Tag: 100-200

Selective cyclooxygenase-2 inhibitors: heteroaryl modified 1,2-diarylimidazoles are potent, orally active antiinflammatory agents was written by Khanna, Ish K.;Yu, Yi;Huff, Renee M.;Weier, Richard M.;Xu, Xiangdong;Koszyk, Francis J.;Collins, Paul W.;Cogburn, J. Nita;Isakson, Peter C.;Koboldt, Carol M.;Masferrer, Jaime L.;Perkins, William E.;Seibert, Karen;Veenhuizen, Amy W.;Yuan, Jinhua;Yang, Dai-Chang;Zhang, Yan Y.. And the article was included in Journal of Medicinal Chemistry in 2000.Name: 3-Methylthiophene-2-carbonitrile This article mentions the following:

A series of heteroaryl modified 1,2-diarylimidazoles has been synthesized and found to be potent and highly selective (1000-9000-fold) inhibitors of the human COX-2. 3-Pyridyl-derived COX-2 selective inhibitor I exhibited excellent activity in acute (carrageenan induced paw edema, ED₅₀ = 5.4 mg/kg) and chronic (adjuvant induced arthritis, ED₅₀ = 0.25 mg/kg) models of inflammation. The relatively long half-life of I in rat and dog prompted investigation of the pyridyl and other heteroaromatic systems containing potential metabolic functionalities. A number of substituted pyridyl and thiazole containing compounds. e.g., II, demonstrated excellent oral activity in every efficacy model evaluated. Several orally active diarylimidazoles exhibited desirable pharmacokinetics profiles and showed no GI toxicity in the rat up to 100 mg/kg in both acute and chronic models. The paper describes facile and practical syntheses of the targeted diarylimidazoles. The structure-activity relationships and antiinflammatory properties of a series of diarylimidazoles are discussed. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Name: 3-Methylthiophene-2-carbonitrile).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) 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. 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.Name: 3-Methylthiophene-2-carbonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Targeting the K_v11.1 (hERG) channel with allosteric modulators. Synthesis and biological evaluation of three novel series of LUF7346 derivatives was written by van Veldhoven, Jacobus P. D.;Campostrini, Giulia;van Gessel, Constantijn J. E.;Ward-van Oostwaard, Dorien;Liu, Rongfang;Mummery, Christine L.;Bellin, Milena;IJzerman, Adriaan P.. And the article was included in European Journal of Medicinal Chemistry in 2021.HPLC of Formula: 60710-80-7 This article mentions the following:

Three novel series of substituted benzophenones for their allosteric modulation of the human Kv11.1 (hERG) channel were synthesized and evaluated. Effects of this is compared with reference compound LUF7346 previously shown to shorten the action potential of cardiomyocytes derived from human stem cells. Most compounds behaved as neg. allosteric modulators (NAMs) of [3H]dofetilide binding to the channel. Compound III [R = 2-Cl; R¹ = CH₂cPr; X= Y = C] was the most potent amongst all ligands, remarkably reducing the affinity of dofetilide in competitive displacement assays. One of the other II [R = H; X = N] tested in a second radioligand binding set-up, displayed unusual displacement characteristics with a pseudo-Hill coefficient significantly distinct from unity, further indicative of its allosteric effects on the channel. Some compounds were evaluated in a more physiol. relevant context in beating cardiomyocytes derived from human induced pluripotent stem cells. Surprisingly, the compounds tested showed effects quite different from the reference NAM LUF7346. For instance, compound I [R = 3-Me] prolonged, rather than shortened, the field potential duration, while it did not influence this parameter when the field potential was already prolonged by dofetilide. In subsequent patch clamp studies on HEK293 cells expressing the hERG channel the compounds behaved as channel blockers. In conclusion, new allosteric modulators of the hERG channel were successfully synthesized and identified . Unexpectedly, their effects differed from the reference compound in functional assays on hERG-HEK293 cells and human cardiomyocytes, to the extent that the compounds behaved as stand-alone channel blockers. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7HPLC of Formula: 60710-80-7).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.HPLC of Formula: 60710-80-7

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Nitrile – Wikipedia,
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Synthesis and antiprotozoal activity of cationic 1,4-diphenyl-1H-1,2,3-triazoles. [Erratum to document cited in CA152:074962] was written by Bakunov, Stanislav A.;Bakunova, Svetlana M.;Wenzler, Tanja;Ghebru, Maedot;Werbovetz, Karl A.;Brun, Reto;Tidwell, Richard R.. And the article was included in Journal of Medicinal Chemistry in 2011.Application In Synthesis of 3-Amino-4-methoxybenzonitrile This article mentions the following:

On page 270, in the left column, the Acknowledgment section was incomplete, and should read: “This work was supported by The Bill and Melinda Gates Foundation and NIH Grant 5U01AI075641.”. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1Application In Synthesis of 3-Amino-4-methoxybenzonitrile).

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).Application In Synthesis of 3-Amino-4-methoxybenzonitrile

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Nitrile – Wikipedia,
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Borrowing Hydrogen Methodology for N-Benzylation using a π-Benzylpalladium System in Water was written by Hikawa, Hidemasa;Koike, Toshitaka;Izumi, Kyoko;Kikkawa, Shoko;Azumaya, Isao. And the article was included in Advanced Synthesis & Catalysis in 2016.Quality Control of 2-Amino-4-(trifluoromethyl)benzonitrile This article mentions the following:

The authors demonstrate a borrowing hydrogen methodol. using the unique reactivity of the π-benzylpalladium system in water, which offers an efficient and environmentally friendly N-monobenzylation of electron-deficient anilines or 2-aminopyridine with non-activated benzylic alcs. under neutral conditions. The crossover experiment using benzyl-α,α-d₂ alc. and 3-methylbenzyl alc. afforded H/D scrambling products, suggesting that the borrowing hydrogen pathway occurred in the authors’ catalytic system. The authors’ simple protocol can accomplish a gram scale reaction of 2-aminobenzonitrile (76% isolated yield), and was performed using only 1 mol % Pd(OAc)₂ and 2 mol % TPPMS without other additives in water. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Quality Control of 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. 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.Quality Control of 2-Amino-4-(trifluoromethyl)benzonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Structure-selectivity relationship in the chemoselective hydrogenation of unsaturated nitriles was written by Kukula, Pavel;Koprivova, Klara. And the article was included in Journal of Catalysis in 2005.Safety of 2-Cyclohexylacetonitrile This article mentions the following:

Several unsaturated nitriles of various structures (cinnamonitrile, cyclohex-1-enyl-acetonitrile, acrylonitrile, 3,3-dimethyl-acrylonitrile, geranylnitrile, and 2- and 3-pentenenitrile) with different substituents at the double bond were hydrogenated over Cr-doped Raney cobalt and nickel and over their undoped equivalent The substitution and the position of the double bond relative to the nitrile group are crucial in determining the chemoselectivity for the unsaturated amine. The double bond is not hydrogenated when it is sterically hindered or if it is too far from the nitrile group (cyclohex-1-enyl-acetonitrile, double bond at C-6 in geranylnitrile). In conjugated systems, such as acrylonitrile or 2-pentenylnitrile, the activated double bond is hydrogenated before the nitrile. An addnl. Me substituent at the double bond enhances the selectivity for unsaturated amines and, thus, 3,3-dimethyl-acrylonitrile and geranylnitrile were hydrogenated with selectivity up to 40%. The highest selectivities for unsaturated amines (up to 90%) were reached during the hydrogenation of nonconjugated systems, such as cyclohex-1-enyl-acetonitrile and 3-pentenylnitrile. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Safety 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. 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 2-Cyclohexylacetonitrile

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Nitrile – Wikipedia,
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Ring opening of 2-substituted 4-nitrothiophenes with pyrrolidine. Access to new functionalized nitro-unsaturated building blocks was written by Dell’Erba, C.;Gabellini, A.;Novi, M.;Petrillo, G.;Tavani, C.;Cosimelli, B.;Spinelli, D.. And the article was included in Tetrahedron in 2001.Application of 42137-24-6 This article mentions the following:

The reaction conditions of the ring-opening processes of 3-nitrothiophene and of 3-nitrobenzo[b]thiophene with pyrrolidine and AgNO₃ were optimized as well as those of the subsequent S-methylation of the ensuing Ag enethiolates to 4-methylthio-2-nitro-1-pyrrolidino-1,3-butadiene (I) and 1-(2-methylthiophenyl)-1-nitro-2-pyrrolidinoethylene (II). Under such conditions 2-substituted 4-nitrothiophenes consistently gave good yields of the corresponding 4-methylthio-2-nitro-1-pyrrolidino-4-R-1,3-butadienes (pyr-MNRB, R = PhS, PhSO₂, MeS, MeSO₂, MeCO, MeCO₂, and CN). The nitroenamine derivatives I, II, and pyr-MNRB were then reacted with p-MeC₆H₄MgBr to furnish moderate to good yields of 4-methylthio-2-nitro-1-(p-tolyl)-4-R-1,3-butadienes (p-tolyl-MNRB) and 1-(2-methylthiophenyl)-1-nitro-2-(p-tolyl)ethylene(III). Stereochem. of the interesting building blocks I–III, pyr-MNRB, and p-tolyl-MNRB was assigned on the grounds of ¹H NMR data and NOE experiments In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Application of 42137-24-6).

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. 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 of 42137-24-6

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Effect of antiprotozoal molecules on hypnospores of Perkinsus spp. parasite was written by Duarte, Samia Sousa;de Moura, Ricardo Olimpio;da Silva, Patricia Mirella. And the article was included in Experimental Parasitology in 2018.Quality Control of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

Perkinsus protozoan parasites have been associated with high mortality of bivalves worldwide, including Brazil. The use of antiproliferative drugs to treat the Perkinsosis is an unusual prophylactic strategy. However, because of their environment impact it could be used to control parasite proliferation in closed system, such as hatchery. This study evaluated the anti-Perkinsus activity potential of synthesized and com. compounds Viability of hypnospores of Perkinsus spp. was assessed in vitro. Cells were incubated with three 2-amino-thiophene (6AMD, 6CN, 5CN) and one acylhydrazone derivatives (AMZ-DCL), at the concentrations of 31.25; 62.5; 125; 250 and 500μM and one com. chlorinated phenoxy phenol derivative, triclosan (2, 5, 10 and 20μM), for 24-48 h. Two synthetic mols. (6CN and AMZ-DCL) caused a significant decline (38 and 39%, resp.) in hypnospores viability, at the highest concentration (500μM), after 48 h. Triclosan was the most cytotoxic compound, causing 100% of mortality at 20μM after 24 h and at 10μM after 48 h. Cytotoxic effects of the compounds 6CN, AMZ-DCL, and triclosan were investigated by measuring parasite’s zoosporulation, morphol. changes and metabolic activities (esterase activity, production of reactive oxygen species and lipid content). Results showed that zoosporulation occurred in few cell. Triclosan caused changes in the morphol. of hypnospores. The 6CN and AMZ-DCL did not alter the metabolic activities studied while Triclosan significantly increased the production of reactive oxygen species and changed the amount and distribution of lipids in the hypnospores. These results suggest that three compounds had potential to be used as antiprotozoal drugs, although further investigation of their mechanism of action must be enlightened. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Quality Control of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile).

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. 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.Quality Control of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Commercial Zinc Oxide: A Facile, Efficient, and Eco-friendly Catalyst for the One-Pot Three-Component Synthesis of Multisubstituted 2-Aminothiophenes via the Gewald Reaction was written by Tayebee, Reza;Ahmadi, S. Javad;Rezaei Seresht, Esmaeil;Javadi, Farzad;Yasemi, Mohammad A.;Hosseinpour, Mohsen;Maleki, Behrouz. And the article was included in Industrial & Engineering Chemistry Research in 2012.Electric Literature of C8H8N2S This article mentions the following:

An eco-friendly, simple, and effective protocol is developed for the synthesis of various multisubstituted 2-aminothiophenes. In the presence of a catalytic amount of ZnO (5 mol %), ketones or aldehydes, malononitrile and elemental sulfur were converted to the corresponding 2-aminothiophene derivatives in moderate to high yields (27%-70%) under solvent-free conditions at 100 °C. Zinc oxide as an efficient, readily available, and reusable catalyst, showed very good catalytic activity for the synthesis of 2-aminothiophene derivatives Thus far, little research has been reported on the Gewald reaction under solvent-free conditions; to the best of our knowledge, this is the first time that it has been proposed as an inexpensive and readily available catalyst for use in the target synthetic route. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Electric Literature of C8H8N2S).

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. 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.Electric Literature of C8H8N2S

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Nitrile – Wikipedia,
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Synthesis of cis- and trans-4-cyanocyclohexanol was written by Praefcke, Klaus;Schmidt, Dietmar. And the article was included in Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie in 1980.Application of 24056-34-6 This article mentions the following:

The title 4-cyanocyclohexanols, whose stereochem. was determined by NMR spectroscopy, were prepared for the first time by the reaction of 4-hydroxycyclohexanone with Me₃COK and p-MeC₆H₄SO₃CH₂NC to give a cis-trans mixture of the title compounds, which was separated via column chromatog. of their benzoates followed by hydrolysis. In the experiment, the researchers used many compounds, for example, 4-Hydroxycyclohexanecarbonitrile (cas: 24056-34-6Application of 24056-34-6).

4-Hydroxycyclohexanecarbonitrile (cas: 24056-34-6) 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.Application of 24056-34-6

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Discovery of a Phosphoinositide 3-Kinase (PI3K) β/δ Inhibitor for the Treatment of Phosphatase and Tensin Homolog (PTEN) Deficient Tumors: Building PI3Kβ Potency in a PI3Kδ-Selective Template by Targeting Nonconserved Asp856 was written by Perreault, Stephane;Chandrasekhar, Jayaraman;Cui, Zhi-Hua;Evarts, Jerry;Hao, Jia;Kaplan, Joshua A.;Kashishian, Adam;Keegan, Kathleen S.;Kenney, Thomas;Koditek, David;Lad, Latesh;Lepist, Eve-Irene;McGrath, Mary E.;Patel, Leena;Phillips, Bart;Therrien, Joseph;Treiberg, Jennifer;Yahiaoui, Anella;Phillips, Gary. And the article was included in Journal of Medicinal Chemistry in 2017.Category: nitriles-buliding-blocks This article mentions the following:

Phosphoinositide 3-kinase (PI3K) beta signaling is required to sustain cancer cell growth in which the tumor suppressor phosphatase and tensin homolog (PTEN) has been deactivated. This manuscript describes the discovery, optimization, and in vivo evaluation of a novel series of PI3Kbeta/delta inhibitors in which PI3Kbeta potency was built in a PI3Kdelta-selective template. This work led to the discovery of a highly selective PI3Kbeta/delta inhibitor displaying excellent pharmacokinetic profile and efficacy in a human PTEN-deficient LNCaP prostate carcinoma xenograft tumor model. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Category: nitriles-buliding-blocks).

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. 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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts