Month: October 2022

COA of Formula: C8H6BrNIn 2020 ,《Regioselective 3-O-Substitution of Unprotected Thiodigalactosides: Direct Route to Galectin Inhibitors》 was published in Chemistry – A European Journal. The article was written by Vasicek, Tomas; Spiwok, Vojtech; Cerveny, Jakub; Petraskova, Lucie; Bumba, Ladislav; Vrbata, David; Pelantova, Helena; Kren, Vladimir; Bojarova, Pavla. The article contains the following contents:

The synthesis of tailored bioactive carbohydrates usually comprises challenging (de)protection steps, which lowers synthetic yields and increases time demands. We present here a regioselective single-step introduction of benzylic substituents at 3-hydroxy groups of β-D-galactopyranosyl-(1→1)-thio-β-D-galactopyranoside (TDG) employing dibutyltin oxide in good yields. These glycomimetics act as inhibitors of galectins-human lectins, which are bio-medically attractive targets for therapeutic inhibition in, for example, cancerogenesis. The affinity of the prepared glycomimetics to galectin-1 and galectin-3 was studied in enzyme-linked immunosorbent (ELISA)-type assays and their potential to inhibit galectin binding on the cell surface was shown. We used our original in vivo biotinylated galectin constructs for easy detection by flow cytometry. The results of the biol. experiments were compared with data from mol. modeling with both galectins. The present work reveals a facile and elegant synthetic route for the preparation of TDG-derived glycomimetics that exhibit differing selectivity and affinity to galectins depending on the choice of 3-O-substitution. The experimental part of the paper was very detailed, including the reaction process of 4-Cyanobenzyl bromide(cas: 17201-43-3COA of Formula: C8H6BrN)

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.COA of Formula: C8H6BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Name: 3-Oxo-3-phenylpropanenitrileIn 2019 ,《Synthesis and DNase I inhibitory properties of some 4-thiazolidinone derivatives》 was published in Journal of Cellular Biochemistry. The article was written by Kolarevic, Ana; Ilic, Budimir S.; Kocic, Gordana; Dzambaski, Zdravko; Smelcerovic, Andrija; Bondzic, Bojan P.. The article contains the following contents:

Twelve new thiazolidinones were synthesized and, together with 41 previously synthesized thiazolidinones, evaluated for inhibitory activity against DNase I (DNase I) in vitro. Ten compounds inhibited com. bovine pancreatic DNase I with an IC50 below 200 μM and showed to be more potent DNase I inhibitors than crystal violet (IC50 = 365.90 ± 47.33 μM), used as a pos. control. Moreover, three compounds were active against DNase I in rat liver homogenate, having an IC50 below 200 μM. (3-Methyl-1,4-dioxothiazolidin-2-ylidene)-N-(2-phenylethyl)ethanamide (41) exhibited the most potent DNase I inhibition against both com. and rat liver DNase I with IC50 values of 115.96 ± 11.70 and 151.36 ± 15.85 μM, resp. Site Finder and mol. docking defined the thiazolidinones interactions with the most important catalytic residues of DNase I, including the H-acceptor interaction with residues His 134 and His 252 and/or H-donor interaction with residues Glu 39 and Asp 168. The three most active compounds against both com. and rat liver DNase I (31, 38, and 41) exhibited favorable physico-chem., pharmacokinetic, and toxicol. properties. These observations could be utilized to guide the rational design and optimization of novel thiazolidinone inhibitors. Thiazolidinones as novel DNase I inhibitors could have potential therapeutic applications due to the significant involvement of DNase I in the pathophysiol. of many disease conditions. In the experiment, the researchers used 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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《C-H chlorination of (hetero)anilines via photo/organo co-catalysis》 was published in Organic & Biomolecular Chemistry in 2022. These research results belong to Xie, Wuchen; Wang, Meng; Yang, Siyu; Chen, Yadong; Feng, Jie; Huang, Yatian. Reference of 2-Amino-3-Bromo-5-chlorobenzonitrile The article mentions the following:

Herein, a photo-redox and organo co-catalyzed chlorination method for anilines to gave chloro-anilines ArNR1R2 [Ar = 4-ClC6H4, 3,4-di-Cl-5-FC6H2, 4-Cl-2,5-di-FC6H2, etc.; R1 = H, Me; R2 = H, Me, C(O)Me, Ph, pyrimidin-2-yl; R1R2 = (CH2)2N(CH3)(CH2)2] was disclose. This method had great substrate generality and excellent mono-chlorination selectivity. Another merit of this method was the late-stage modification of drug mols., which would be useful in medicinal chem.2-Amino-3-Bromo-5-chlorobenzonitrile(cas: 914636-84-3Reference of 2-Amino-3-Bromo-5-chlorobenzonitrile) was used in this study.

2-Amino-3-Bromo-5-chlorobenzonitrile(cas: 914636-84-3) belongs to anime. Nitrous acid converts secondary amines (aliphatic or aromatic) to N-nitroso compounds (nitrosamines): R2NH + HNO2 → R2N―NO. Some nitrosamines are potent cancer-inducing substances, and their possible formation is a serious consideration when nitrites, which are salts of nitrous acid, are present in foods or pharmaceutical preparations. Tertiary amines give rise to nitrosamines more slowly; an alkyl group is eliminated as an aldehyde or ketone, along with nitrous oxide, N2O.Reference of 2-Amino-3-Bromo-5-chlorobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Koeysal, Oguz; Okutan, Mustafa; San, S. Eren; Dabrowski, Roman; Ecevit, F. Necati published an article in Materials Chemistry and Physics. The title of the article was 《Molecular orientation and photorefractive effects in single-wall carbon nanotubes doped nitrile-ester mixture liquid crystals》.Computed Properties of C18H16FNO2 The author mentioned the following in the article:

The authors report the electrooptical properties of liquid crystal cells containing pure nitrile-ester mixture liquid crystal (NEMLC) and its doped form with 0.05% (weight/weight) single-wall C nanotubes (SWCNT). Diffraction efficiencies of 441-nm pump and 632-nm probe beams were measured in two-wave mixing experiment Efficiencies and rise time increase in SWCNT doped nematic liquid crystals. A maximum diffraction efficiency of ∼15% was found for cell doped with SWCNT, while cells without SWCNT had a maximum efficiency of 7%. Also photoconductivity in SWCNT doped liquid crystals is highly dependent on the light intensity. This is attributed to the doping, which enhances the efficient photo-charge generation, combined with enlarged conductivity After reading the article, we found that the author used 4-Cyano-3-fluorophenyl 4-butylbenzoate(cas: 86776-52-5Computed Properties of C18H16FNO2)

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).Computed Properties of C18H16FNO2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Aromatic amidines. Comparison of their ability to block respiratory syncytial virus induced cell fusion and to inhibit plasmin, urokinase, thrombin, and trypsin》 were Tidwell, R. R.; Geratz, J. D.; Dubovi, E. J.. And the article was published in Journal of Medicinal Chemistry in 1983. Category: nitriles-buliding-blocks The author mentioned the following in the article:

The title compounds I (R = H, H2NC:NH, NO2; R1 = H or H2NC:NH; R2 = H, Me, Et, benzyl, substituted benzyl; R3 = H, COEt; R4 = H, COH, Ac, COCF3, or Bz) some of which were prepared from the corresponding nitrile derivatives and benzimidazoles by a modified Pinner amidine synthesis, and investigated to determine if the correlation between inhibition of plasmin  [9001-90-5] and(or) urokinase  [9039-53-6] with fusion-blocking activity exists with these compounds 6-amidino-1H-indole-3-carboxaldehyde  [83783-19-1] Was a selective inhibitor of plasmin over thrombin  [9002-04-4], and 5-amidino-1-(4-amidino-2-chlorobenzyl)-1H-indole  [80531-08-4] is a potent new blocker of virus-induced cell fusion. In the experimental materials used by the author, we found 3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9Category: nitriles-buliding-blocks)

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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2005,Albrecht, Uwe; Goerdes, Dirk; Schmidt, Enrico; Thurow, Kerstin; Lalk, Michael; Langer, Peter published 《Synthesis and structure-activity relationships of 2-alkylidenethiazolidine-4,5-diones as antibiotic agents》.Bioorganic & Medicinal Chemistry published the findings.Computed Properties of C8H6BrN The information in the text is summarized as follows:

2-Alkylidenethiazolidine-4,5-diones were prepared by novel one-pot cyclizations of arylacetonitriles with isothiocyanates and Et 2-chloro-2-oxoacetate. The products show antibiotic activity against the Gram-pos. bacteria Bacillus subtilis and Staphylococcus aureus. The results came from multiple reactions, including the reaction of 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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2018,Kong, Weiguang; Zhou, Yao; Song, Qiuling published 《Lewis-acid Promoted Chemoselective Condensation of 2-Aminobenzimidazoles or 3-Aminoindazoles with 3-Ethoxycyclobutanones to Construct Fused Nitrogen heterocycles》.Advanced Synthesis & Catalysis published the findings.Name: 4-Bromo-2-fluorobenzonitrile The information in the text is summarized as follows:

A Lewis-acid promoted chemoselective condensation of 2-aminobenzimidazoles YNH2 (Y = benzoimidazol-2-yl, 5-fluoro-1H-benzoimidazol-2-yl, 5,6-diphenyl-1H-benzoimidazol-2-yl, etc.) or 3-aminoindazoles Y1NH2 (Y1 = 1H-indazol-3-yl, 1H-pyrazolo[3,4-b]pyridin-3-yl, 4-cyano-1H-pyrazole-3-yl, etc.) with 3-ethoxycyclobutanones I (R = H, CH3; X = CH3CHCH3, cyclobutanyl, phenylethyl, etc.) was presented. Diverse fused heterocycles benzo[4,5]-imidazo[1,2-a]pyrimidines II (R1 = H, 7-F, 8-Cl, 7,8-(C6H5)2, etc.) and pyrimido[1,2-b]-indazole derivatives III (R2 = CN, C(O)OCH2CH3, C(O)NH2; R2, R3 = -CH=CH-CH=CH-, -CH=C(OCH3)-CH=CH-, -CH=CH-CH=NH-, etc.) were obtained in moderate to high yields under mild conditions, and the reaction mechanism of which was in sharp contrast to previous [3+3] annulation reaction of 3-ethoxycyclobutanones. In the experiment, the researchers used 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Name: 4-Bromo-2-fluorobenzonitrile)

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.Name: 4-Bromo-2-fluorobenzonitrile 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 2018,Journal of Medicinal Chemistry included an article by Dianati, Vahid; Navals, Pauline; Couture, Frederic; Desjardins, Roxane; Dame, Anthony; Kwiatkowska, Anna; Day, Robert; Dory, Yves L.. Product Details of 105942-08-3. The article was titled 《Improving the Selectivity of PACE4 Inhibitors through Modifications of the P1 Residue》. The information in the text is summarized as follows:

Paired basic amino acid cleaving enzyme 4 (PACE4), a serine endoprotease of the proprotein convertases family, has been recognized as a promising target for prostate cancer. We previously reported a selective and potent peptide-based inhibitor for PACE4, named the multi-Leu peptide (Ac-LLLLRVKR-NH2 sequence), which was then modified into a more potent and stable compound named C23 with the following structure: Ac-DLeu-LLLRVK-Amba (Amba: 4-amidinobenzylamide). Despite improvements in both in vitro and in vivo profiles of C23, its selectivity for PACE4 over furin was significantly reduced. We examined other Arg-mimetics instead of Amba to regain the lost selectivity. Our results indicated that the replacement of Amba with 5-(aminomethyl)picolinimidamide increased affinity for PACE4 and restored selectivity. Our results also provide a better insight on how structural differences between S1 pockets of PACE4 and furin could be employed in the rational design of selective inhibitors. 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 OLED intermediate, Pharmaceutical, electronic and chemical intermediate.Product Details of 105942-08-3 It is used in the synthesis of heterocycles and liquid crystals.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,Asian Journal of Organic Chemistry included an article by Kim, Jihyeon; Golime, Gangadhararao; Kim, Hun Young; Oh, Kyungsoo. Safety of 4-Fluorobenzonitrile. The article was titled 《Copper(II)-Catalyzed Aerobic Oxidation of Amines: Divergent Reaction Pathways by Solvent Control to Imines and Nitriles》. The information in the text is summarized as follows:

The Cu(OAc)2-catalyzed aerobic oxidations of amines to imines RR1CH=NR2 [R = H, Me; R1 = Ph, 4-MeC6H4, 2-thienyl, etc.; R2 = cyclohexyl, Ph, Bn, etc.] and nitriles R3CN [R3 = n-heptyl, Ph, 2-thienyl, etc.] were identified under solvent control conditions and in the presence of mol. oxygen. By modulating the aerobic oxidation pathways of Cu(OAc)2 catalyst in different reaction solvents, the selective formations of homo-coupled imines, cross-coupled imines and nitriles were achieved from amine derivatives In the experiment, the researchers used 4-Fluorobenzonitrile(cas: 1194-02-1Safety of 4-Fluorobenzonitrile)

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,Journal of Medicinal Chemistry included an article by Pirzer, Anna S.; Lasch, Roman; Friedrich, Heike; Huebner, Harald; Gmeiner, Peter; Heinrich, Markus R.. COA of Formula: C8H6BrN. The article was titled 《Benzyl Phenylsemicarbazides: A Chemistry-Driven Approach Leading to G Protein-Biased Dopamine D4 Receptor Agonists with High Subtype Selectivity》. The information in the text is summarized as follows:

Many subtype-selective dopamine receptor ligands developed for the D2-D4 family incorporate a 1-arylpiperazine-derived primary recognition motif, which is connected to a lipophilic moiety occupying an extended binding pocket (EBP) of the receptor via an aliphatic linker of variable lengths. The evaluation of a novel group of dopamine receptor ligands now showed that highly subtype-selective ligands [up to Ki(D4.4) = 0.25 nM, D2L/D4.4 = 320, D3/D4.4 = 710 for APH199 (17)] can be obtained by choosing a relatively large and conformationally flexible 1-benzyl-1-phenylsemicarbazide substructure to fill the EBP. The novel chemotype APH199 (17) was found to act as a full agonist at the D4 receptor showing significant bias toward G protein activation over β-arrestin recruitment in comparison to quinpirole. In the experiment, the researchers used many compounds, for example, 4-Cyanobenzyl bromide(cas: 17201-43-3COA of Formula: C8H6BrN)

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.COA of Formula: C8H6BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts