Category: 5098-14-6

Taylor, Edward C. published the artcilePteridines. XXXIV. Synthesis of 8-hydroxy-7(8H)-pteridinones (pteridine hydroxamic acids), Formula: C10H11N3O3S, the publication is Journal of Organic Chemistry (1975), 40(16), 2332-6, database is CAplus and MEDLINE.

A series of 2,4-diamino-6-alkyl-substituted 8-hydroxy-7(8H)-pteridinones (pteridinehydroxamic acids) (I) was prepared from 2,4-diamino-6-substituted pteridine 8-oxides by chlorination in glacial AcOH, followed by cleavage of the resulting pteridinehydroxamic acid anhydrides II with ethanolic HCl. An alternative but less satisfactory route to 2,4-diamino-6-methyl-8-hydroxy-7(8H)-pteridinone involved condensation of pyruvohydroxamoyl chloride with aminomalononitrile tosylate to give 2-amino-3-cyano-5-methyl-6-chloropyrazine 1-oxide, hydrolysis to the pyrazinehydroxamic acid III, and cyclization with guanidine.

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 C12H15ClO3, Formula: C10H11N3O3S.

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

Taylor, Edward C. published the artcilePteridines. XXXVII. A total synthesis of L-erythro-biopterin and some related 6-(polyhydroxyalkyl)pterins, Safety of 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Journal of the American Chemical Society (1976), 98(8), 2301-7, database is CAplus and MEDLINE.

6-(1-Erythro-1′,2′-dihydroxypropyl)pterin was prepared by cupric acetate oxidation of 5-deoxy-L-arabinose to its osone, transoximation with acetone oxime to the α-ketoaldoxime, condensation with benzyl α-aminocyanoacetate methanesulfate to give II, cyclization with guanidine to biopterin 8-oxide, and deoxygenation with sodium dithionite. The overall yield was 12%. In analogous fashion, 6-(D-arabino-tetrahydroxybutyl)pterin and 6-D-threo-trihydroxypropyl)pterin were prepared from D-glucose and D-xylose, resp.

Journal of the American Chemical Society 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 C28H29NO4, Safety of 2-Aminomalononitrile 4-methylbenzenesulfonate.

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

Hennen, William J. published the artcileSynthesis of 4-substituted 5-amino-2-(β-D-ribofuranosyl)thiazoles and 4-substituted 5-amino-2-(β-D-ribofuranosyl)selenazoles, and their respective conversion into 2-(β-D-ribofuranosyl)thiazolo[5,4-d]pyrimidines and 2-(β-D-ribofuranosyl)selenazolo[5,4-d]pyrimidines. A new synthesis of tiazofurin and selenazofurin, Application In Synthesis of 5098-14-6, the publication is Journal of Organic Chemistry (1985), 50(10), 1741-6, database is CAplus.

Anhydroallonothioate (I; Z = S) and -selenoate (I; Z = Se), prepared by treatment of anhydroallonimidate (I; Z = NH) with H₂S and H₂Se, underwent cyclocondensation with H₂NCH(CN)₂, NCCN(NH₂)CONH₂, or NCCH(NH₂)CO₂Et to give C-nucleosides II (X = S, R = NH₂, R¹ = cyano; X = S, Se, R = NH₂, R¹ = CONH₂; X = S, Se, R = NH₂, R¹ = CO₂Et). II (X = S, R = NH₂, R¹ = cyano; X = S, Se, R = NH₂, R¹ = CONH₂) were further cyclized with H₂NCH:NH or HC(OEt)₃ to give thiazolo- and selenazolopyrimidine C-nucleosides, e.g., III (X = S, Se). II (X = S, Se, R = NH₂, R¹ = CO₂Et) were converted in 2 steps into tiazofurin and selenazofurin (II; X = S, Se, R = H, R¹ = CONH₂), resp.

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 C10H11N3O3S, Application In Synthesis of 5098-14-6.

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

Sircar, Ila published the artcileNonpeptide angiotensin II receptor antagonists. 2. Design, synthesis, and structure-activity relationships of 2-alkyl-4-(1H-pyrrol-l-yl)-1H-imidazole derivatives: profile of 2-propyl-1-[[2′-(1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl]-methyl]-4-[2-(trifluoroacetyl)-1H-pyrrol-1-yl]-1H-imidazole-5-carboxylic acid (CI-996), Synthetic Route of 5098-14-6, the publication is Journal of Medicinal Chemistry (1993), 36(16), 2253-65, database is CAplus and MEDLINE.

A novel series of nonpeptide angiotensin II (AII) receptor antagonists containing a 1H-pyrrol-1-yl moiety at the 4-position of the imidazole have been developed. The pyrrole group occupies the same lipophilic pocket at the receptor as the chloro group in DuP 753 and EXP 3174 (I; R = Bu, R¹ = CH₂OH, CO₂H, R² = Cl, resp.) and the pentafluoro group in DuP 532 (I; R = Pr, R¹ = CO₂H, R² = CF₂CF₃). The impetus for its selection came from bioisosteric considerations based on hydrophobic and electronic substituent constants An extensive study of the structure-activity relationships revealed several highly potent AII receptor antagonists. An acyl substitution at the 2-position of the pyrrole ring improved activity, most notably in the in vivo rat model. In addition, the 2-substituted pyrrole compounds improved chem. stability toward extremely facile decarboxylation reaction associated with unsubstituted pyrrole analogs, thus facilitating development of these agents. The IC₅₀‘s of I [R = Pr, R¹ = CO₂H, R² = 2-(trifluoroacetyl)- (18), 2,5-dimethyl-, or 2,5-dichloro-1H-pyrrol-1-yl] (<1 nM) were better than the reference compounds EXP 3174 and DuP 532. These compounds were selective AII antagonists that compete at the AT₁ receptor and showed no affinity at the AT₂ receptor at concentrations up to 10 M. Upon i.v. administration in a normotensive rat model, compound 18 inhibited the AII-induced responses with ED₅₀ of 6 g/kg per min. In a renal hypertensive rat model, the antihypertensive potency of compound 18, at a dose of 10 mg/kg, was very similar to those of DuP 753 and EXP 3174, resp. Compound 18 demonstrated a dose-related (3-30 mg/kg) decrease in blood pressure that was sustained for greater than 24 h. On the basis of its profile, compound 18, designated as CI-996, has been selected for in-depth studies. The design, synthesis, in vitro, and in vivo structure-activity relationships are described.

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 C6H16OSi, Synthetic Route of 5098-14-6.

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

Nikseresht, Ahmad published the artcile[Cu₃(BTC)₂]: A metal-organic framework as an environment-friendly and economically catalyst for the synthesis of tacrine analogues by Friedlaender reaction under conventional and ultrasound irradiation, Recommanded Product: 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Polyhedron (2018), 112-117, database is CAplus.

Using a green and simple route with ultrasound illumination, atm. pressure and room temperature, for synthesizing tacrine analogs in the presence of [Cu₃(BTC)₂] as an environment-friendly and economically catalyst was considered. [Cu₃(BTC)₂] is one of the heterogeneous catalysts on hand capable of being employed, in the Friedlaender reaction, whenever 5-amino-4-cyano-2-phenyl-1,3-oxazole and appropriately substituted carbonyl derivatives under conventional and ultrasonic irradiation The results of this study indicate that the active sites in the [Cu₃(BTC)₂] for synthesis of cyclohepta[b]oxazolo[4,5-e]pyridine are mainly copper atoms and the role of Bronsted acid organic ligand in the MOF is negligible. These procedures were properly arranged to provide the utmost yields in a short while. The crystal stability in the process of catalysis was studied by various techniques such as XRD, BET and ICP that demonstrate excellent stability in reaction conditions.

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

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

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

Bizzarri, Bruno Mattia published the artcileAminomalononitrile inspired prebiotic chemistry as a novel multicomponent tool for the synthesis of imidazole and purine derivatives with anti-influenza A virus activity, SDS of cas: 5098-14-6, the publication is RSC Advances (2021), 11(48), 30020-30029, database is CAplus and MEDLINE.

Amino imidazole carbonitrile derivatives decorated with α-amino acid side-chains have been synthesized by a multicomponent microwave assisted reaction inspired by the prebiotic chem. of aminomalononitrile as a tool for generating high chem. diversity. These compounds were used as annulation synthons for the preparation of 8,9-disubstituted-6,9-dihydro-1H-purin-6-ones by reaction with formic acid as a simple C-1 donor reagent. The novel heterocycles were characterized by significant activity against influenza A virus, amino imidazole carbonitrile derivatives showing the highest activity. Thus, the chem. complexity generated by prebiotic chem. furnished a general tool for the identification of novel antiviral agents.

RSC Advances 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, SDS of cas: 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

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

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