Category: 5098-14-6

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. 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

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

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

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

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

Rosowsky, Andre published the artcileMethotrexate analogs. 4. 7-Methyl derivatives of methotrexate and dichloromethotrexate. New synthesis and some biological studies, HPLC of Formula: 5098-14-6, the publication is Journal of Medicinal Chemistry (1974), 17(12), 1308-11, database is CAplus and MEDLINE.

Conversion of methotrexate (I) [59-05-2] and 3′,5′-dichloromethotrexate (II) [528-74-5] to their 7-methyl analogs III [35190-25-1] and IV [53729-18-3], resp., to prevent metabolism in vivo to the inactive 7-hydroxy derivatives resulted in marked loss of antileukemic activity in mice and in vitro and loss of inhibitory potency against purified dihydrofolate reductase [9002-03-3] from Lactobacillus casei and L1210-FR8 tumor. The lack of antitumor activity presumably resulted from impaired enzyme binding. III was prepared from 2-amino-5-chloromethyl-3-cyano-6-methylpyrazine 1-oxide [53661-20-4] and diethyl N-(p-N-methylaminobenzoyl)glutamate [2378-95-2] by the method of E. C. Taylor, et al. (1973).

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, HPLC of Formula: 5098-14-6.

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

Jeong, Susan published the artcileMacrocyclic Triarylethylenes via Heck Endocyclization: A System Relevant to Diazonamide Synthesis, COA of Formula: C10H11N3O3S, the publication is Journal of Organic Chemistry (1998), 63(24), 8640-8641, database is CAplus.

The author’s approach the preparation of diazonamide A (I) synthesis is described. Initial results show that Heck endocyclization can form highly functionalized lactam rings containing an imbedded 1,2-diaryl-1-(5-oxazolyl)ethylene. Thus, cross-coupling of vinylstannane II (PMB = p-methoxybenzyl) with functionalized oxazole III (prepared in 2 steps from Boc-Val-OH and aminomalononitrile tosylate) gave phenol IV in 89% yield after deprotection. Peptide coupling of IV with a protected O-benzyl-3-iodotyrosine derivative, followed by Pd-catalyzed macrocyclization gave macrocycle V, which contains the diazonamide AEF ring system.

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, COA of Formula: C10H11N3O3S.

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

Bartlett, Robert T. published the artcileSynthesis and pharmacological evaluation of a series of analogs of 1-methylisoguanosine, Recommanded Product: 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Journal of Medicinal Chemistry (1981), 24(8), 947-54, database is CAplus and MEDLINE.

Analogs of 1-methylisoguanosine (I, R = Me, R¹ = H, R² = OH) were evaluated as muscle relaxants, antiinflammatory agents, allergy inhibitors, and for cardiovascular activity. Cyclizing imidazole nucleoside II with RNCO (R = Et, Bu, octyl, Ph) and deprotecting gave I (R = Et, Bu, octyl, Ph; R¹ = H, R² = OH). Bromination of I (R = Me, R¹ = H, R² = OH) with Br₂-H₂O gave I (R = Me, R¹ = Br, R² = OH) which reacted with N₂H₄ to give I (R = Me, R¹ = NHNH₂, R² = OH). This was cleaved with Raney Ni to give I (R = Me, R¹ = NH₂, R² = OH). Deamination of 1-methylguanosine with NaNO₂ in aqueous AcOH gave 1-methylxanthosine. Iodination of I (R = Me, R¹ = H, R² = OH) with Me(PhO)₃P⁺I^– gave I (R = Me, R¹ = H, R² = iodo) which was cyclized to III or deiodinated to I (R = Me, R¹ = R² = H). The phosphate ester I (R = Me, R¹ = H, R² = OPO₃^2-) was prepared as well as cyclic phosphate IV. C-Nucleoside V was prepared from Me β-D-ribofuranosyl-1-carboximidate. Cyclizing the 9-(2-hydroxyethoxy)methyl analog of II with MeNCO gave acyclic analog VI. Similarly prepared was the β-D-arabinofuranosyl analog of I (R = Me, R¹ = H, R² = OH).

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, Recommanded Product: 2-Aminomalononitrile 4-methylbenzenesulfonate.

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

Tuo, Wei published the artcileDevelopment of novel oxazolo[5,4-d]pyrimidines as competitive CB₂ neutral antagonists based on scaffold hopping, Application In Synthesis of 5098-14-6, the publication is European Journal of Medicinal Chemistry (2018), 68-78, database is CAplus and MEDLINE.

A series of novel oxazolo[5,4-d]pyrimidines I [R¹ = H, Cl, F, CF₃; R² = H, Me; R³ = n-Bu, cyclohexylmethyl, 1-methylpiperazinyl, etc.] was designed via a scaffold hopping strategy and synthesized through a newly developed approach. All these compounds I were evaluated for their biol. activity toward CB₁/CB₂ cannabinoid receptors, their metabolic stability in mice liver microsomes and their cytotoxicity against several cell lines. Eight compounds I [R¹ = Cl, CF₃; R² = H, Me; R³ = 1-methylpiperazinyl, 1-ethylpiperazinyl, 1-acetylpiperazinyl] were identified as CB₂ ligands with K_i values less than 1 ΜM. It was noteworthy that compounds I [R¹ = Cl; R² = Me; R³ = 1-methylpiperazinyl, 1-ethylpiperazinyl] showed CB₂ binding affinity in the nanomolar range and significant selectivity over CB₁ receptors. Interestingly, functionality studies imply that they behaved as competitive neutral antagonists. Moreover, all tested compounds I were devoid of cytotoxicity toward several cell lines, including Chinese hamster ovary cells (CHO) and human colorectal adenocarcinoma cells HT29.

European 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 C12H16O3, Application In Synthesis of 5098-14-6.

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