Author: Jessica.F

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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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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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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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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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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Pyrolysis of aryl azides. V. Characterization of phenylazo, benzoyl and formyl as neighboring groups was written by Dickson, Noel J.;Dyall, Leonard K.. And the article was included in Australian Journal of Chemistry in 1980.HPLC of Formula: 68385-95-5 This article mentions the following:

The enhancements of the thermolysis rate of PhN₃ produced by o-PhN:N, o-Bz and o-HCO substituents are 21,780, 70.0 and 22.8 (Decalin solutions). The same ortho substituents produce much smaller enhancements (169, 8.56 and 10.7, resp.) in the pyrolysis rate of 2,4-Br₂C₆H₃N₃. These results are interpreted as steric effects on an electrocyclic thermolysis mechanism, and are not consistent with the alternative pathway of intramol. 1,3-dipolar addition In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5HPLC of Formula: 68385-95-5).

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. 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. HPLC of Formula: 68385-95-5

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Dissociative ionization of 7-dialkylaminocoumarins under electron impact was written by Gorozhankin, S. K.;Kirpichenok, M. A.;Klyuev, N. A.;Zhil’nikov, V. G.. And the article was included in Izvestiya Timiryazevskoi Sel’skokhozyaistvennoi Akademii in 1987.Quality Control of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile This article mentions the following:

The behavior of 19 substituted 7-aminocoumarins, eg, I (R = OEt, CF₃, R¹ = H; R = Me, R¹ = thiocyanato; R = CF₃, R¹ = cyano), II (R = Ac, R¹ = H; R = H, R¹ = Cl), and III (R = Me, R¹ = H, CH₂CO₂Et; R = H, R¹ = CO₂ Et; R = CF₃, R¹ = H), under electron impact mass spectroscopic conditions was studied. The pyrone ring in I–III was more stable to degradation than in other coumarins. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Quality Control of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Quality Control of 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile

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Cobalt-catalyzed asymmetric hydrogenation of ketones: A remarkable additive effect on enantioselectivity was written by Du, Tian;Wang, Biwen;Wang, Chao;Xiao, Jianliang;Tang, Weijun. And the article was included in Chinese Chemical Letters in 2021.Related Products of 101219-69-6 This article mentions the following:

A chiral cobalt pincer complex, when combined with an achiral electron-rich mono-phosphine ligand, catalyzes efficient asym. hydrogenation of a wide range of aryl ketones, affording chiral alcs. with high yields and moderate to excellent enantioselectivities (29 examples, up to 93% ee). Notably, the achiral mono-phosphine ligand showed a remarkable effect on the enantioselectivity of the reaction. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Related Products of 101219-69-6).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) 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. 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.Related Products of 101219-69-6

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New heterocyclic Meisenheimer complexes. Action of methoxide and hydride ions on 2,4-substituted thiophenes and selenophenes was written by Paulmier, Claude;Simonnin, Marie Paule;Chatrousse, Alain Pierre;Terrier, Francois. And the article was included in Tetrahedron Letters in 1973.Electric Literature of C5H2N2O2S This article mentions the following:

Meisenheimer complexes, formed by addition of MeOK to 2,4-disubstituted thiophenes and selenophenes (I; X = S, Se; R, R1 = NO2, CN), were assigned structure II (R2 = OMe) from NMR data. Addition of Me4NBH4 to I (X = S; R = NO2, CN, R1 = NO2) gave analogous II (R = NO2, CN; R1 = NO2; R2 = H), but with I (X = S, R = NO2, R1 = CN; X = Se, R, R1 = NO2, CN) ring-opening occurred. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Electric Literature 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Electric Literature of C5H2N2O2S

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Silver co-ordination compounds with aliphatic nitriles containing amino nitrogen as H bond donor or additional metal binding site: formation of a ring, a chain, a polymeric sheet and a 3D polymeric channeled structure was written by Erxleben, Andrea. And the article was included in CrystEngComm in 2002.HPLC of Formula: 7528-78-1 This article mentions the following:

Three coordination polymers and a discrete 20-membered macrometallacycle were prepared by crystallization of Ag salts with the conformationally flexible, polyfunctional ligands N-(2-cyanoethyl)glycine (ceg), 3,3-iminodipropionitrile (idpn) and tris(2-cyanoethyl)amine (tca). Single-crystal x-ray analyses of [Ag₂(tca)₂](ClO₄)₂ (1), [Ag(idpn)]ClO₄ (2), [Ag(ceg)]CF₃SO₃ (3) and [Ag(ceg)]ClO₄·0.5H₂O (4) revealed a bimetallic macrocycle (1), a 2-dimensional sheet structure with 4.8² topol. (2), a 3-dimensional network structure with rhomboid channels (3) and a 1-dimensional chain structure (4). The rhomboid channels in 3 are generated by 36-membered macrometallacyclic subunits consisting of four Ag atoms and four ceg ligands with ceg binding through the carboxylate group and the nitrile N. The amino N of ceg is protonated and serves as a H bond donor for the triflate anions that are incorporated into the macrocycles, thus stabilizing the channeled structure. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1HPLC of Formula: 7528-78-1).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) 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).HPLC of Formula: 7528-78-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts