Month: January 2023

Guanidine derivatives. XVI. Synthesis of alkylated 4-alkoxyphenylacetonitriles and substituted guanidines was written by Ovsepyan, T. R.;Petrosyan, A. S.;Aroyan, A. A.. And the article was included in Armyanskii Khimicheskii Zhurnal in 1973.Recommanded Product: 5351-07-5 This article mentions the following:

4-ROC6H4CR1R2CN (I; R,R2 = Me, Et, Pr; R1 = H, Me, Et, Pr) were prepared (38.3-70.2%) by the reaction of 4-ROC6H4CH2CN with NaNH2 and the corresponding R1X and R2X (X = halo). Catalytic reduction of I over Ni-Cr2O3 gave 64.2-85.5% 4-ROC6H4CR1R2CH2NH2 (II). Reaction of II with MeSC(:NH)NH2.5H2SO4 gave, 36.7-74.1% 4-ROC6H4CR1R2CH2NHC(:NH)NH2.5H2SO4. 4-ROC6H4CH2NHCSNHNHC(:NH)NH2.HNO3 (R = Me, Et, Pr) were prepared (13.9-19.0%) by the reaction of 4-ROC6H4CH2NCS with H2NNHC(:NH)NH2.HNO3. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5Recommanded Product: 5351-07-5).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) 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.Recommanded Product: 5351-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Quantum chemistry calculations of 2-aminopyrimidine-5-carbonitrile Dye sensitizer for solar cells was written by Arul, S.;Senthilnathan, T.. And the article was included in Journal of Ultra Chemistry in 2017.Name: 2-Aminopyrimidine-5-carbonitrile This article mentions the following:

Quantum chem. calculations of energies, geometries, electronic structures, polarizabilities, and hyperpolarizabilities of organic dye sensitizer 2-aminopyrimidine-5-carbonitrile were studied based on ab initio HF and D. Functional Theory (DFT) using the hybrid functionals B3LYP. UV-visible (UV-Vis) spectrum was investigated by Time Dependent DFT (TDDFT). Features of the electronic absorption spectrum in the visible and near-UV regions were assigned based on TDDFT calculations The electronic absorption bands are assigned to π→π* transitions. Calculated results suggest that the three excited states with the lowest excited energies in 2-aminopyrimidine-5-carbonitrile is due to photo induced electron transfer processes. The interfacial electron transfer between semiconductor TiO₂ electrode and dye sensitizer 2-aminopyrimidine-5-carbonitrile is due to an electron injection process from excited dye to the semiconductor’s conduction band. The role of amine and nitrile group in 2-aminopyrimidine-5-carbonitrile geometries, electronic structures, and electronic absorption spectra were analyzed in Dye sensitizer solar cell (DSSC) give good conversion efficiency. In the experiment, the researchers used many compounds, for example, 2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6Name: 2-Aminopyrimidine-5-carbonitrile).

2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6) 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. 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.Name: 2-Aminopyrimidine-5-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Par-4 secretion: stoichiometry of 3-arylquinoline binding to vimentin was written by Sviripa, Vitaliy M.;Burikhanov, Ravshan;Obiero, Josiah M.;Yuan, Yaxia;Nickell, Justin R.;Dwoskin, Linda P.;Zhan, Chang-Guo;Liu, Chunming;Tsodikov, Oleg V.;Rangnekar, Vivek M.;Watt, David S.. And the article was included in Organic & Biomolecular Chemistry in 2016.Product Details of 3218-45-9 This article mentions the following:

Advanced prostate tumors usually metastasize to the lung, bone, and other vital tissues and are resistant to conventional therapy. Prostate apoptosis response-4 protein (Par-4) is a tumor suppressor that causes apoptosis in therapy-resistant prostate cancer cells by binding specifically to a receptor, Glucose-regulated protein-78 (GRP78), found only on the surface of cancer cells. 3-Arylquinolines or “arylquins” induce normal cells to release Par-4 from the intermediate filament protein, vimentin and promote Par-4 secretion that targets cancer cells in a paracrine manner. A structure-activity study identified arylquins that promote Par-4 secretion, and an evaluation of arylquin binding to the hERG potassium ion channel using a [³H]-dofetilide binding assay permitted the identification of structural features that separated this undesired activity from the desired Par-4 secretory activity. A binding study that relied on the natural fluorescence of arylquins and that used the purified rod domain of vimentin (residues 99-411) suggested that the mechanism behind Par-4 release involved arylquin binding to multiple sites in the rod domain. In the experiment, the researchers used many compounds, for example, 2-(2,3-Dichlorophenyl)acetonitrile (cas: 3218-45-9Product Details of 3218-45-9).

2-(2,3-Dichlorophenyl)acetonitrile (cas: 3218-45-9) 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.Product Details of 3218-45-9

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Superacidic Cyclization of Activated Anthranilonitriles into 2-Unsubstituted-4-aminoquinolines was written by Lavrard, Hubert;Larini, Paolo;Popowycz, Florence. And the article was included in Organic Letters in 2017.Category: nitriles-buliding-blocks This article mentions the following:

4-Aminoquinolines were prepared in a three-step synthesis starting from substituted anthranilonitriles. The condensation on 1,1,1-trichloro-4-ethoxybut-3-enone proceeded efficiently either neat or in refluxing EtOH. Cyclization in superacidic trifluoromethanesulfonic acid provided unstable intermediate, which upon treatment with NaOEt in ethanol, afforded the expected esters. Theor. investigations pointed out a monoprotonated nitrilium as the reactive species during the cyclization process. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Category: nitriles-buliding-blocks).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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. 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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Thienopyridines: nitric oxide synthase inhibitors with potent In vivo activity was written by Beaton, H.;Boughton-Smith, N.;Hamley, P.;Ghelani, A.;Nicholls, D. J.;Tinker, A. C.;Wallace, A. V.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2001.Related Products of 55406-13-8 This article mentions the following:

5-Substituted 7-amino-4,5-tetrahydrothieno[2,3-c]pyridines and 6-substituted 4-amino-6,7-dihydrothieno[3,2-c]pyridines were shown to be exceptionally potent inhibitors of inducible and neuronal nitric oxide synthase. Selectivity and potency could be modulated by variation of the 5- or 6-substituent. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Related Products of 55406-13-8).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Selective Synthesis of Secondary and Tertiary Amines by Reductive N-Alkylation of Nitriles and N-Alkylation of Amines and Ammonium Formate Catalyzed by Ruthenium Complex was written by Alshakova, Iryna D.;Nikonov, Georgii I.. And the article was included in ChemCatChem in 2019.HPLC of Formula: 4714-63-0 This article mentions the following:

A ruthenium catalytic system for the syntheses of secondary and tertiary amines via reductive N-alkylation of nitriles and N-alkylation of primary amines is proposed. Isomeric ruthenium complexes catalyzed transfer hydrogenation and N-alkylation of nitriles in ethanol to give secondary amines. Unsym. secondary amines can be produced by N-alkylation of primary amines with alcs. via the borrowing hydrogen methodol. Aliphatic amines were obtained with excellent yields, while only moderate conversions were observed for anilines. Based on kinetic and mechanistic studies, it is suggested that the rate determining step is the hydrogenation of intermediate imine to amine. Finally, ammonium formate was applied as the amination reagent for alcs. in the presence of ruthenium catalyst. Secondary amines were obtained from primary alcs. within 24 h at 100 °C, and tertiary amines can be produced after prolonged heating. Secondary alcs. can only be converted to secondary amines with moderate yield. Based on mechanistic studies, the process is suggested to proceed through an ammonium alkoxy carbonate intermediate, where carbonate acts as an efficient leaving group. In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0HPLC of Formula: 4714-63-0).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Nucleophilic and Radical Heptafluoroisopropoxylation with Redox-Active Reagents was written by Tong, Chao-Lai;Xu, Xiu-Hua;Qing, Feng-Ling. And the article was included in Angewandte Chemie, International Edition in 2021.Category: nitriles-buliding-blocks This article mentions the following:

The practical and efficient heptafluoroisopropoxylation reactions through the invention of a series of redox-active N-OCF(CF₃)₂ reagents e.g., I were described. These reagents were readily prepared from the oxidative heptafluoroisopropylation of hydroxylamines e.g., II with AgCF(CF₃)₂. The substitutions on the nitrogen atom significantly affected the properties and reactivities of N-OCF(CF₃)₂ reagents. Accordingly, two types of N-OCF(CF₃)₂ reagents including I and III were used as OCF(CF₃)₂ anion and radical precursors, resp. This protocol enables the direct heptafluoroisopropoxylation of a range of substrates, delivering the corresponding products in moderate to excellent yields. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Category: nitriles-buliding-blocks).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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

Divergent synthesis of 2-methylthioindole and 2-unsubstituted indole derivatives mediated by SOCl₂ and dimethyl/diethyl sulfoxides was written by Zhang, Jingran;Zhang, Beibei;He, Jiaxin;Shi, Haofeng;Du, Yunfei. And the article was included in Organic & Biomolecular Chemistry in 2022.Application of 1483-54-1 This article mentions the following:

A metal-free divergent synthesis of indole compounds dependent on a reagent via intramol. C(sp²)-H amination was described. The reaction of 2-vinylanilines with DMSO/SOCl₂ at 70 ° was found to give 2-thiomethylindoles, while replacing DMSO with di-Et sulfoxide afforded 2-unsubstituted indoles in a highly selective manner. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Application of 1483-54-1).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Exploring Homogeneous Conditions for Mild Buchwald-Hartwig Amination in Batch and Flow was written by Kashani, Saeed K.;Jessiman, Jacob E.;Newman, Stephen G.. And the article was included in Organic Process Research & Development in 2020.Name: 4-(Benzylamino)benzonitrile This article mentions the following:

The use of high throughput experimentation to identify a number of conditions that enable Buchwald-Hartwig reactions to be carried out using readily available ligands (e.g. XantPhos) with DBU as a soluble, functional group tolerant, homogeneous base was described. Application of this system to diverse aminations in batch and flow were demonstrated, as was the translation of this technique to performing continuous Mizoroki-Heck and Sonogashira coupling reactions. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Name: 4-(Benzylamino)benzonitrile).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A novel multiple-stage antimalarial agent that inhibits protein synthesis was written by Baragana, Beatriz;Hallyburton, Irene;Lee, Marcus C. S.;Norcross, Neil R.;Grimaldi, Raffaella;Otto, Thomas D.;Proto, William R.;Blagborough, Andrew M.;Meister, Stephan;Wirjanata, Grennady;Ruecker, Andrea;Upton, Leanna M.;Abraham, Tara S.;Almeida, Mariana J.;Pradhan, Anupam;Porzelle, Achim;Martinez, Maria Santos;Bolscher, Judith M.;Woodland, Andrew;Luksch, Torsten;Norval, Suzanne;Zuccotto, Fabio;Thomas, John;Simeons, Frederick;Stojanovski, Laste;Osuna-Cabello, Maria;Brock, Paddy M.;Churcher, Tom S.;Sala, Katarzyna A.;Zakutansky, Sara E.;Jimenez-Diaz, Maria Belen;Sanz, Laura Maria;Riley, Jennifer;Basak, Rajshekhar;Campbell, Michael;Avery, Vicky M.;Sauerwein, Robert W.;Dechering, Koen J.;Noviyanti, Rintis;Campo, Brice;Frearson, Julie A.;Angulo-Barturen, Inigo;Ferrer-Bazaga, Santiago;Gamo, Francisco Javier;Wyatt, Paul G.;Leroy, Didier;Siegl, Peter;Delves, Michael J.;Kyle, Dennis E.;Wittlin, Sergio;Marfurt, Jutta;Price, Ric N.;Sinden, Robert E.;Winzeler, Elizabeth A.;Charman, Susan A.;Bebrevska, Lidiya;Gray, David W.;Campbell, Simon;Fairlamb, Alan H.;Willis, Paul A.;Rayner, Julian C.;Fidock, David A.;Read, Kevin D.;Gilbert, Ian H.. And the article was included in Nature (London, United Kingdom) in 2015.Formula: C12H14N2O This article mentions the following:

There is an urgent need for new drugs to treat malaria, with broad therapeutic potential and novel modes of action, to widen the scope of treatment and to overcome emerging drug resistance. Here we describe the discovery of DDD107498, a compound with a potent and novel spectrum of antimalarial activity against multiple life-cycle stages of the Plasmodium parasite, with good pharmacokinetic properties and an acceptable safety profile. DDD107498 demonstrates potential to address a variety of clin. needs, including single-dose treatment, transmission blocking and chemoprotection. DDD107498 was developed from a screening program against blood-stage malaria parasites; its mol. target has been identified as translation elongation factor 2 (eEF2), which is responsible for the GTP-dependent translocation of the ribosome along mRNA, and is essential for protein synthesis. This discovery of eEF2 as a viable antimalarial drug target opens up new possibilities for drug discovery. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Formula: C12H14N2O).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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. Formula: C12H14N2O

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts