Month: December 2022

Guerrero-Corella, Andrea published the artcile2-Hydroxybenzophenone as a Chemical Auxiliary for the Activation of Ketiminoesters for Highly Enantioselective Addition to Nitroalkenes under Bifunctional Catalysis, Safety of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Angewandte Chemie, International Edition (2018), 57(19), 5350-5354, database is CAplus and MEDLINE.

An organocatalytic system is presented for the Michael addition of monoactivated glycine ketimine ylides with a bifunctional catalyst. The ketimine bears an ortho hydroxy group, which increases the acidity of the methylene hydrogen atoms and enhances the reactivity, thus allowing the synthesis of a large variety of α,γ-diamino acid derivatives with excellent stereoselectivity.

Angewandte Chemie, International Edition published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Safety of (E)-4-(2-Nitrovinyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Eskandariyan, Zahra published the artcileSynthesis of thioether derivatives of quinazoline-4-one-2-thione and evaluation of their antiplatelet aggregation activity, Category: nitriles-buliding-blocks, the publication is Archives of Pharmacal Research (2014), 37(3), 332-339, database is CAplus and MEDLINE.

A series of 2-(arylmethylthio)-3-phenylquinazolin-4-one derivatives have been synthesized and their antiplatelet aggregation activities were assessed against ADP and arachidonic acid-induced platelet aggregation in human plasma. Among the tested thioethers, derivative 2, 3, 5 and 16 were the most potent compounds with satisfactory IC₅₀ for inhibition of platelet aggregation induced by ADP. Anal. of global physicochem. parameters shows some correlations between activities and mol. volume and also surface area of the studied derivatives

Archives of Pharmacal Research published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Category: nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Abu-Shanab, Fathi A. published the artcileα,α-Dioxoketene dithioacetals as starting materials for the synthesis of polysubstituted pyridines, Category: nitriles-buliding-blocks, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1994), 1449-52, database is CAplus.

Reactions of 3-acetyl-4,4-bis(methylthio)but-3-en-2-one and Me 2-acetyl-3,3-bis(methylthio)-prop-2-enoate with cyanothioacetamide, cyanoacetamide, or 2-amino-1,3,3-tricyanoprop-1-ene and base, followed by treatment with acid, give polysubstituted pyridines. Further elaboration of these products leads to bicyclic systems such as thieno[2,3-b]pyridines and pyrazolo[3,4-c]pyridine and then to tricyclic systems including pyrazolo[3,4-d]thieno[2,3-b]pyridine and dipyrazolo[3,4-b:3′,4′-d]pyridine.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about 57663-05-5. 57663-05-5 belongs to nitriles-buliding-blocks, auxiliary class Fused/Partially Saturated Cycles,Tetrahydropyrimidins, name is 6-Methyl-4-(methylthio)-2-oxo-1,2-dihydropyridine-3-carbonitrile, and the molecular formula is C8H8N2OS, Category: nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Yosef, Hisham Abdallah A. published the artcileSynthesis and biological evaluation of some novel chiral carbamates and 4-imino-2- oxazolidinones derived from selected optically active cyanohydrins, Application of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Pharma Chemica (2017), 9(16), 6-21, database is CAplus.

The reaction of tert-Bu isocyanate with the optically active cyanohydrins was accompanied with inversion of configuration giving the chiral (S)-enantiomers of the resp. carbamate derivatives On the other hand, reactions of aryl isocyanate reagents Ar-N=C=O with cyanohydrins gave the corresponding optically active 4-imino-2-oxazolidinone derivatives in the form of their S-configuration. Moreover, the same reactions were also applied for the racemic cyanohydrins to afford the corresponding carbamates and/or 4-imino-2-oxazolidinones as racemic mixtures Structures of the new products were elucidated with compatible micro anal. and spectroscopic (IR, ¹H-NMR, ¹³C-NMR and MS) measurements. The X-ray crystallog. anal. provided an efficient tool in confirming the structure and configuration of the new chiral compounds The antimicrobial activity of selected new derivatives against four bacterial species (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa) and two fungi (Aspergillus flavus and Candida albicans) were evaluated. Moreover, some of the new products were screened for their in-vitro antitumor activity against the human solid cancer cell lines, human carcinoma (HCT116), human hepatocellular liver carcinoma (HepG2) and human breast adenocarcinoma (MCF-7) cell lines. Generally, most of the investigated compounds were showed moderate to high activities in comparison with the standard drugs. The structure-activity relationship (SAR) was also discussed.

Pharma Chemica published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C2H5BF3K, Application of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Chen, Yi-Hung published the artcilePreparation and Application of Solid, Salt-Stabilized Zinc Amide Enolates with Enhanced Air and Moisture Stability, Recommanded Product: 2-(Chloromethyl)benzonitrile, the publication is Angewandte Chemie, International Edition (2017), 56(16), 4612-4616, database is CAplus and MEDLINE.

The treatment of various N-morpholino amides with TMPZnCl·LiCl (TMP=2,2,6,6-tetramethylpiperidyl) and Mg(OPiv)₂ in THF at 25 °C provides solid zinc enolates with enhanced air and moisture stability (t_1/2 in air: 1-3 h) after solvent evaporation These enolates undergo Pd- and Cu-catalyzed cross-couplings with (hetero)aryl bromides as well as allylic and benzylic halides. The arylated N-morpholino amides were converted into various ketones by LaCl₃·2 LiCl mediated acylation with Grignard reagents. The new, solid enolates were used to prepare a potent anti-breast-cancer drug candidate in six steps and 23 % overall yield.

Angewandte Chemie, International Edition published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Recommanded Product: 2-(Chloromethyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Carreiras, M. Carmo published the artcileSynthesis and Friedlander reactions of 5-amino-4-cyano-1,3-oxazoles, Synthetic Route of 5098-14-6, the publication is Heterocycles (2007), 71(10), 2249-2262, database is CAplus.

The synthesis of a series of 2-substituted 5-amino-4-cyano-1,3-oxazoles and the Friedlander-type reaction of some of them with cyclic ketones was described. Oxazolo[5,4-b]quinoline derivatives were tacrine analogs provided by the Friedlander reaction. Their anticholinesterase activity has been investigated and the compound I was found to be the most active (60% inhibition), at the maximum soluble concentration

Heterocycles published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, Synthetic Route of 5098-14-6.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Cristalli, Gloria published the artcileAdenosine deaminase inhibitors: synthesis and structure activity relationships of imidazole analogs of erythro-9-(2-hydroxy-3-nonyl)adenine, Quality Control of 5098-14-6, the publication is Journal of Medicinal Chemistry (1991), 34(3), 1187-92, database is CAplus and MEDLINE.

A series of erythro-1-(2-hydroxy-3-nonyl)imidazole derivatives were synthesized and evaluated for adenosine deaminase (ADA) inhibitory activity, in order to introduce simplifications in the ADA inhibitors erythro-9-(2-hydroxy-3-nonyl)adenine [EHNA, (I; X = N)] and 3-deaza-I (X = CH). Opening the pyrimidine or pyridine ring of I (X = N, CH), resp. led to compounds which are still ADA inhibitors. The most potent compound was erythro-1-(2-hydroxy-3-nonyl)imidazole-4-carboxamide (II; K_i = 3.53 × 10^-8 M), which provided potential donor and acceptor sites for hydrogen bonding. Lack of one of this sites could account for the order of potency of all compounds examined in this series. Opening the same ring in adenosine and in 3-deazaadenosine led to fully inactive compounds These results support the hypothesis of the existence, at or near the enzyme active site, of a hydrophobic region able to bind the erythro-nonyl moiety.

Journal of Medicinal Chemistry published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, Quality Control of 5098-14-6.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Ferris, J. P. published the artcileThe effect of clays on the oligomerization of hydrocyanic acid, Name: 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Journal of Molecular Evolution (1979), 13(4), 317-30, database is CAplus and MEDLINE.

The possible role of clays in prebiotic evolution was studied using the primitive Earth model in which aqueous solutions of HCN and diaminomaleonitrile (I) react with clay mineral sediments. The reaction of 0.1M HCN and dilute solutions of I at pH 8-9 and 25° in the presence of suspensions of montmorillonite (bentonite) clays were investigated. Montmorillonite clays inhibited the oligomerization of aqueous solutions of HCN. Yields of colored oligomers, urea, and I were all diminished by clays, but the rate of loss of cyanide was not significantly decreased. The inhibition of oligomer formation was due to the clay-catalyzed decomposition of I. The absence of strong binding of I to clays was suggested by the failure to detect I when a clay that was incubated with I was washed with spermidine (6 × 10^-3 g/L). I did not simply bind to the clays as the bulk of radioactivity was recovered from the supernatant in the reaction of I–¹⁴C with montmorillonite. The clay-catalyzed decomposition of I was observed when montmorillonite from 2 different sources was used and with a variety of homoionic montmorillonites and bentonites. A modification of the established procedure for using the cyanide electrode for cyanide analyses was used to follow the release of HCN from I. This new method could be used in both the acidic and basic pH range and did not result in the destruction of I by the reagents used for the anal. Quant. anal. of the reaction solution from the clay-catalyzed decompositions of I revealed the formation of 1-2 equiv HCN/mol I. The possible significance of these clay-catalyzed reactions in prebiotic evolution is discussed.

Journal of Molecular Evolution published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, Name: 2-Aminomalononitrile 4-methylbenzenesulfonate.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Liao, Tzu-Ying published the artcileAminomalononitrile-Assisted Multifunctional Antibacterial Coatings, Synthetic Route of 5098-14-6, the publication is ACS Biomaterials Science & Engineering (2020), 6(6), 3349-3360, database is CAplus and MEDLINE.

Medical device associated infections remain a significant problem for all classes of devices at this point in time. Here, we have developed a surface modification technique to fabricate multifunctional coatings that combine antifouling and antimicrobial properties. Zwitterionic polymers providing antifouling properties and quaternary ammonium containing polymers providing antimicrobial properties were combined in these coatings. Throughout this study, aminomalononitrile (AMN) was used to achieve one-step coatings incorporating different polymers. The characterization of coatings was carried out using static water contact angle (WCA) measurements, XPS, profilometry, and SEM, whereas the biol. response in vitro was analyzed using Staphylococcus epidermidis and Escherichia coli as well as L929 fibroblast cells. Zwitterionic polymers synthesized from sulfobetaine methacrylate and 2-aminoethyl methacrylate were demonstrated to reduce bacterial attachment when incorporated in AMN assisted coatings. However, bacteria in suspension were not affected by this approach. On the other hand, alkylated polyethylenimine polymers, synthesized to provide quaternary ammonium groups, were demonstrated to have contact killing properties when incorporated in AMN assisted coatings. However, the high bacterial attachment observed on these surfaces may be detrimental in applications requiring longer-term bactericidal activity. Therefore, AMN-assisted coatings containing both quaternary and zwitterionic polymers were fabricated. These multifunctional coatings were demonstrated to significantly reduce the number of live bacteria not only on the modified surfaces, but also in suspension. This approach is expected to be of interest in a range of biomedical device applications.

ACS Biomaterials Science & Engineering published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, Synthetic Route of 5098-14-6.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Taylor, Edward C. published the artcilePteridines. 49. Synthesis of 2,4-diamino-6,8-dihydro-7-aryl-8-oxopyrrolo[3,4-g]pteridines, Application In Synthesis of 5098-14-6, the publication is Journal of Organic Chemistry (1982), 47(1), 116-19, database is CAplus.

Reaction of Et 4-chloro-2-oximino-3-oxobutyrate with aminomalononitrile tosylate followed by deoxygenation of the resulting pyrazine 1-oxide provides the cyanopyrazine (I). Treatment of I with arylamines gives the (arylaminomethyl)cyanopyrazines II (R = H, Me) which are readily cyclized to the oxopyrrolopyrazines III. Condensation of III with guanidine acetate in DMF then provides the title compounds IV (R = H, Me).

Journal of Organic Chemistry published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C23H28N2O4, Application In Synthesis of 5098-14-6.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts