Category: 57663-05-5

Smyth, Lynette A. published the artcileSynthesis and reactivity of 3-amino-1H-pyrazolo[4,3-c]pyridin-4(5H)-ones: development of a novel kinase-focussed library, HPLC of Formula: 57663-05-5, the publication is Tetrahedron (2010), 66(15), 2843-2854, database is CAplus.

3-Amino-1H-pyrazolo[4,3-c]pyridin-4(5H)-ones represent a potentially attractive heteroaromatic scaffold for drug-discovery chem. In particular, the arrangement of hydrogen bond donor and acceptor groups in the bicyclic core can fulfil the requirements for ATP competitive binding to kinase enzymes. Efficient and regioselective routes from simple starting materials to novel functionalized 3-amino-1H-pyrazolo[4,3-c]pyridin-4(5H)-ones and related 3-amino-2H-pyrazolo[4,3-c]pyridines were explored and adapted for parallel synthesis, resulting in a library of compounds suitable for screening against kinases and other cancer drug targets. Methods for substituent variation at five distinct positions around the bicyclic core were devised to generate sets of compounds containing two- or three-point diversity.

Tetrahedron 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 C14H31NO2, HPLC of Formula: 57663-05-5.

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

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

Tominaga, Yoshinori published the artcileSynthesis of 4-(methylthio)-2(1H)-pyridone derivatives using ketene dithio acetals, Quality Control of 57663-05-5, the publication is Journal of Heterocyclic Chemistry (1987), 24(5), 1325-31, database is CAplus.

Reaction of active methylene compounds with ketene dithioacetals, (MeS)₂C:C(CN)₂ and (MeS)₂C:C(CN)CONH₂ gave cyanomethylthiopyridone I [R = Me, CH₂CH₂CO₂H, (un)substituted Ph; R¹ = H, Me, Ac, CO₂Et, CH₂CO₂H; RR¹ = (CH₂)₄]. The transformation of 4-methylthiooxopyrancarbonitriles II (R² = Ph, C₆H₄Br-4, C₆H₄OMe-4, Me, styryl) into I was also described.

Journal of Heterocyclic Chemistry 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 C11H16BNO3, Quality Control of 57663-05-5.

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

Kumar, Arvind published the artcileKetene dithioacetals. Part 11. Reaction of 3-cyano-4-methylthio-2(1H)-pyridones with hydrazine and guanidine: synthesis of novel substituted and fused pyrazolo[4,3-c]pyridone and pyrido[4,3-d]pyrimidine derivatives, HPLC of Formula: 57663-05-5, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1978), 857-62, database is CAplus.

The N-methylpyridones I [R = Me, R¹ = H, R² = 4-R³C₆H₄, R³ = H, Me, MeO, Cl, Br; R = R² = Me, R¹ = H; R = Me, R¹R² = (CH₂)₃, (CH₂)₄] and the benzoquinolone II (R = Me, R¹ = H, n = 1) were prepared by alkylation of I (R = H, R¹, R² as before) and II (R = R¹ = H, n = 1), resp., with Me₂SO₄-NaOMe, followed by heating the mixture of N-Me and O-Me products with MeI. Treatment of I (R = H, Me, R¹ = H, R² = 4-R³C₆H₄, R³ = H, Me, MeO, Cl, Br; R = R² = Me, R¹ = H; R = R¹ = H, R² = 3-, 4-pyridyl; R = H, R¹ = Ph, R² = Me) with NH₂NH₂ in refluxing Me₂CHOH gave 70-90% pyrazolopyridones III. Similar treatment of I [R = H, Me, R¹R² = (CH₂)₃, (CH₂)₄; R = H, R¹R² = (CH₂)₅] and II (R = H, Me, MeO, R¹ = H, n = 1; R = R¹ = H, n = 2) gave 68-80% III (R, R¹, R² as before) and 64-78% pyrazolopyridone IV (R, R¹, n as before), resp. Reaction of I [R = Me, R¹ = H, R² = 4-R³C₆H₄, R³ = H, Me, MeO, Cl, Br; R = Me, R¹R² = (CH₂)₃, (CH₂)₄] and II (R = Me, R¹ = H, n = 1) with guanidine in the presence of 2 mol of NaOEt gave 31-71% pyridopyrimidinone V (R, R¹, R² as before) and 41% pyrimidoquinolinone VI.

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, HPLC of Formula: 57663-05-5.

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

Rastogi, Roopa R. published the artcileNovel method for the synthesis of substituted and fused 3-cyano-4-(methylmercapto)-2(1H)-pyridones using α-oxoketene S,S-diacetals, Synthetic Route of 57663-05-5, the publication is Journal of the Chemical Society, Chemical Communications (1975), 645, database is CAplus.

RCOCH:C(SMe)2 (R = Me, p-MeC6H4, 3-pyridyl) with cyanoacetamide and Me2CHONa in refluxing Me2CHOH gave 65-85% pyridone I. Similar reaction of the cycloalkanones II (n = 1 and 2) and III gave 77% pyrindinone IV (n = 1), 76% quinolinone IV (n = 2), and 65% benzoquinoline V.

Journal of the Chemical Society, Chemical Communications 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, Synthetic Route of 57663-05-5.

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

Abu-Shanab, Fathi A. published the artcileα,α-Dioxoketene dithioacetals as starting materials for the synthesis of polysubstituted pyridines, Category: nitriles-buliding-blocks, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1994), 1449-52, database is CAplus.

Reactions of 3-acetyl-4,4-bis(methylthio)but-3-en-2-one and Me 2-acetyl-3,3-bis(methylthio)-prop-2-enoate with cyanothioacetamide, cyanoacetamide, or 2-amino-1,3,3-tricyanoprop-1-ene and base, followed by treatment with acid, give polysubstituted pyridines. Further elaboration of these products leads to bicyclic systems such as thieno[2,3-b]pyridines and pyrazolo[3,4-c]pyridine and then to tricyclic systems including pyrazolo[3,4-d]thieno[2,3-b]pyridine and dipyrazolo[3,4-b:3′,4′-d]pyridine.

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, Category: nitriles-buliding-blocks.

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

Khanna, Avinash published the artcileDesign, Synthesis, and Pharmacological Evaluation of Second Generation EZH2 Inhibitors with Long Residence Time, HPLC of Formula: 57663-05-5, the publication is ACS Medicinal Chemistry Letters (2020), 11(6), 1205-1212, database is CAplus and MEDLINE.

Histone methyltransferase EZH2, which is the catalytic subunit of the PRC2 complex, catalyzes the methylation of histone H3K27-a transcriptionally repressive post-translational modification (PTM). EZH2 is commonly mutated in hematol. malignancies and frequently overexpressed in solid tumors, where its expression level often correlates with poor prognosis. First generation EZH2 inhibitors are beginning to show clin. benefit, and we believe that a second generation EZH2 inhibitor could further build upon this foundation to fully realize the therapeutic potential of EZH2 inhibition. During our medicinal chem. campaign, we identified 4-thiomethyl pyridone as a key modification that led to significantly increased potency and prolonged residence time. Leveraging this finding, we optimized a series of EZH2 inhibitors, with enhanced antitumor activity and improved physiochem. properties, which have the potential to expand the clin. use of EZH2 inhibition.

ACS Medicinal Chemistry Letters 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, HPLC of Formula: 57663-05-5.

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

Stuckey, Jacob I. published the artcileIdentification and characterization of second-generation EZH2 inhibitors with extended residence times and improved biological activity, Product Details of C8H8N2OS, the publication is Journal of Biological Chemistry (2021), 100349, database is CAplus and MEDLINE.

Kinetic methodologies for studying EZH2-inhibitor-binding kinetics that had allowed to identify a unique structural modification that results in significant increases in the drug-target residence times of all EZH2 inhibitor scaffolds was studied. The unexpected residence time enhancement bestowed by this modification had enabled us to create a series of second-generation EZH2 inhibitors with sub-pM binding affinities. Both biophys. evidence validating this sub-pM potency and biol. evidence demonstrating the utility and relevance of such high-affinity interactions with EZH2 was provided.

Journal of Biological Chemistry 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 C12H10F2Si, Product Details of C8H8N2OS.

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