TNFα and IL-6 in serum. Identified MNK1/2 inhibitors represent a novel class of immunomodulatory compounds with a potential for the treatment of inflammatory diseases including sepsis. The results came from multiple reactions, including the reaction of 4-Cyanobenzyl bromide(cas: 17201-43-3Formula: C8H6BrN)

4-Cyanobenzyl bromide(cas: 17201-43-3) is an important intermediate for pharmaceutical production. It can be used for the synthesis of a series of piperidine-linked aromatic diimidazolines, which have been synthesized as conformationally restricted congeners of the anti-Pneumocystis carinii (PCP) drug, Pentamidine.Formula: C8H6BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Wang, Xing-Rong; Wang, Shuai; Li, Wen-Bo; Xu, Kai-Yan; Qiao, Xue-Peng; Jing, Xue-Li; Wang, Zi-Xiao; Yang, Chang-jiang; Chen, Shi-Wu published an article in 2021. The article was titled 《Design, synthesis and biological evaluation of novel 2-(4-(1H-indazol-6-yl)-1H-pyrazol-1-yl)acetamide derivatives as potent VEGFR-2 inhibitors》, and you may find the article in European Journal of Medicinal Chemistry.Product Details of 105942-08-3 The information in the text is summarized as follows:

Vascular endothelial growth factor-2 (VEGFR-2) plays a pivotal role in tumor angiogenesis. Herein, a library of novel 2-(4-(1H-indazol-6-yl)-1H-pyrazol-1-yl)acetamide derivatives were designed and synthesized as VEGFR-2 inhibitors based on scaffold hopping strategy. These compounds exhibited excellent inhibitory activity in both VEGFR-2 and tumor cell proliferation. Especially, compound I possessed potent VEGFR-2 inhibition with IC50 = 1.6 nM and anti-proliferation against HGC-27 tumor cells with IC50 = 0.36 +/- 0.11μM, as well as less toxicity against normal GES-1 cells with IC50 = 187.46 +/- 10.13μM. Moreover, I obviously inhibited colony formation, migration and invasion of HGC-27 cells by adjusting the expression of MMP-9 and E-cadherin, and induced HGC-27 cells apoptosis by increasing ROS production and regulates the expression of apoptotic proteins. Furthermore, I blocked the PI3K-Akt-mTOR signaling pathway in HGC-27 cells. In addition, anti-angiogenesis of I was proved by inhibition tube formation and the expression of p-VEGFR-2 in HUVEC cells. All the results demonstrated that I could be developed as a promising anticancer agent for gastric cancer therapy. After reading the article, we found that the author used 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Product Details of 105942-08-3)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a OLED intermediate, Pharmaceutical, electronic and chemical intermediate.Product Details of 105942-08-3 It is used in the synthesis of heterocycles and liquid crystals.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ghadermazi, Mohammad; Molaei, Somayeh; Ghadermazi, Nahid published an article in 2021. The article was titled 《Introduction of Fe into mesoporous MCM-41 for the synthesis of 5-substituted 1H-Tetrazoles from aryl nitriles in water》, and you may find the article in Microporous and Mesoporous Materials.Safety of 2-Bromobenzonitrile The information in the text is summarized as follows:

In this exploration, new recyclable mesoporous-supported iron particles with the ligand and without ligand (MCM-41@ 3,4,5-tri hydroxyphenyl acetic acid @Fe and MCM-41@Fe) have been developed through post-functionalization modification of silica MCM-41. These catalysts were demonstrated to be novel, effective, and green for the synthesis of 5-substituted 1H-tetrazoles from aryl nitriles in water. In these systems, 5-substituted 1H-tetrazoles are produced as the only product. Fe3+ species were identified as active sites. The ordered mesoporous iron-silica catalyst with the ligand displayed better catalytic activity compared to iron-silica catalyst without the ligand, which was ascribed to the improvement of the inter-action of iron with the support. The catalysts can be easily separated using simple recovery and reused several times with consistent activity. After reading the article, we found that the author used 2-Bromobenzonitrile(cas: 2042-37-7Safety of 2-Bromobenzonitrile)

2-Bromobenzonitrile(cas: 2042-37-7) is used as a starting material to synthesize novel benzothiophene derivatives that were found to exhibit antibacterial and antifungal activity. It is commonly employed in reactions that require an electron-rich species to carry out nucleophilic substitution (or addition) reactions.Safety of 2-Bromobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Traxler, Michael; Gisbertz, Sebastian; Pachfule, Pradip; Schmidt, Johannes; Roeser, Jerome; Reischauer, Susanne; Rabeah, Jabor; Pieber, Bartholomaus; Thomas, Arne published an article in 2022. The article was titled 《Acridine-Functionalized Covalent Organic Frameworks (COFs) as Photocatalysts for Metallaphotocatalytic C-N Cross-Coupling》, and you may find the article in Angewandte Chemie, International Edition.Formula: C7H4BrN The information in the text is summarized as follows:

Covalent organic frameworks (COFs) are structurally tuneable, porous and crystalline polymers constructed through the covalent attachment of small organic building blocks as elementary units. Using the myriad of such building blocks, a broad spectrum of functionalities has been applied for COF syntheses for broad applications, including heterogeneous catalysis. Herein, we report the synthesis of a new family of porous and crystalline COFs using a novel acridine linker and benzene-1,3,5-tricarbaldehyde derivatives bearing a variable number of hydroxy groups. With the broad absorption in the visible light region, the COFs were applied as photocatalysts in metallaphotocatalytic C-N cross-coupling. The fully β-ketoenamine linked COF showed the highest activity, due to the increased charge separation upon irradiation The COF showed good to excellent yields for several aryl bromides, good recyclability and even catalyzed the organic transformation in presence of green light as energy source. The results came from multiple reactions, including the reaction of 2-Bromobenzonitrile(cas: 2042-37-7Formula: C7H4BrN)

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. In addition, 2-bromobenzonitrile can be used for the Suzuki coupling reaction.Formula: C7H4BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

SDS of cas: 614-16-4In 2021 ,《Mechanistic selectivity investigation and 2D-QSAR study of some new antiproliferative pyrazoles and pyrazolopyridines as potential CDK2 inhibitors》 appeared in European Journal of Medicinal Chemistry. The author of the article were Hassan, Ghaneya S.; Georgey, Hanan H.; Mohammed, Esraa Z.; George, Riham F.; Mahmoud, Walaa R.; Omar, Farghaly A.. The article conveys some information:

Novel series of diphenyl-1H-pyrazoles (Z/E)I (Ar = C6H5, 4-BrC6H4, 2-thienyl, etc.) and pyrazolo[3,4-b]pyridines II and III (R = H, OMe, Cl; X = CH2, O, NCH3) were synthesized and evaluated for their antiproliferative activity against breast cancer cell line (MCF7) and Hepatocellular carcinoma cell line (HepG2). The highest MCF7 growth inhibition activity was attained via compounds (Z/E)I (Ar = 4-CH3OC6H4) and III (R = OMe; X = O) (IC50 = 1.29 and 0.93μM, resp.), while compounds II (4-FC6H4) and III (R = OMe; X = NMe) were the most active ones against HepG2 (IC50 = 1.57 and 1.33μM, resp.) compared to doxorubicin (IC50 = 1.88 and 7.30μM, resp.). Cell cycle anal. showed arrest at S and G2-M phases in MCF7 cells treated with (Z/E)I (Ar = 4-CH3OC6H4) and III (R = OMe; X = O), and at G2-M and G1/S phases in HepG2 cells treated with II (4-FC6H4) and III (R = OMe; X = NMe), resp. Apoptotic effect of compounds (Z/E)I (Ar = 4-CH3OC6H4), II (4-FC6H4), III (R = OMe; X = O, NMe) was indicated via their pre-G1 early and late apoptotic effects and augmented levels of caspase-9/MCF7 and caspase-3/HepG2. A worthy safety profile was assessed for compounds (Z/E)I (Ar = 4-CH3OC6H4) and III (R = OMe; X = O) on MCF10A and compounds II (4-FC6H4) and III (R = OMe; X = NMe) on THLE2 treated normal cells. Furthermore, compounds (Z/E)I (Ar = 4-CH3OC6H4), II (4-FC6H4) and III (R = OMe; X = NMe) displayed a promising selective profile for CDK2 inhibition vs. CDK1, CDK4, and CDK7 isoforms are proved from their selectivity index. Docking in CDK2 ATP binding site, co-crystallized with R-Roscovitine, demonstrated analogous interactions and comparable binding energy with the native ligand. 2D QSAR sighted the possible structural features governing the CDK2 inhibition activity elicited by the studied pyrazolo[3,4-b]pyridines II and III. These findings present compounds (Z/E)I (Ar = 4-CH3OC6H4), II (4-FC6H4) and III (R = OMe; X = NMe) as selective CDK2 inhibitors with promising antiproliferative activity against MCF7 and HepG2 cancer cells.3-Oxo-3-phenylpropanenitrile(cas: 614-16-4SDS of cas: 614-16-4) was used in this study.

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.SDS of cas: 614-16-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts