Category: 5098-14-6

Hosmane, Ramachandra S. published the artcileRearrangements in heterocyclic synthesis: a novel translocation of an (N-amino-N-methylamino)methylene group from a heterocyclic N-amino-N-methylformamidine side chain to the vinylogous nitrile function, Recommanded Product: 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Journal of Organic Chemistry (1988), 53(2), 382-6, database is CAplus.

Reaction of imidazole I (R = OMe) (II) with 1 equiv of N₂H₄ gave 1-amino-9-benzyl-6-iminopurine (III), which upon treatment with excess N₂H₄, rearranged to 9-benzyl-6-hydrazinopurine (IV). Reaction of II with MeNHNH₂ gave I (R = H₂NNMe) (V). Thermolysis of V in refluxing PhMe-MeOH containing CF₃CO₂H gave an equimolar mixture of 5-amino-1-benzyl-4-cyanoimidazole (VI) and triazole VII. VI was recycled to V via II. The structure of VII was established by spectral data and an unequivocal synthesis. The conversion of V to VII represents a novel translocative rearrangement involving the transfer of an H₂NNMeCH: group from the imidazole 5-position to the nitrile function at C-4. The rearrangement also occurs in the analogous pyrazole 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, Recommanded Product: 2-Aminomalononitrile 4-methylbenzenesulfonate.

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

Ioannidis, Stephanos published the artcileDiscovery of pyrazol-3-ylamino pyrazines as novel JAK2 inhibitors, Product Details of C10H11N3O3S, the publication is Bioorganic & Medicinal Chemistry Letters (2009), 19(23), 6524-6528, database is CAplus and MEDLINE.

Pyridineethyl- and pyrimidineethyl-substituted pyrazoleaminopyrazines such as I (R = Me; X = N) and I (R = H; X = CH) are prepared as selective JAK2 kinase inhibitors for potential use as anticancer agents; the GI₅₀ values for their JAK2 and JAK3 kinase inhibition are determined The activities of selected pyridineethyl- and pyrimidineethyl-substituted pyrazoleaminopyrazines in a functional phosphorylation model in mice and their inhibition of aurora B kinase, cyclin-dependent kinase 2, and TrkA are determined; the pharmacokinetics and pharmacodynamics of I (R = Me; X = N) and of I (R = H; X = CH) in rats and beagles are also determined

Bioorganic & 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, Product Details of C10H11N3O3S.

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

Yang, Mu published the artcileToll-like receptor 7 and 8 imidazoquinoline-based agonist/antagonist pairs, Synthetic Route of 5098-14-6, the publication is Bioorganic & Medicinal Chemistry Letters (2022), 128548, database is CAplus and MEDLINE.

Toll-like receptors (TLRs) 7 and 8 are key targets in the development of immunomodulatory drugs for treating infectious disease, cancer, and autoimmune disorders. These receptors can adopt both agonist and antagonist binding conformations that switch the receptor signal on or off to the downstream production of cytokines. In this study, we examined the effect of simple isomeric substitutions to the C2-Bu group of two imidazoquinoline agonists and evaluated the activity of these analogs using both TLR7 and TLR8 reporter cells and cytokine induction assays. the C2-iso-Bu and C2-cyclopropylmethyl isomers are both mixed TLR7/8 competitive antagonists of the parent agonist [4-Amino-1-(4-(aminomethyl)benzyl)-2-butyl-7-methoxycarbonyl-1H-imidazo[4,5-c]quinoline], indicating the conformation of the dimeric receptor complex is highly sensitive to steric perturbations to the ligand binding pocket. This observation is consistent with prior work demonstrating TLR7 and TLR8 activity is directly correlated to C2-alkyl substitutions that project into a hydrophobic pocket at the dimer interface of the receptor. The close structural relationship of the agonist/antagonist pairs identified here highlights the importance of this pocket in tipping the balance between the agonist and antagonist binding states of the receptor which may have significant ramifications to the design of imidazoquinoline-based immunomodulatory agents.

Bioorganic & 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 C6H6N2O, Synthetic Route of 5098-14-6.

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

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

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

Hirota, Kosaku published the artcileNovel and efficient synthesis of 8-oxoadenine derivatives, Safety of 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Heterocycles (2001), 55(12), 2279-2282, database is CAplus.

A novel synthetic method for the preparation of 8-oxoadenine derivatives was reported. This widely applicable synthetic method was realized through the use of 5-amino-2,3-dihydro-2-oxo-1-(phenylmethyl)-1H-imidazole-4-carbonitrile as the key intermediates. A variety of substituents were successfully introduced to the 2- and 9-position of the 8-oxoadenine nucleus.

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, Safety of 2-Aminomalononitrile 4-methylbenzenesulfonate.

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

Freeman, Fillmore published the artcileReaction of aminopropanedinitrile 4-methylbenzenesulfonate [aminomalononitrile p-toluenesulfonate (tosylate)] with aromatic aldehydes, SDS of cas: 5098-14-6, the publication is Journal of Organic Chemistry (1991), 56(2), 657-63, database is CAplus.

(NC)₂CHNH₂·HO₃SC₆H₄Me-4 reacts with aromatic aldehydes in NaOAc-MeOH to give diastereoselectively (E,E)-RCH:NC(CN):C(NH₂)OMe (R = C₆H₄R¹-4, R¹ = OMe, OEt, OAc, H, Br, NO₂, CO₂Me; R = 3-pyridyl, 3-thienyl) and trans-3,6-diaryl-2,2,5,5-tetracyanopiperazines I (same R). The product distribution depends on the ratio of reactants and the structures of the substrates. Electron-releasing groups on the 4-position of the Ph ring favor piperazine formation. The formation of piperazines may involve synthetically useful N-protonated aryl- and cyano-stabilized azomethine ylide (prototropic 1,3-dipoles) intermediates which could have resulted from an imine-azomethine ylide tautomerism of prior formed 1-aryl-3,3-dicyano-2-aza-1-propenes. [4+2]-1,3-Dipolar cycloaddition reactions of the highly reactive azomethine ylides with MeO₂CCCCO₂Me give 3,4-dicarbomethoxy-2-cyano-5-aryl-3-pyrrolines, which undergo facile dehydrocyanation to 3,4-dicarbomethoxy-2-cyano-5-arylpyrroles. The possible intermediacy of ketenimines and of aryl- and cyano-stabilized 2-azaallyl anionic intermediates in equilibrium with azomethine ylides is also considered.

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, SDS of cas: 5098-14-6.

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

Freeman, Fillmore published the artcileReaction of aminopropanedinitrile 4-methylbenzenesulfonate (aminomalononitrile p-toluenesulfonate (tosylate)) with isothiocyanates, Computed Properties of 5098-14-6, the publication is Journal of Organic Chemistry (1991), 56(15), 4645-8, database is CAplus.

Aminopropanedinitrile tosylate reacts with isothiocyanates RNCS (R = Bu, 4-MeOC₆H₄, Ph, 4-ClC₆H₄, 4-O₂NC₆H₄, 1-naphthyl) in 1-methyl-2-pyrrolidinone to give 2,5-diaminothiazole-4-carbonitriles I. I (R = 4-MeOC₆H₄, Ph) react with H₂NCH:NH.AcOH to give thiazolopyrimidines II (R¹ = H). I (R = Ph) also reacts with MeC(OEt)₃ to give II (R = Ph, R¹ = 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 C10H11N3O3S, Computed Properties of 5098-14-6.

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

Freeman, Fillmore published the artcilePreparation of (E,E)-4-amino-1-aryl-3-cyano-4-methoxy-2-azabutadienes, Formula: C10H11N3O3S, the publication is Synthesis (1989), 698-9, database is CAplus.

Treatment of (NC)₂CHN⁺H₃ 4-MeC₆H₄SO₃^– with NaOAc and RCHO (R = Ph, 2-BrC₆H₄, 2-ClC₆H₄, 2-O₂NC₆H₄, 4-O₂NC₆H₄, 4-HOC₆H₄, 2-naphthyl) in MeOH gave 23-99% (E,E)-RCH:NC(CN):C(OMe)NH₂.

Synthesis 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, Formula: C10H11N3O3S.

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