Author: Jessica.F

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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Nitrile – Wikipedia,
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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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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Stereoselective synthesis of spirocyclohexadiene-pyrazolones via organic base and/or hydrogen bonding assisted [3+3] annulation reactions was written by Sun, Bing-Bing;Zhang, Jun-Qi;Chen, Jun-Bo;Fan, Wei-Tai;Yu, Jie-Qiang;Hu, Jia-Ming;Wang, Xing-Wang. And the article was included in Organic Chemistry Frontiers in 2019.SDS of cas: 55490-87-4 This article mentions the following:

The 1,4-diazabicyclo[2.2.2]octane (DABCO)-catalyzed [3+3] cycloaddition reaction of α-arylidene pyrazolinones I (R¹ = Ph, 3-fluorophenyl, 2-naphthyl, 2-thienyl, etc.; R² = Ph, 4-methylphenyl, 4-methoxyphenyl, 4-fluorophenyl; R³ = Ph, 3-chlorophenyl, 4-cyanophenyl, 4-methylphenyl, 4-methoxyphenyl) and 2-benzylidenemalononitriles R⁴CH=C(CN)₂ (R² = Ph, 2-chlorophenyl, 9-anthracenyl, etc.) under mild reaction conditions has been reported, which afforded the spirocyclohexadiene-pyrazolones II in good yields with moderate to good diastereoselectivities. By the use of a cinchona alkaloid derived bifunctional squaramide-tertiary amine catalyst, an asym. variant of this [3 + 3] cycloaddition reaction has also been developed to provide optically active spirocyclohexadiene-pyrazolones bearing an all-carbon quaternary chiral center III in good yields with excellent enantioselectivities and moderate diastereoselectivities. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4SDS of cas: 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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.SDS of cas: 55490-87-4

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Second harmonic generation from the single crystals of N-substituted 4-cyanoanilines was written by Hashimoto, H.;Okada, Y.;Okamoto, N.;Matsushima, R.. And the article was included in Journal of Luminescence in 2000.Category: nitriles-buliding-blocks This article mentions the following:

Six N-substituted derivatives of 4-cyanoaniline (pCA) were synthesized and their phys. and optical properties were examined in the search for 2nd-order nonlinear optical materials with enough crystal dimensions together with blue-light transparency. Among the derivatives examined, N-diphenylmethyl-pCA and N-2-naphthylmethyl-pCA afforded single crystals that lack a center of symmetry. Although the 2nd harmonic (SH) activities of these derivatives were not enough for the practical purposes, their cut-off wavelengths were shorter than 330 nm and showed sufficient blue-light transparency. Quant. prediction of the SH activity was also attempted. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Category: nitriles-buliding-blocks).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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

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Nitrile – Wikipedia,
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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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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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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Optimization of N-benzyl-5-nitrofuran-2-carboxamide as an antitubercular agent was written by Gallardo-Macias, Ricardo;Kumar, Pradeep;Jaskowski, Mark;Richmann, Todd;Shrestha, Riju;Russo, Riccardo;Singleton, Eric;Zimmerman, Matthew D.;Ho, Hsin Pin;Dartois, Veronique;Connell, Nancy;Alland, David;Freundlich, Joel S.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2019.Recommanded Product: 37812-51-4 This article mentions the following:

The optimization campaign for a nitrofuran antitubercular hit (N-benzyl-5-nitrofuran-2-carboxamide; JSF-3449) led to the design, synthesis, and biol. profiling of a family of analogs. These compounds exhibited potent in vitro antitubercular activity (MIC = 0.019-0.20 μM) against the Mycobacterium tuberculosis H37Rv strain and low in vitro cytotoxicity (CC₅₀ = 40- > 120 μM) towards Vero cells. Significant improvements in mouse liver microsomal stability and mouse pharmacokinetic profile were realized by introduction of an α,α-dimethylbenzyl moiety. Among these compounds, JSF-4088 (I) is highlighted due to its in vitro antitubercular potency (MIC = 0.019 μM) and Vero cell cytotoxicity (CC₅₀ > 120 μM). The findings suggest a rationale for the continued evolution of this promising series of antitubercular small mols. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Recommanded Product: 37812-51-4).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) 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. 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: 37812-51-4

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Nitrile – Wikipedia,
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Iron-Catalyzed Oxidative Amination of Benzylic C(sp³)-H Bonds with Anilines was written by Song, Yan-Ling;Li, Bei;Xie, Zhen-Biao;Wang, Dan;Sun, Hong-Mei. And the article was included in Journal of Organic Chemistry in 2021.Safety of 4-(Benzylamino)benzonitrile This article mentions the following:

Iron-catalyzed oxidative amination of benzylic C(sp³)-H bonds with anilines bearing electron-withdrawing groups (EWGs) or electron-donating groups (EDGs) has been realized based on simple variations of N-substituents on imidazolium cations in novel ionic Fe(III) complexes. The structural modification of the imidazolium cation resulted in regulation of the redox potential and the catalytic performance of the iron metal center. Using DTBP as oxidant, [HItBu][FeBr₄] (1,3-di-tert-butylimidazolium iron tetrabromide) showed the highest catalytic activity for anilines bearing EWGs, while [HIPym][FeBr₄] (1,3-bis(pyrimidin-2-yl)imidazolium iron tetrabromide) was more efficient for EDG-substituted anilines. This work provides an alternative access to benzylamines, e.g., RN(R¹)CH₂Ph [R = 4-O₂NC₆H₄, 2-pyrimidinyl, 8-isoquinolinyl, etc., R¹ = H, Me,], with advantages of both a wide substrate scope and iron catalysis. 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 carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Safety of 4-(Benzylamino)benzonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Heterocyclic Meisenheimer complexes: kinetic and equilibrium data for methoxide ion attack on various disubstituted 2,4-Y,Z-thiophenes and -selenophenes in methanol was written by Terrier, Francois;Chatrousse, Alain-Pierre;Paulmier, Claude. And the article was included in Journal of Organic Chemistry in 1979.Category: nitriles-buliding-blocks This article mentions the following:

The stabilities of I (R, R¹ = NO₂, NO₂; CN, NO₂; NO₂, CN; X = Se, S) decreased in the stated order of R, R¹ and of X, but different trends were found in kinetic studies. II (R = CN; R¹ = NO₂; X = Se, S) reacted differently with MeO^– than the other II. An ortho-like NO₂ group may affect nucleophilic substitution more than a para-like NO₂ group. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Category: nitriles-buliding-blocks).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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

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CNDO/2 calculations of molecules. 3. Ionization potential and charge distribution was written by Koppel, I.;Molder, U.. And the article was included in Organic Reactivity (Tartu) in 1981.Recommanded Product: 7528-78-1 This article mentions the following:

For several classes of aliphatic compounds, (e.g., ether, amines), a linear relation is established between ionization energy of the electron localized on a certain atom and semiempirical CNDO/2 charges on the latter. The charge distribution was calculated according to the Mulliken procedure. The correction for the intramol. Madelung potential was introduced into the valence shell ionization potentials. A method for the determination of the ionization potential of the lone pair from photoelectron spectra was suggested. The linearity between CNDO/2 and ab initio (STO-3G and 4-31G basis sets) charge densities was found. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Recommanded Product: 7528-78-1).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts