Month: January 2023

Structurally novel PI3Kδ/γ dual inhibitors characterized by a seven-membered spirocyclic spacer: The SARs investigation and PK evaluation was written by Tao, Qiangqiang;Chen, Yuqing;Liang, Xiao;Hu, Yongzhou;Li, Jiaming;Fang, Fang;Wang, Huchuan;Meng, Chang;Liang, Jingtai;Ma, Xiaodong;Gui, Shuangying. And the article was included in European Journal of Medicinal Chemistry in 2020.HPLC of Formula: 60025-09-4 This article mentions the following:

Herein, we communicate our recent medicinal chem. efforts which have culminated in a series of PI3Kδ/γ dual inhibitors structurally featuring a seven-membered spirocyclic spacer. Compound 26, the most potent one among them, exhibited superior PI3Kδ inhibitory activity (IC₅₀ = 1.0 nM) to that of the approved PI3Kδ inhibitor Idelalisib. Besides, it exerted remarkable anti-proliferative efficacy against human malignant B-cell line SU-DHL-6 with GI₅₀ value of 33 nM. The biochem. assay against the other three class I PI3K isoforms identified compound 26 as a potent PI3Kδ/γ dual inhibitor with considerable selectivity over PI3Kα and PI3Kβ. In SU-DHL-6 cells, a dramatic down-regulation of PI3K signaling was observed following compound 26-treatment at the concentration as low as 10 nM. Inspiringly, the pharmacokinetic (PK) study in Sprague-Dawley (SD) rats revealed it was orally available with a favorable bioavailability (F = 87.5%). Overall, compound 26, a promising PI3Kδ/γ dual inhibitor, has the potential to emerge as a clin. candidate for the treatment of leukocyte-mediated malignancies after extensive functional investigation. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4HPLC of Formula: 60025-09-4).

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.HPLC of Formula: 60025-09-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Iridium-catalyzed α-alkylation of acetonitrile with primary and secondary alcohols was written by Sawaguchi, Takuya;Obora, Yasushi. And the article was included in Chemistry Letters in 2011.Application In Synthesis of 2-Cyclohexylacetonitrile This article mentions the following:

Acetonitrile is successfully alkylated with primary and secondary alcs. in the presence of t-BuOK using [Ir(OH)(cod)]₂ as a catalyst. This method provides a very clean and atom-economical convenient direct route to substituted nitriles, which are very important raw materials in organic and industrial chem. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Application In Synthesis of 2-Cyclohexylacetonitrile).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Application In Synthesis of 2-Cyclohexylacetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Anodic cyanation of tert-butylated anisoles: competitive aromatic additions and substitutions was written by Yoshida, Kunihisa;Takeda, Kazusada;Fueno, Takayuki. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1993.Computed Properties of C11H13N This article mentions the following:

The electrooxidation of several tert-butylated anisoles has been carried out in methanol containing sodium cyanide at a Pt anode in a divided cell. Two types of reactions occurred competitively, aromatic-ring addition and substitution. Increasing the level of tert-Bu substitution raises the relative extent of addition to the aromatic ring. The order of orientational preference for substitution of the aromatic hydrogen of alkylanisole cation radicals is explained in terms of the LUMO electron densities calculated for the cation radicals. The effect of structure on the oxidation potential of alkylanisoles has also been studied. Para substitution lowers the oxidation potential while ortho substitution raises the potential. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)benzonitrile (cas: 154532-34-0Computed Properties of C11H13N).

3-(tert-Butyl)benzonitrile (cas: 154532-34-0) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Computed Properties of C11H13N

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Cobalt in N-doped carbon matrix catalyst for chemoselective hydrogenation of nitroarenes was written by Dai, Yihu;Jiang, Chunyang;Xu, Min;Bian, Bo;Lu, Di;Yang, Yanhui. And the article was included in Applied Catalysis, A: General in 2019.Recommanded Product: 2-Amino-4-(trifluoromethyl)benzonitrile This article mentions the following:

Anilines as important intermediates for both organic synthesis and industrial manufactory are densely substituted with a variety of functional moieties, and the transformation of nitroarenes into corresponding anilines requires catalytically selective hydrogenation catalyst. Herein, we describe a simple pyrolysis strategy to prepare cobalt catalysts in nitrogen-doped carbon matrix applied in the selective hydrogenation of nitroarenes with mol. hydrogen. The Co/NC catalysts are obtained through thermal treatment of mixed precursors of cobalt phthalocyanine and melamine. The surface-modified Co particles with Co₃O₄ and CoNx sites are surrounded by N-doped carbon layers according to a series of structural characterization results. These Co/NC catalysts are capable of efficiently selective hydrogenation of nitrobenzene and various substituted nitroarenes into corresponding anilines under relatively mild reaction conditions. The optimal catalytic hydrogenation performance is contributed to the fast rate of H₂ dissociated activation on the CoN_x active sites and the facile adsorption of the reactant substances, which is verified by the isotopic H₂-D₂ exchange experiments, reactant adsorption and the ORR reaction tests. Furthermore, the heterogeneous Co/NC catalyst is highly stable without the Co leaching and deactivation issues during the recycling reaction runs. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Recommanded Product: 2-Amino-4-(trifluoromethyl)benzonitrile).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Recommanded Product: 2-Amino-4-(trifluoromethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Iron-Catalyzed Tandem Radical Addition/Cyclization: Highly Efficient Access to Methylated Quinoline-2,4-diones was written by Sun, Huan;Jiang, Yue;Lu, Ming-Kun;Li, Yun-Yun;Li, Li;Liu, Ji-Kai. And the article was included in Synlett in 2020.Product Details of 1483-54-1 This article mentions the following:

A visible-light-induced and iron-catalyzed oxidative radical addition/cyclization cascade reaction of N-(o-cyanoaryl)acrylamides I [R¹ = 4-Cl, 5-CF₃, 3-Br, etc.; R² = Me, Bn; R³ = Me, [(2,2-dimethylpropanoyl)oxy]methyl, Bn, Ph, (acetyloxy)methyl, (1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl] with DMSO has been developed. The method exhibits a wide substrate scope and an excellent functional-group tolerance, thus providing an efficient and convenient access to a variety of methylated quinoline-2,4-diones II (R⁴ = 6-Cl, 6-CF₃, 5-Br, etc.). In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Product Details of 1483-54-1).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Product Details of 1483-54-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A new synthesis of 4-amino-2-quinolinones was written by Bergman, Jan;Brynolf, Anna;Vuorinen, Eino. And the article was included in Tetrahedron in 1986.Recommanded Product: 68385-95-5 This article mentions the following:

Addition of Grignard or organolithium reagents to N-(α-haloacyl)-N-alkylsubstituted anthranilonitriles, e.g. N-(2-bromopropionyl)-N-methyl-2-cyanoaniline, induced anion formation followed by cyclization to 4-amino-2-quinolinones, e.g. 4-amino-1,3-dimethyl-2-quinolinone (I). Substrates lacking α-hydrogen atoms, such as N-(α-bromoisobutyryl)-2-cyanoaniline, also yielded 3,3-dimethylquinolinedione by cyclization. In these cases the initial step is a halogen-metal exchange reaction. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Recommanded Product: 68385-95-5).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Recommanded Product: 68385-95-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and Biological Evaluation of 2-(Alkoxycarbonyl)-3-Anilinobenzo[b]thiophenes and Thieno[2,3-b]pyridines as New Potent Anticancer Agents was written by Romagnoli, Romeo;Baraldi, Pier Giovanni;Kimatrai Salvador, Maria;Preti, Delia;Aghazadeh Tabrizi, Mojgan;Bassetto, Marcella;Brancale, Andrea;Hamel, Ernest;Castagliuolo, Ignazio;Bortolozzi, Roberta;Basso, Giuseppe;Viola, Giampietro. And the article was included in Journal of Medicinal Chemistry in 2013.HPLC of Formula: 64113-86-6 This article mentions the following:

Two new series of inhibitors of tubulin polymerization based on the 2-(alkoxycarbonyl)-3-(3′,4′,5′-trimethoxyanilino)benzo[b]thiophene and thieno[2,3-b]pyridine mol. skeletons were synthesized and evaluated for antiproliferative activity on a panel of cancer cell lines, inhibition of tubulin polymerization, cell cycle effects, and in vivo potency. Antiproliferative activity was strongly dependent on the position of the Me group on the benzene portion of the benzo[b]thiophene nucleus, with the greatest activity observed when the Me was located at the C-6 position. Also, in the smaller thieno[2,3-b]pyridine series, the introduction of the Me group at the C-6 position resulted in improvement of antiproliferative activity to the nanomolar level. The most active compounds I and II did not induce cell death in normal human lymphocytes, suggesting that the compounds may be selective against cancer cells. Compound I significantly inhibited in vivo the growth of a syngeneic hepatocellular carcinoma in Balb/c mice. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6HPLC of Formula: 64113-86-6).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.HPLC of Formula: 64113-86-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electrophilic Activation of [1.1.1]Propellane for the Synthesis of Nitrogen-Substituted Bicyclo[1.1.1]pentanes was written by Livesley, Sarah;Sterling, Alistair J.;Robertson, Craig M.;Goundry, William R. F.;Morris, James A.;Duarte, Fernanda;Aissa, Christophe. And the article was included in Angewandte Chemie, International Edition in 2022.Safety of 4-(Benzylamino)benzonitrile This article mentions the following:

Herein, the electrophilic activation of [1.1.1]propellane in a halogen bond complex was reported, which enabled its reaction with electron-neutral nucleophiles such as anilines/azoles to give nitrogen-substituted bicyclo[1.1.1]pentanes (BCP)s such as I [R = H, Ph, Bn, etc.; Ar = Ph, 4-CNPh, 3,5-di-FPh, etc.] that were prominent motifs in drug discovery. A detailed computational anal. indicated that the key halogen bonding interaction promotes nucleophilic attack without sacrificing cage stabilization. Overall, this work rehabilitates electrophilic activation of [1.1.1]propellane as a valuable strategy for accessing functionalised BCPs. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Safety of 4-(Benzylamino)benzonitrile).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Safety of 4-(Benzylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Copper-Catalyzed Coupling of Alkylamines and Aryl Iodides: An Efficient System Even in an Air Atmosphere was written by Kwong, Fuk Yee;Klapars, Artis;Buchwald, Stephen L.. And the article was included in Organic Letters in 2002.Quality Control of 4-(Benzylamino)benzonitrile This article mentions the following:

A mild method for the copper-catalyzed amination of aryl iodides is reported. This operationally simple C-N bond-forming protocol uses CuI as the catalyst and ethylene glycol as ligand in 2-propanol. A variety of functionalized aryl iodides as well as several amines were efficiently coupled using this method. This catalytic amination procedure is relatively insensitive to moisture and can be performed under an air atm. with comparable yield. Preliminary results on the amination of aryl bromides are also described. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Quality Control of 4-(Benzylamino)benzonitrile).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Quality Control of 4-(Benzylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and mesomorphic properties of some 3-substituted-4-cyanophenyl esters, 4′-cyano-3-substituted-4-biphenyl esters of 4-(trans-4-alkylcyclohexyl) benzoic, 4-alkyl-1,3-substituted biphenyl-4′-carboxylic, trans-4-alkylcyclohexanecarboxylic and 4-alkylbenzoic acids and electrooptic parameters of liquid-crystalline mixtures containing these compounds was written by Bezborodov, V. S.;Lapanik, V. I.;Adomenas, P.;Sirutkaitis, R.. And the article was included in Liquid Crystals in 1992.Computed Properties of C7H4BrNO This article mentions the following:

The reaction of trans-4-alkylcyclohexanecarboxylic acid chlorides, 4-alkylbenzoic, 4-(trans-4-alkylcyclohexyl)-benzoic, 4-alkyl-3-substituted biphenyl-4′-carboxylic acids with 4-hydroxy-3′-substituted benzonitriles and 4-hydroxy-3′-substituted-4′-cyanobiphenyls produced the corresponding esters. The mesomorphic properties of the esters and electrooptic and dynamic parameters of the mixtures containing these compound were studied. The liquid-crystalline mixtures containing 4-cyano-3-substituted-4′-biphenyl esters of 4-alkylbenzoic and trans-4-alkyl-cyclohexanecarboxylic acids have higher threshold voltages and saturation voltages in comparison with the analogous mixtures containing 4-cyano-3-substituted Ph esters of 4-(trans-4-alkylcyclohexyl)benzoic acids. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4Computed Properties of C7H4BrNO).

2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Computed Properties of C7H4BrNO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts