Author: Jessica.F

Rastogi, R. R. published the artcileKetene SS-acetals. Part 9. Reaction of α-oxo- and α-cyano-ketene SS-acetals with cyanoacetamide: a new general method for substituted and fused 4-alkylthio-3-cyano-2(1H)-pyridones and formation of novel pyridones through base-induced rearrangements, Safety of 6-Methyl-4-(methylthio)-2-oxo-1,2-dihydropyridine-3-carbonitrile, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1978), 549-53, database is CAplus.

Fourteen acylketene S,S-acetals RCOCR¹:C(SR²)₂ (R = aryl, pyridyl, alkyl; R¹ = H, aryl; R² = alkyl, aralkyl), on treatment with NCCH₂CONH₂ in base, gave 65-85% pyridones I. α-Cyanoacetals NCCR:C(SMe)₂ (R = CN, Ph, p-ClC₆H₄, p-MeC₆H₄) gave lower yields of the corresponding 6-aminopyridones. The method was successfully extended to cyclic ketene S,S-acetals, giving fused pyridones, benzoquinolone derivatives, and a (benzocyclohepta)pyridone derivative α-Alkyl-α-acylketene S,S-acetals with NCCH₂CONH₂ gave novel pyridones, e.g. II (R = MeSCH₂, CH₂:CH), formed by initial base induced proton migration in these acetals.

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, Safety of 6-Methyl-4-(methylthio)-2-oxo-1,2-dihydropyridine-3-carbonitrile.

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

Larson, Peter published the artcileDesign and Synthesis of N1-Modified Imidazoquinoline Agonists for Selective Activation of Toll-like Receptors 7 and 8, Application In Synthesis of 5098-14-6, the publication is ACS Medicinal Chemistry Letters (2017), 8(11), 1148-1152, database is CAplus and MEDLINE.

A series of N1-modified imidazoquinolines were synthesized and screened for Toll-like receptors (TLR) 7 and 8 activities to identify recognition elements that confer high affinity binding and selectivity. These receptors are key targets in the development of immunomodulatory agents that signal the NF-κB mediated transcription of pro-inflammatory chemokines and cytokines. Results are presented showing both TLR7/8 activations are highly correlated to N1-substitution, with TLR8 selectivity achieved through inclusion of an ethyl-, propyl-, or butylamino group at this position. While the structure-activity relationship anal. indicates TLR7 activity is less sensitive to N1-modification, extension of the aminoalkyl chain length to pentyl and p-methylbenzyl elicited high affinity TLR7 binding. Cytokine profiles are also reported that show the pure TLR8 agonist [4-amino-2-butyl-1-(2-aminoethyl)-7-methoxycarbonyl-1H-imidazo[4,5-c]quinoline] (I) induces higher levels of IL-1β, IL-12, and IFNγ when compared with TLR7 selective or mixed TLR7/8 agonists. The results are consistent with previous work suggesting TLR8 agonists are Th1 polarizing and may help promote cell-mediated immunity.

ACS Medicinal Chemistry Letters 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

Cox, Oakley B. published the artcileA poised fragment library enables rapid synthetic expansion yielding the first reported inhibitors of PHIP(2), an atypical bromodomain, Category: nitriles-buliding-blocks, the publication is Chemical Science (2016), 7(3), 2322-2330, database is CAplus and MEDLINE.

Research into the chem. biol. of bromodomains has been driven by the development of acetyl-lysine mimetics. The ligands are typically anchored by binding to a highly conserved asparagine residue. Atypical bromodomains, for which the asparagine is mutated, have thus far proven elusive targets, including PHIP(2) whose parent protein, PHIP, has been linked to disease progression in diabetes and cancers. The PHIP(2) binding site contains a threonine in place of asparagine, and solution screening have yielded no convincing hits. We have overcome this hurdle by combining the sensitivity of X-ray crystallog., used as the primary fragment screen, with a strategy for rapid follow-up synthesis using a chem.-poised fragment library, which allows hits to be readily modified by parallel chem. both peripherally and in the core. Our approach yielded the first reported hit compounds of PHIP(2) with measurable IC₅₀ values by an AlphaScreen competition assay. The follow-up libraries of four poised fragment hits improved potency into the sub-mM range while showing good ligand efficiency and detailed structural data.

Chemical Science 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, Category: nitriles-buliding-blocks.

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

Tam Huynh Dinh published the artcileSynthesis of C-nucleosides. VII. β-D-Ribofuranosyl-2- and -8-adenines, Related Products of nitriles-buliding-blocks, the publication is Journal of Heterocyclic Chemistry (1975), 12(1), 111-17, database is CAplus.

Benzyl (O-benzoyl-5-D-ribofuranosyl)thioformimidate reacted with aminomalodinitrile or with 5-amino-4-cyanoimidazole to yield the two C-nucleoside analogs I and II of adenosine. The β-configuration was determined with NMR and CD spectra.

Journal of Heterocyclic 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 C9H9BrO2, Related Products of nitriles-buliding-blocks.

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

Van Genderen, H. published the artcileToxicological properties of the herbicide dichlobenil, 2,6-dichlorobenzonitrile, in warm-blooded animals, SDS of cas: 3336-34-3, the publication is Mededelingen Rijksfaculteit Landbouwwetenschappen, Gent (1966), 31(3), 1026-31, database is CAplus.

After oral administration of 100 mg. dichlobenil/kg. body weight, rabbits converted approx. 23% into 2,6-dichloro-3-hydroxybenzonitrile (I) and 2% into the 4-hydroxy analog (II). Rats excreted, resp., 22% and 9% of I and II. In mice the i.p. LD50 for I and II was 83 mg./kg. and 50 mg./kg., resp. The oral toxicity for mice and rabbits was very much lower. The effects of I and II were studied on the respiration of bakers’ yeast, on the ATPase induction in isolated mitochondria, on the contraction of isolated rat diaphragm, and on single beating rat heart cells in tissue culture. It was concluded that I and II, like other chlorophenols, were uncoupling agents of oxidative phosphorylation with approx. the same potency as 2,4-dinitrophenol. Liver function tests with dichlobenil showed different results for rats and rabbits. The effect on the liver of the rat seemed to be reversible, but, at a critical dose level for the rabbit, it was irreversible. It was suggested that in the rat liver cells the conjugation of the phenols to glucuronides and sulfates could keep pace with their formation.

Mededelingen Rijksfaculteit Landbouwwetenschappen, Gent published new progress about 3336-34-3. 3336-34-3 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Phenol, name is 2,6-Dichloro-3-hydroxybenzonitrile, and the molecular formula is C8H10S, SDS of cas: 3336-34-3.

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

Taylor, Edward C. published the artcilePteridines. XXXII. 2-Amino-3-cyano-5-chloromethylpyrazine 1-oxide and its conversion to 6-alkenyl-substituted pteridines, HPLC of Formula: 5098-14-6, the publication is Journal of Organic Chemistry (1973), 38(16), 2817-21, database is CAplus.

2-Amino-3-cyano-5-chloromethylpyrazine 1-oxide (I), prepared by the condensation of β-chloropyruvaldoxime with aminomalononitrile tosylate, was deoxygenated with PCl3 to 2-amino-3-cyano-5-chloromethylpyrazine (II). Both I and II were converted by conventional procedures to triphenylphosphonium ylides (Wittig reagents) and, hence, by condensation with aldehydes, to parallel series of 5-alkenylpyrazines (III and IV). Cyclization of IV with guanidine gave 2,4-diamino-6-alkenylpteridines, of interest as intermediates for the synthesis of biopterin and biopterin analogs. Some addnl. reactions of the above pyrazine intermediates are also described.

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 C10H16O2, HPLC of Formula: 5098-14-6.

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

Taylor, Edward C. published the artcilePteridines. XXXIX. Synthesis of 2,4-diamino-7-alkenylpteridines and their 8-oxides, Product Details of C10H11N3O3S, the publication is Journal of Organic Chemistry (1976), 41(8), 1299-303, database is CAplus.

A versatile and flexible route to a variety of 2,4-diamino-7-alkenylpteridines was described. Condensation of aminomalononitrile with α-oximino-β-chloroaldehydes R1COC(:NOH)CClR2R3 [R1-R3 = H; R1 = R2 = H, R3 = Me, Pr; R1R2 = (CH2)3, R3 = H] (prepared by the addition of nitrosyl chloride to α,β-unsaturated aldehydes) gave 2-amino-3-cyano-6-(1-chloroalkyl)pyrazine 1-oxides I. The 6-chloromethyl compound I (R1-R3 = H) was converted to a stable phosphorane which was condensed with aldehydes to give a series of 2-amino-3-cyano-6-alkenylpyrazine 1-oxides II (R = Me, CH2OH, CO2H, Ph, 3,4-Cl2C6H3, 3,4-(OCH2O)C6H3, 2-thienyl, 3-pyridyl) which were cyclized with guanidine to 2,4-diamino-7-alkenylpteridine 8-oxides III (n = 1). Deoxygenation of I (R1-R3 = H) with PCl3 in THF gave 2-amino-3-cyano-6-chloromethylpyrazine, which analogously gave a series of 2,4-diamino-7-alkenylpteridines III (n = 0).

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 C21H24O8, Product Details of C10H11N3O3S.

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

Kuroda, Chiaki published the artcileReaction of Aminomalononitrile and Benzylic Compounds as a Plausible Route to Phenylalanine, COA of Formula: C10H11N3O3S, the publication is Natural Product Communications (2020), 15(1), 1934578X20901417, database is CAplus.

As a possible route to phenylalanine, reaction of aminomalononitrile with benzylic compounds was studied. 2-Benzyl-2-aminomalononitrile was obtained in a good yield when aminomalononitrile p-toluenesulfonate was treated with benzyl bromide in THF using triethylamine as a base. The reaction proceeded in the presence of water. 2-Benzyl-2-aminomalononitrile was hydrolyzed to afford phenylalanine. The aminomalononitrile route can explain the presence of not only 1 methylene in aromatic amino acids, but also α-hydrogen in all 20 proteinogenic amino acids.

Natural Product Communications 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

Noe, Christian R. published the artcileChiral lactols. XIII. On the determination of the absolute configuration of aromatic cyanohydrins and structurally related compounds, Quality Control of 13312-84-0, the publication is Liebigs Annalen (1995), 1353-60, database is CAplus.

Synthesis and conformational anal. of diastereomeric acetals, e.g. I, of aromatic cyanohydrins and structurally related compounds are described. Based on ¹H-NMR spectroscopic and x-ray data it is shown that the absolute configuration of such compounds can be assigned according to a method, which has been presented previously for secondary arylalkyl alcs.

Liebigs Annalen 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 C8H6ClNO, Quality Control of 13312-84-0.

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

Noe, C. R. published the artcileAmino alcohols. II: Preparation of enantiomerically pure pharmacologically active β-amino alcohols, Computed Properties of 13312-84-0, the publication is Monatshefte fuer Chemie (1995), 126(4), 481-94, database is CAplus.

A synthesis of β-amino alcs. is described starting from racemic or enantiomerically pure α-hydroxynitriles which were O-protected using enantiomerically pure acetal type protective groups. Reduction with lithium aluminum hydride yielded O-protected β-amino alcs. Whenever diastereomeric O-protected cyanohydrins could not be separated, the mixture was reduced and the resulting O-protected amino alcs. were separated Removal of the protective group using hydrogen chloride and methanol yielded enantiomerically pure β-amino alcs. or their corresponding hydrochlorides. For example, the chiral synthesis of (R)-1-amino-3-(1-naphthalenyloxy)-2-propanol and (S)-1-amino-3-(1-naphthalenyloxy)-2-propanol was accomplished via resolution of (±)-2-hydroxy-3-(1-naphthalenyloxy)propanenitrile.

Monatshefte fuer Chemie 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 C8H6ClNO, Computed Properties of 13312-84-0.

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