Month: October 2022

《Synthesis and evaluation of new 1,2,4-oxadiazole based trans-acrylic acid derivatives as potential PPAR-α/γ dual agonists》 was written by Kaur, Paranjeet; Bhat, Zahid Rafiq; Bhat, Sana; Kumar, Rakesh; Kumar, Rajan; Tikoo, Kulbhushan; Gupta, Jeena; Khurana, Navneet; Kaur, Jaskiran; Khatik, Gopal L.. Formula: C7H4FN And the article was included in Bioorganic Chemistry in 2020. The article conveys some information:

New 1,2,4-oxadiazole-containing trans-cinnamic acids I (R = Ph, 2-MeOC6H4, 3-MeOC6H4, 4-FC6H4, 4-ClC6H4, 4-MeC6H4) were synthesized and evaluated as dual PPAR-α/γ agonists. Using AutoDock Vina, compounds I were identified as potential PPAR α/γ dual agonists comparable to PPAR γ agonist Pioglitazone on the basis of their affinity scores, in-silico toxicity and in-silico ADME properties. These compounds showed better calculated lipophilicity (iLogP), which was found to be from 0.92 to 3.19. Compounds I (R = Ph, 4-FC6H4) were found to be most potent on both PPAR α and γ receptors with EC50 of 0.07 ± 0.0006μM, 0.06 ± 0.0005μM and 0.781 ± 0.008μM, 3.29μM ± 0.03 resp. compared to pioglitazone having EC50 of 32.38 ± 0.2 and 38.03 ± 0.13 for both receptors. The in-vivo evaluation found to reduce the plasma glucose level and total cholesterol level significantly in diabetic rats compared to pioglitazone at 5 mg/kg/day dose for 7 days of treatment. Thus, trans-cinnamic acids I can be further developed as oral therapeutic agents for diabetic interventions as PPAR α/γ dual agonists. 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

Product Details of 1194-02-1In 2021 ,《Pyridine-Bridged Polybenzimidazole for Use in High-Temperature PEM Fuel Cells》 appeared in ACS Applied Energy Materials. The author of the article were Harilal; Shukla, Avanish; Ghosh, Prakash Chandra; Jana, Tushar. The article conveys some information:

Although pyridine bridged oxypolybenzimidazole (PyOPBI) membranes are considered to be promising high-temperature proton exchange membrane (HT-PEM) materials that have the potential to overcome many obstacles such as solubility, membrane processability, cost, etc., of the mainstream conventional polybenzimidazole (PBI)-based HT-PEM, the weak structural stability of PyOPBI in concentrated phosphoric acid (PA) and poor dimensional and mech. stability have been the crucial issues restraining the performance. To mitigate these bottlenecks, in this work, we successfully synthesized three types of PyOPBIs with flexible aryl ether backbones and bulky substituents by polycondensation reaction of various aryl diacids and pyridine-bridged tetraamine 2,6-bis(3′,4′-diaminophenyl)-4-phenylpyridine (PyTAB) in Eaton’s reagent followed by casting as HT-PEMs. Three designed bulky substitute containing PyOPBI membranes showed considerably high PA loading capacity (16-22 mol of PA/repeat unit) and proton conductivity (0.04-0.078 S/cm) at 180°C as compared to earlier reported unsubstituted PyOPBI membranes (14 mol of PA/repeat unit and 0.007 S/cm at 180°C). In addition, the obtained membranes showcased good chem., mech., thermal, and long-term conductivity stabilities and outstanding stability in concentrated PA. The pendent groups and the bulkiness of the backbone are believed to be the cause behind better stability and facilitating proton transport that results in higher proton conductivity The single cell made from the membrane electrode assembly of these bulky substituted PyOPBI membranes displayed a peak power d. in the range of 144-240 mW cm-2 under H2/O2 at 160°C, which is considerably higher than that for unsubstituted PyOPBI membrane (90.4 mW cm-2). Overall, the current results provide an effective strategy to explore the benefits of structural modulation of PyOPBI using various structurally divergent diacids to enhance HT-PEM properties and suggest a scalable route for the advancement of PBI-based HT-PEM fuel cells. In the experiment, the researchers used 4-Fluorobenzonitrile(cas: 1194-02-1Product Details 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.Product Details of 1194-02-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of C7H4FNIn 2022 ,《Development of a ruthenium-aquo complex for utilization in synthesis and catalysis for selective hydration of nitriles and alkynes》 was published in New Journal of Chemistry. The article was written by Saha, Rumpa; Mukherjee, Aparajita; Bhattacharya, Samaresh. The article contains the following contents:

Synthesis of a ruthenium(II)-aquo complex bearing 2,2′ : 6′,2”-terpyridine and a 1,4-diazabutadiene ligand, and exploration of its synthetic utility and catalytic activity are described. Ag+-assisted displacement of the coordinated chloride from the previously reported [Ru(trpy)(L-OCH3)Cl]ClO4 complex [denoted as complex 1; where L-OCH3 represents 1,4-di-(p-methoxyphenyl)azabutadiene] in aqueous ethanol affords the [Ru(trpy)(L-OCH3)(H2O)]2+ complex cation, which was isolated as a perchlorate salt (complex 1a). Complex 1a undergoes facile substitution of the aquo ligand by neutral monodentate ligands giving complexes of type [Ru(trpy)(L-OCH3)(L’)]2+, also isolated as perchlorate salts [L’ = acetonitrile (complex 1b); L’ = DMSO (complex 1c); L’ = 4-picoline (complex 1d) and L’ = PPh3 (complex 1e)]. Complexes 1b-1e can also be synthesized directly from complex 1via the Ag+-assisted displacement of coordinated chloride by the resp. monodentate L’ ligand. The crystal structures of complexes 1a, 1b and 1d were determined The complexes show intense absorptions in the visible and UV regions, the origin of which was probed into with the help of the TDDFT method. Cyclic voltammetry of the complexes shows an irreversible Ru(II)-Ru(III) oxidation within 0.9-1.6 v vs. SCE, and two ligand (trpy and L-R) based reductions on the neg. side of the SCE. The aquo-complex (1a) is found to serve as an efficient catalyst for the hydration of aryl nitriles to the corresponding amides, and aryl alkynes to aldehydes. In the experiment, the researchers used 4-Fluorobenzonitrile(cas: 1194-02-1Synthetic Route of 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.Synthetic Route of C7H4FN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Product Details of 53005-44-0On September 21, 2012 ,《Pd(OAc)2-Catalyzed Alkoxylation of Arylnitriles via sp2 C-H Bond Activation Using Cyano as the Directing Group》 was published in Journal of Organic Chemistry. The article was written by Li, Wu; Sun, Peipei. The article contains the following contents:

A Pd(OAc)2-catalyzed ortho-alkoxylation of arylnitrile was described. Using cyano as a directing group, the aromatic C-H bond can be functionalized efficiently to generate ortho-alkoxylated arylnitrile derivatives with moderate yields. The optimal reaction conditions were identified after examining various factors such as oxidant, solvent, and reaction temperature The method was compatible to the arylnitriles with either electron-withdrawing or electron-donating groups. The experimental process involved the reaction of 2-Methoxy-6-methylbenzonitrile(cas: 53005-44-0Product Details of 53005-44-0)

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. Product Details of 53005-44-0 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.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Gladkov, Anton A.; Chernov, Grigory N.; Levin, Vitalij V.; Kokorekin, Vladimir A.; Dilman, Alexander D. published their research in Organic Letters on December 17 ,2021. The article was titled 《Photoredox Activation of Organozinc Reagents: Barbier-Type Reaction of Alkyl Halides with α-(Trifluoromethyl)styrenes》.Safety of 2,4,6-Tris(diphenylamino)-3,5-difluorobenzonitrile The article contains the following contents:

Organozinc reagents were activated under blue light irradiation using an organic photocatalyst to generate alkyl radicals. The radicals were trapped by α-(trifluoromethyl)styrenes leading to gem-difluorinated products after elimination of fluoride. The reaction was conveniently performed under Barbier conditions starting from organic iodides and bromides and elemental zinc. The experimental part of the paper was very detailed, including the reaction process of 2,4,6-Tris(diphenylamino)-3,5-difluorobenzonitrile(cas: 1403850-00-9Safety of 2,4,6-Tris(diphenylamino)-3,5-difluorobenzonitrile)

2,4,6-Tris(diphenylamino)-3,5-difluorobenzonitrile(cas: 1403850-00-9) is cyanoarene-based donor-acceptor photocatalyst developed by the Zeitler group. While this catalyst has a balanced redox profile, allowing for its use in a variety of transformations, it stands out as the most reducing catalyst of the family.Safety of 2,4,6-Tris(diphenylamino)-3,5-difluorobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Molecular dynamics of 4-cyano-3-fluorophenyl 4-butylbenzoate (4CFPB) glass-forming liquid crystal in unidirectional silicon nanopores》 were Rozwadowski, Tomasz; Massalska-Arodz, Maria; Krawczyk, Jan; Juszynska-Galazka, Ewa. And the article was published in Liquid Crystals in 2014. Application of 86776-52-5 The author mentioned the following in the article:

Complex dynamics of 4-cyano-3-fluorophenyl 4-butylbenzoate (4CFPB) in cylindrical non-intersecting nanopores, mean diameters 6 nm and 8 nm was studied by broadband dielec. spectroscopy. For relaxation processes ascribed to the flip-flop, reptation-like and collective motions, the short- and long-range time correlations were estimated and discussed. Size effect and differences in ordering of mols. in pores during cooling and heating runs were found. On cooling, vitrification occurred in pores, similarly as in bulk, while on heating two-step ordering of mols. along pore walls was evidenced by subsequent diminishing of ε”max(T). Explanation based on data concerning solid state polymorphism of 4CFPB in bulk is given. The experimental part of the paper was very detailed, including the reaction process of 4-Cyano-3-fluorophenyl 4-butylbenzoate(cas: 86776-52-5Application of 86776-52-5)

4-Cyano-3-fluorophenyl 4-butylbenzoate(cas: 86776-52-5) is a member of aromaticfluorinated building blocks. Depending on which substituents are present, fluoroaromatic intermediates can be converted into fluorinated or fluorine-free commercial end products.Fluorine-containing aromatics have been incorporated into drugs (hypnotics, tranquilizers, antiinflammatory agents, analgesics, antibacterials).Application of 86776-52-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2017,Hammann, Jeffrey M.; Thomas, Lucie; Chen, Yi-Hung; Haas, Diana; Knochel, Paul published 《Cobalt-Catalyzed Cross-Couplings of Bench-Stable Alkynylzinc Pivalates with (Hetero)Aryl and Alkenyl Halides》.Organic Letters published the findings.Product Details of 105942-08-3 The information in the text is summarized as follows:

In the presence of CoCl2·2LiCl and TMEDA, selected terminal alkynylzinc pivalates underwent coupling with electron-deficient aryl and heteroaryl chlorides, bromides, and iodides and two alkenyl bromides to yield aryl alkynes and enynes chemoselectively; coupling of a silylethynylzinc pivalate with an (E)-alkenyl bromide and a (Z)-bromoacrylate yielded the corresponding (E)-enyne and (Z)-enynoate in 99:1 dr. In the experiment, the researchers used many compounds, for example, 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 reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Product Details of 105942-08-3 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,CrystEngComm included an article by Gayathri, Parthasarathy; Karthikeyan, Subramanian; Pannipara, Mehboobali; Al-Sehemi, Abdullah G.; Moon, Dohyun; Anthony, Savarimuthu Philip. Related Products of 31938-07-5. The article was titled 《Aggregation-enhanced emissive mechanofluorochromic carbazole-halogen positional isomers: tunable fluorescence via conformational polymorphism and crystallization-induced fluorescence switching》. The information in the text is summarized as follows:

Carbazole-based donor-acceptor derivatives of halogen-substituted positional isomers were synthesized and the effect of the halogen and position on the solid-state fluorescence and mechanofluorochromism was explored. All compounds showed good solid-state fluorescence (Φf = 15.67 to 31.32%). Interestingly, the crystallization of the positional isomers produced concomitant blue and green fluorescent polymorphs and tunable solid-state fluorescence. Solid-state structural anal. revealed a subtle conformational change in the acceptor unit, which led to polymorphism and tunable fluorescence. Halogen substitution induced a higher conformational twist and a large fluorescence shift between the polymorphs. The supramol. interactions (H-bonding, C-H···π and π···π) observed in the crystal lattice rigidified the fluorophores and enhanced the solid-state fluorescence. Computational studies were performed to gain insights into the electronic energy level of the fluorophore and fluorescence modulation. All fluorophores showed mechanofluorochromism (MFC), reversible fluorescence switching, upon crushing and heating. The crushed solids also showed self-reversible fluorescence switching with a longer time. Interestingly, OFF-ON reversible fluorescence switching was also demonstrated by melting and warming/scratching. The powder X-ray diffraction studies supported self-reversible and crystallization-induced fluorescence switching. In the experimental materials used by the author, we found 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Related Products 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.Related Products of 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《2-Mercapto Benzthiazole Coupled Benzyl Triazoles as New COX-2 Inhibitors: Design, Synthesis, Biological Testing and Molecular Modeling Studies》 were Yatam, Satyanarayana; Jadav, Surender Singh; Gundla, Krishna Prasadh; Paidikondala, Kalyani; Ankireddy, Ashok Reddy; Babu, Bathini Nagendra; Ahsan, Mohamed Jawed; Gundla, Rambabu. And the article was published in ChemistrySelect in 2019. Recommanded Product: 4-Cyanobenzyl bromide The author mentioned the following in the article:

A series of 2-mercapto benzothiazole linked with triazoles I (R = 4-tert-butylphenyl, naphthalen-2-yl, 3,4-dichlorolphenyl, etc.) was designed based on our previous exptl. evaluation of benzothiazole allied oxadiazoles and synthesized in two step starting from the 2-mercaptan precursor. The insilico binding mode interpretations in both COX-1/COX-2 was investigated, and their probable binding energies were predicted and ADMET properties were calculated The mol. level interactions of the designed library indicated, the aryl ring united with triazole was occupying as mefenamic acid in COX-2 active site. All the benzothiazoles were evaluated for their COX inhibitory activities as per the standard protocol reported elsewhere. The compounds I (R = 2-chlorophenyl (A), 4-carboxyphenyl and 4-carbamoylphenyl) based benzothiazoles showed the most significant COX-2 inhibitory activity with an IC50 of 4.1, 4.3 and 5.4 μM resp. The time dependant increase in inhibition of inflammation of above COX-2 inhibitors in invivo anti-inflammatory evaluation was noticed. Addnl., I (R = 3-fluorophenyl) expressed the significant DPPH scavenging activity with 80.45 percent inhibition at 100 μM and an IC50 of 27.8 μM. Furthermore, the 50 ns mol. dynamic simulations of (A) to interpret the constant residue interactions that might liable for the COX selectivity were presented. Later, they also have been tested for cancer lines at NCI and the obtained data were provided. In the part of experimental materials, we found many familiar compounds, such as 4-Cyanobenzyl bromide(cas: 17201-43-3Recommanded Product: 4-Cyanobenzyl bromide)

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.Recommanded Product: 4-Cyanobenzyl bromide

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Synthesis and in-vitro anti-proliferative evaluation of some pyrazolo[1,5-a]pyrimidines as novel larotrectinib analogs》 was published in Bioorganic Chemistry in 2020. These research results belong to Attia, Mohamed H.; Elrazaz, Eman Z.; El-Emam, Soad Z.; Taher, Azza T.; Abdel-Aziz, Hatem A.; Abouzid, Khaled A. M.. Quality Control of 3-Oxo-3-phenylpropanenitrile The article mentions the following:

A series of pyrazolo[1,5-a]pyrimidine-3-carbonitriles I [R = H; Ar = 2-furanyl, Ph, 2-naphthalenyl, etc.] and pyrazolo[1,5-a]pyrimidine-3,6-dicarbonitriles I [R = cyano; Ar = 2-furanyl, Ph, 4-methoxyphenyl] was synthesized by the reaction of 5-amino-3-phenyl-1H-pyrazole-4-carbonitrile with 3-(dimethylamino)-1-arylprop-2-en-1-ones or 2-aryl-3-(dimethylamino)acrylonitriles, resp. In addition, 7-amino-5-oxo-2-phenyl-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile II was prepared from the reaction of dimethylformamide-dimethylacetal with Et cyanoacetate. The anticancer activity of the newly synthesized compounds against Huh-7, HeLa, MCF-7 and MDA-MB231 cell lines showed moderate activity of compound I [R = H, Ar = 4-chlorophenyl] as anti-proliferative agent against Huh-7 cell line with IC50 = 6.3μM when compared with doxorubicin (IC50 = 3.2μM). On the other hand, compound I [R = cyano, Ar = 4-methoxyphenyl] revealed potent anti-proliferative activity against HeLa cell line with IC50 = 7.8μM when compared with doxorubicinι (IC50 = 8.1μM). Also compound I [R = H, Ar = 2-naphthalenyl] exhibited a promising anti-proliferative activity against MCF-7 cell line (IC50 = 3.0μM) whereas IC50 of doxorubicin = 5.9μM, finally compounds I [R = H, Ar = 2-naphthalenyl] and I [R = cyano, Ar = 24-methoxyphenyl] have potent activity as anti-proliferative agents against MDA-MB231 cell line with IC50 = 4.32 and 5.74μM, resp. when compared with doxorubicin (IC50 = 6.0μM). The experimental part of the paper was very detailed, including the reaction process of 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Quality Control of 3-Oxo-3-phenylpropanenitrile)

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.Quality Control of 3-Oxo-3-phenylpropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts