Tag: M.W=250-300

Hirota, Kosaku published the artcileSynthesis and biological evaluation of 2,8-disubstituted 9-benzyladenines: discovery of 8-mercaptoadenines as potent interferon-inducers, COA of Formula: C10H11N3O3S, the publication is Bioorganic & Medicinal Chemistry (2003), 11(13), 2715-2722, database is CAplus and MEDLINE.

Recently, we have identified 9-benzyl-8-hydroxyadenines bearing an appropriate substituent (a butoxy, propylthio or butylamino group) at the 2-position as potent interferon (IFN)-inducers. Herein we report the design, synthesis, and IFN-inducing activity of 8-substituted 9-benzyladenines possessing such an appropriate substituent at the 2-position. Introduction of the appropriate substituent into the 2-position of the adenine nucleus gave rise to expression of the activity even in 9-benzyladenines bearing no hydroxyl group at the 8-position. An amino group at the 6-position and a hydroxyl or thiol group carrying an acidic proton at the 8-position are required to express excellent IFN-inducing activity. 9-Benzyl-2-butoxy-8-mercaptoadenine indicated the most potent activity with MEC of 0.001 μM.

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, COA of Formula: C10H11N3O3S.

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

Hirota, Kosaku published the artcileEfficient synthesis of 2,9-disubstituted 8-hydroxyadenine derivatives, Quality Control of 5098-14-6, the publication is Organic & Biomolecular Chemistry (2003), 1(8), 1354-1365, database is CAplus and MEDLINE.

An efficient and general method for the synthesis of 2,9-disubstituted 8-hydroxyadenines, e.g. I, which are expected to have various biol. activities, was realized. 5-Amino-4-cyano-2-hydroxyimidazoles, e.g. II, were prepared from aminomalononitrile and isocyanates as key intermediates. The condensation of II with amidines, imidates, guanidine, urea and thioureas afforded 8-hydroxyadenines, e.g. III, possessing various substituents at the 2-position. Furthermore, selective alkylation of 2-amino- and 2-hydroxyadenines (IV and V) successively proceeded to give the corresponding 2-alkylamino- and 2-alkoxyadenines, resp. 2-Alkylthioadenines, e.g. VI, were prepared by an analogous reaction of II with benzoyl isothiocyanate and subsequent S-alkylation. The imidazoles, e.g. II, are most useful intermediates for the synthesis of 8-hydroxyadenine derivatives

Organic & Biomolecular 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

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

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

Barnathan, Gilles published the artcileSynthesis of C-nucleosides. XI. 2-D-Arabinofuranosylimidazoles and 8-D-arabinofuranosylpurines, Related Products of nitriles-buliding-blocks, the publication is European Journal of Medicinal Chemistry (1976), 11(1), 67-72, database is CAplus.

The nucleoside analogs I (R = NH2, SH, R1 = H) were prepared by treating II (R1 = R2 = Bz, R3 = Cl, Br) with Hg(CN)2, cleaving benzoyl groups from II (R1 = R2 = Bz, R3 = CN), treating II (R1 = Bz, R2 = H, R3 = CN) with PhCH2SH, cyclizing II (R1 = Bz, R2 = H, R3 = CH(:NH)SCH2Ph) with H2NCH(CN)2, cyclizing II (R1 = Bz, R2 =H, R3 = 4-cyano-5-amino-2-imidazolyl) with HC(:NH)NH2 or HC(OEt)3 and NaSH, and cleaving the benzoyl groups from I (R1 = Bz).

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 C10H11N3O3S, Related Products of nitriles-buliding-blocks.

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

Steven, Alan published the artcileUse of a Curtius Rearrangement as Part of the Multikilogram Manufacture of a Pyrazine Building Block, Computed Properties of 5098-14-6, the publication is Organic Process Research & Development (2018), 22(1), 77-81, database is CAplus.

2-Amino-5-methylpyrazine I was prepared on multikilogram scale as an intermediate in the preparation of a glucokinase activator using the Curtius rearrangement of an acyl azide derived from 5-methyl-2-pyrazinecarboxylic acid as the key step. The formation of an acyl azide for the Curtius rearrangement required a process safety control strategy to be put in place. The process developed was used to successfully deliver multikilogram quantities of I in an overall yield of 68% starting from 5-methylpyrazine-2-carboxylic acid.

Organic Process Research & Development 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 C3H12Cl2N2, Computed Properties 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

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

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

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