Category: nitriles-buliding-blocks

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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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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Nitrile – Wikipedia,
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Amination of Alcohols Catalyzed by Copper-Aluminum Hydrotalcite: A Green Synthesis of Amines was written by Likhar, Pravin R.;Arundhathi, Racha;Kantam, Mannepalli Lakshmi;Prathima, Parvathaneni Sai. And the article was included in European Journal of Organic Chemistry in 2009.Safety of 4-(Benzylamino)benzonitrile This article mentions the following:

Copper-aluminum hydrotalcite (CuAl-HT)/K₂CO₃ has been employed in the activation of various benzyl alcs. with benzylamines to afford the corresponding amines in good to high yields. Experimentation showed that the reaction takes place through sequential transformations: the oxidation of alcs. into carbonyl compounds, imine formation between amines and carbonyl compounds, and then reduction of imines to amines, heterogeneously catalyzed by non-noble Cu-Al HT catalyst in a one-pot and straightforward fashion. The process was further extended to amination of alcs. with anilines which are often resistant to alkylation reactions when substituted with strong electron-withdrawing groups. 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 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).Safety of 4-(Benzylamino)benzonitrile

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Nitrile – Wikipedia,
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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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Nitrile – Wikipedia,
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“Water Strider” Legs with a Self-Assembled Coating of Single-Crystalline Nanowires of an Organic Semiconductor was written by Jiang, Lang;Yao, Xi;Li, Hongxiang;Fu, Yanyan;Chen, Li;Meng, Qing;Hu, Wenping;Jiang, Lei. And the article was included in Advanced Materials (Weinheim, Germany) in 2010.Synthetic Route of C18H10N2 This article mentions the following:

Superhydrophobic surfaces are reported composed of crystalline nanowires of an organic semiconductor. Model copper waterstriders weighing 259.6 mg with self-assembled crystalline nanowires on their legs can easily stand on the surface of water. 1.0 Mg of such organic crystalline nanowires assembled on the legs could maximum float a 372 mg model strider. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Synthetic Route of C18H10N2).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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.Synthetic Route of C18H10N2

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Reductive Amination Revisited: Reduction of Aldimines with Trichlorosilane Catalyzed by Dimethylformamide – Functional Groups Tolerance, Scope, and Limitations was written by Popov, Kirill K.;Campbell, Joanna L. P.;Kysilka, Ondrej;Hosek, Jan;Davies, Christopher D.;Pour, Milan;Kocovsky, Pavel. And the article was included in Journal of Organic Chemistry in 2022.Related Products of 10282-32-3 This article mentions the following:

Aldimines R¹CH₂NHR² (R¹ = but-3-yn-1-yl, Ph, thiophen-2-yl, etc.; R² = Bu, Bn, cyclohexyl, 5-methyl-1,3,4-thiadiazol-2-yl, etc.), generated in situ from aliphatic, aromatic, and heteroaromatic aldehydes R¹CHO and aliphatic, aromatic, and heteroaromatic primary or secondary amines R²NH₂, can be reduced with trichlorosilane in the presence of DMF (DMF) as an organocatalyst (≤10 mol%) in toluene or CH₂Cl₂ at room temperature The reduction tolerates ketone carbonyls, esters, amides, nitriles, sulfones, sulfonamides, NO₂, SF₅, and CF₃ groups, boronic esters, azides, phosphine oxides, C=C and CC bonds, and ferrocenyl nucleus but sulfoxides and N-oxides are reduced. α,β-Unsaturated aldimines undergo 1,2-reduction only, leaving the C=C bond intact. N-Monoalkylation of primary amines is attained with a 1:1 aldehyde to amine ratio, whereas excess of the aldehyde (≥2:1) allows second alkylation, giving rise to tertiary amines. Reductive N-alkylation of α-amino acids proceeds without racemization; the resulting products, containing a CC bond or N₃ group, are suitable for click chem. This reaction thus offers advantages over the traditional methods (borohydride reduction or catalytic hydrogenation) in terms of efficiency and chemoselectivity. Solubility of some of the reacting partners appears to be the only limitation. The byproducts generated by the workup with aqueous NaHCO₃ (i.e., NaCl and silica) are environmentally benign. As a greener alternative, DMA can be employed as a catalyst instead of DMF. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Related Products of 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Related Products of 10282-32-3

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Cyanobenzyl sulfates as alkylating agents. Alkylation of amines with bis(cyanobenzyl)sulfate was written by Grochowski, E.;Boleslawska, T.. And the article was included in Bulletin de l’Academie Polonaise des Sciences, Serie des Sciences Chimiques in 1972.HPLC of Formula: 37812-51-4 This article mentions the following:

(2-NCC6H4CH2)2SO4 (I) and (4-NCC6H4CH2)2SO4 (II) are powerful alkylating agents for amines. Thus the resp. mono-(cyanobenzyl) derivatives were obtained in 95-8% yield by treating I with morpholine or pyridine or treating II with PhNH2, PhCH2NH2, cyclohexylamine, morpholine, or pyridine. II was prepared in 68% yield from 4-NCC6H4CH2Br and Ag2SO4. Reaction of I with primary amines gave iminoisoindoles, however. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4HPLC of Formula: 37812-51-4).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).HPLC of Formula: 37812-51-4

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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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Nitrile – Wikipedia,
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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

Spontaneous Charge Separation and Sublimation Processes are Ubiquitous in Nature and in Ionization Processes in Mass Spectrometry was written by Trimpin, Sarah;Lu, I-Chung;Rauschenbach, Stephan;Hoang, Khoa;Wang, Beixi;Chubatyi, Nicholas D.;Zhang, Wen-Jing;Inutan, Ellen D.;Pophristic, Milan;Sidorenko, Alexander;McEwen, Charles N.. And the article was included in Journal of the American Society for Mass Spectrometry in 2018.Recommanded Product: 5-Methyl-2-nitrobenzonitrile This article mentions the following:

Ionization processes have been discovered by which small and large as well as volatile and nonvolatile compounds are converted to gas-phase ions when associated with a matrix and exposed to sub-atm. pressure. Here, we discuss experiments further defining these simple and unexpected processes. Charge separation is found to be a common process for small mol. chems., solids and liquids, passed through an inlet tube from a higher to a lower pressure region, with and without heat applied. This charge separation process produces pos.- and neg.-charged particles with widely different efficiencies depending on the compound and its phys. state. Circumstantial evidence is presented suggesting that in the new ionization process, charged particles carry analyte into the gas phase, and desolvation of these particles produce the bare ions similar to electrospray ionization, except that solid particles appear likely to be involved. This mechanistic proposition is in agreement with previous theor. work related to ion emission from ice. [Figure not available: see fulltext.]. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6Recommanded Product: 5-Methyl-2-nitrobenzonitrile).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) 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: 5-Methyl-2-nitrobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts