Category: nitriles-buliding-blocks

Man, Hon-Wah published the artcileA Highly Enantioselective and Diastereoselective Synthesis of Cyclobutanes via Boronic Esters, COA of Formula: C10H18BNO2, the publication is Organic Letters (1999), 1(3), 379-381, database is CAplus and MEDLINE.

Deprotonation of enantiopure (R,R)-1,2-dicyclohexyl-1,2-ethanediol 1-chloro-4-cyanobutylboronates with LDA followed by treatment with anhydrous magnesium bromide yields (R)-(trans-2-cyanocyclobutyl)boronic esters 7 in high diastereomeric and enantiomeric purity. No cyclobutane formation has been observed in the absence of at least a catalytic amount of magnesium halide.

Organic Letters published new progress about 238088-16-9. 238088-16-9 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Aliphatic cyclic hydrocarbon,Boronic Acids,Boronate Esters, name is 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile, and the molecular formula is C10H18BNO2, COA of Formula: C10H18BNO2.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Sircar, Ila published the artcileNonpeptide angiotensin II receptor antagonists. 2. Design, synthesis, and structure-activity relationships of 2-alkyl-4-(1H-pyrrol-l-yl)-1H-imidazole derivatives: profile of 2-propyl-1-[[2′-(1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl]-methyl]-4-[2-(trifluoroacetyl)-1H-pyrrol-1-yl]-1H-imidazole-5-carboxylic acid (CI-996), Synthetic Route of 5098-14-6, the publication is Journal of Medicinal Chemistry (1993), 36(16), 2253-65, database is CAplus and MEDLINE.

A novel series of nonpeptide angiotensin II (AII) receptor antagonists containing a 1H-pyrrol-1-yl moiety at the 4-position of the imidazole have been developed. The pyrrole group occupies the same lipophilic pocket at the receptor as the chloro group in DuP 753 and EXP 3174 (I; R = Bu, R¹ = CH₂OH, CO₂H, R² = Cl, resp.) and the pentafluoro group in DuP 532 (I; R = Pr, R¹ = CO₂H, R² = CF₂CF₃). The impetus for its selection came from bioisosteric considerations based on hydrophobic and electronic substituent constants An extensive study of the structure-activity relationships revealed several highly potent AII receptor antagonists. An acyl substitution at the 2-position of the pyrrole ring improved activity, most notably in the in vivo rat model. In addition, the 2-substituted pyrrole compounds improved chem. stability toward extremely facile decarboxylation reaction associated with unsubstituted pyrrole analogs, thus facilitating development of these agents. The IC₅₀‘s of I [R = Pr, R¹ = CO₂H, R² = 2-(trifluoroacetyl)- (18), 2,5-dimethyl-, or 2,5-dichloro-1H-pyrrol-1-yl] (<1 nM) were better than the reference compounds EXP 3174 and DuP 532. These compounds were selective AII antagonists that compete at the AT₁ receptor and showed no affinity at the AT₂ receptor at concentrations up to 10 M. Upon i.v. administration in a normotensive rat model, compound 18 inhibited the AII-induced responses with ED₅₀ of 6 g/kg per min. In a renal hypertensive rat model, the antihypertensive potency of compound 18, at a dose of 10 mg/kg, was very similar to those of DuP 753 and EXP 3174, resp. Compound 18 demonstrated a dose-related (3-30 mg/kg) decrease in blood pressure that was sustained for greater than 24 h. On the basis of its profile, compound 18, designated as CI-996, has been selected for in-depth studies. The design, synthesis, in vitro, and in vivo structure-activity relationships are described.

Journal of Medicinal Chemistry published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C6H16OSi, Synthetic Route of 5098-14-6.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Sakata, Yoko published the artcileFunctionalized metallonanobelt derivatives having quinoxaline scaffold prepared from a common precursor, Name: Tetrakis(acetonitrile)palladium(II) Ditriflate, the publication is Tetrahedron Letters (2019), 60(31), 2049-2053, database is CAplus.

Synthesis of functionalized pentamer metallonanobelts was accomplished by using a series of triptycene ligands, which were synthesized by quinoxaline formation from 2,3,6,7,14,15-hexaaminotriptycene as a common precursor. It was also found that two kinds of template-bound metal complexes were selectively formed by changing the ratio of Pd²⁺/ligand.

Tetrahedron Letters published new progress about 68569-14-2. 68569-14-2 belongs to nitriles-buliding-blocks, auxiliary class Palladium, name is Tetrakis(acetonitrile)palladium(II) Ditriflate, and the molecular formula is C10H12F6N4O6PdS2, Name: Tetrakis(acetonitrile)palladium(II) Ditriflate.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Sau, Abhijit published the artcilePalladium-Catalyzed α-Stereoselective O-Glycosylation of O(3)-Acylated Glycals, Formula: C10H12F6N4O6PdS2, the publication is Organic Letters (2017), 19(11), 2857-2860, database is CAplus and MEDLINE.

Pd(MeCN)₂Cl₂ enables the α-stereoselective catalytic synthesis of 2,3-unsaturated O-glycosides from O(3)-acylated glycals without the requirement for additives to pre-activate either donor or nucleophile. Mechanistic studies suggest that, unlike traditional (η3-allyl)palladium-mediated processes, the reaction proceeds via an alkoxy-palladium intermediate that increases the proton acidity and oxygen nucleophilicity of the alc. The method is exemplified with the synthesis of a range of glycosides and glycoconjugates of synthetic utility.

Organic Letters published new progress about 68569-14-2. 68569-14-2 belongs to nitriles-buliding-blocks, auxiliary class Palladium, name is Tetrakis(acetonitrile)palladium(II) Ditriflate, and the molecular formula is C10H12F6N4O6PdS2, Formula: C10H12F6N4O6PdS2.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Wan, Jinlin published the artcileDesign, synthesis and anti-bacterial evaluation of novel 1,3,4-thiadiazole derivatives bearing a semicarbazone moiety, Application In Synthesis of 612-13-5, the publication is Phosphorus, Sulfur and Silicon and the Related Elements (2018), 193(7), 443-450, database is CAplus.

(Alkylthio)thiadiazolyl semicarbazones of 2-chloro-3-indolecarboxaldehyde I (R = R¹CH₂, Me, Et, n-Pr, Bu, BuCH₂; R¹ = Ph, 2-ClC₆H₄, 3-ClC₆H₄, 4-ClC₆H₄, 2-MeOC₆H₄, 3-MeOC₆H₄, 4-MeOC₆H₄, 2-MeC₆H₄, 3-MeC₆H₄, 4-MeC₆H₄, 2-FC₆H₄, 4-FC₆H₄, 2-NCC₆H₄, 2,4-Cl₂C₆H₃) were prepared as agrochem. antibacterial agents for treatment of rice bacterial leaf blight (Xanthomonas oryzae pv. oryzae, Xoo) and citrus canker (Xanthomonas axonopodis pv. citri, Xac). I were prepared in four steps from 5-amino-1,3,4-thiadiazole-2-thiol, benzyl chlorides or alkyl bromides, and 2-chloro-3-indolecarboxaldehyde (prepared in one step from oxindole). Many of the tested compounds exhibited excellent activity (≥74.19%) against Xoo at a concentration of 200 μg/mL, with 50% effective concentration (EC₅₀) values ranging from 12.21 to 67.20 μg/mL, superior to the com. antibacterial agent bismerthiazol (EC₅₀ = 92.23 μg/mL). I (R = 2-ClC₆H₄CH₂) demonstrated good inhibitory activity against Xac (89.46% at 200 μg/mL) and Xoo (EC₅₀ = 18.28 μg/mL), while I (R = 4-MeOC₆H₄CH₂) displayed excellent activity against Xoo with an EC₅₀ value of 12.21 μg/mL.

Phosphorus, Sulfur and Silicon and the Related Elements published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C15H14Cl2S2, Application In Synthesis of 612-13-5.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Shan, Xiaojie published the artcile2,2′-Azodi(2-methylbutyronitrile) (AMBN) Promoted Alkenylation of Cyclic Ethers via Radical Addition to β-Nitrostyrenes, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is ChemistrySelect (2022), 7(13), e202200425, database is CAplus.

It is reported the alkenylation of cyclic ethers via radical addition to β-nitrostyrenes in the presence of AMBN without any other additives under mild conditions. A wide range of β-nitrostyrenes and various ethers are tested in this reaction, most cases are happed smoothly with excellent to good yields. Cyclohexane also could be reacted under the conditions with moderate yield. According to the control experiments, the reaction mechanism was proposed. It is found that AMBN could induce to hydrogen abstraction from sp³ carbon under oxygen atm. This reaction system possesses the advantages of very high reactivity, stability, and convenient preparation method. Especially, it is very useful in the pharmacy industry due to the metal-free and easy treatment conditions.

ChemistrySelect published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C15H21BO2, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Sun, Huihui published the artcileExpression, characterization of a novel nitrilase PpL19 from Pseudomonas psychrotolerans with S-selectivity toward mandelonitrile present in active inclusion bodies, Name: 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Biotechnology Letters (2016), 38(3), 455-461, database is CAplus and MEDLINE.

Objectives: To identify a novel nitrilase with S-selectivity toward mandelonitrile that can produce (S)-mandelic acid in one step. Results: A novel nitrilase PpL19 from Pseudomonas psychrotolerans L19 was discovered by genome mining. It showed S-selectivity with an enantiomeric excess of 52.7% when used to hydrolyze (R,S)-mandelonitrile. No byproduct was observed PpL19 was overexpressed in Escherichia coli BL21 (DE3) and formed inclusion bodies that were active toward mandelonitrile and stable across a broad range of temperature and pH. In addition, PpL19 hydrolyzed nitriles with diverse structures; arylacetonitriles were the optimal substrates. Homol. modeling and docking studies of both enantiomers of mandelonitrile in the active site of nitrilase PpL19 shed light on the enantioselectivity. Conclusions: A novel nitrilase PpL19 from P. psychrotolerans L19 was mined and distinguished from other nitrilases as it was expressed as an active inclusion body and showed S-selectivity toward mandelonitrile.

Biotechnology Letters published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C10H9NO, Name: 2-(2-Chlorophenyl)-2-hydroxyacetonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Sun, Huihui published the artcileCloning, purification and evaluation of the enzymatic properties of a novel arylacetonitrilase from Luminiphilus syltensis NOR5-1B: a potential biocatalyst for the synthesis of mandelic acid and its derivatives, Category: nitriles-buliding-blocks, the publication is Biotechnology Letters (2015), 37(8), 1655-1661, database is CAplus and MEDLINE.

Objective: To examine nitrilase-mediated hydrolysis of nitriles to produce optically pure α-hydroxycarboxylic acids. Results: A novel nitrilase, GPnor51, from Luminiphilus syltensis NOR5-1B was discovered by genomic data mining. It could hydrolyze racemic o-chloromandelonitrile to (R)-o-chloromandelic acid with high enantioselectivity (ee 98.2 %). GPnor51 was overexpressed in Escherichia coli BL21 (DE3), purified, and its catalytic properties studied. GPnor51 had a broad substrate acceptance toward various nitriles with structure diversity. It was an arylacetonitrilase that uses arylacetonitriles as optimal substrates. The V_max and K_m of GPnor51 towards o-chloromandelonitrile were 1.9 μmol min^-1 mg^-1 protein and 0.38 mM, resp. GPnor51 also demonstrated high enantioselectivity toward mandelonitrile and other substituted mandelonitrile. Conclusion: This enzyme has a great potential for com. production of optically pure (R)-mandelic acid and its derivatives

Biotechnology Letters published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C10H13NO2, Category: nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Wang, Hualei published the artcileProtein engineering of a nitrilase from Burkholderia cenocepacia J2315 for efficient and enantioselective production of (R)-o-chloromandelic acid, Related Products of nitriles-buliding-blocks, the publication is Applied and Environmental Microbiology (2015), 81(24), 8469-8477, database is CAplus and MEDLINE.

The nitrilase-mediated pathway has significant advantages in the production of optically pure aromatic α-hydroxy carboxylic acids. However, low enantioselectivity and activity are observed on hydrolyzing o-chloromandelonitrile to produce optically pure (R)-o-chloromandelic acid. A protein engineering approach was successfully used to enhance the performance of nitrilase obtained from Burkholderia cenocepacia strain J2315 (BCJ2315) in hydrolyzing o-chloromandelonitrile. Four hot spots (T49, I113, Y199, and T310) responsible for the enantioselectivity and activity of BCJ2315 were identified by random mutagenesis. An effective double mutant (I113M/Y199G [encoding the replacement of I with M at position 113 and Y with G at position 199]), which demonstrated remarkably enhanced enantioselectivity (99.1% enantiomeric excess [ee] compared to 89.2% ee for the wild type) and relative activity (360% of the wild type), was created by two rounds of site saturation mutagenesis, first at each of the four hot spots and subsequently at position 199 for combination with the selected beneficial mutation I113M. Notably, this mutant also demonstrated dramatically enhanced enantioselectivity and activity toward other mandelonitrile derivatives and, thus, broadened the substrate scope of this nitrilase. Using an Et acetate-water (1:9) biphasic system, o-chloromandelonitrile (500 mM) was completely hydrolyzed in 3 h by this mutant with a small amount of biocatalyst (10 g/L wet cells), resulting in a high concentration of (R)-o-chloromandelic acid with 98.7% ee, to the authors’ knowledge the highest ever reported. This result highlights a promising method for industrial production of optically pure (R)-o-chloromandelic acid. Insight into the source of enantioselectivity and activity was gained by homol. modeling and mol. docking experiments

Applied and Environmental Microbiology published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C18H10, Related Products of nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Nikseresht, Ahmad published the artcile[Cu₃(BTC)₂]: A metal-organic framework as an environment-friendly and economically catalyst for the synthesis of tacrine analogues by Friedlaender reaction under conventional and ultrasound irradiation, Recommanded Product: 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Polyhedron (2018), 112-117, database is CAplus.

Using a green and simple route with ultrasound illumination, atm. pressure and room temperature, for synthesizing tacrine analogs in the presence of [Cu₃(BTC)₂] as an environment-friendly and economically catalyst was considered. [Cu₃(BTC)₂] is one of the heterogeneous catalysts on hand capable of being employed, in the Friedlaender reaction, whenever 5-amino-4-cyano-2-phenyl-1,3-oxazole and appropriately substituted carbonyl derivatives under conventional and ultrasonic irradiation The results of this study indicate that the active sites in the [Cu₃(BTC)₂] for synthesis of cyclohepta[b]oxazolo[4,5-e]pyridine are mainly copper atoms and the role of Bronsted acid organic ligand in the MOF is negligible. These procedures were properly arranged to provide the utmost yields in a short while. The crystal stability in the process of catalysis was studied by various techniques such as XRD, BET and ICP that demonstrate excellent stability in reaction conditions.

Polyhedron published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, Recommanded Product: 2-Aminomalononitrile 4-methylbenzenesulfonate.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts