Tag: 100-200

In 2006,Balskus, Emily P.; Jacobsen, Eric N. published 《α,β-Unsaturated β-silyl imide substrates for catalytic, enantioselective conjugate additions: A total synthesis of (+)-lactacystin and the discovery of a new proteasome inhibitor》.Journal of the American Chemical Society published the findings.Name: 2-(3-Bromophenyl)acetonitrile The information in the text is summarized as follows:

Chiral (salen)Al μ-oxo dimer catalyzes the highly enantioselective conjugate addition of carbon-centered nucleophiles to α,β-unsaturated silyl imides. Allyldimethylsilane-substituted imide I was identified as an optimal substrate, undergoing addition reactions with a variety of nitrile nucleophiles in high yield and enantiomeric excess. The silicon-containing products are synthetically useful chiral building blocks, as demonstrated by their application to an enantioselective total synthesis of the potent proteasome inhibitor (+)-lactacystin. Elaboration of lactam II to the natural product was effected in 12 steps and in 11% overall yield and proceeded through an unusual spiro β-lactone intermediate. This compound was found to inhibit the chymotrypsin-like site of the 26S proteasome at similar levels to known inhibitor clasto-lactacystin β-lactone (omuralide). In the experimental materials used by the author, we found 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Name: 2-(3-Bromophenyl)acetonitrile)

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.Name: 2-(3-Bromophenyl)acetonitrile

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Zhang, Mingkai; Xu, Peilin; Vendola, Alex J.; Allais, Christophe; Dechert Schmitt, Anne-Marie; Singer, Robert A.; Morken, James P. published an article in Angewandte Chemie, International Edition. The title of the article was 《Stereocontrolled Pericyclic and Radical Cycloaddition Reactions of Readily Accessible Chiral Alkenyl Diazaborolidines》.SDS of cas: 1019607-55-6 The author mentioned the following in the article:

In this paper is described an easily synthesized chiral diazaborolidine that is inexpensive, stable, and provides excellent stereoselection across a number of reaction classes. These versatile compounds possess utility in four different classes of cycloaddition reactions, offering good yield and stereoselectivity. X-ray structure anal. provides insight about the origin of stereocontrol. In the experiment, the researchers used 4-(Cyclopropylamino)benzonitrile(cas: 1019607-55-6SDS of cas: 1019607-55-6)

4-(Cyclopropylamino)benzonitrile(cas: 1019607-55-6) belongs to anime. Amines can be classified according to the nature and number of substituents on nitrogen. Aliphatic amines contain only H and alkyl substituents. Aromatic amines have the nitrogen atom connected to an aromatic ring.Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine (NClH2).SDS of cas: 1019607-55-6

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In 2012,Bioorganic & Medicinal Chemistry Letters included an article by Bryan, Marian C.; Biswas, Kaustav; Peterkin, Tanya A. N.; Rzasa, Robert M.; Arik, Leyla; Lehto, Sonya G.; Sun, Hong; Hsieh, Feng-Yin; Xu, Cen; Fremeau, Robert T.; Allen, Jennifer R.. Safety of 2-Methoxy-6-methylbenzonitrile. The article was titled 《Chromenones as potent bradykinin B1 antagonists》. The information in the text is summarized as follows:

A series of fused 6,6-bicyclic chromenones was investigated for activity against the bradykinin B1 receptor. SAR studies based on a pharmacophore model revealed compounds with high affinity for both human and rabbit B1. These compounds demonstrated favorable pharmacokinetic properties and 5-chlorochromenone I was efficacious in a carrageenan-induced mech. hyperalgesia model for chronic pain. The experimental part of the paper was very detailed, including the reaction process of 2-Methoxy-6-methylbenzonitrile(cas: 53005-44-0Safety of 2-Methoxy-6-methylbenzonitrile)

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. Safety of 2-Methoxy-6-methylbenzonitrile 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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COA of Formula: C9H7NOIn 2019 ,《Highly efficient thermally activated delayed fluorescence emitter developed by replacing carbazole with 1,3,6,8-tetramethyl-carbazole》 was published in Frontiers in Chemistry (Lausanne, Switzerland). The article was written by Cai, Jia-Lin; Liu, Wei; Wang, Kai; Chen, Jia-Xiong; Shi, Yi-Zhong; Zhang, Ming; Zheng, Cai-Jun; Tao, Si-Lu; Zhang, Xiao-Hong. The article contains the following contents:

Carbazole (Cz) is the one of the most popular electron donors to develop thermally activated delayed fluorescence (TADF) emitters, but addnl. groups are generally required in the mols. to enhance the steric hindrance between Cz and electron acceptor segments. To address this issue, we replaced Cz with its derivative 1,3,6,8-tetramethyl-carbazole (tMCz) to develop TADF emitters. Two novel compounds, 6-(4-(carbazol-9-yl)phenyl)-2,4-diphenylnicotinonitrile (CzPN) and 2,4-diphenyl-6-(4-(1,3,6,8-tetramethyl-carbazol-9-yl)phenyl) nicotinonitrile (tMCzPN) were designed and synthesized accordingly. With the same and simple mol. framework, tMCzPN successfully exhibits TADF behavior, while CzPN is a non-TADF fluorophor, as the addnl. steric hindrance of Me groups leads to a more twisted structure of tMCzPN. In the organic light-emitting diodes (OLEDs), tMCzPN exhibits extremely high forward-viewing maximum external quantum efficiency of 26.0%, without any light out-coupling enhancement, which is significantly higher than that of 5.3% for CzPN. These results indicate that tMCzPN is an excellent TADF emitter and proves that tMCz is a more appropriate candidate than Cz to develop TADF emitters. In the part of experimental materials, we found many familiar compounds, such as 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4COA of Formula: C9H7NO)

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.COA of Formula: C9H7NO

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Garcia-Monroy, Ricardo; Gonzalez-Calderon, Davir; Ramirez-Villalva, Alejandra; Mastachi-Loza, Salvador; Aguirre-de Paz, Jose G.; Fuentes-Benites, Aydee; Gonzalez-Romero, Carlos published their research in Journal of the Mexican Chemical Society in 2021. The article was titled 《Synthesis of novel benzylic 1,2,3-triazole-4-carboxamides and their in vitro activity against clinically common fungal species》.Formula: C9H7NO The article contains the following contents:

A library of novel benzylic 1,2,3-triazole-4-carboxamides I (R = Ph, 4-methylphenyl, 4-phenylphenyl; R1 = 4-methoxyphenyl, 2,6-dichlorophenyl, 2H-1,3-benzodioxol-5-yl, etc.) were obtained with acceptable yields via a one-pot procedure. The series of compounds I was screened for fungicidal activity and evaluated in vitro against four filamentous fungi and four Candida species. The former consisted of Aspergillus fumigatus, Trichosporon cutaneum, Rhizopus oryzae and Mucor hiemalis, and the latter consisted of C. krusei, C. albicans, C. utilis and C. glabrata. According to the in vitro assays, I (R = Ph, R1 = 2,6-dichlorophenyl; R = Ph, R1 = 2H-1,3-benzodioxol-5-yl) were the most efficient fungicidal agents (of all the test compounds) against R. oryzae, even better than the reference drug (itraconazole). Thus, I (R = Ph, R1 = 2,6-dichlorophenyl; R = Ph, R1 = 2H-1,3-benzodioxol-5-yl) represent important scaffolds that can be modified to increase antifungal activity. Addnl., they are candidates for complementary studies on the inhibition of clin. infections produced by Rhizopus spp. strains.3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Formula: C9H7NO) was used in this study.

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.Formula: C9H7NO

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The author of 《nBu4NI-catalyzed C3-formylation of indoles with N-methylaniline》 were Li, Lan-Tao; Huang, Juan; Li, Hong-Ying; Wen, Li-Juan; Wang, Peng; Wang, Bin. And the article was published in Chemical Communications (Cambridge, United Kingdom) in 2012. Synthetic Route of C10H6N2O The author mentioned the following in the article:

NBu4NI-catalyzed C3-selective formylation of N-H and N-substituted indoles by using N-methylaniline as a formylating reagent was first successfully demonstrated. The experimental process involved the reaction of 3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9Synthetic Route 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.Synthetic Route of C10H6N2O

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Stepannikova, Kateryna O.; Vashchenko, Bohdan V.; Grygorenko, Oleksandr O.; Gorichko, Marian V.; Cherepakha, Artem Yu.; Moroz, Yurii S.; Volovenko, Yulian M.; Zhersh, Serhii published their research in European Journal of Organic Chemistry on December 21 ,2021. The article was titled 《Synthesis of Spirocyclic β- and γ-Sultams by One-Pot Reductive Cyclization of Cyanoalkylsulfonyl Fluorides》.Computed Properties of C9H13NO2 The article contains the following contents:

One-pot intramol. cyclization of novel sp3-enriched cyanoalkylsulfonyl fluorides into spirocyclic β- or γ-sultams is disclosed. The method relies on nitrile group reduction followed by sulfonylation of amino group thus formed upon mild conditions (NaBH4, NiCl2·6H2O in MeOH). Cyclization proceeds smoothly with considerable efficiency (48-84%, 10 examples) on up to 30 g scale. The cyanoalkylsulfonyl fluoride intermediates can be obtained via S-nucleophilic substitution in β-functionalized alkanenitriles or double alkylation of α-alkylthioacetonitrile, followed by oxidative chlorination with Cl2 and further reaction with KHF2. The title mono- and bifunctional sultams are advanced sp3-enriched building blocks for drug discovery and organic synthesis providing novel substitution patterns and frameworks mimicking saturated nitrogen heterocycles such as pyrrolidine/pyrrolidone. In the experiment, the researchers used Ethyl 1-cyanocyclopentane-1-carboxylate(cas: 28247-14-5Computed Properties of C9H13NO2)

Ethyl 1-cyanocyclopentane-1-carboxylate(cas: 28247-14-5) is a member of cyclopentanes. Although cyclopentane itself doesn’t have a single highly favoured conformation, a substituent on the cyclopentane ring can upset the balance of strains thereby favouring either the envelope or the half-chair.Computed Properties of C9H13NO2

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《Design, synthesis, biological evaluation and molecular docking of new uracil analogs-1,2,4-oxadiazole hybrids as potential anticancer agents》 was written by El Mansouri, Az-Eddine; Oubella, Ali; Maatallah, Mohamed; AitItto, Moulay Youssef; Zahouily, Mohamed; Morjani, Hamid; Lazrek, Hassan B.. Recommanded Product: 4-Cyanobenzyl bromideThis research focused onuracil oxadiazole hybrid preparation caspase mol docking anticancer agent; 1,2,4-Oxadiazole; Anticancer activity; Apoptosis; Heterogeneous catalyst; Hybrid molecules; Molecular docking; Uracil analogues. The article conveys some information:

A new series of uracil analogs-1,2,4-oxadiazole hybrid derivatives were synthesized by a new, simple, and efficient method using for the first time HAP-SO3H as an heterogeneous acid catalyst for the condensation and cyclization between amidoxime and aldehyde. The new derivatives were characterized by HRMS, FTIR, 1H NMR, and 13C NMR spectroscopy techniques. The synthesized 1,2,4-oxadiazole hybrids were evaluated for their cytotoxic activity in five human cancer cell lines: melanoma (A-375), fibrosarcoma (HT-1080), breast (MCF-7 and MDA-MB-231), and lung carcinoma (A-549). Compounds 1-[4-(5-Biphenyl-4-yl-[1,2,4]oxadiazol-3-yl)-benzyl]-5-fluoro-1H-pyrimidine-2,4-dione and 5-Fluoro-1-{4-[5-(4′-methoxy-biphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]-benzyl}-1H-pyrimidine-2,4-dione were potent cytotoxic agents against HT-1080 and MFC-7 cells with IC50 inferior to 1μM. The possible mechanism of apoptosis induction by the derivatives was studied using Annexin v staining, caspase-3/7 activity, mitochondrial membrane potential measurement, and anal. cell cycle progression. The compound 1-[4-(5-Biphenyl-4-yl-[1,2,4]oxadiazol-3-yl)-benzyl]-5-fluoro-1H-pyrimidine-2,4-dione induced apoptosis through caspase-3/7 activation and S-phase arrest in HT-1080 and A549 cells. The mol. docking showed that compound 1-[4-(5-Biphenyl-4-yl-[1,2,4]oxadiazol-3-yl)-benzyl]-5-fluoro-1H-pyrimidine-2,4-dione activated the caspase-3 by forming a stable protein-ligand complex. In the experiment, the researchers used many compounds, for example, 4-Cyanobenzyl bromide(cas: 17201-43-3Recommanded Product: 4-Cyanobenzyl bromide)

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.Recommanded Product: 4-Cyanobenzyl bromide

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《Asymmetric Alkylation of Ketones Catalyzed by Engineered TrpB》 was written by Watkins-Dulaney, Ella J.; Dunham, Noah P.; Straathof, Sabine; Turi, Soma; Arnold, Frances H.; Buller, Andrew R.. Electric Literature of C9H7NOThis research focused onTrpB ketone alkylation catalysis propiophenone; asymmetric catalysis; biocatalysis; directed evolution; ketones; nitrogen heterocycles. The article conveys some information:

The β-subunit of tryptophan synthase (TrpB) catalyzes a PLP-mediated β-substitution reaction between indole and serine to form -Trp. A succession of TrpB protein engineering campaigns to expand the enzyme′s nucleophile substrate range has enabled the biocatalytic production of diverse non-canonical amino acids (ncAAs). Here, we show that ketone-derived enolates can serve as nucleophiles in the TrpB reaction to achieve the asym. alkylation of ketones, an outstanding challenge in synthetic chem. We engineered TrpB by directed evolution to catalyze the asym. alkylation of propiophenone and 2-fluoroacetophenone with a high degree of selectivity. In reactions with propiophenone, preference for the opposite product diastereomer emerges over the course of evolution, demonstrating that full control over the stereochem. at the new chiral center can be achieved. The addition of this new reaction to the TrpB platform is a crucial first step toward the development of efficient methods to synthesize non-canonical prolines and other chirally dense nitrogen heterocycles. In the part of experimental materials, we found many familiar compounds, such as 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Electric Literature of C9H7NO)

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.Electric Literature of C9H7NO

Referemce:
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In 2022,Ataie, Saeed; Ovens, Jeffrey S.; Tom Baker, R. published an article in Chemical Communications (Cambridge, United Kingdom). The title of the article was 《Solvent-free Zn (NSNO) complex-catalysed dihydroboration of nitriles》.Name: 2-Bromobenzonitrile The author mentioned the following in the article:

N-donors are the most commonly employed Lewis bases in ligand-assisted catalysis. A dimeric zinc complex (Zn-1) employing a tetradentate pyridine-thioether-anilido-aryloxide NSNO ligand (L) effects the quant. conversion of nitriles to the corresponding double hydroborated products at 1 mol% catalyst loading. Variable Time Normalization Anal. kinetic studies showed a first-order dependence with respect to the nitrile, pinacolborane and zinc and clear evidence for catalyst deactivation. A plausible ligand-assisted reaction pathway involves B-H bond activation by the aryloxide (vs. anilido) donor. After reading the article, we found that the author used 2-Bromobenzonitrile(cas: 2042-37-7Name: 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.Name: 2-Bromobenzonitrile

Referemce:
Nitrile – Wikipedia,
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