Tag: 100-200

《Revision of the Regioselectivity of the Beirut Reaction of Monosubstituted Benzofuroxans with Benzoylacetonitrile. 6-Substituted quinoxaline-2-carbonitrile 1,4- dioxides: Structural Characterization and Estimation of Anticancer Activity and Hypoxia Selectivity》 was written by Buravchenko, Galina I.; Scherbakov, Alexander M.; Korlukov, Alexander A.; Dorovatovskii, Pavel V.; Shchekotikhin, Andrey E.. Name: 3-Oxo-3-phenylpropanenitrileThis research focused ontirapazamine benzofuroxan anticancer agent hypoxia normoxia adenocarcinoma; 6(7)-substituted-3-phenylquinoxaline-2-carbonitrile 1,4-dioxides; Beirut reaction; CIGAR-HMBC method; X-ray structural analysis; antiproliferative activity; hypoxia-selective cytotoxins; structural isomers.. The article conveys some information:

Objective: The preparation, isolation, structure characterization, and screening for anticancer activity of the first representatives of 6-substituted quinoxaline-2-carbonitrile 1,4-dioxides have been described. Materials and Methods: A series of 7- and 6-halogeno-3-phenylquinoxaline-2-carbonitrile 1,4-dioxides was synthesized by the Beirut reaction. The cytotoxicity was assessed by MTT test (72 h incubation) in normoxia (21% O2) and hypoxia (1% O2) conditions. Results: We found that during the Beirut reaction between a benzofuroxan bearing an electron withdrawing group and benzoylacetonitrile in the presence of triethylamine, in addition to well-known 7-substituted quinoxaline-2-carbonitrile 1,4-dioxides 7-11a, the 6-isomers 7-11b are formed. Moreover, the yield of the 6- isomers increased with the increase in the electron-withdrawing character of the substituent. For benzofuroxans with CO2Me and CF3 groups, 6-substituted quinoxaline-2-carbonitrile 1,4-dioxides 10-11b were the major products. Despite similarities in physicochem. and spectroscopic properties, the obtained isomers exhibit considerable differences in their anticancer activity and hypoxia selectivity. Conclusion: Substituents and their electronic effects play a key role in the formation of 7- and 6-substituted quinoxaline-2-carbonitrile 1,4-dioxides in the Beirut reaction and in the cytotoxicity properties of the obtained isomers. The experimental process involved the reaction of 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Name: 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.Name: 3-Oxo-3-phenylpropanenitrile

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《Anodic oxidations. VII. Nuclear cyanation of methylanisoles》 was published in Journal of Organic Chemistry in 1975. These research results belong to Yoshida, Kunihisa; Shigi, Masataka; Fueno, Takayuki. COA of Formula: C9H9NO The article mentions the following:

Addnl. data considered in abstracting and indexing are available from a source cited in the original document. Electrochem. oxidation of methylanisoles in MeOH containing NaCN was investigated. The anodic cyanation in MeOH is compared to anodic cyanation in MeCn containing Et4NCN. In the cases of o- and m-substituted methylanisoles, nuclear cyanation took place preferentially. With p-methylanisole [104-93-8], side chain methoxylation surpassed nuclear cyanation. The data obtained are compared with those of other electron-transfer reactions such as the anodic acetoxylation and the acetoxylation and chlorination by metal oxidizing agents. Factors controlling the competition between nuclear and side-chain substitution in alkyl aromatic compounds are ascribable to the degree of pos. charge on the aromatic C atoms in the cation radicals as well as the nucleophilicity of attacking agents. The experimental process involved the reaction of 2-Methoxy-6-methylbenzonitrile(cas: 53005-44-0COA of Formula: C9H9NO)

2-Methoxy-6-methylbenzonitrile(cas: 53005-44-0) 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. COA of Formula: C9H9NO Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.

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Application In Synthesis of 2-(3-Bromophenyl)acetonitrileIn 2012 ,《Conformational Restriction Approach to β-Secretase (BACE1) Inhibitors: Effect of a Cyclopropane Ring To Induce an Alternative Binding Mode》 was published in Journal of Medicinal Chemistry. The article was written by Yonezawa, Shuji; Yamamoto, Takahiko; Yamakawa, Hidekuni; Muto, Chie; Hosono, Motoko; Hattori, Kazunari; Higashino, Kenichi; Yutsudo, Takashi; Iwamoto, Hideo; Kondo, Yutaka; Sakagami, Masahiro; Togame, Hiroko; Tanaka, Yoshikazu; Nakano, Toru; Takemoto, Hiroshi; Arisawa, Mitsuhiro; Shuto, Satoshi. The article contains the following contents:

Improvement of a drug’s binding activity using the conformational restriction approach with sp3 hybridized carbons is becoming a key strategy in drug discovery. We applied this approach to BACE1 inhibitors and designed four stereoisomeric cyclopropane compounds in which the ethylene linker of a known amidine-type inhibitor I was replaced with chiral cyclopropane rings. The synthesis and biol. evaluation of these compounds revealed that the cis-(1S,2R) isomer II exhibited the most potent BACE1 inhibitory activity among them. X-ray structure anal. of the complex of II and BACE1 revealed that its unique binding mode is due to the apparent CH-π interaction between the rigid cyclopropane ring and the Tyr71 side chain. A derivatization study using II as a lead mol. led to the development of highly potent inhibitors in which the structure-activity relationship as well as the binding mode of the compounds clearly differ from those of known amidine-type inhibitors. After reading the article, we found that the author used 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Application In Synthesis of 2-(3-Bromophenyl)acetonitrile)

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.Application In Synthesis of 2-(3-Bromophenyl)acetonitrile

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Related Products of 1194-02-1In 2019 ,《Ru (III) Schiff-base complex anchored on nanosilica as an efficient and retrievable catalyst for hydration of nitriles》 was published in Applied Organometallic Chemistry. The article was written by Sultana, Samim; Borah, Geetika; Gogoi, Pradip K.. The article contains the following contents:

Synthesis of a new solid supported Ru (III) Schiff base complex, Ru@imine-nanoSiO2 immobilized on nanosilica obtained from rice husk was reported. The complex was characterized by FTIR, powder X-ray diffraction, BET surface area measurement, UV-vis, SEM-EDX, TEM, ESR, XPS and ICP-AES anal. Using Ru@imine-nanoSiO2 as the catalyst, the hydration of nitriles in i-PrOH at 40 ° was studied which resulted in good isolated yields (60-99%). The catalyst can be recycled and reused up to 5th cycle without any loss in activity. The products were characterized by FTIR, GC-MS and 1H-NMR spectroscopy and compared with authentic samples. After reading the article, we found that the author used 4-Fluorobenzonitrile(cas: 1194-02-1Related Products of 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.Related Products of 1194-02-1

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In 2022,Salaverri, Noelia; Carli, Benedetta; Gratal, Patricia B.; Marzo, Leyre; Aleman, Jose published an article in Advanced Synthesis & Catalysis. The title of the article was 《Remote Giese Radical Addition by Photocatalytic Ring Opening of Activated Cycloalkanols》.Application In Synthesis of 3-Oxo-3-phenylpropanenitrile The author mentioned the following in the article:

The addition of these remote alkyl radicals RC(R1)(R2)OH [R = Me, 4-methoxyphenyl, furan-2-yl, etc.; R1R2 = -(CH2)5-, -CH2S(CH2)2-, -CH2N(Boc)(CH2)3-, etc.] to electron deficient double bonds R3CH=C(R4)CN (R3 = Ph, thiophen-2-yl, naphthalen-1-yl, etc.; R4 = CN, C(O)Ph, 4-nitrophenyl, etc.) under photoorganocatalyzation and very mild conditions was reported. The method not only applicable to diactivated double bonds, but monoactivated ones are also accessible using more stabilized alkyl radicals, and alkyl chains of any length can be introduced. The final products RC(O)(CH2)nCH2C(R3)CH(R4)CN (n = 2, 4, 6, etc.) can be easily converted into more complex structures via a one-pot process, and the activating functional groups were transformed in the more versatile Me esters. Mechanistic investigations support a mechanistic proposal based on a PCET process. After reading the article, we found that the author used 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Application In Synthesis 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.Application In Synthesis of 3-Oxo-3-phenylpropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zhang, Xin-Yang; Lu, Yao; Du, Ye; Wang, Wen-Long; Yang, Lu-Lin; Wu, Qian-Yuan published an article in 2021. The article was titled 《Comprehensive GCxGC-qMS with a mass-to-charge ratio difference extraction method to identify new brominated byproducts during ozonation and their toxicity assessment》, and you may find the article in Journal of Hazardous Materials.Product Details of 31938-07-5 The information in the text is summarized as follows:

Ozonation might increase the risk of wastewater due to byproduct formation, especially in the presence of bromide. In this study, a new anal. method was developed to identify new brominated disinfection byproducts (Br-DBPs) during ozonation, using comprehensive two-dimensional gas chromatog.-single quadrupole mass spectrometry (GCxGC-qMS) connected with an electron capture detector in parallel. The obtained data were analyzed using a mass-to-charge ratio (m/z) difference extraction method. Over 1304 DBPs were detected in an ozonated phenylalanine solution Further screening of 635 DBPs was conducted using the m/z difference extraction method. Finally, the structures for 12 Br-DBPs were confirmed and for 4 Br-DBPs were tentatively proposed by comparison with the NIST library and standard compounds Eight of the confirmed Br-DBPs are first reported and identified: 2-bromostyrene, 1-bromo-1-phenylethylene, 2-bromobenzaldehyde, 3-bromobenzaldehyde, 4-bromobenzaldehyde, 2-bromophenylacetonitrile, 3-bromophenylacetonitrile and 4-bromophenylacetonitrile. These DBPs and 2,4,6-tribromophenol were detected at nanogram- to microgram-per-liter concentrations during ozonation of authentic water samples like algal bloom waters, wastewater treatment plant effluents, and surface water. The toxicities of these compounds were generally higher than that of bromate. The developed anal. method is a powerful technique for analyzing complex compounds and provides a novel way of identifying byproducts in future studies. In the experiment, the researchers used 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Product Details of 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.Product Details of 31938-07-5

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Rohde, Jason M.; Karavadhi, Surendra; Pragani, Rajan; Liu, Li; Fang, Yuhong; Zhang, Weihe; McIver, Andrew; Zheng, Hongchao; Liu, Qingyang; Davis, Mindy I.; Urban, Daniel J.; Lee, Tobie D.; Cheff, Dorian M.; Hollingshead, Melinda; Henderson, Mark J.; Martinez, Natalia J.; Brimacombe, Kyle R.; Yasgar, Adam; Zhao, Wei; Klumpp-Thomas, Carleen; Michael, Sam; Covey, Joseph; Moore, William J.; Stott, Gordon M.; Li, Zhuyin; Simeonov, Anton; Jadhav, Ajit; Frye, Stephen; Hall, Matthew D.; Shen, Min; Wang, Xiaodong; Patnaik, Samarjit; Boxer, Matthew B. published their research in Journal of Medicinal Chemistry in 2021. The article was titled 《Discovery and Optimization of 2H-1λ2-Pyridin-2-one Inhibitors of Mutant Isocitrate Dehydrogenase 1 for the Treatment of Cancer》.Computed Properties of C8H6BrN The article contains the following contents:

Neomorphic mutations in isocitrate dehydrogenase 1 (IDH1) are oncogenic for a number of malignancies, primarily low-grade gliomas and acute myeloid leukemia. We report a medicinal chem. campaign around a 7,7-dimethyl-7,8-dihydro-2H-1λ2-quinoline-2,5(6H)-dione screening hit against the R132H and R132C mutant forms of isocitrate dehydrogenase (IDH1). Systematic SAR efforts produced a series of potent pyrid-2-one mIDH1 inhibitors, including the atropisomer (+)-119 (NCATS-SM5637, NSC 791985). In an engineered mIDH1-U87-xenograft mouse model, after a single oral dose of 30 mg/kg, 16 h post dose, between 16 and 48 h, (+)-119(I) showed higher tumoral concentrations that corresponded to lower 2-HG concentrations, when compared with the approved drug AG-120 (ivosidenib). In the experimental materials used by the author, we found 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Computed Properties of C8H6BrN)

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.Computed Properties of C8H6BrN

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Akkoc, Mitat; Bugday, Nesrin; Altin, Serdar; Kiraz, Nadir; Yasar, Sedat; Ozdemir, Ismail published their research in Journal of Organometallic Chemistry in 2021. The article was titled 《N-heterocyclic carbene Pd(II) complex supported on Fe3O4@SiO2: Highly active, reusable and magnetically separable catalyst for Suzuki-Miyaura cross-coupling reactions in aqueous media》.Related Products of 623-00-7 The article contains the following contents:

A new type magnetic nano Fe3O4@SiO2@NHC@Pd-MNPs heterogeneous catalyst was fabricated and characterized by Fourier Transform IR (FTIR) spectroscopy, Transmission Electron Microscopy (TEM), X-Ray Diffraction (XRD), XPS, Energy Disperse X-ray anal. (EDX), Thermogravimetric Anal. (TGA), DTA (DTA), and SEM (SEM). The loading amount of palladium (Pd) to magnetic nano Fe3O4@SiO2@NHC@Pd-MNPs was measured by Inductively Coupled Plasma-Optical Emission Spectroscopy (ICP-OES) anal. The catalytic activity of magnetic nano Fe3O4@SiO2@NHC@Pd-MNPs heterogeneous catalyst was examined on Suzuki-Miyaura cross-coupling reactions of aryl halides with different substituted arylboronic acid derivatives All coupling reactions yielded excellent results and high TOF (up to 76528 h-1) in the presence of 2 mg of Fe3O4@SiO2@NHC@Pd-MNPs catalyst (0.0197 mmolg-1, 0.00394 mmol%Pd) at 80° in 2-propanol/H2O (1:2). In addition, the magnetic nano Fe3O4@SiO2@NHC@Pd-MNPs catalyst was easily recovered by using an external Nd-magnet and reused for the Suzuki cross-coupling reactions. The catalyst showed strong structural and chem. stability and was reused six times without losing its catalytic activity substantially. In the experimental materials used by the author, we found 4-Bromobenzonitrile(cas: 623-00-7Related Products 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,Related Products 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.

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Saidi, Lamia; Samet, Amira; Dammak, Thameur; Pillet, Sebastien; Abid, Younes published their research in Physical Chemistry Chemical Physics in 2021. The article was titled 《Down and up conversion luminescence of the lead-free organic metal halide material: (C9H8NO)2SnCl6·2H2O》.HPLC of Formula: 614-16-4 The article contains the following contents:

The present work deals with the optical properties of hybrid organic metal halide material namely (C9H8NO)2SnCl6.2H2O. Its structure is built up from isolated [SnCl6]2- octahedral dianions surrounded by Hydroxyl quinolinium organic cations (C9H8NO)+, abbreviated as [HQ]+. Unlike the usual hybrid materials, where metal halide ions are luminescent semiconductors while the organic ones are optically inactive, [HQ]2SnCl6.2H2O contains two optically active entities: [HQ]+ organic cations and [SnCl6]2- dianions. The optical properties of the synthesized crystals were studied by optical absorption spectroscopy, photoluminescence measurements and DFT calculations of electronic d. of states. These studies have shown that both organic and inorganic entities have very close HOMO-LUMO gaps and very similar band alignments favoring the resonant energy transfer process. In addition, measurements of luminescence under variable excitations reveal an intense green luminescence around 497 nm under UV excitation (down conversion) and IR excitation (up conversion luminescence). The down conversion luminescence is assigned to the π-π* transition within the [HQ]+ organic cations involving charge transfer between the organic and inorganic entities, whereas the up-conversion luminescence is based on the triplet-triplet annihilation mechanism (TTA). The experimental part of the paper was very detailed, including the reaction process of 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4HPLC of Formula: 614-16-4)

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.HPLC of Formula: 614-16-4

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《Chiral Chalcogenyl-Substituted Naphthyl- and Acenaphthyl-Silanes and Their Cations》 was published in Chemistry – A European Journal in 2020. These research results belong to Kuenzler, Sandra; Rathjen, Saskia; Rueger, Katherina; Wuerdemann, Marie S.; Wernke, Marcel; Tholen, Patrik; Girschik, Corinna; Schmidtmann, Marc; Landais, Yannick; Mueller, Thomas. HPLC of Formula: 1194-02-1 The article mentions the following:

Cyclic silylated chalconium borates 13[B(C6F5)4] and 14[B(C6F5)4] with peri-acenaphthyl and peri-naphthyl skeletons were synthesized from unsym. substituted silanes 3, 4, 6, 7, 9 and 10 using the standard Corey protocol (Chalcogen Ch=O, S, Se, Te). The configuration at the chalcogen atom is trigonal pyramidal for Ch=S, Se, Te, leading to the formation of cis- and trans-isomers in the case of phenylmethylsilyl cations. With the bulkier tert-Bu group at silicon, the configuration at the chalcogen atoms is predetermined to give almost exclusively the trans-configurated cyclic silylchalconium ions. The barriers for the inversion of the configuration at the sulfur atoms of sulfonium ions 13 c and 14 a are substantial (72-74 kJ mol-1) as shown by variable temperature NMR spectroscopy. The neighboring group effect of the thiophenyl substituent is sufficiently strong to preserve chiral information at the silicon atom at low temperatures In the experiment, the researchers used many compounds, for example, 4-Fluorobenzonitrile(cas: 1194-02-1HPLC of Formula: 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.HPLC of Formula: 1194-02-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts