Month: January 2023

A transient outward potassium current activator recapitulates the electrocardiographic manifestations of Brugada syndrome was written by Calloe, Kirstine;Cordeiro, Jonathan M.;Di Diego, Jose M.;Hansen, Rie S.;Grunnet, Morten;Olesen, Soren Peter;Antzelevitch, Charles. And the article was included in Cardiovascular Research in 2009.Computed Properties of C7H4Br2N2 This article mentions the following:

Aims: Transient outward potassium current (I_to) is thought to be central to the pathogenesis of the Brugada syndrome (BrS). However, an I_to activator has not been available with which to validate this hypothesis. Here, we provide a direct test of the hypothesis using a novel I_to activator, NS 5806 (I). Methods and results: Isolated canine ventricular myocytes and coronary-perfused wedge preparations were used. Whole-cell patch-clamp studies showed that I (10 μM) increased peak I_to at +40 mV by 79 ± 4% (24.5 ± 2.2 to 43.6 ± 3.4 pA/pF, n = 7) and slowed the time constant of inactivation from 12.6 ± 3.2 to 20.3 ± 2.9 ms (n = 7). The total charge carried by I_to increased by 186% (from 363.9 ± 40.0 to 1042.0 ± 103.5 pA·ms/pF, n = 7). In ventricular wedge preparations, I increased phase 1 and notch amplitude of the action potential in the epicardium, but not in the endocardium, and accentuated the ECG J-wave, leading to the development of phase 2 re-entry and polymorphic ventricular tachycardia (n = 9). Although sodium and calcium channel blockers are capable of inducing BrS only in right ventricular (RV) wedge preparations, the I_to activator was able to induce the phenotype in wedges from both ventricles. I induced BrS in 4/6 right and 2/10 left ventricular wedge preparations Conclusion: The I_to activator I recapitulates the electrog. and arrhythmic manifestation of BrS, providing evidence in support of its pivotal role in the genesis of the disease. Our findings also suggest that a genetic defect leading to a gain of function of I_to could explain variants of BrS, in which ST-segment elevation or J-waves are evident in both right and left ECG leads. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Computed Properties of C7H4Br2N2).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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.Computed Properties of C7H4Br2N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Emission characteristics of new laser dyes for the green and red spectral regions was written by Krymova, A. I.;Petukhov, V. A.;Popov, M. B.. And the article was included in Kvantovaya Elektronika (Moscow) in 1985.SDS of cas: 51473-74-6 This article mentions the following:

Emission characteristics were studies of solutions of certain new dyes from the classes of coumarins, naphthalimides, and benzanthrones under transverse pumping by the ruby laser 2nd-harmonic radiation. Most of the compounds showed laser action in the blue, green, and red spectral regions. A comparison was made of these substances with laser dyes widely used in the given spectral intervals. Compounds were found the lasing efficiency of which exceeds substantially that of uranin in the green region and that of Cresyl Violet in the red region and which are not inferior to them by photostability. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6SDS of cas: 51473-74-6).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) 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. SDS of cas: 51473-74-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Preparation of Tertiary Amines from Tris(2-cyanoethyl)amine Using Three Successive Cobalt-Catalyzed Electrophilic Aminations with Organozinc Halides was written by Grassl, Simon;Knochel, Paul. And the article was included in Organic Letters in 2020.Category: nitriles-buliding-blocks This article mentions the following:

A stepwise preparation of triple alkylated or arylated tertiary amines, starting from com. available tris(2-cyanoethyl)amine using three successive reaction sequences involving a selective oxidation (formation of an N-oxide followed by a Cope elimination) leading to an intermediate hydroxylamine, a benzoylation, and a cobalt-catalyzed electrophilic amination with organozinc halides is reported. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Category: nitriles-buliding-blocks).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) belongs to nitriles. Nitrile carbon shifts are in the range of 115â€?25 ppm whereas in isonitriles the shifts are around 155â€?65 ppm. 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

Immobilized Iron Metal-Containing Ionic Liquid-Catalyzed Chemoselective Transfer Hydrogenation of Nitroarenes into Anilines was written by Patil, Nilesh M.;Sasaki, Takehiko;Bhanage, Bhalchandra M.. And the article was included in ACS Sustainable Chemistry & Engineering in 2016.Computed Properties of C8H8N2 This article mentions the following:

The chemoselective transfer hydrogenation of nitroarenes into anilines was investigated using immobilized iron metal containing ionic liquid (ImmFe-IL) as a versatile heterogeneous catalyst. The present protocol has high atom efficiency with excellent chemoselectivity and regioselectivity. Selective reduction of the nitro group was observed in the presence of other reducing functional groups such as nitrile, ketone, acid, amide, ester, halogens, hydroxyl, olefin, and heterocycles. The developed protocol is also highly selective toward conversion of dinitroarenes into nitroanilines. The present catalytic system uses environmentally benign ethylene glycol as a solvent which is inexpensive, easily available, nontoxic, nonvolatile, nonflammable, thermally stable, and biodegradable. The catalyst was reused up to four consecutive cycles with high activity and selectivity. The fresh catalyst and recycle catalyst was well characterized by XPS anal. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Computed Properties of C8H8N2).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Computed Properties of C8H8N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Nitration of moderately deactivated arenes with nitrogen dioxide and molecular oxygen under neutral conditions. Zeolite-induced enhancement of regioselectivity and reversal of isomer ratios was written by Peng, Xinhua;Fukui, Naoyuki;Mizuta, Masayuki;Suzuki, Hitomi. And the article was included in Organic & Biomolecular Chemistry in 2003.SDS of cas: 64113-86-6 This article mentions the following:

In the presence of zeolites, moderately deactivated arenes such as 1-nitronaphthalene, naphthonitriles, and methylated benzonitriles can be smoothly nitrated at room temperature by the combined action of nitrogen dioxide and mol. oxygen. The regioselectivity is considerably improved as compared with the conventional nitration methodol. based on nitric and sulfuric acids. In some cases, the minor isomer became favored to a significant extent, resulting in the reversal of ordinary isomer ratios of nitration products. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6SDS of cas: 64113-86-6).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Copper-Catalyzed Enantioselective Hydrosilylation of Ketones by Using Monodentate Binaphthophosphepine Ligands was written by Junge, Kathrin;Wendt, Bianca;Addis, Daniele;Zhou, Shaolin;Das, Shoubhik;Beller, Matthias. And the article was included in Chemistry – A European Journal in 2010.Formula: C9H9NO This article mentions the following:

The first copper-catalyzed asym. hydrosilylation of carbonyl compounds by using chiral monodentate ligands is presented. Under comparably mild conditions, high yields and enantioselectivities (up to 96% ee) are achieved for a broad range of carbonyl compounds such as aryl alkyl, cyclic, heterocyclic and aliphatic ketones. Compared to other known asym. hydrosilylation catalysts, advantageously no base or fluoride activation is necessary. 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. 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.Formula: C9H9NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

New Genetic Bomb Trigger: Design, Synthesis, Molecular Dynamics Simulation, and Biological Evaluation of Novel BIBR1532-Related Analogs Targeting Telomerase against Non-Small Cell Lung Cancer was written by Tawfik, Haytham O.;El-Hamaky, Anwar A.;El-Bastawissy, Eman A.;Shcherbakov, Kirill A.;Veselovsky, Alexander V.;Gladilina, Yulia A.;Zhdanov, Dmitry D.;El-Hamamsy, Mervat H.. And the article was included in Pharmaceuticals in 2022.Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

Telomeres serve a critical function in cell replication and proliferation at every stage of the cell cycle. Telomerase is a ribonucleoprotein, responsible for maintaining the telomere length and chromosomal integrity of frequently dividing cells. Although it is silenced in most human somatic cells, telomere restoration occurs in cancer cells because of telomerase activation or alternative telomere lengthening. The telomerase enzyme is a universal anticancer target that is expressed in 85-95% of cancers. BIBR1532 is a selective non-nucleoside potent telomerase inhibitor that acts by direct noncompetitive inhibition. Relying on its structural features, three different series were designed, and 30 novel compounds were synthesized and biol. evaluated as telomerase inhibitors using a telomeric repeat amplification protocol (TRAP) assay. Target compounds 29a, 36b, and 39b reported the greatest inhibitory effect on telomerase enzyme with IC50 values of 1.7, 0.3, and 2.0 μM, resp., while BIBR1532 displayed IC50 = 0.2 μM. Compounds 29a, 36b, and 39b were subsequently tested using a living-cell TRAP assay and were able to penetrate the cell membrane and inhibit telomerase inside living cancer cells. Compound 36b was tested for cytotoxicity against 60 cancer cell lines using the NCI (USA) procedure, and the % growth was minimally impacted, indicating telomerase enzyme selectivity. To investigate the interaction of compound 36b with the telomerase allosteric binding site, mol. docking and mol. dynamics simulations were used. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Safety 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. Nitrile carbon shifts are in the range of 115�25 ppm whereas in isonitriles the shifts are around 155�65 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.Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Spectroscopic and theoretical studies of arylmethylenemalonitriles. II. Frequencies and intensities of the nitrile groups: LFER and Hueckel MO approaches was written by Binev, I.;Vitanov, D.;Yukhnovski, I.;Kaneti, Kh.. And the article was included in Izvestiya po Khimiya in 1979.Computed Properties of C18H10N2 This article mentions the following:

The IR frequencies and integrated intensities of the nitrile group were measured in HCCl₃ for a series of arylidenemalononitriles. The data correlated satisfactorily with substituent constants, as well as with CN bond orders and changes in the π-dipole moment during the ν_CN vibration. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Computed Properties of C18H10N2).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ozonation treatment increases chlorophenylacetonitrile formation in downstream chlorination or chloramination was written by Zhang, Di;Bond, Tom;Li, Mingli;Dong, Shengkun;Pan, Yang;Du, Erdeng;Xiao, Rong;Chu, Wenhai. And the article was included in Environmental Science & Technology in 2021.HPLC of Formula: 3218-45-9 This article mentions the following:

Chlorophenylacetonitriles (CPANs) are an emerging group of aromatic nitrogenous disinfection byproducts (DBPs). However, their dominant precursors and formation pathways remain unclear, which hinders the further development of effective control strategies. For the first time, CPAN precursors were screened by conducting formation potential (FP) tests on real water samples from six drinking water treatment plants (DWTPs). The average overall removal of CPAN precursors across all six DWTPs was only 10%. Moreover, ozonation increased CPAN precursors by 140% on average Fluorescence spectroscopy showed a dramatic reduction in aromatic proteins, tyrosine-like proteins, and tryptophan-like proteins following ozonation. Low-apparent-mol.-weight (AMW) (<1 kDa) substances were correlated with the CPAN FP in these samples. We therefore hypothesized that protein fragments with low AMW, such as amino acids, are important CPAN precursors during downstream chlor(am)ination. Two aromatic free amino acids, tyrosine and tryptophan, were selected to investigate the formation of CPANs during chlor(am)ination. Both amino acids were found to act as CPAN precursors for the first time. CPAN formation pathways from these model precursors were proposed based on the frontier MO theory and intermediate products identified using high-resolution mass spectrometry. This study provides a powerful theor. foundation for controlling CPAN formation in drinking water. In the experiment, the researchers used many compounds, for example, 2-(2,3-Dichlorophenyl)acetonitrile (cas: 3218-45-9HPLC of Formula: 3218-45-9).

2-(2,3-Dichlorophenyl)acetonitrile (cas: 3218-45-9) 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. 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.HPLC of Formula: 3218-45-9

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Thio amides. V. Preparation of some N-substituted p-alkoxythiobenzamides was written by Reynaud, Pierre;Moreau, Robert C.;Samama, Jean Paul. And the article was included in Bulletin de la Societe Chimique de France in 1965.HPLC of Formula: 5203-15-6 This article mentions the following:

A series of p-RC₆H₄NHC(S)C₆H₄OR¹-p (I) was prepared as analogs of the antitubercular thioureas; in formula I, R is an alkoxy group, Me₂N, or Cl, and R¹ is Bu, iso-Bu, or iso-Am. p-NCC₆H₄OH (1 mole), 1 mole NaOEt, and 1.10 mole appropriate alkyl bromide refluxed 24 hrs. with stirring gave the corresponding p-ROC₆H₄CN (R, b.p./mm., n²⁵_D, and % yield given): Bu (II), 133°/0.3, 1.5351, 82; iso-Bu, 122°/0.3, 1.5350, 51; iso-Am, 155.5°/0.3, 1.5260, 80. II (27.5 g.) in 30 cc. CHCl₃ and 15 g. absolute EtOH treated at about -5° with dry HCl to a weight increase of 7 g., kept 4 hrs. at -5°, and refrigerated 10 days, and the crystalline product treated at -20° in 200 cc. dry Et₂O with stirring with dry NH₃ yielded 80% p-BuOC₆H₄C(:NH)OEt (III), b_0.05 118-19°, n²⁵_D 1.5315. Similarly were prepared p-iso-BuOC₆H₄C(:NH)OEt (IV), 88%, b_0.05 122-5°, n²⁵_D 1.5282, and p-iso-AmOC₆H₄C(:NH)OEt (V), 89%, b_0.05 123°, m, 25°, n²⁵_D 1.515. III (22.10 g.) and 35 g. dry C₅H₅N treated at about 0° with dry H₂S to a weight increase of 7 g. and kept overnight yielded 23.2 g. yellow p-BuOC₆H₄C(S)OEt (VI), m. 71° (absolute EtOH). Similarly were prepared p-isoBuOC₆H₄C(S)OEt, 97%, b_0.1 134-5°, m. 25°, and p-iso-AmOC₆H₄C(S)OEt, 100%, m. 53° (EtOH), from IV and V, resp. p-AcNHC₆H₄OH was converted by the method of Gutekunst and Gray (CA 16, 3089) to p-BuOC₆H₄NH₂ (VII), b₁₂ 143-4° p-iso-BuOC₆H₄NH₂, b₁₀ 145-6°, and p-iso-AmOC₆H₄NH₂, b₁₅ 149-50°. VII (4.95 g.) in 15 cc. Et₂O added dropwise with stirring to EtMgBr from 0.03 mole EtBr in 30 cc. dry Et₂O, refluxed 15 min., treated with 3.57 g. VI in the min. amount Et₂O, refluxed 1 hr., and evaporated, and the residue treated with 100 cc. HCl and ice gave 92% I (R = BuO, R¹ = Bu), m. 152° (MeOH-C₆H₆); method A. VI (0.015 mole) treated similarly with the reaction mixture from p-Me₂NC₆H₄NH₂ and EtMgBr, and the residue decomposed with dilute iced HCl and extracted with Et₂O yielded 94% I (R = Me₂N, R¹ = Bu), m. 154.5° (EtOH); method B. Similarly were prepared the following I (R¹= Bu) (R, m.p., method and % yield, given): EtO, 155° (MePh), A, 90; iso-BuO, 164° (AcOEt), A, 95.2; AmO, 151° (MeOH-C₆H₆), A, 64; Cl, 185° (AcOEt), A, 89. Similarly were prepared the following I (R¹ = iso-Bu) (same data given): EtO, 178° (MePh), A, 99; BuO, 164° (EtOH), A, 97; iso-BuO, 159° (AcOEt), A, 97; AmO, 149° (EtOH), A, 99; Cl, 210° (Me₂CO), A, 87; Me₂N, 173° (EtOH), B, 92. Similarly were prepared the following I (R¹ = isoAm) (same data given): EtO, 162-3° (MePh), A, 99; BuO, 159° (EtOH), A, 87; iso-BuO, 164° (AcOEt), A, 95; AmO, 95° (AcOEt), A, 95; Cl, 194° (AcOEt), A, 90; Me₂N, 159° (EtOH), B, 91. The ir spectra of III, V, AmC(:NH)OEt, and EtC(:NH)OEt are recorded and the ir maximum of III, IV, V, and PhC(:NH)OEt are tabulated. In the experiment, the researchers used many compounds, for example, 4-iso-Butoxybenzonitrile (cas: 5203-15-6HPLC of Formula: 5203-15-6).

4-iso-Butoxybenzonitrile (cas: 5203-15-6) 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. 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.HPLC of Formula: 5203-15-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts