Month: October 2022

The author of 《Supported organometallic palladium catalyst into mesoporous channels of magnetic MCM-41 nanoparticles for phosphine-free C-C coupling reactions》 were Ghorbani-Choghamarani, Arash; Tahmasbi, Bahman; Hudson, Robert H. E.; Heidari, Ali. And the article was published in Microporous and Mesoporous Materials in 2019. Formula: C7H4BrN The author mentioned the following in the article:

Magnetic MCM-41 nanoparticles were synthesized via Fe3O4-doped into mesoporous channels of MCM-41 nanoparticles and further, a new organometallic complex of palladium was supported on its inner surface (Pd-imi@MCM-41/Fe3O4). This immobilized catalyst was applied as highly efficient, heterogeneous and magnetically recoverable nanocatalyst in the various C-C coupling reactions such as Suzuki-Miyaura and Mizoroki-Heck reactions under phosphine-free conditions at atm. pressure. This catalyst has advantages of both magnetic nanoparticles and mesoporous materials. The structure of prepared nanomaterial has been characterized by various techniques such as N2 adsorption-desorption isotherms, TEM, SEM, EDS, WDX, FT-IR, XRD, TGA, ICP, AAS, and VSM. SEM images of this catalyst demonstrate that the particles size are less than 100 nm in diameter VSM curve of the catalyst shows that this catalyst can be recovered using an external magnet; therefore, this catalyst can be reused for several times without significant loss of its catalytic efficiency or palladium leaching. Also, all products were obtained in high TON and TOF numbers, which reveals this catalyst has high activity and selectivity in described coupling reactions. Heterogeneity and stability of this nanocatalyst were confirmed by hot filtration test and AAS technique.4-Bromobenzonitrile(cas: 623-00-7Formula: C7H4BrN) was used in this study.

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

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,
Nitriles – Chemistry LibreTexts

《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:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Synthesis of difluoromethyl and deuterium-labeled difluoromethyl thioethers from aliphatic electrophiles》 was published in Chemical Communications (Cambridge, United Kingdom) in 2020. These research results belong to Ding, Tianqi; Jiang, Lvqi; Yi, Wenbin. SDS of cas: 17201-43-3 The article mentions the following:

A one-pot difluoromethylthiolation of alkyl electrophiles with thiourea and di-Et bromodifluoromethylphosphonate is described. The transition-metal-free approach, readily available reagents, and mild conditions provide a practical way for the synthesis of difluoromethyl thioethers. By changing the “”H”” source to the most commonly used “”D”” sources CD3OD and D2O, this strategy enables efficient synthesis of SCF2D-substituted mols. in good yields with high levels of D incorporation. In addition to this study using 4-Cyanobenzyl bromide, there are many other studies that have used 4-Cyanobenzyl bromide(cas: 17201-43-3SDS of cas: 17201-43-3) was used in this study.

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.SDS of cas: 17201-43-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zhang, Linlin; Qi, Lin; Chen, Jia-Min; Dong, Wei; Fang, Zhuo-Yue; Cao, Tong-Yang; Li, Wei; Wang, Li-Jing published their research in Chemical Communications (Cambridge, United Kingdom) in 2021. The article was titled 《Preparation of selenyl 1,3-oxazines via PhICl2/Cu2O-promoted aminoselenation of O-homoallyl benzimidates with diselenides》.Computed Properties of C7H4FN The article contains the following contents:

A practical electrophilic aminoselenation of O-homoallyl benzimidate with diselenides promoted by PhICl2/Cu2O had been developed. The easily available and stable diselenides were used as selenium sources. Various selenyl 1,3-oxazines I [Ar = Ph, 4-MeC6H4, 2-naphthyl, etc.; R1 = H, Me; R2 = H, Ph; R3 = Me, n-Bu, Ph, etc.], which were important frameworks in medicinal and biol. chem., were easily obtained in moderate to good yields for the first time. Easy scaleup and scalability made this method attractive for the preparation of other valuable organoselenides. The experimental process involved the reaction of 4-Fluorobenzonitrile(cas: 1194-02-1Computed Properties of C7H4FN)

4-Fluorobenzonitrile(cas: 1194-02-1) is used in the synthesis of flurenones, pharmaceutical prerequisites, as well as opiod receptor antagonists.Computed Properties of C7H4FN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Zhu, Da-Liang; Jiang, Shan; Young, David James; Wu, Qi; Li, Hai-Yan; Li, Hong-Xi published an article in Chemical Communications (Cambridge, United Kingdom). The title of the article was 《Visible-light-driven C(sp2)-H arylation of phenols with arylbromides enabled by electron donor-acceptor excitation》.Related Products of 2042-37-7 The author mentioned the following in the article:

A catalyst-free visible-light-driven C(sp2)-H arylation of unprotected phenols ROH (R = Ph, naphthalen-2-yl, 3,5-dibromophenyl, etc.) with arylbromides R1Br (R1 = 4-cyclopropanecarbonylbenzen-1-yl, 2-cyanobenzen-1-yl, 3-cyano-5-(trifluoromethyl)phenyl, etc.) to give 2-arylated phenols RR1 have been developed. This reaction proceeds through the excitation of an electron donor-acceptor complex between a phenolate and arylbromide, electron transfer, and debrominative C(sp2)-C(sp2) coupling. The results came from multiple reactions, including the reaction of 2-Bromobenzonitrile(cas: 2042-37-7Related Products of 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.Related Products of 2042-37-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Category: nitriles-buliding-blocksIn 2020 ,《Synthesis, Characterization, Antimicrobial Activity and Anticancer of Some New Pyrazolo[1,5-a]pyrimidines and Pyrazolo[5,1-c]1,2,4-triazines》 appeared in Medicinal Chemistry (Sharjah, United Arab Emirates). The author of the article were Hosny, Mona A.; Zaki, Yasser H.; Mokbel, Wafaa A.; Abdelhamid, Abdou O.. The article conveys some information:

Background: Pyrazole and its derivatives are known to exhibit significant biol. and pharmacol. activities such as anticancer, anti-inflammatory, antioxidant, antibacterial, analgesic, antiviral, antimicrobial, antifungal, anti-glycemic, antiamoebic, and antidepressive. Considering the immense biol. properties, pyrazole is one of the most widely studied nitrogen- containing heterocyclic nuclei. Fused pyrazole derivatives are composed of the pyrazole nucleus attached to other heterocyclic moieties. Objective: The objective of this article is the synthesis of some new pyrazolo[1,5-a]pyrimidine and pyrazolo[5,1-c]1,2,4-triazine derivatives with potential anticancer and antimicrobial activities. Methods: The in vitro growth inhibitory rates (%) and inhibitory growth activity (as measured by IC50) of the newly synthesized compounds were determined against the MCF-7 human breast carcinoma cell line in comparison with the well-known anticancer drug doxorubicin as the standard, using the MTT viability assay. The data generated were used to plot a dose-response curve from which the concentration (μM) of tested compounds required to kill 50% of the cell population (IC50) was determined Cytotoxic activity was expressed as the mean IC50 of three independent experiments The difference between inhibitory activities of all compounds with different concentrations was statistically significant p < 0.001. All compounds were structurally characterized by different spectroscopic techniques EI-MS, 1H-NMR, and 13C-NMR, and evaluated for their anticancer and antimicrobial activities (antibacterial and antifungal). Results: Several pyrazolo[1,5-a]pyrimidine derivatives were synthesized from the reaction of 2-(4- (5-amino-1H-pyrazol-3-yl)phenyl)-1H-indene-1,3(2H)-dione with the appropriate active methylene compounds in boiling ethanol. Also, pyrazolo[5,1-c]triazines were obtained through the reaction of 2-(4-(5-(chlorodiazenyl)-1H-pyrazol-3-yl)phenyl)-1H-indene-1,3(2H)-dione with various active methylene compounds in ethanol containing sodium acetate at 0-5 °C. The structures of the newly synthesized compounds were elucidated on the basis of elemental anal., spectral data, and alternative synthetic routes whenever possible. The newly synthesized compounds were evaluated for their antitumor activity against a breast cancer cell line (MCF-7) and a human colon cancer cell line (HCT-116). The results revealed that the tested compounds showed high variation in the inhibitory growth rates and activities against the tested tumor cell lines. All newly synthesized compounds screen towards microorganisms e.g. Gram-neg. bacteria, Gram-pos. bacteria, and Fungi. Conclusion: 2-(4-(5-Amino-1H-pyrazol-3-yl)phenyl)isoindoline-1,3-dione proved to be a useful precursor for the synthesis of various pyrazolo[1,5-a]pyrimidine and pyrazolo[5,1-c]-1,2,4-triazines. The structures of the newly synthesized compounds were confirmed by spectral data and elemental analyses. The newly synthesized compounds were tested in vitro against the MCF-7, HCT-116 human cancer cell line and compared with doxorubicin as the standard, using the MTT viability assay. Most of the tested compounds were found to have moderate to high anticancer activity. The results came from multiple reactions, including 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 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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts