Tag: 100-200

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

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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

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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

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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

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Nitrile – Wikipedia,
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Magic matrices for ionization in mass spectrometry was written by Trimpin, Sarah;Lutomski, Corinne A.;El-Baba, Tarick J.;Woodall, Daniel W.;Foley, Casey D.;Manly, Cory D.;Wang, Beixi;Liu, Chih-Wei;Harless, Bryan M.;Kumar, Ruby;Imperial, Lorelie F.;Inutan, Ellen D.. And the article was included in International Journal of Mass Spectrometry in 2015.Category: nitriles-buliding-blocks This article mentions the following:

The initial discovery that a heated inlet tube of a mass spectrometer is an ionization source producing ions from volatile, nonvolatile, small, and large mols. with charge states similar to electrospray ionization has been advanced to ionization requiring only the vacuum inherent with a mass spectrometer and a suitable matrix. This spontaneous ionization method was first applicable with the matrix 3-nitrobenzonitrile. Here we report that over 40 compounds have now been discovered that spontaneously convert mols. to gas-phase ions when exposed to sub-atm. pressure, some with remarkable sensitivity (10 fmol of protein insulin). The commonality of all matrixes is the ability to sublime, preferably near room temperature, through exposure to vacuum, and the ability to create charge separation under these conditions. The effect of vacuum, airflow, temperature (-80 to +150 °C) and pH (1-9) on the effectiveness of these newly discovered matrixes to ionize peptides and proteins is presented. Compounds with and without acidic hydrogen atoms act as matrixes and ionize specific compound classes. The new matrixes extend applications from peptides, proteins and drugs to compound classes without basic functionality such as lipids and synthetic polymers in the neg. and pos. modes. Mass resolution and ion mobility spectrometry aspects are also discussed. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6Category: nitriles-buliding-blocks).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) 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. 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. Category: nitriles-buliding-blocks

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Nitrile – Wikipedia,
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Pyridyl Radical Cation for C-H Amination of Arenes was written by Roessler, Simon L.;Jelier, Benson J.;Tripet, Pascal F.;Shemet, Andrej;Jeschke, Gunnar;Togni, Antonio;Carreira, Erick M.. And the article was included in Angewandte Chemie, International Edition in 2019.Category: nitriles-buliding-blocks This article mentions the following:

Electron-transfer photocatalysis provides access to the elusive and unprecedented N-pyridyl radical cation from selected N-substituted pyridinium reagents. The resulting C(sp²)-H functionalization of (hetero)arenes furnishes versatile intermediates for the development of valuable aminated aryl scaffolds. Mechanistic studies that include the first spectroscopic evidence of a spin-trapped N-pyridyl radical adduct implicate SET-triggered, pseudo-mesolytic cleavage of the N-X pyridinium reagents mediated by visible light. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1Category: nitriles-buliding-blocks).

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) 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.Category: nitriles-buliding-blocks

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Nitrile – Wikipedia,
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Highly efficient conjugate reduction of α,β-unsaturated nitriles catalyzed by copper/xanthene-type bisphosphine complexes was written by Kim, Daesung;Park, Bu-Mahn;Yun, Jaesook. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2005.COA of Formula: C8H13N This article mentions the following:

α,β-Unsaturated nitriles are chemoselectively reduced to the corresponding saturated nitriles in high yields using a copper-DPEphos or Xantphos complex as catalyst in the presence of polymethylhydrosiloxane (PMHS) as the stoichiometric reducing agent and tert-butanol as additive. The use of tert-butanol as additive was key to success of this method. PMHS was used as stoichiometric reducing agent. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7COA of Formula: C8H13N).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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. COA of Formula: C8H13N

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Nitrile – Wikipedia,
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Design, synthesis, biological evaluation and molecular modeling study of new thieno[2,3-d]pyrimidines with anti-proliferative activity on pancreatic cancer cell lines was written by Salem, Mohamed S. H.;Abdel Aziz, Yasmine M.;Elgawish, Mohamed S.;Said, Mohamed M.;Abouzid, Khaled A. M.. And the article was included in Bioorganic Chemistry in 2020.Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

In this study, twenty eight new compounds based on thieno[2,3-d]pyrimidine scaffold I [R = (2-methylphenyl)aminyl, diphenylaminyl, 2-naphthyloxy, etc.] and II [X = O, S; R¹ = Ph, 4-fluorophenyl, ethyl] were synthesized as anti-pancreatic cancer agents mimicking the benzofuro[3,2-d]pyrimidine derivative, amuvatinib. Various linkers including amides, esters, ketones, urea and thiourea derivatives were utilized to study their effect on the anti-proliferative activity of these compounds Most of the tested compounds revealed good cytotoxic activities against pancreatic carcinoma cell line PANC-1. Compound I [R = (4-chlorophenyl)aminyl] (A) showed the highest cytotoxicity with an IC₅₀ value of 5.4μM. Furthermore, (A) showed excellent platelet derived growth factor receptor (PDGFR-α) inhibitory activity, with IC₅₀ value 0.155μM. Docking study was carried out into PDGFR-α active site which showed comparable binding mode to that of FDA approved PDGFR-α inhibitor, imatinib. 3D-Quant. structure activity relationship (QSAR) model was built up with five-featured pharmacophore which could be implemented for emerging effective lead structures. These compounds could serve as a new chemotype for discovering new agents for pancreatic cancer therapy. 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 compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. 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.Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Antioxidant-based inhibitors of leukotriene biosynthesis. The discovery of 6-[1-[2-(hydroxymethyl)phenyl]-1-propen-3-yl]-2,3-dihydro-5-benzofuranol, a potent topical antiinflammatory agent was written by Hammond, Milton L.;Zambias, Robert A.;Chang, Michael N.;Jensen, Norman P.;McDonald, John;Thompson, Kathryn;Boulton, David A.;Kopka, Ihor E.;Hand, Karen M.. And the article was included in Journal of Medicinal Chemistry in 1990.Synthetic Route of C5H2N2O2S This article mentions the following:

The leukotrienes, metabolites of arachidonic acid produced through the action of the enzyme 5-lipoxygenase, are important mediators of immediate hypersensitivity and inflammation. Among the variety of diseases in which the leukotrienes may play a symptomatic or causative role is the dermatol. condition psoriasis, a chronic proliferative disease of the skin. This study reports the synthesis and comparative biol. activities of various ortho-substituted phenols including 4-methoxyphenols, 6-hydroxy-1,2,3,4-tetrahydrobenzopyrans, 2,3-dihydro-5-benzofuranols, and 5-benzofuranols. The phenols prepared in this study were evaluated for their ability to inhibit the production of leukotriene B₄ (LTB₄) in isolated human polymorphonuclear leukocytes (PMNs) and to inhibit a topical inflammatory response in the topical mouse ear (TME) model. In the former case, when the log IC₅₀ was plotted vs. the log of the octanol/water partition coefficient (log P), to eliminate the effect of lipophilicity, the 2,3-dihydro-5-benzofuranol ring system was more potent than the other ring systems examined throughout the range of partition coefficients studied. The ability to inhibit leukotriene production in vitro in human PMNs can be rationalized on the basis of a model that suggests that the observed inhibition is dependent on the kinetic ability of the inhibitor to reduce a radical species and on the fraction of inhibitor that is partitioned into the cell membrane. While the in vivo antiinflammatory activity as measured by the TME did not correlate with the in vitro data, it was felt that the TME represented a valuable measure of the ability of a compound to penetrate the skin to the site of an ongoing inflammatory response. The title compound I was chosen for further development. 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. 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Synthetic Route of C5H2N2O2S

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N-Demethylation of N,N-Dimethylanilines by the Benzotriazole N-Oxyl Radical: Evidence for a Two-Step Electron Transfer-Proton Transfer Mechanism was written by Baciocchi, Enrico;Bietti, Massimo;Lanzalunga, Osvaldo;Lapi, Andrea;Raponi, Daniele. And the article was included in Journal of Organic Chemistry in 2010.COA of Formula: C9H10N2 This article mentions the following:

The reaction of the benzotriazole N-oxyl radical (BTNO) with a series of 4-X-N,N-dimethylanilines (X = CN, CF₃, CO₂CH₂CH₃, CH₃, OC₆H₅, OCH₃) has been investigated in CH₃CN. Product anal. shows that the radical, 4-X-C₆H₄N(CH₃)CH₂^·, is first formed, which can lead to the N-demethylated product or the product of coupling with BTNO. Reaction rates were found to increase significantly by increasing the electron-donating power of the aryl substituents (ρ⁺ = -3.8). With electron-donating substituents (X = CH₃, OC₆H₅, OCH₃), no intermol. deuterium kinetic isotope effect (DKIE) and a substantial intramol. DKIE are observed With electron-withdrawing substituents (X = CN, CF₃, CO₂CH₂CH₃), substantial values of both intermol. and intramol. DKIEs are observed These results can be interpreted on the basis of an electron-transfer mechanism from the N,N-dimethylanilines to the BTNO radical followed by deprotonation of the anilinium radical cation (ET-PT mechanism). By applying the Marcus equation to the kinetic data for X = CH₃, OC₆H₅, OCH₃ (rate-determining ET), a reorganization energy for the ET reaction was determined (λ_BTNO/DMA = 32.1 kcal mol^-1). From the self-exchange reorganization energy for the BTNO/BTNO^– couple, a self-exchange reorganization energy value of 31.9 kcal mol^-1 was calculated for the DMA^·1/DMA couple. In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0COA of Formula: C9H10N2).

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. 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. COA of Formula: C9H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts