Tag: 100-200

Immobilized Iron Metal-Containing Ionic Liquid-Catalyzed Chemoselective Transfer Hydrogenation of Nitroarenes into Anilines was written by Patil, Nilesh M.;Sasaki, Takehiko;Bhanage, Bhalchandra M.. And the article was included in ACS Sustainable Chemistry & Engineering in 2016.Computed Properties of C8H8N2 This article mentions the following:

The chemoselective transfer hydrogenation of nitroarenes into anilines was investigated using immobilized iron metal containing ionic liquid (ImmFe-IL) as a versatile heterogeneous catalyst. The present protocol has high atom efficiency with excellent chemoselectivity and regioselectivity. Selective reduction of the nitro group was observed in the presence of other reducing functional groups such as nitrile, ketone, acid, amide, ester, halogens, hydroxyl, olefin, and heterocycles. The developed protocol is also highly selective toward conversion of dinitroarenes into nitroanilines. The present catalytic system uses environmentally benign ethylene glycol as a solvent which is inexpensive, easily available, nontoxic, nonvolatile, nonflammable, thermally stable, and biodegradable. The catalyst was reused up to four consecutive cycles with high activity and selectivity. The fresh catalyst and recycle catalyst was well characterized by XPS anal. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Computed Properties of C8H8N2).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) 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. 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 C8H8N2

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Preparation of Tertiary Amines from Tris(2-cyanoethyl)amine Using Three Successive Cobalt-Catalyzed Electrophilic Aminations with Organozinc Halides was written by Grassl, Simon;Knochel, Paul. And the article was included in Organic Letters in 2020.Category: nitriles-buliding-blocks This article mentions the following:

A stepwise preparation of triple alkylated or arylated tertiary amines, starting from com. available tris(2-cyanoethyl)amine using three successive reaction sequences involving a selective oxidation (formation of an N-oxide followed by a Cope elimination) leading to an intermediate hydroxylamine, a benzoylation, and a cobalt-catalyzed electrophilic amination with organozinc halides is reported. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Category: nitriles-buliding-blocks).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) belongs to nitriles. Nitrile carbon shifts are in the range of 115â€?25 ppm whereas in isonitriles the shifts are around 155â€?65 ppm. 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.Category: nitriles-buliding-blocks

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Syntheses of cyanothiophenes from halothiophenes was written by Nishimura, Shoji;Imoto, Eiji. And the article was included in Nippon Kagaku Zasshi in 1961.Synthetic Route of C5H2N2O2S This article mentions the following:

2-Iodothiophene (42 g.), 20 g. Cu₂(CN)₂, and 120 cc. pyridine were refluxed 3 hrs., 5060 cc. pyridine distilled, 150 cc. C₆H₆ added, and the mixture refluxed 30 min., cooled, and filtered to give 14.3 g. 2-cyanothiophene (I), b₂₁ 88-90°. A mixture of 2-bromothiophene (32.6 g.), 20 g. Cu₂(CN)₂, and 150 cc. quinoline was refluxed 4 hrs., distilled, and treated with HCl to give 11.3 g.I. Similarly, 3-bromothiophene gave 70% 3-cyanothiophene. Similarly, the following cyanothiophenes were obtained (substituent on the starting material, reaction period in hrs., and % yield given): 2,5-BrNO₂, 4.0, 32; 2,5INO₂, 3.0, 70; 2,3-BrNO₂, 4.0, 35; 3,2-BrNO₂, 4.0, 54; 3,4-Br-NO₂, 4.5, 24; 2,4-BrNO₂, 4.5, 20; 2,5-AcI, 4.5, 44; 2,5-AcBr, 7.0, 20; 2,5-AcCl, 7.0, 0; 2,5-BrCO₂Me, 7.0, 0. The results indicate that reactivity of halogens is I > Br > Cl and the activating ability of substituents is NO₂ Ac > CO₂Me. Reactions of 5- acetyl- 2- bromo- 3- nitrothiophene, 2- bromo- 5- methoxycarbonyl-3-nitrothiophene, 2-bromo- 5- carboxy- 3- nitrothiophene, and 2,5-dibromo-3-nitrothiophene yielded 17% 2-acetyl-4-nitrothiophene, 10% 2-methoxycarbonyl-4-nitrothiophene, 15% 2cyano-3-nitrothiophene (II), and 35% II, resp. Hydrolysis of cyano compounds was carried out by heating with concentrated HCl for 2-3 hrs. but II, 3-cyano-2-nitrothiophene, and 3-cyano-4-nitrothiophene were recovered unchanged. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Synthetic Route of C5H2N2O2S).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) 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.Synthetic Route of C5H2N2O2S

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INCB050465 (Parsaclisib), a Novel Next-Generation Inhibitor of Phosphoinositide 3-Kinase Delta (PI3Kδ) was written by Yue, Eddy W.;Li, Yun-Long;Douty, Brent;He, Chunhong;Mei, Song;Wayland, Brian;Maduskuie, Thomas;Falahatpisheh, Nikoo;Sparks, Richard B.;Polam, Padmaja;Zhu, Wenyu;Glenn, Joseph;Feng, Hao;Zhang, Ke;Li, Yanlong;He, Xin;Katiyar, Kamna;Covington, Maryanne;Feldman, Patricia;Shin, Niu;Wang, Kathy He;Diamond, Sharon;Li, Yu;Koblish, Holly K.;Hall, Leslie;Scherle, Peggy;Yeleswaram, Swamy;Xue, Chu-Biao;Metcalf, Brian;Combs, Andrew P.;Yao, Wenqing. And the article was included in ACS Medicinal Chemistry Letters in 2019.Recommanded Product: 60025-09-4 This article mentions the following:

A medicinal chem. effort focused on identifying a structurally diverse candidate for phosphoinositide 3-kinase delta (PI3Kδ) led to the discovery of clin. candidate INCB050465 (20, parsaclisib). The unique structure of 20 contains a pyrazolopyrimidine hinge-binder in place of a purine motif that is present in other PI3Kδ inhibitors, such as idelalisib (1), duvelisib (2), and INCB040093 (3, dezapelisib). Parsaclisib (20) is a potent and highly selective inhibitor of PI3Kδ with drug-like ADME properties that exhibited an excellent in vivo profile as demonstrated through pharmacokinetic studies in rats, dogs, and monkeys and through pharmacodynamic and efficacy studies in a mouse Pfeiffer xenograft model. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Recommanded Product: 60025-09-4).

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) 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 addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Recommanded Product: 60025-09-4

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Preparation of Tertiary Benzylic Nitriles from Aryl Fluorides was written by Caron, Stephane;Vazquez, Enrique;Wojcik, Jill M.. And the article was included in Journal of the American Chemical Society in 2000.Safety of 2-(4-Methoxyphenyl)-2-methylpropanenitrile This article mentions the following:

An efficient method for the addition of secondary nitriles to fluoroarenes was described. The reaction is specific to hexamethyldisilazane potassium salt, but proceeds with a variety of substrates. For example, the reaction of 1-fluoro-2-methoxybenzene with 2-methylpropanenitrile in the presence of hexamethyldisilazane potassium salt in toluene or THF gave 2-methoxy-α,α-dimethylbenzeneacetonitrile. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5Safety of 2-(4-Methoxyphenyl)-2-methylpropanenitrile).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) 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.Safety of 2-(4-Methoxyphenyl)-2-methylpropanenitrile

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Design, Synthesis, and Molecular-modeling Study of Aminothienopyridine Analogues of Tacrine for Alzheimer’s Disease was written by Badran, Mohga M.;Abdel Hakeem, Maha;Abuel-Maaty, Suzan M.;El-Malah, Afaf;Abdel Salam, Rania M.. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2010.Reference of 70291-62-2 This article mentions the following:

2-Amino-3-cyanothiophenes were successfully condensed with a number of cycloalkanones to afford tacrine analogs in a one-step reaction mediated with Lewis acid. The newly synthesized compounds have been tested for their ability to inhibit acetylcholine esterase (AChE) activity using tacrine as standard drug. Some of the tested compounds showed moderate inhibitory activity in comparison with tacrine, especially compounds 6a (I) which displayed the highest inhibitory activity. Furthermore, mol.-modeling studies were performed in order to rationalize the obtained biol. results. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Reference of 70291-62-2).

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

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Structure-Activity Relationship Exploration of NNIBP Tolerant Region I Leads to Potent HIV-1 NNRTIs was written by Kang, Dongwei;Sun, Yanying;Murugan, N. Arul;Feng, Da;Wei, Fenju;Li, Jing;Jiang, Xiangyi;De Clercq, Erik;Pannecouque, Christophe;Zhan, Peng;Liu, Xinyong. And the article was included in ACS Infectious Diseases in 2020.Related Products of 1753-48-6 This article mentions the following:

Previous efforts in our lab have led to the development of human immunodeficiency virus type 1 (HIV-1) non-nucleoside reverse transcriptase inhibitor (NNRTI) thiophene[3,2-d]pyrimidine compound 1 (K-5a2) with promising activity against wild-type and mutant HIV-1 strains. In this work, a series of novel diarylpyrimidines derivatives carrying a structurally diverse motif at the right wing of the lead K-5a2 was designed and synthesized as potential anti-HIV-1 agents. The results demonstrated that 8a yielded exceptionally potent activity against HIV-1 wild-type (50% effective concentration (EC₅₀) = 3.30 nM) and mutant strain RES056 (EC₅₀ = 22.6 nM) in MT-4 cells; in the reverse transcriptase inhibitory assay, 8a (half maximal inhibitory concentration (IC₅₀) = 0.028μM) was remarkably superior to that of K-5a2 (IC₅₀ = 0.300μM) and comparable to that of etravirine (ETR; IC₅₀ = 0.011μM). Notably, 8a exhibited better druggability than that of K-5a2, including significantly reduced CYP enzymic inhibitory activity (IC₅₀ > 50μM), lower human ether-á-go-go related gene (hERG) inhibition (IC₅₀ > 30μM), and improved metabolic stability (short half-life, T_1/2 = 77.5 min) in vitro. In the experiment, the researchers used many compounds, for example, 2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6Related Products of 1753-48-6).

2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6) 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. 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.Related Products of 1753-48-6

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Oxadiazole Derivatives as Dual Orexin Receptor Antagonists: Synthesis, Structure-Activity Relationships, and Sleep-Promoting Properties in Rats was written by Brotschi, Christine;Roch, Catherine;Gatfield, John;Treiber, Alexander;Williams, Jodi T.;Sifferlen, Thierry;Heidmann, Bibia;Jenck, Francois;Bolli, Martin H.;Boss, Christoph. And the article was included in ChemMedChem in 2019.Name: 2-(Trifluoromethoxy)benzonitrile This article mentions the following:

The orexin system plays an important role in the regulation of wakefulness. Suvorexant, a dual orexin receptor antagonist (DORA) is approved for the treatment of primary insomnia. Herein, we outline our optimization efforts toward a novel DORA. We started our investigation with rac-[3-(5-chloro-benzoxazol-2-ylamino)piperidin-1-yl]-(5-methyl-2-[1,2,3]triazol-2-ylphenyl)methanone (3, I), a structural hybrid of suvorexant and a piperidine-containing DORA. During the optimization, we resolved liabilities such as chem. instability, CYP3A4 inhibition, and low brain penetration potential. Furthermore, structural modification of the piperidine scaffold was essential to improve potency at the orexin 2 receptor. This work led to the identification of (5-methoxy-4-methyl-2-[1,2,3]triazol-2-ylphenyl)-{(S)-2-[5-(2-trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]pyrrolidin-1-yl}methanone (51, II), a potent, brain-penetrating DORA with in vivo efficacy similar to that of suvorexant in rats. 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 compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. 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

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Synthesis and target annotation of the alkaloid GB18 was written by Woo, Stone;Shenvi, Ryan A.. And the article was included in Nature (London, United Kingdom) in 2022.Name: 4-methoxypicolinonitrile This article mentions the following:

Ingestion of alkaloid metabolites from the bark of Galbulimima (GB) sp. leads to psychotropic and excitatory effects in humans1-4. Limited, variable supply of GB alkaloids5, however, has impeded their biol. exploration and clin. development6. Here we report a solution to the supply of GB18, a structural outlier and putative psychotropic principle of Galbulimima bark. Efficient access to its challenging tetrahedral attached-ring motif required the development of a ligand-controlled endo-selective cross-electrophile coupling and a diastereoselective hydrogenation of a rotationally dynamic pyridine. Reliable, gram-scale access to GB18 enabled its assignment as a potent antagonist of κ- and μ-opioid receptors-the first new targets in 35 years-and lays the foundation to navigate and understand the biol. activity of Galbulimima metabolites. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Name: 4-methoxypicolinonitrile).

4-methoxypicolinonitrile (cas: 36057-44-0) 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.Name: 4-methoxypicolinonitrile

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Synthesis and structural elucidation of novel 2,4-disubstituted 1,3-oxazole analogues for pharmacological properties was written by Venugopala, Katharigatta N.. And the article was included in Asian Journal of Chemistry in 2018.Reference of 60979-25-1 This article mentions the following:

Novel 2,4-disubstituted 1,3-oxazole analogs (3a-i) were designed and synthesized between 1-[3,5-bis(trifluoromethyl)-phenyl]-2-bromoethan-1-one and substituted amides by microwave assisted method. 2,4-Disubstituted 1,3-oxazole analogs obtained were at excellent yields and purity of the compound was ascertained by HPLC. The chem. structure of these compounds was elucidated by spectrometric (FTIR, NMR and LCMS) and elemental anal. Microwave method influenced the better yield and reduction in reaction time when compared to conventional reflux method. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1Reference of 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Reference of 60979-25-1

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts