Month: October 2022

In 2014,Yan, Zi-Hong; Wu, Hai-Qiu; Chen, Wen-Xue; Wu, Yan; Piao, Hu-Ri; He, Qiu-Qin; Chen, Fen-Er; De Clercq, Erik; Pannecouque, Christophe published 《Synthesis and biological evaluation of CHX-DAPYs as HIV-1 non-nucleoside reverse transcriptase inhibitors》.Bioorganic & Medicinal Chemistry published the findings.Product Details of 31938-07-5 The information in the text is summarized as follows:

A series of new diarylpyrimidines (DAPYs) characterized by a halogen atom on the methylene linker between wing I and the central pyrimidine ring was synthesized and evaluated for their anti-HIV activity in MT-4 cell cultures. The two most promising compounds 7f and 7g showed excellent activity against wild-type HIV-1 with low nanomolar EC50 values of 0.005 and 0.009μM, resp., which were comparable to or more potent than all the reference drugs zidovudine (AZT), lamivudine (3TC), nevirapine (NEV), efavirenz (EFV), delavirdine (DLV) and etravirine (ETV). In particular, 7g also displayed strong activity against the double mutant strain 103N + 181C with an EC50 value of 8.2μM. The preliminary structure-activity relationship (SAR) and mol. docking anal. of this new series of CHX-DAPYs were also investigated. In the part of experimental materials, we found many familiar compounds, such as 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Product Details of 31938-07-5)

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.Product Details of 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2014,Yan, Zi-Hong; Huang, Xia-Yun; Wu, Hai-Qiu; Chen, Wen-Xue; He, Qiu-Qin; Chen, Fen-Er; De Clercq, Erik; Pannecouque, Christophe published 《Structural modifications of CH(OH)-DAPYs as new HIV-1 non-nucleoside reverse transcriptase inhibitors》.Bioorganic & Medicinal Chemistry published the findings.Product Details of 31938-07-5 The information in the text is summarized as follows:

A series of CR2(OH)-diarylpyrimidine derivatives (CR2(OH)-DAPYs) featuring a hydrophobic group at CH(OH) linker between wing I and the central pyrimidine were synthesized and evaluated for their anti-HIV activity in MT-4 cell cultures. All the target compounds except for compound 3k displayed inhibitory activity against HIV-1 wild-type with EC50 values ranging from 7.21 ± 1.99 to 0.067 ± 0.006μM. Among them, compound 3d showed the most potent anti-HIV-1 activity (EC50 = 0.067 ± 0.006μM, SI > 592), which was approx. 2-fold more potent than the reference drugs nevirapine (NVP) and delavirdine (DLV) in the same assay. In addition, the binding modes with HIV-1 RT and the preliminary SAR studies of these new derivatives were also investigated.2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Product Details of 31938-07-5) 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.Product Details of 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2018,Zhou, Qiang; Zhu, Jinjin; Chen, Jinglei; Ji, Peng; Qiao, Chunhua published 《N-Arylsulfonylsubstituted-1H indole derivatives as small molecule dual inhibitors of signal transducer and activator of transcription 3 (STAT3) and tubulin》.Bioorganic & Medicinal Chemistry published the findings.Computed Properties of C7H3BrFN The information in the text is summarized as follows:

Signal transducer and activator of transcription (STAT3) is a proposed therapeutic target for the development of anti-cancer agents. In this report, a series of N-arylsulfonylsubstituted-1H indole derivatives were designed and synthesized as STAT3 inhibitors, their anti-proliferative activities were evaluated against a number of tumor cells, some potent compounds exhibited IC50 values less than 10μM. The most potent compound 4a was further confirmed to inhibit STAT3 phosphorylation at Tyr705. It was further revealed that 4a arrested the cell cycle at the G2/M phase and inhibited tubulin polymerization This study describes a series of N-arylsulfonylsubstituted-1H indole derivatives as potent anti-cancer agents targeting both STAT3 and tubulin. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Computed Properties of C7H3BrFN)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Computed Properties of C7H3BrFN 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Sulfuryl Fluoride Mediated Conversion of Aldehydes to Nitriles》 were Gurjar, Jitendra; Bater, Jorick; Fokin, Valery V.. And the article was published in Chemistry – A European Journal in 2019. Electric Literature of C7H4BrN The author mentioned the following in the article:

Aliphatic, aromatic, and heteroaromatic aldehydes were readily converted to corresponding nitriles in a one-pot reaction sequence with hydroxylamine and sulfuryl fluoride. The reaction proceeds at room temperature, does not require metal catalysts and special precautions, and produces nitriles in excellent yields. It is compatible with a variety of functional groups, can be performed in aqueous and organic solvents, and is readily scalable to multigram quantities. Mild conditions and high selectivity of the reaction enabled the construction of polyfunctional probes containing nitrile, alkyne, azide, and fluorosulfate groups for further orthogonal derivatization. The experimental part of the paper was very detailed, including the reaction process 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

The author of 《In-situ ultrasonic synthesis of Palladium nanorods into mesoporous channel of SBA-15 and its enhanced catalytic activity for Suzuki coupling reaction》 were Li, Jiazhe; Bai, Xuefeng; Lv, Hongfei. And the article was published in Microporous and Mesoporous Materials in 2019. Synthetic Route of C7H4BrN The author mentioned the following in the article:

Palladium nanorods (PdNRs) into mesoporous channels of SBA-15 nanocatalyst (PdNRs/SBA-15) were synthesized by a green and surfactant-free ultrasonic method without any surfactants and complex chem. modification and chem. method in absence of ultrasound, resp. The PdNRs/SBA-15 catalysts were characterized by XRD, TEM, XPS, N2 absorption-desorption and FT-IR anal. The results showed that PdNRs with 15.96 ± 3.89 nm long and 5.69 nm wide were highly dispersed into mesoporous channels exploiting the confinement effect of SBA-15 pore channel, while reunited PdNPs were distributed on the outside surface of SBA-15 in PdNPs/SBA-15 prepared by chem. method. The in-situ ultrasonic reduction of PdNRs/SBA-15 by the reductive radical (induced by ultrasonic process) was good for higher dispersion of Pd species and the formation of Pd species inside the mesoporous channel of SBA-15 without any structure-directing agents or surfactants. The yield of Suzuki coupling reaction between 4-bromotoluene and phenylboronic acid catalyzed by PdNRs (5)/SBA-15 reached 96.4%, which was much higher than that of PdNPs(5)/SBA-15 prepared without ultrasound (76.3%). PdNRs (5)/SBA-15 could be reused up to five times without a significant activity loss due to the strong chem. interaction and the unblocked channel. The experimental part of the paper was very detailed, including the reaction process of 4-Bromobenzonitrile(cas: 623-00-7Synthetic Route of C7H4BrN)

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

Choudhury, Shubhranshu Shekhar; Mahapatra, Shivam; Biswal, Himansu S. published an article in 2022. The article was titled 《Hydrogen bond mediated conversion of benzenenitriles and arylacetonitriles to amides: an “”on/in-water”” reaction strategy》, and you may find the article in Green Chemistry.COA of Formula: C7H4BrN The information in the text is summarized as follows:

Owing to the myriad of applications that amides have, hydration of nitriles has emerged as one of the most preferred atom-efficient synthesis methods. Being kinetically slow, this strategy requires some efficient catalysts. Herein, authors discovered choline hydroxide as an environmentally benign, metal-free and inexpensive catalyst for the hydration of aromatic and heteroaromatic nitriles on/in water with excellent yields. All the reactions proceeded under mild/moderate conditions, facilitated by the hydrogen bonds between the catalyst and the reactant or intermediate. D. functional theory (DFT) studies were used to propose the plausible reaction mechanism, which was further corroborated with kinetics measurements using quant. 19F NMR spectroscopy, thereby revealing the presence of H-bond mediated catalysis which brought down the activation energy barrier even lower than those in previous reports on using H2SO4 or Ru(OH)x/Al2O3 as catalysts. This work offers an “”on/in-water”” reaction strategy for the efficient hydration of nitriles and will pave the path towards novel routes for the com. synthesis of amides. In the experiment, the researchers used 2-Bromobenzonitrile(cas: 2042-37-7COA of Formula: 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.COA of Formula: C7H4BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Moeini, Nazanin; Ghadermazi, Mohammad; Molaei, Somayeh published an article in Journal of Molecular Structure. The title of the article was 《Synthesis and characterization of magnetic Fe3O4@Creatinine@Zr nanoparticles as novel catalyst for the synthesis of 5-substituted 1H-tetrazoles in water and the selective oxidation of sulfides with classical and ultrasonic methods》.Reference of 2-Bromobenzonitrile The author mentioned the following in the article:

Tetrazoles and sulfoxide compounds have a wide range of applications in industries and are of great expectation to be environmentally friendly and cost-effective. This paper reports the introduction of zirconium supported on Fe3O4 nanoparticles through creatinine post-functionalization modification of Fe3O4 (Fe3O4@Creatinine@Zr). The Fe3O4@Creatinine@Zr was characterized by a vibrating sample magnetometer, X-ray powder diffractometry, Fourier transforms IR, scanning electron microscope, energy dispersive X-Ray anal., thermogravimetric anal., and inductively coupled plasma. Fourier transform-IR spectroscopy results confirmed that creatinine was successfully immobilized on the surface of Fe3O4-Cl with the presence of ν(C = N), and ν(C = O) bands of creatinine. X-ray diffraction data confirmed that the crystalline phase of Fe3O4 was not destroyed after modification. Vibrating sample magnetometer anal. showed that the saturation magnetization of the Fe3O4@Creatinine@Zr was 28.6 emu/g. The SEM-EDX results revealed that the zirconium complex was successfully incorporated into the structure of Fe3O4. This catalyst displayed high catalytic performance in the synthesis of 5-substituted 1H-tetrazoles and the selective oxidation of sulfides with classical and ultrasonic methods. The catalyst conferred strong Lewis’s acidity sites for the activity and selectivity of the reactions. The obtained results showed that the fast oxidation of sulfides occurred with 0.2 mmol g -1 of zirconium immobilized on the Fe3O4 nanoparticle at optimum condition (sulfide (1 mmol), H2O2 (0.6 mL), ethanol (3 mL) and catalyst (Fe3O4@Creatinine@Zr, 60 mg) at room temperature). The results showed that ultrasonic was an appropriate method for the oxidation of sulfides to the related sulfoxide at the optimum condition. The 5-substituted 1H-tetrazoles were afforded at optimum condition (nitrile (1 mmol), NaN3 (1.2 mmol), H2O (3 mL), catalyst (100 mg) at 90°C). The catalyst was separated by simple recovery and reused for seven cycles without any remarkable decrease in the catalysis activity and selectivity. The output of this research can open a window for the synthesis the other organic materials under mild condition. In the experimental materials used by the author, we found 2-Bromobenzonitrile(cas: 2042-37-7Reference 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.Reference of 2-Bromobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Kulkarni, Pravin S.; Sarda, Swapnil R.; Khandebharad, Amol U.; Farooqui, Mazahar; Agrawal, Brijmohan R. published an article in Asian Journal of Chemistry. The title of the article was 《Synthesis and biological screening of novel 5-(5-aryl-1-phenyl-1H-pyrazol-3-yl)-3-aryl-1,2,4-oxadiazole derivatives》.Safety of 4-Fluorobenzonitrile The author mentioned the following in the article:

A new series of 5-(5-aryl-1-phenyl-1H-pyrazol-3-yl)-3-aryl-1,2,4-oxadiazole I [R = H, 4-Cl, 3,4-(OCH3)2; R1 = H, 4-F, 2-CH3, 3-CH3, 4-CH3] have been synthesized by a cyclocondensation reaction of Et 5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carboxylate II with aryl imidoxime R1C6H4C(=NOH)NH2. The newly synthesized pyrazolyl-1,2,4-oxadiazole derivatives I were characterized by spectroscopic techniques and screened for in vitro antibacterial activity against Bacillus subtilis (NCIM 2063), Staphylococcus albus (NCIM 2178), Escherichia coli (NCIM 2574), Proteus mirabilis (NCIM 2388) and in vitro antifungal activity against Aspergillus niger (ATCC 504) Candida albicans (NCIM 3100). The experimental process involved the reaction of 4-Fluorobenzonitrile(cas: 1194-02-1Safety of 4-Fluorobenzonitrile)

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.Safety of 4-Fluorobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 105942-08-3In 2018 ,《Palladium-Catalyzed Tandem Reaction of Quinazolinone-Based Nitriles with Arylboronic Acids: Synthesis of 2-(4-Arylquinazolin-2-yl)anilines》 appeared in Advanced Synthesis & Catalysis. The author of the article were Zhang, Yetong; Shao, Yinlin; Gong, Julin; Hu, Kun; Cheng, Tianxing; Chen, Jiuxi. The article conveys some information:

A palladium-catalyzed tandem reaction of 2-(quinazolinone-3(4H)-yl)benzonitriles with arylboronic acids has been developed, allowing access to a class of 2-(4-arylquinazolin-2-yl)anilines that were often difficult to prepare using previous methods. In particular, the newly produced amino group is amenable to further synthetic elaborations, thereby broadening the diversity of the products. The structure of the newly synthesized 2-(4-arylquinazolin-2-yl)anilines was unambiguously confirmed by X-ray crystallog. Moreover, a possible mechanism for the formation of 2-(4-arylquinazolin-2-yl)anilines is discussed. The experimental process involved the reaction of 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Related Products of 105942-08-3)

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Safety of 2-BromobenzonitrileIn 2022 ,《VU6036720: the first potent and selective in vitro inhibitor of heteromeric Kir4.1/5.1 inward rectifier potassium channels》 appeared in Molecular Pharmacology. The author of the article were McClenahan, Samantha J.; Kent, Caitlin N.; Kharade, Sujay V.; Isaeva, Elena; Williams, Jade C.; Han, Changho; Terker, Andrew; Gresham, Robert III; Lazarenko, Roman M.; Days, Emily L.; Romaine, Ian M.; Bauer, Joshua A.; Boutaud, Olivier; Sulikowski, Gary A.; Harris, Raymond; Weaver, C. David; Staruschenko, Alexander; Lindsley, Craig W.; Denton, Jerod S.. The article conveys some information:

Heteromeric Kir4.1/Kir5.1 (KCNJ10/KCNJ16) inward rectifier potassium (Kir) channels play key roles in the brain and kidney, but pharmacol. tools for probing their physiol. and therapeutic potential have not been developed. Here, we report the discovery, in a high-throughput screening of 80,475 compounds, of the moderately potent and selective inhibitor VU0493690, which we selected for characterization and chem. optimization. VU0493690 concentration-dependently inhibits Kir4.1/5.1 with an IC50 of 0.96 μM and exhibits at least 10-fold selectivity over Kir4.1 and ten other Kir channels. Multidimensional chem. optimization of VU0493690 led to the development of VU6036720, the most potent (IC50 = 0.24 μM) and selective (>40-fold over Kir4.1) Kir4.1/5.1 inhibitor reported to date. Cell-attached patch single-channel recordings revealed that VU6036720 inhibits Kir4.1/5.1 activity through a reduction of channel open-state probability and single-channel current amplitude. Elevating extracellular potassium ion by 20 mM shifted the IC50 6.8-fold, suggesting that VU6036720 is a pore blocker that binds in the ion-conduction pathway. Mutation of the “”rectification controller”” asparagine 161 to glutamate (N161E), which is equivalent to small-mol. binding sites in other Kir channels, led to a strong reduction of inhibition by VU6036720. Renal clearance studies in mice failed to show a diuretic response that would be consistent with inhibition of Kir4.1/5.1 in the renal tubule. Drug metabolism and pharmacokinetics profiling revealed that high VU6036720 clearance and plasma protein binding may prevent target engagement in vivo. In conclusion, VU6036720 represents the current state-of-the-art Kir4.1/5.1 inhibitor that should be useful for probing the functions of Kir4.1/5.1 in vitro and ex vivo. In the part of experimental materials, we found many familiar compounds, such as 2-Bromobenzonitrile(cas: 2042-37-7Safety of 2-Bromobenzonitrile)

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.Safety of 2-Bromobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts