Month: January 2023

Design, synthesis, and biological evaluation of 1,2,4-oxadiazole-containing pyrazolo[3,4-b]pyridinones as a new series of AMPKα1β1γ1 activators was written by Xiao, Zhihong;Peng, Yajun;Zheng, Bifeng;Chang, Qi;Guo, Yating;Chen, Zhuo;Li, Qianbin;Hu, Gaoyun. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2021.Name: 2-(Trifluoromethoxy)benzonitrile This article mentions the following:

Three series of 1,2,4-oxadiazole-containing pyrazolo[3,4-b]pyridinone derivatives I [R¹ = 2-Me, 3-OMe, 4-F, etc.; R² = CF₃, COOH; R³ = H, 4-methoxybenzyl; R⁴ = H, 4-methoxybenzyl] were synthesized and reported as AMPKα1β1γ1 activators. The in vitro biol. assay demonstrated that compounds I [R¹ = 4-Cl; R² = CF3; R³ = H; R⁴ = H] (EC₅₀[AMPKα1γ1β1] = 180 nM) and I [R¹ = 3-CF₃; R² = COOH; R³ = H; R⁴ = H] (EC₅₀[AMPKα1γ1β1] = 2 nM) displayed significant enzyme activation. Mechanism studies indicated that both compounds reduced the levels of reactive oxygen species in a rat kidney fibroblast cell line (NRK-49F) stimulated by transforming growth factor-β and induced early apoptosis of NRK-49F cells at 10μM. Mol. docking studies suggested that compoundI [R¹ = 3-CF₃; R² = COOH; R³ = H; R⁴ = H] exhibited critical hydrogen-bond interactions with the critical amino acid residues Lys29, Lys31, Asn111, and Asp88 at the binding site of the AMPK protein. These results enriched the structure pool of AMPK activators and provided novel lead compounds for the subsequent development of compounds with a promising therapeutic potential against DN. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4Name: 2-(Trifluoromethoxy)benzonitrile).

2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4) 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. 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.Name: 2-(Trifluoromethoxy)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

KG-60-piperazine as a new heterogeneous catalyst for Gewald three-component reaction was written by Rezaei-Seresht, Esmail;Tayebee, Reza;Yasemi, Mohammad. And the article was included in Synthetic Communications in 2013.Category: nitriles-buliding-blocks This article mentions the following:

Piperazine supported on amorphous silica (KG-60-piperazine) as a basic catalyst acts in the Gewald three-component reaction of some aldehydes and ketones with malononitrile as well as Et cyanoacetate. The catalyst shows general utility with a variety of starting carbonyl compounds Moreover, the catalyst can be reused for four addnl. cycles without significant loss of the activity. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Category: nitriles-buliding-blocks).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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. 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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Thermal chlorination of n-heptane was written by Galanina, R. S.. And the article was included in Doklady Akademii Nauk SSSR in 1953.Computed Properties of C7H11NO This article mentions the following:

Continuous thermal chlorination of n-C₇H₁₆ was studied in a continuous-flow apparatus (cf. first reference above) with rapid removal of RCl from the reaction zone. With a ratio RH:Cl₂ of 10:1 at 0.73 space velocity 50% RCl with only a trace of dichlorides is formed at 180°. At higher temperatures the yield of RCl rises and the dichloride disappears. At 260° is obtained the best yield, 96.5% RCl. At this temperature the yield of RCl rises steadily as the RH:Cl₂ ratio is increased although both 8:1 and 10:1 ratios give the same high yield of 96.5%. Fractionation of the RCl gave 2 fractions, b. 134-6° and b. 147-50°, corresponding, resp., to 2-and 1-chloroheptane, identified further by d. and n. No tertiary halides were found, showing there is no isomerization of RH. At the temperature employed, the rate of substitution of primary H is greater than that of the secondary H atoms, but at lower temperatures the reverse is true. Chlorination of the crude RCl was run to obtain the dichlorides; with a 6:1 ratio of RCl: Cl₂ at 0.45 space velocity of Cl₂, the yield of dichlorides was 79.7% at 240°, 90% at 260°, and 99.2% at 280°. Fractionation gave 1,7-, 1,1- and 1,2-dichloroheptanes. Only at 220-40° does equilibrium exist in the rates of replacement of primary and secondary H atoms by Cl, while at 260° the highest rate of primary H replacement occurs (cf. Nekrasova, C.A. 48, 2560d, for chlorination in the liquid phase). The yields and properties of the isomeric dichlorides follow: 1,1, 31.5%, b₂₀ 82°, d₂₀ 1.0088, n²⁰_D 1.4440; 1,2, 15%, b₇ 68-72°, d₂₀ 1.0625, n²⁰_D 1.4480; 1,7, 53.1%, b₂₈ 120°, d₂₀ 1.048, n²⁰_D 1.4500. In the experiment, the researchers used many compounds, for example, 4-Hydroxycyclohexanecarbonitrile (cas: 24056-34-6Computed Properties of C7H11NO).

4-Hydroxycyclohexanecarbonitrile (cas: 24056-34-6) 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. 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.Computed Properties of C7H11NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Heterogeneous Gold-Catalyzed Cascade Hydrogen-Transfer Strategy for Selective Synthesis of Quinazolinones in Water was written by Tang, Lin;Zhao, Xianghua;Zou, Guodong;Zhou, Yuqiang;Yang, Xingkun. And the article was included in Asian Journal of Organic Chemistry in 2016.Application In Synthesis of 5-Methyl-2-nitrobenzonitrile This article mentions the following:

Efficient and selective synthesis of quinazolinones from 2-nitrobenzonitriles and benzylic alcs. catalyzed by TiO₂-supported gold nanoparticles (Au/TiO₂) was developed. Various transformations, such as dehydrogenative oxidation of C-O and C-N bonds, reduction of nitro groups, condensation of aldehydes with amines, hydration of cyano groups and cyclization, was achieved in the tandem hydrogen-transfer reaction. This protocol presents broad substrate scope, good tolerance to air and water, excellent recycling of the catalyst and did not require any additive, oxidant or reductant, which enables straightforward, practical and environmentally benign C-N and C-O bond formation. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6Application In Synthesis of 5-Methyl-2-nitrobenzonitrile).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Application In Synthesis of 5-Methyl-2-nitrobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of 2-azastilbene derivatives with intramolecular charge transfer was written by Kokars, V.;Yanishevskii, A.;Kampars, V.. And the article was included in Chemistry of Heterocyclic Compounds (New York, NY, United States)(Translation of Khimiya Geterotsiklicheskikh Soedinenii) in 2002.Formula: C7H5N3O2 This article mentions the following:

The condensation reaction of 2-cyanomethyl-5-nitropyridine with benzaldehydes 4-RC₆H₄CHO (R = H, Cl, NMe₂, OMe, cyano) gave 2-azastilbene derivatives I. The electronic absorption spectra of these compounds showed intramol. charge-transfer, which depends on the ionization potential of the donor fragment, i.e. the σ⁺-constant of the R substituent. Introduction of the heteroatom into the acceptor part when changing from the stilbene to the 2-azastilbene system is accompanied by a decrease in the energy and increase in the intensity of the charge-transfer electronic transition. In the experiment, the researchers used many compounds, for example, 2-(5-Nitro-2-pyridinyl)acetonitrile (cas: 123846-66-2Formula: C7H5N3O2).

2-(5-Nitro-2-pyridinyl)acetonitrile (cas: 123846-66-2) 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.Formula: C7H5N3O2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Nucleic acid components and their analogs. CLVIII. Preparation of some substituted 2-amino- and 2-mercaptopyrimidines from trimethinium salts was written by Holy, Antonin;Arnold, Zdenek. And the article was included in Collection of Czechoslovak Chemical Communications in 1973.Reference of 1753-48-6 This article mentions the following:

Condensation of Me2NCR:CR1CH:N(+)Me2(ClO4)(-) (I) (R = H, alkyl, NMe2; R1 = H, alkyl, halo, CN, CO2Et, OCH2Ph) with (H2N)2C:NH or (H2N)2C:S gave II (R2 = NH2) and II (R2 = SH), resp. I (R = H; R1 = OCH2Ph) was prepared from PhCH2OCH2CH(OEt)2 by reaction with ClCH:N(+)Me2Cl(-), hydrolysis, and treatment with Me2NH. I (R = NMe2; R1 = CO2Et) and I (R = NMe2; R1 = CN) were prepared analogously from Me2NCOCH2CO2Et and Me2NCOCH2CN, resp. 5-Methyl-2-pyrimidinone was prepared from II (R = H; R1 = Me; R2 = SH) and ClCH2CO2H. Reaction of II (R = H; R1 = OCH2Ph; R2 = NH2) and II (R = H; R1 = OEt; R2 = NH2) in aqueous dioxane with HONO gave 5-benzyloxy-2-pyrimidinone and 5-ethoxy-2-pyrimidinone, resp. In the experiment, the researchers used many compounds, for example, 2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6Reference of 1753-48-6).

2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6) 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. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Reference of 1753-48-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Cathodic behaviour of 1-cycloalken-1-yl phenyl sulfones. I. Competition among dimerization, cleavage, isomerization and oligomerization processes in aprotic media was written by Prigent, Sylvie;Cauliez, Pascal;Simonet, Jacques;Peters, Dennis G.. And the article was included in Acta Chemica Scandinavica in 1999.Application of 4435-14-7 This article mentions the following:

1-Cycloalken-1-yl Ph sulfones (1-cyclopenten-1-yl Ph sulfone and 1-cyclohexen-1-yl Ph sulfone) were studied electrochem. in aprotic media (DMF, DMSO, or acetonitrile containing tetraalkylammonium salts) at a mercury electrode. Their behavior was compared with that of 2-norbornen-2-yl Ph sulfone. The expected cleavage reaction is accompanied by a concomitant isomerization process into allyl sulfones that is triggered by electrogenerated bases. A quant. determination of the product distribution during controlled-potential electrolyzes suggests the formation of dimers and oligomeric species, arising through a Michael addition of the sulfone anions to the activated double bond of these sulfones. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Application of 4435-14-7).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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. 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.Application of 4435-14-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Selective reduction of α,β-unsaturated nitriles with sodium hydrogen telluride was written by Blay, Gonzalo;Cardona, Luz;Garcia, Begona;Pedro, Jose R.. And the article was included in Synlett in 1995.Formula: C8H13N This article mentions the following:

Sodium hydrogen telluride reacts chemoselectively with α,β-unsaturated nitriles linked to aromatic and aliphatic substituents, e.g., (E)-4-NCC₆H₄CH:CHCN, to give the corresponding saturated nitriles with good yields. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Formula: C8H13N).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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.Formula: C8H13N

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Design, synthesis and biological evaluation of novel 4-(2-fluorophenoxy)quinoline derivatives as selective c-Met inhibitors was written by Wang, Xiaoqiang;Jiang, Nan;Zhao, Sijia;Xi, Shuancheng;Wang, Jiao;Jing, Tongfei;Zhang, Wenyu;Guo, Ming;Gong, Ping;Zhai, Xin. And the article was included in Bioorganic & Medicinal Chemistry in 2017.Name: 2-(Trifluoromethoxy)benzonitrile This article mentions the following:

Two novel series of 6,7-disubstituted-4-(2-fluorophenoxy)quinoline derivatives bearing 1H-imidazole-4-carboxamido or (E)-3-hydrosulfonylacrylamido motifs were designed, synthesized and evaluated for their in vitro cytotoxic activity. Most of the compounds exhibited moderate to excellent potency against tested three cell lines, and fifteen compounds were further examined for their inhibitory activity against c-Met kinase. The most promising compound I (c-Met kinase [IC₅₀] = 1.1 nM) demonstrated high selectivity and remarkable cytotoxicity against HT-29, MKN-45 and A549 cells with IC₅₀ values of 0.08, 0.22 and 0.07 μM, which were 3.1-, 1.4- and 2.1-fold more active than Foretinib. The preliminary structure-activity relationships as well as mol. docking disclosed that 1H-imidazole-4-carboxamido as a linker was of great importance for the antitumor activity. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4Name: 2-(Trifluoromethoxy)benzonitrile).

2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. 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.Name: 2-(Trifluoromethoxy)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A comparison of the properties of some 2-aminothiophene-derived disperse dyes was written by Hallas, Geoffrey;Towns, Andrew D.. And the article was included in Dyes and Pigments in 1996.Computed Properties of C12H14N2O4S This article mentions the following:

In the course of an investigation into the properties of monoazo disperse dyes synthesized from aminothiophene diazo components, significant discrepancies were observed between the spectroscopic and fastness data of some thienyl-2-azo dyes compared to that previously reported for closely related analogs. Considerable differences in λ_max and ε_max values were noted; in some cases, light fastness ratings were at variance with previously disclosed figures. In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Computed Properties of C12H14N2O4S).

Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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 C12H14N2O4S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts