Nitriles-buliding-blocks

New diarylsulfonamide inhibitors of Leishmania infantum amastigotes was written by Gonzalez, Myriam;Alcolea, Pedro Jose;Alvarez, Raquel;Medarde, Manuel;Larraga, Vicente;Pelaez, Rafael. And the article was included in International Journal of Parasitology: Drugs and Drug Resistance in 2021.Recommanded Product: 60979-25-1 This article mentions the following:

New drugs against visceral leishmaniasis with mechanisms of action differing from existing treatments and with adequate cost, stability, and properties are urgently needed. No antitubulin drug is currently in the clinic against Leishmania infantum, the causative agent of visceral leishmaniasis in the Mediterranean area. We have designed and synthesized a focused library of 350 compounds against the Leishmania tubulin based on the structure-activity relationship (SAR) and sequence differences between host and parasite. The compounds synthesized are accessible, stable, and appropriately soluble in water. We assayed the library against Leishmania promastigotes, axenic, and intracellular amastigotes and found 0, 8, and 16 active compounds, resp., with a high success rate against intracellular amastigotes of over 10%, not including the cytotoxic compounds Five compounds have a similar or better potency than the clin. used miltefosine. 14 compounds showed a host-dependent mechanism of action that might be advantageous as it may render them less susceptible to the development of drug resistance. The active compounds cluster in five chem. classes that provide structure-activity relationships for further hit improvement and facilitate series development. Mol. docking is consistent with the proposed mechanism of action, supported by the observed structure-activity relationships, and suggests a potential extension to other Leishmania species due to sequence similarities. A new family of diarylsulfonamides designed against the parasite tubulins is active against Leishmania infantum and represents a new class of potential drugs with favorable cost, stability, and aqueous solubility for the treatment of visceral leishmaniasis (VL). These results could be extended to other clin. relevant species of Leishmania spp. 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 compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. 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.Recommanded Product: 60979-25-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electronic effects of para-substitution on acetophenones in the reaction of rat liver 3α-hydroxysteroid dehydrogenase was written by Uwai, Koji;Konno, Noboru;Yasuta, Yuka;Takeshita, Mitsuhiro. And the article was included in Bioorganic & Medicinal Chemistry in 2008.Formula: C9H9NO This article mentions the following:

Stereoselective reductive metabolism of various p-substituted acetophenone derivatives was studied using isolated rat liver 3α-hydroxysteroid dehydrogenase (3α-HSD). Kinetic experiments were performed and analyzed by measuring the products by HPLC using a chiral column. The results demonstrated that the presence of an electron-withdrawing substituent on the benzene ring plays an important role in determining the reduction rate in the syntheses of various (S)-alcs. from their corresponding carbonyl compounds A plot of log {(V_max/K_m)X/(V_max/K_m)H} vs. the substituent parameter (π, σ_para, Es) shows an increasing rate mainly for electron-withdrawing substituents, with a correlation coefficient (r²) of 0.97 which was obtained for triplicate data that were significant at the p < 0.0001 level. With this in mind, new drugs can be designed that exploit this reduction pathway by introducing an electron-withdrawing group adjacent to the reduction site when a reduction reaction is desired, or by adding an electron-donating group when minimization of the reduction pathway is desired. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Formula: C9H9NO).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Formula: C9H9NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A real-time colorimetric and ratiometric fluorescent probe for sulfite was written by Wu, Ming-Yu;He, Ting;Li, Kun;Wu, Ming-Bo;Huang, Zheng;Yu, Xiao-Qi. And the article was included in Analyst (Cambridge, United Kingdom) in 2013.Category: nitriles-buliding-blocks This article mentions the following:

A real-time colorimetric and ratiometric fluorescent probe based on modulating the intramol. charge transfer (ICT) of the coumarin platform for selective detection of sulfite is presented. This reaction based probe used the Michael addition to the dicyano-vinyl group with the detection limit of 5.8 × 10^-5 M The probe displayed a high selectivity for sulfite over other anions and reactive sulfur especially for biothiols including cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), with ∼100 nm blue shift and >230 times intensity ratios change of the emission spectrum. Meanwhile, it could be easily observed that the probe for sulfite changes from red to pale yellow by the naked eye, and from red to blue under UV lamp immediately after the sulfite is added. It is the fastest response probe for sulfite ever reported, which could give a colorimetric and ratiometric fluorescent response instantly. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Category: nitriles-buliding-blocks).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Use of correlation equations in gas chromatographic identification of oxygen and nitrogen-containing organic substances was written by Zakirov, N. S.. And the article was included in Zhurnal Analiticheskoi Khimii in 1980.Reference of 7528-78-1 This article mentions the following:

Coefficients of linear equations, which describe the dependence of the logarithm of relative retention time values on the C number of a mol. were determined for substances of different natures, e.g. nitriles, alcs., amines, aldehydes, aliphatic hydrocarbons, on phases containing cyano groups. The constants obtained can be used for the identification of components of complicated mixtures In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Reference of 7528-78-1).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Reference of 7528-78-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A Boron-Nitrogen Double Transborylation Strategy for Borane-Catalyzed Hydroboration of Nitriles was written by Pradhan, Subham;Sankar, Raman Vijaya;Gunanathan, Chidambaram. And the article was included in Journal of Organic Chemistry in 2022.Reference of 4435-14-7 This article mentions the following:

Organoborane-catalyzed hydroboration of nitriles provides N,N-diborylamines, which act as efficient synthons for the synthesis of primary amines and secondary amides. Known nitrile hydroboration methods are dominated by metal catalysis. Simple and metal-free hydroboration of nitriles using diborane [H-B-9-BBN]₂ as a catalyst and pinacolborane as a turnover reagent is reported. The reaction of monomeric H-B-9-BBN with nitriles leads to the hydrido-bridged diborylimine intermediate; a subsequent sequential double hydroboration-transborylation pathway involving B-N/B-H σ bond metathesis is proposed. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Reference of 4435-14-7).

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. 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.Reference of 4435-14-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

One pot synthesis of fused pyrimidines from 2-[N-(methylthiothiocarbonyl)amino]acetate was written by Chowdhury, A. Z. M. Shaifullah;Shibata, Yasuyuki;Morita, Masatoshi;Kaya, Kunimitsu;Sano, Tomoharu. And the article was included in Heterocycles in 2001.Recommanded Product: 70291-62-2 This article mentions the following:

A variety of 3-substituted fused pyrimidines are readily obtained from the 2-amino esters with 2-[N-(methylthiothiocarbonyl)amino]acetate (I). Condensed imidazo[1,2-c]pyrimidine ring system was also constructed in a one-pot process by reacting heteroaromatic 2-amino nitriles with I, obtaining a number of novel tri- and tetracyclic compounds In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Recommanded Product: 70291-62-2).

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. Recommanded Product: 70291-62-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

1,3-Diaryltriazenes: a new class of anorectic agents was written by Hill, David T.;Stanley, Kerry G.;Williams, Janice E. Karoglan;Loev, Bernard;Fowler, Phillip J.;McCafferty, James P.;Macko, Edward;Berkoff, Charles E.;Ladd, Christine B.. And the article was included in Journal of Medicinal Chemistry in 1983.Recommanded Product: 2-Amino-4-(trifluoromethyl)benzonitrile This article mentions the following:

The title compounds I (R = H, Ac, ClCH₂CO, EtCO, etc.; R¹ = H, Br, Cl, CN, CF₃, MeO, CO₂Me; R² = H, Cl, CF₃; R³ = H, Br, Cl, CN, CF₃, MeO, CO₂H, CO₂Me; R⁴ = H, Cl, CF₃, CO₂H) prepared in part from the aniline precursors II (R = Br, Cl, CN, MeO, CF₃, CO₂H, CO₂Me; R¹ = Cl or CF₃) were evaluated as anorectic and antiobesity agents in dog, rat, and squirrel monkey. 1,3-bis[2-cyano-5-(trifluoromethyl)phenyl]triazene  [58458-08-5] Was the most effective compound Structure activity relations are discussed. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Recommanded Product: 2-Amino-4-(trifluoromethyl)benzonitrile).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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. 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: 2-Amino-4-(trifluoromethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis with nitriles. 92. Synthesis of 5-formylcytosine derivatives was written by Jachak, Madhukar;Mittelbach, Martin;Junek, Hans. And the article was included in Heterocycles in 1993.Recommanded Product: 2-Aminopyrimidine-5-carbonitrile This article mentions the following:

The reactivity of 3-dimethylamino-2-formylpropenenitrile (I) with various amino compounds is studied. Thus, condensation of I with anilines gives the corresponding azomethines. Reaction of I with thiourea and guanidine, resp., leads to 5-formylthiocytosine (II) and 2-amino-5-cyanopyrimidine. Also, 2-formyl-3-ureidopropenenitriles can be obtained by reaction of I with urea and substituted ureas. The 2-formyl-3-ureidopropenenitriles can easily be cyclized to 3-substituted 5-formylcytosines. In the experiment, the researchers used many compounds, for example, 2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6Recommanded Product: 2-Aminopyrimidine-5-carbonitrile).

2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6) 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Recommanded Product: 2-Aminopyrimidine-5-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A recyclable Cu-catalyzed C-N coupling reaction in water and its application to synthesis of imidazo[1,2-a]quinoxaline was written by Huang, Liye;Yu, Ruina;Zhu, Xinhai;Wan, Yiqian. And the article was included in Tetrahedron in 2013.Quality Control of 4-(Benzylamino)benzonitrile This article mentions the following:

Polystyrene-supported pyrrole-2-carbohydrazide was synthesized and combined with CuI to make up a recyclable heterogeneous catalytic system for Ullmann-type C-N coupling reaction in water. In which, a variety of functionalized aryl halides reacted efficiently with anilines, benzylamine, aliphatic amines, and imidazole. its preliminary application resulted in a more practical synthesis of imidazo[1,2-a]quinoxaline. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Quality Control of 4-(Benzylamino)benzonitrile).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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. 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.Quality Control of 4-(Benzylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Direct N-Alkylation/Fluoroalkylation of Amines Using Carboxylic Acids via Transition-Metal-Free Catalysis was written by Lu, Chunlei;Qiu, Zetian;Xuan, Maojie;Huang, Yan;Lou, Yongjia;Zhu, Yiling;Shen, Hao;Lin, Bo-Lin. And the article was included in Advanced Synthesis & Catalysis in 2020.Reference of 4714-63-0 This article mentions the following:

A scalable protocol of direct N-mono/di-alkyl/fluoroalkylation of primary/secondary amines was constructed with various carboxylic acids as coupling agents under the catalysis of a simple air-tolerant inorganic salt, K₃PO₄. Advantageous features include 100 examples, 10 drugs and drug-like amines, fluorinated complex tertiary amines, gram-scale synthesis and isotope-labeling amine, thus demonstrating the potential applicability in industry of this methodol. The involvement of relatively less reactive silicon-hydride compared with the traditional reactive metal-hydride or boron-hydride species required to reduce the amide intermediates presumably contributes to the remarkable functional group compatibility. In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0Reference of 4714-63-0).

4-(Ethylamino)benzonitrile (cas: 4714-63-0) 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.Reference of 4714-63-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts