Tag: M.W=150-200

Han, Xinya published the artcileBiological evaluation and SAR analysis of novel covalent inhibitors against fructose-1,6-bisphosphatase, Formula: C9H6N2O2, the publication is Bioorganic & Medicinal Chemistry (2020), 28(18), 115624, database is CAplus and MEDLINE.

Herein, a series of nitrostyrene derivatives I (R¹ = H, F, Me, etc.; R² = H, Cl, Me, etc.; R³ = H, Cl, Br, Me) were synthesized, and their inhibitory activities against Fructose-1,6-bisphosphatase (FBPase) were investigated in vitro. Most of the prepared compounds exhibit potent FBPase inhibition (IC₅₀ < 10μM). Specifically, when the substituents of F, Cl, OMe, CF₃, OH, CO₂H, or 2-nitrovinyl were installed at the R² (meta-) position of the benzene ring, the FBPase inhibitory activities of the resulting compounds increased 4.5-55 folds compared to those compounds with the same groups at the R¹ (para-) position. In addition, the preferred substituents at the R³ position were Cl or Br, thus compound I (R¹ = NO₂; R² = H; R³ = Cl) exhibited the most potent inhibitory activity (IC₅₀ = 0.15μM). The mol. docking and site-directed mutation suggest that C128 and N125 are essential for the binding of I (R¹ = NO₂; R² = H; R³ = Cl) and FBPase, which is consistent with the C128-N125-S123 allosteric inhibition mechanism. The reaction enthalpy calculations show that the order of the reactions of compounds with thiol groups at the R³ position is Cl > H > CH₃. CoMSIA anal. is consistent with proposed binding mode. The effect of compounds I (R¹ = 1,2,4-triazol-1-yl; R² = H; R³ = H) and I (R¹ = NO₂; R² = H; R³ = Cl) on glucose production in primary mouse hepatocytes were further evaluated, showing that the inhibition was 71% and 41% at 100μM, resp.

Bioorganic & Medicinal Chemistry published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Formula: C9H6N2O2.

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

Moreland, D. E. published the artcileComparative effects of dichlobenil and its phenolic alteration products on photo- and oxidative phosphorylation, Name: 2,6-Dichloro-3-hydroxybenzonitrile, the publication is Pesticide Biochemistry and Physiology (1974), 4(3), 356-64, database is CAplus.

The effects of dichlobenil (2,6-dichlorobenzonitrile)(I) [1194-65-6] and its phenolic degradation products, 2,6-dichloro-3-hydroxybenzonitrile (II) [3336-34-3] and 2,6-dichloro-4-hydroxybenzonitrile (III) [3336-19-4] on electron transport and phosphorylation were studied in isolated spinach (Spinacia oleracea) chloroplasts and mung bean (Phaseolus aureus) mitochondria. II and III inhibited photoreduction, coupled phosphorylation, and cyclic phosphorylation in chloroplasts and acted as uncouplers of oxidative phosphorylation in mitochondria. II and III also decreased ATP in mung bean hypocotyls. In all assays only limited inhibition was caused by I, even at relatively high concentrations (1.0 mM).

Pesticide Biochemistry and Physiology 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 C7H3Cl2NO, Name: 2,6-Dichloro-3-hydroxybenzonitrile.

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

Rani, Dixita published the artcileAqueous synthesis of 2-aryl-3-nitro-2H-chromenes via L-prolinamide mediated tandem oxa-Michael Henry reactions, Category: nitriles-buliding-blocks, the publication is Journal of Molecular Structure (2022), 133341, database is CAplus.

An efficient and aqueous protocol was developed for the synthesis of 2-aryl-3-nitro-2H-chromene derivatives This protocol involves the L-prolinamide mediated tandem oxa-Michael Henry reaction between a variety of β-nitrostyrenes and salicylaldehyde. Among the screened solvents, the catalytic efficiency of prolinamides was found to be high in chloroform, but the best results were obtained in water to provide the 2-phenyl-3-nitro-2H-chromene in excellent yields. Substrate scope was also investigated using various substituted β-Nitrostyrenes. All reactions worked well to provide the corresponding products in very high yields. Theor. calculations were performed to find out the reaction pathways and nature of transition state at 3-21G* basis set and TS1 corresponding to the product (S)-3a, was found favorable by 1.13 kcal/mol over TS2 corresponding to the product (R)-3a.

Journal of Molecular Structure published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Category: nitriles-buliding-blocks.

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

Wang, Hai-Jun published the artcilePd/C-Catalyzed Dehydrogenative [3+2] Cycloaddition for the Synthesis of Functionalized Tropanes, Name: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is European Journal of Organic Chemistry (2018), 2018(39), 5456-5459, database is CAplus.

A Pd/C-catalyzed cascade approach for the synthesis of attractive benzo-fused tropanes was developed. The reaction proceeds through a sequential Pd/C-catalyzed dehydrogenative formation of azomethine ylides from amines and 1,3-dipolar cycloaddition It gave structurally complex benzo-fused tropanes in good yields with excellent diastereoselectivities under mild reaction conditions. Preliminary results of asym. version of the reaction reveal that the copper catalyst and chiral monophosphoramidite ligand can furnish optically active products with moderate ee.

European Journal of Organic Chemistry published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C6H5BFNO4, Name: (E)-4-(2-Nitrovinyl)benzonitrile.

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

Deng, Lijuan published the artcileLigustrazine derivatives. Part 4: Design, synthesis, and biological evaluation of novel ligustrazine-based stilbene derivatives as potential cardiovascular agents, Synthetic Route of 612-13-5, the publication is Chemical Biology & Drug Design (2012), 79(5), 731-739, database is CAplus and MEDLINE.

A series of novel stilbene derivatives containing ligustrazinyl moiety was designed, synthesized, and assayed for their protective effects on damaged endothelial cells. The results showed that most ligustrazinyl stilbene derivatives exhibited high protective effects on the human umbilical vascular endothelial cells (HUVECs) damaged by hydrogen peroxide in comparison with Ligustrazine. Structure-activity relationships were briefly discussed.

Chemical Biology & Drug Design published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Synthetic Route of 612-13-5.

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

Zhang, Wenjun published the artcileSynthesis of aryl acetamides by aminocarbonylation of benzylic chlorides using carbamoylsilane as an amide source, SDS of cas: 612-13-5, the publication is Synthetic Communications (2017), 47(7), 704-709, database is CAplus.

Using N-methyl-N-(1-phenyl)ethylcarbamoyl(trimethyl)silane as an amide source, the direct transformation of benzylic chlorides into the corresponding aryl acetamides through palladium-catalyzed aminocarbonylation is described. The electronic property and the relative position of substituents on the aromatic ring impact the coupling efficiency.

Synthetic Communications published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C5H5BrN2, SDS of cas: 612-13-5.

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

Dou, Xiaowei published the artcileFrom the Feist-Benary reaction to organocatalytic domino Michael-alkylation reactions: asymmetric synthesis of 3(2 H)-furanones, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Chemistry – A European Journal (2012), 18(1), 85-89, S85/1-S85/45, database is CAplus and MEDLINE.

A modified Feist-Benary reaction by employing a domino Michael-alkylation sequence for the enantioselective preparation of 3(2H)-furanones is introduced. A L-threonine-derived tertiary amine/thiourea catalyst was synthesized to promote the domino Michael-alkylation reaction efficiently, affording the title compounds in high yields and excellent enantioselectivities.

Chemistry – A European Journal published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile.

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

Xu, Hong-mei published the artcilePreparation of (R)-o-chloromandelic acid through dynamic kinetic resolution of o-chloromandelonitrile by whole cells of Alcaligenes faecalis CGMCC 1.2006, Quality Control of 13312-84-0, the publication is Fenzi Cuihua (2014), 28(2), 174-181, database is CAplus.

Alcaligenes faecalis CGMCC 1.2006 with higher arylacetonitrilase activity and moderate enantioselectivity towards o-chloromandelonitrile was screened from six microbial strains belonging to Alcaligenes faecalis. The regulating effects of reaction medium on both activity and enantioselectivity of arylacetonitrilase were studied. The addition of water-soluble co-solvents such as methanol into the reaction medium decreased the activity of arylacetonitrilase, but enhanced the enantioselectivity significantly. Addition of non-ionic surfactants possessed the reverse effects. The effects of reaction conditions such as substrate concentration, cell concentration, pH, temperature and reaction time on the activity and enantioselectivity of arylacetonitrilase were also optimized systematically. Under the optimal reaction conditions, the fed-batch production of (R)-o-chloromandelic acid was attained with 32.2 g/L productivity within 22 h, in 82.4% yield and 93.1% ee. With o-chlorobenzaldehyde and potassium cyanide as the substrates, (R)-o-chloromandelic acid was also produced in 89.5% yield and 98.6% ee.

Fenzi Cuihua 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 C12H23N3S, Quality Control of 13312-84-0.

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