Tag: M.W=250-300

Toh, Rou Jun published the artcileDeposition of Aminomalononitrile-Based Films: Kinetics, Chemistry, and Morphology, HPLC of Formula: 5098-14-6, the publication is Langmuir (2019), 35(30), 9896-9903, database is CAplus and MEDLINE.

In the last few years, the development of versatile coating chemistries has become a hot topic in surface science after the discovery that catecholamines can lead to conformal coatings upon oxidation from aqueous solutions Recently, it was found that aminomalononitrile (AMN), a mol. implicated in the appearance of life on earth, is an excellent prototype of novel material-independent surface functionalizing agents leading to conformal and biocompatible coatings in a simple and direct chem. process from aqueous solutions So far, very little insight has been gained regarding the mechanisms underlying coating deposition. In this paper, we show that the chem. evolution of AMN film deposition under slightly basic conditions is different in solution and on silica. Thereon, the coating proceeds via a nucleation process followed by further deposition of islands which evolve to produce nitrogen-rich superhydrophilic fibrillar structures. Addnl., we show that AMN-based material can form films at the air-solution interface from unshaken solutions These results open new vistas into the chem. of HCN-derived species of potential relevance in materials science.

Langmuir 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 C17H18N2O6, HPLC of Formula: 5098-14-6.

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

Jeng, Huey-Jiuan published the artcileFormation of pyrrole derivatives from heteroatom-substituted acetonitriles, Synthetic Route of 5098-14-6, the publication is Journal of the Chinese Chemical Society (Taipei) (1994), 41(6), 803-11, database is CAplus.

Aminomalononitrile reacted with conjugated carbonyl compounds to give 3H-pyrrolines. Treatment of 2-chloro-2-phenylthioacetonitrile with alkenes in the presence of potassium t-butoxide afforded 1-phenylthiocyclopropanecarbonitriles, which reacted with nucleophiles in 1,2-, 1,4- or 1,6-addition modes. The 1,2-adducts (cyclopropylimines) rearranged in situ to give substituted pyrroles.

Journal of the Chinese Chemical Society (Taipei) 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

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

Taylor, Edward C. published the artcilePteridines. 47. Preparation and chemistry of 2-amino-6-carbalkoxy-3-cyano-5-substituted pyrazine 1-oxides: synthesis of pterin-6-carboxaldehyde, HPLC of Formula: 5098-14-6, the publication is Journal of Organic Chemistry (1980), 45(12), 2485-9, database is CAplus.

A new procedure for the synthesis of 2-amino-3-cyano-5-substituted pyrazines I [R = CH(OMe)₂, Me], useful intermediates for the synthesis of pteridines, is described. Oximation of β-oxo esters followed by reaction with aminomalononitrile provides 2-amino-6-carbalkoxy-3-cyano-5-substituted pyrazine 1-oxides II. Protection of the amino group as its (dimethylamino)methylenamino derivative I followed by S_N2 decarbalkoxylation provides pyrazines, which on removal of the protecting group and deoxygenation give pyrazines III. This method is designed to be of use in cases where the β-oxo ester cannot be converted directly to the corresponding α-oxo aldoxime. The procedure is applied to the synthesis of III [R = CH(OMe)₂], an intermediate in the synthesis of pterin-6-carboxaldehyde.

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 C5H8N2O, HPLC of Formula: 5098-14-6.

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

Taylor, Edward C. published the artcilePteridines. 48. Utilization of 3,3-dimethoxy-2-pyrrolidinopropene for the synthesis of folic acid, N²‘-acetyl-7-folic acid, and 5-deaza-7-folic acid, Recommanded Product: 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Journal of Organic Chemistry (1981), 46(7), 1394-402, database is CAplus.

Pyrrolidinopropene I was treated with NOCl and hydrolyzed to give (MeO)₂CHCOCH:NOH which was treated with NCCH(NH₂)CN to give II, a known precursor for III (R = CHO, R¹ = H). Treating I with 4-MeC₆H₄SO₃N:C(CN)₂ and then with NH₄OH gave IV [R² = H, R³ = (MeO)₂CH] which gave III (R = H, R¹ = CHO) (V) by guanidine cyclization. VI (R⁴ = CHO, R⁵ = H, X = CH) was prepared by treating I with MeOCH:C(CN)₂ followed by cyclizing with NH₄OH to give VII which was treated with HN:C(NH₂)₂, NaOH, and then HCl. Refluxing V with Ac₂O followed by condensation with 4-H₂NC₆H₄COGlu(OCMe₃)OCMe₃ gave VI (R⁴ = CH:NC₆H₄CO-Glu(OCMe₃)OCMe₃-4, R⁵ = Ac, X = N] which was reduced by NaBH₄ to give 37% VI (R⁴ = CH₂NHC₆H₄CO-Glu(OCMe₃)OCMe₃-4]. Similarly refluxing VI (R⁴ = CHO, R⁵ = H, X = CH) with 4-H₂NC₆H₄CO-Glu(OMe)OMe followed by reduction by NaBH₄ gave ∼40% VI [R⁴ = CH₂NHC₆H₄CO-Glu(OMe)OMe-4].

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 C8H8O3, Recommanded Product: 2-Aminomalononitrile 4-methylbenzenesulfonate.

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

Marco, Jose L. published the artcileSynthesis, biological evaluation and molecular modelling of diversely functionalized heterocyclic derivatives as inhibitors of acetylcholinesterase/butyrylcholinesterase and modulators of Ca²⁺ channels and nicotinic receptors, HPLC of Formula: 5098-14-6, the publication is Bioorganic & Medicinal Chemistry (2004), 12(9), 2199-2218, database is CAplus and MEDLINE.

The synthesis and the biol. activity of heterocyclic derivatives as inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), as well as modulators of voltage-dependent Ca²⁺ channels and nicotinic receptors, are described. These mols. are tacrine analogs, which have been prepared from polyfunctionalized 6-amino-5-cyano-4H-pyrans, 6-amino-5-cyano-pyridines and 5-amino-2-aryl-3-cyano-1,3-oxazoles via Friedlander reaction with selected cycloalkanones. These compounds are moderate acetylcholinesterase and butyrylcholinesterase inhibitors, the BuChE/AChE selectivity of the most active mols. ranges from 10.0 to 76.9. Interestingly, the oxazolo-tacrine’ derivatives are devoid of any activity. All compounds showed an important inhibitory effect on the nicotinic acetylcholine receptor. Most of them also blocked L-type Ca²⁺ channels, and three of them blocked the non-L type of Ca²⁺ channels. Mol. modeling studies suggest that these compounds might bind at the peripheral binding site of AChE, which opens the possibility to design inhibitors able to bind at both, the catalytic and peripheral binding sites of the enzyme.

Bioorganic & 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, HPLC of Formula: 5098-14-6.

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