Month: January 2023

A new synthesis of aryl substituted quinazolin-4(1H)-ones was written by Roth, Gary A.;Tai, Jimmy J.. And the article was included in Journal of Heterocyclic Chemistry in 1996.Product Details of 53312-77-9 This article mentions the following:

Treatment of a variety of substituted 2-aminobenzonitriles I (R¹ = H, 3-F, R² = 3-Me, 5-NO₂, 5-OMe, 3-F, 3-Cl, 5-Cl, 6-Cl) with formic acid under strong acid catalysis provides the corresponding quinazolin-4(1H)-ones II in good yield. A potential reaction pathway is described. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Product Details of 53312-77-9).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.Product Details of 53312-77-9

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Acylpyridines. III. Reaction of 1-methoxy-4-alkoxypyridinium salts with potassium cyanide was written by Nishimoto, Nobushige;Nakashima, Tatsumi. And the article was included in Yakugaku Zasshi in 1962.Safety of 4-methoxypicolinonitrile This article mentions the following:

By the reaction of 1, 4-dimethoxypyridinium iodide with KCN in MeOH, 4-MeOC₅H₄N (1), Me 4-cyanopicolinimidate, Me 4-methoxypicolinimidate, di-Me 3,4-pyridinecarboximidate, 4-methoxypicolinamide, 2,4,6-tris(4-methoxy-2-pyridyl)- 1,3,5-triazine, 4-cyanopicolinamide (II), and 2,4-pyridinecarboxamide (III) were produced but a very little of the expected 4-methoxypicolinonitrile (IV) was obtained. When dioxane was used instead of MeOH, IV was obtained in 30% yield, besides a small amount of I and 2,4-pyridinedicarbonitrile (V). On the other hand, 1-methoxy-4-ethoxypyridinium iodide treated with KCN in MeOH gave 4-ethoxypyridine, 4-ethoxypicolinamide, II, and III. In dioxane, 4-ethoxypicolinonitrile was obtained in 32% yield, together with V and 4-EtOC₅H₄N. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Safety of 4-methoxypicolinonitrile).

4-methoxypicolinonitrile (cas: 36057-44-0) 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. 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.Safety of 4-methoxypicolinonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Asymmetric catalytic reduction of carbonyl compounds using C₂ symmetric diamines as chiral ligands was written by Gamez, Patrick;Fache, Fabienne;Lemaire, Marc. And the article was included in Tetrahedron: Asymmetry in 1995.Safety of (R)-4-(1-Hydroxyethyl)benzonitrile This article mentions the following:

The catalytic asym. reduction of prochiral ketones by hydride transfer using various C₂ sym. chiral diamines as ligands and rhodium complexes is studied. Kinetic studies show an increase in the enantiomeric excess with the conversion. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Safety of (R)-4-(1-Hydroxyethyl)benzonitrile).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. 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 (R)-4-(1-Hydroxyethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Decomposition of thiopyrans to thiophenes under electron impact was written by Bogdanowicz-Szwed, Krystyna;Nagraba, Krzysztof. And the article was included in Organic Mass Spectrometry in 1984.Synthetic Route of C8H8N2S This article mentions the following:

Fragmentation patterns for I (n = 3, 4, 5; R = H, Cl, Br, Me) are discussed. The mass spectra of I showed peaks of high intensity in the mol. ion region, with rel. abundance varying from 20 to 60% of the base peak. The fragmentation of the [I]⁺· occurred as a one-step process with ejection of RC₆H₄NC as well as by a two-step process involving loss of RC₆H₄· and CN· radicals. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Synthetic Route of C8H8N2S).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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.Synthetic Route of C8H8N2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

New thiophene-acridine compounds: Synthesis, antileishmanial activity, DNA binding, chemometric, and molecular docking studies was written by Serafim, Vanessa de Lima;Felix, Mayara Barbalho;Silva, Daiana Karla Frade;Rodrigues, Klinger Antonio da Franca;Andrade, Patricia Neris;Vitalino de Almeida, Sinara Monica;de Albuquerque dos Santos, Sanderssonilo;Ferreira de Oliveira, Jamerson;Alves de Lima, Maria do Carmo;Mendonca-Junior, Francisco Jaime Bezerra;Scotti, Marcus Tullius;Rosa de Oliveira, Marcia;Olimpio de Moura, Ricardo. And the article was included in Chemical Biology & Drug Design in 2018.Synthetic Route of C8H8N2S This article mentions the following:

In this study, we synthesized eight new compounds containing the 2-amino-cycloalkyl[b]thiophene and acridine moieties (ACT₀₁ and ACS₀₁-ACS₀₇). None tested compounds presented human erythrocyte cytotoxicity. The new compounds presented antipromastigote activity, where ACS₀₁ and ACS₀₂ derivatives presented significant antileishmanial activity, with better performance than the reference drugs (tri and pentavalent antimonials), with resp. IC₅₀ values of 9.60 ± 3.19 and 10.95 ± 3.96 μm. Addnl., these two derivatives were effective against antimony-resistant Leishmania (Leishmania) amazonensis strains. In addition, binding and fragmentation DNA assays were performed. It was observed that the antileishmanial activity of ACS₀₁ is not associated with DNA fragmentation of the promastigote forms. However, it interacted with DNA with a binding constant of 10⁴ M^-1. In partial least-squares studies, it was observed that the most active compounds (ACS₀₁ and ACS₀₂) showed lower values of amphiphilic moment descriptor, but there was a correlation between the lipophilicity of the mols. and antileishmanial activity. Furthermore, the docking mol. studies showed interactions between thiophene-acridine derivatives and the active site of pyruvate kinase enzyme with the major contribution of asparagine 152 residue for the interaction with thiophene moiety. Thus, the results suggested that the new thiophene-acridine derivatives are promising mols. as potential drug candidates. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Synthetic Route of C8H8N2S).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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. Synthetic Route of C8H8N2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The taste of 1-alkoxy- and 1-halo-2-amino-4-cyanobenzenes was written by Blanksma, J. J.;Petri, E. M.. And the article was included in Recueil des Travaux Chimiques des Pays-Bas et de la Belgique in 1947.Recommanded Product: 60979-25-1 This article mentions the following:

The 1-alkoxy- and 1-halo-2-amino-4-cyanobenzenes are less sweet than the corresponding nitrobenzenes, though still much sweeter than cane sugar, the 1-methoxy-(I) being 180, 1-ethoxy-(II) 900, 1-propoxy-(III) 2,500, 1-chloro-(IV) 300, and 1-bromo-2-amino-4-cyanobenzene (V) 500 times as sweet as sucrose. Acylation destroyed the sweet taste. I, m. 84°, was prepared by treating 4,2-NC(O₂N)C₆H₃Cl with MeONa and reducing the product with Na₂S₂; N-Ac, m. 186°, Bz, m. 117°, and carbethoxy derivative, m. 103°, were tasteless as were 1-methoxy-2-nitro-4-carbamylbenzene, m. 117°, and 1-methoxy-2-nitro-4-aminobenzene, m. 49°. Similarly II, m. 112°, its N-Ac, m. 168°, Bz, m. 140°, and carbethoxy derivatives, m. 89°, and 1-ethoxy-2-nitro-4-carbamylbenzene (VI), m. 175°, were prepared VI and NaOCl produced tasteless 1-ethoxy-2-nitro-4-aminobenzene, m. 41°. 1-Propoxy-2-nitro-4-cyanobenzene (VII), m. 105°, was prepared and reduced to III, m. 99° (N-Ac, m. 178°, Bz, m. 135°, and carbethoxy derivatives, m. 66°). The hydrolysis of III to 1-propoxy-2-amino-4-carbamylbenzene (VIII), m. 171°, destroyed the sweetness; Ac derivative of VIII m. 198°; Bz derivative m. 198°. 1-Propoxy-2-nitro-4-carbamylbenzene, m. 158°, is also tasteless. 4-Chlorobenzamide is tasteless but 1-chloro-2-nitro-4-cyanobenzene is 75 times and 1-chloro-2-amino-4-cyanobenzene (IX), m. 92°, 300 times as sweet as sucrose; the Ac derivative of IX, m. 158°, Bz derivative, m. 166°, and 3,5-di-Br derivative, m. 171°, are all tasteless. 1-Chloro-2-nitro-4-carbamylbenzene, m. 156°, 1-chloro-2-amino-4-carbamylbenzene (X), m. 164°, and its 2-AcNH, m. 220°, 2-Ac₂N, m. 200°, 2-BzNH, m. 215°, 2-carbethoxyamino, m. 162°, and 3,5-di-Br derivative, m. 248°, are also tasteless. V, m. 99°, was prepared by reducing 2,4-O₂N(NC)C₆H₃Br; its Ac, m. 185°, Bz, m. 160°, carbethoxy, m. 115°, and 3,5-di-Br derivative, m. 180°. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1Recommanded Product: 60979-25-1).

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) 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. Recommanded Product: 60979-25-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Heterometallic Coordination Polymers Assembled from Trigonal Trinuclear Fe₂Ni-Pivalate Blocks and Polypyridine Spacers: Topological Diversity, Sorption, and Catalytic Properties was written by Sotnik, Svetlana A.;Polunin, Ruslan A.;Kiskin, Mikhail A.;Kirillov, Alexander M.;Dorofeeva, Victoria N.;Gavrilenko, Konstantin S.;Eremenko, Igor L.;Novotortsev, Vladimir M.;Kolotilov, Sergey V.. And the article was included in Inorganic Chemistry in 2015.Recommanded Product: 55490-87-4 This article mentions the following:

Linkage of the trigonal complex [Fe₂NiO(Piv)₆] (Piv^– = pivalate) by polypyridine ligands, namely, tris(4-pyridyl)triazine (L²), 2,6-bis(3-pyridyl)-4-(4-pyridyl)pyridine (L³), N-(bis-2,2-(4-pyridyloxymethyl)-3-(4-pyridyloxy)propyl)pyridone-4 (L⁴), and 4-(N,N-diethylamino)phenyl-bis-2,6-(4-pyridyl)pyridine (L⁵) gave novel coordination polymers [Fe₂NiO(Piv)₆(L²)]_n (2), [Fe₂NiO(Piv)₆(L³)]_n (3), [Fe₂NiO(Piv)₆(L⁴)]_n·nHPiv (4), and [{Fe₂NiO(Piv)₆}₄{L⁵}₆]_n·3nDEF (5, where DEF is N,N-diethylformamide), which were crystallog. characterized. The topol. anal. of 3, 4, and 5 disclosed the 3,3,4,4-connected 2-dimensional (3, 4) or 3,4,4-connected 1-dimensional (5) underlying networks which, upon further simplification, gave rise to the uninodal 3-connected nets with the resp. fes (3, 4) or SP 1-periodic net (4,4)(0,2) (5) topologies, driven by the cluster [Fe₂Ni(μ₃-O)(μ-Piv)₆] nodes and the polypyridine μ₃-L^3,4 or μ₂-L⁵ blocks. The obtained topologies were compared with those identified in other closely related derivatives [Fe₂NiO(Piv)₆(L¹)]_n (1) and {Fe₂NiO(Piv)₆}₈{L⁶}₁₂ (6), where L¹ and L⁶ are tris(4-pyridyl)pyridine and 4-(N,N-dimethylamino)phenyl-bis-2,6-(4-pyridyl)pyridine, resp. A key structure-driven role in defining the dimensionality and topol. of the resulting coordination network is played by the type of polypyridine spacer. Compounds 2 and 3 possess a porous structure, as confirmed by the N₂ and H₂ sorption data at 78 K. Methanol and ethanol sorption by 2 was also studied indicating that the pores filled by these substrates did not induce any structural rearrangement of this sorbent. Addnl., porous coordination polymer 2 was also applied as a heterogeneous catalyst for the condensation of salicylaldehyde or 9-anthracenecarbaldehyde with malononitrile. The best activity of 2 was observed in the case of salicylaldehyde substrate, resulting in up to 88% conversion into 2-imino-2H-chromen-3-carbonitrile. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Recommanded Product: 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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. 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.Recommanded Product: 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some amine derivatives of acrylonitrile was written by Wiedemann, O. F.;Montgomery, W. H.. And the article was included in Journal of the American Chemical Society in 1945.Recommanded Product: 3,3′,3”-Nitrilotripropanenitrile This article mentions the following:

Correction. In C.A. 40, 832.2 the m.p. of IV is 59°, not 99°. n_D²⁵ of VI is 1.4802, not 1.4910. (CH₂)₂O in line 38 should read HOCH₂CH₂CN. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Recommanded Product: 3,3′,3”-Nitrilotripropanenitrile).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) 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.Recommanded Product: 3,3′,3”-Nitrilotripropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Discovery of 4-aminopyrimidine analogs as highly potent dual P70S6K/Akt inhibitors was written by Xiao, Yufang;Huck, Bayard R.;Lan, Ruoxi;DeSelm, Lizbeth;Chen, Xiaoling;Qiu, Hui;Neagu, Constantin;Johnson, Theresa;Mochalkin, Igor;Gardberg, Anna;Jiang, Xuliang;Tian, Hui;Dutt, Vikram;Santos, Dusica;Head, Jared;Jackson, Jennifer;Syed, Sakeena;Lin, Jing;Wilker, Erik;Ma, Jianguo;Clark, Anderson;Machl, Andreas;Bankston, Donald;Jones, Christopher C. V.;Goutopoulos, Andreas;Sherer, Brian. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2021.Safety of 4-Amino-6-chloropyrimidine-5-carbonitrile This article mentions the following:

Activation of the PI3K/Akt/mTOR kinase pathway is associated with human cancers. A dual p70S6K/Akt inhibitor is sufficient to inhibit strong tumor growth and to block neg. impact of the compensatory Akt feedback loop activation. A scaffold docking strategy based on an existing quinazoline carboxamide series identified 6-[4-(2-Amino-1-phenyl-ethyl)-piperazin-1-yl]-5-(4-fluoro-phenyl)-pyrimidin-4-ylamine, which showed a single-digit nanomolar and a micromolar potencies in p70S6K and Akt enzymic assays. SAR optimization improved Akt enzymic and p70S6K cellular potencies, reduced hERG liability, and ultimately discovered the promising candidate 4-Amino-6-{4-[1-(2-azetidin-1-yl-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}pyrimidine-5-carboxylic acid amide, which exhibited with a single digit nanomolar value in both p70S6K and Akt biochem. assays, and hERG activities (IC50 = 17.4 μM). This agent demonstrated dose-dependent efficacy in inhibiting mice breast cancer tumor growth and covered more than 90% pS6 inhibition up to 24 h at a dose of 200 mg/kg po. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Safety of 4-Amino-6-chloropyrimidine-5-carbonitrile).

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. 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-Amino-6-chloropyrimidine-5-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Novel pyrazolo[1,5-a]pyridines as p110α-selective PI3 kinase inhibitors: Exploring the benzenesulfonohydrazide SAR was written by Kendall, Jackie D.;Giddens, Anna C.;Tsang, Kit Yee;Frederick, Raphael;Marshall, Elaine S.;Singh, Ripudaman;Lill, Claire L.;Lee, Woo-Jeong;Kolekar, Sharada;Chao, Mindy;Malik, Alisha;Yu, Shuqiao;Chaussade, Claire;Buchanan, Christina;Rewcastle, Gordon W.;Baguley, Bruce C.;Flanagan, Jack U.;Jamieson, Stephen M. F.;Denny, William A.;Shepherd, Peter R.. And the article was included in Bioorganic & Medicinal Chemistry in 2012.SDS of cas: 60710-80-7 This article mentions the following:

Structure-activity relationship studies of the pyrazolo[1,5-a]pyridine class of PI3 kinase inhibitors show that substitution off the hydrazone nitrogen and replacement of the sulfonyl both gave a loss of p110α selectivity, with the exception of an N-hydroxyethyl analog. Limited substitutions were tolerated around the Ph ring; in particular the 2,5-substitution pattern was important for PI3 kinase activity. The N-hydroxyethyl compound also showed good inhibition of cell proliferation and inhibition of phosphorylation of Akt/PKB, a downstream marker of PI3 kinase activity. It had suitable pharmacokinetics for evaluation in vivo, and showed tumor growth inhibition in two human tumor cell lines in xenograft studies. This work has provided suggestions for the design of more soluble analogs. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7SDS of cas: 60710-80-7).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) 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.SDS of cas: 60710-80-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts