Category: 5153-73-1

Huang, Yunyuan published the artcileDiscovery of novel allosteric site and covalent inhibitors of FBPase with potent hypoglycemic effects, Related Products of nitriles-buliding-blocks, the publication is European Journal of Medicinal Chemistry (2019), 111749, database is CAplus and MEDLINE.

Fructose-1,6-bisphosphatase (FBPase) is an essential enzyme of GNG pathway. Significant advances demonstrate the FBPase plays a critical role in treatment of diabetes. Numerous FBPase inhibitors were developed by targeting AMP site, nevertheless, none of these inhibitors has exhibited suitable potency and druggability. Herein, a new allosteric site (C128) on FBPase was discovered, and several nitrostyrene compounds exhibiting potent FBPase inhibitions were found covalently bind to C128 site on FBPase. Mutagenesis suggest that C128 is the only cysteine that can influence FBPase inhibition, the N125-S124-S123 pathway was most likely involved in allosteric signaling transmission between C128 and active site. However, these nitrostyrenes may bind with multiple cysteine besides C128 in FBPase. To improve pocket selectivity, a series of novel compounds (14a-14n) were re-designed rationally by integrating fragment-based covalent virtual screening and machine-learning-based synthetic complexity evaluation. As expected, the mass spectrometry validated that the proportion of title compounds binding to the C128 in FBPase was significantly higher than that of nitrostyrenes. Notably, under physiol. and pathol. conditions, the treatment of compounds 14b(I), 14c(II), 14i(III) or 14n(IV) led to potent inhibition of glucose production, as well as decreased triglyceride and total cholesterol levels in mouse primary hepatocytes. We highlight a novel paradigm that mol. targeting C128 site on FBPase can have potent hypoglycemic effect.

European Journal of 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, Related Products of nitriles-buliding-blocks.

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

Wu, Lulu published the artcileSynthesis of Optically Active 2H-Thiopyrano[2,3-b]quinolines with Three Contiguous Stereocenters via an Organocatalytic Asymmetric Tandem Michael-Henry Reaction [Erratum to document cited in CA160:033796], COA of Formula: C9H6N2O2, the publication is Advanced Synthesis & Catalysis (2014), 356(6), 1134, database is CAplus.

The authors were made of aware of an error regarding the x-ray anal. data for the absolute configuration of compound 5ad; the corrected structure is given and the NMR data and spectra can be found in the Supporting Information.

Advanced Synthesis & Catalysis 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 C8H11NO, COA of Formula: C9H6N2O2.

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

Luo, Jie published the artcileHighly diastereoselective and enantioselective direct Michael addition of phthalide derivatives to nitroolefins, Computed Properties of 5153-73-1, the publication is Chemical Communications (Cambridge, United Kingdom) (2013), 49(51), 5775-5777, database is CAplus and MEDLINE.

The first asym. Michael addition of 3-substituted phthalides to nitroolefins promoted by amino acid-incorporating multifunctional catalysts has been developed. The reported method led to the synthesis of 3,3-disubstituted phthalide derivatives in high yields, and in a highly diastereoselective and enantioselective manner. Facile synthesis of a chiral bicyclic lactam has also been demonstrated.

Chemical Communications (Cambridge, United Kingdom) 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, Computed Properties of 5153-73-1.

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

Scettri, Arrigo published the artcileMukaiyama-Michael vinylogous additions to nitroalkenes under solvent-free conditions, Application In Synthesis of 5153-73-1, the publication is Central European Journal of Chemistry (2012), 10(1), 47-53, database is CAplus.

The first Mukaiyama-Michael vinylogous reaction of a dioxin-derived silyl ether to nitroalkenes is reported. The conjugate addition is performed in absence of a catalyst under solvent-free conditions. Using as starting materials silyl enol ether (i.e., masked acetoacetate ester) 2,2-dimethyl-4-methylene-6-[(trimethylsilyl)oxy]-4H-1,3-dioxin or 2-[(trimethylsilyl)oxy]furan, the synthesis of the target compounds was achieved with satisfactory efficiency with variously substituted (nitro)alkene derivatives Moreover, an organocatalyst for this Mukaiyama-Michael vinylogous reaction of (trimethylsilyloxy)furan to nitroalkenes was developed [i.e., 4-hydroxydinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin 4-oxide, BINOL hydrogen phosphate]. The reaction is promoted by Bronsted acids under solvent-free conditions, providing products in moderate to good yield with variously substituted nitroalkenes.

Central European Journal of 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, Application In Synthesis of 5153-73-1.

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

Wu, Lulu published the artcileSynthesis of Optically Active 2H-Thiopyrano[2,3-b]quinolines with Three Contiguous Stereocenters via an Organocatalytic Asymmetric Tandem Michael-Henry Reaction, SDS of cas: 5153-73-1, the publication is Advanced Synthesis & Catalysis (2013), 355(6), 1053-1057, database is CAplus.

Optically active 2H-thiopyrano[2,3-b]quinolines with three contiguous stereocenters were synthesized via a chiral bifunctional squaramide-catalyzed tandem thia-Michael-Henry reaction between 2-mercaptoquinoline-3-carboxaldehydes and nitroolefins. The reactions proceeded in high yields to give the title compounds, e.g., I, with high levels of diastereo- and enantioselectivity (up to >99/1 dr and >99% ee, resp.).

Advanced Synthesis & Catalysis 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 C7H8BClO2, SDS of cas: 5153-73-1.

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

Li, Wei published the artcileFacile synthesis of 1,2,4-trisubstituted imidazoles via aerobic copper catalyzed ligand-free [3+2] cycloaddition, Application of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Letters in Organic Chemistry (2014), 11(5), 386-392, database is CAplus.

A simple and facile approach to highly functionalized imidazoles in moderate to good yields was developed. This method involves Cu-catalyzed aerobic [3+2] cycloaddition of amidines with nitro olefins in absence of ligand. Based on observation of the intermediates, possible reaction mechanism different from the same reported approach was proposed.

Letters in 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 C9H6N2O2, Application of (E)-4-(2-Nitrovinyl)benzonitrile.

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

Feng, Huan-Xi published the artcileAn Efficient One-Pot Approach to the Construction of Chiral Nitrogen-Containing Heterocycles under Mild Conditions, Related Products of nitriles-buliding-blocks, the publication is Organic Letters (2015), 17(15), 3794-3797, database is CAplus and MEDLINE.

A new, general, and practical procedure for the highly enantioselective synthesis of functionalized nitrogen-containing heterocycles, e.g., I, has been developed. The simple cyclic hemiaminals were directly catalyzed for the first time as nucleophiles in an enamine-based asym. conjugate addition reaction. The practical approach recycles the catalyst and solvent which make it possible for large-scale and diversity-oriented chem. production

Organic Letters 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, Related Products of nitriles-buliding-blocks.

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

Szczesniak, Piotr published the artcileAsymmetric Synthesis of Cyclic Nitrones via Organocatalytic Michael Addition of Aldehydes to Nitroolefins and Subsequent Reductive Cyclization., HPLC of Formula: 5153-73-1, the publication is ChemistrySelect (2017), 2(9), 2670-2676, database is CAplus.

A direct approach to the synthesis of optically active five-membered cyclic nitrones I [R¹ = H, Me, OBn, etc., R² = H, Et, Ph, etc.; R¹R² = (CH₂)₄, (CH₂)₅; R³ = Ph, 2-naphthyl, 2-thienyl, etc.] was described. The presented strategy was based on organocatalytic Michael addition of aldehydes to trans-nitroalkenes to afford γ-nitroaldehydes II and subsequent reductive cyclization to form 4-substituted-3-(aryl)-3,4-dihydro-2H-pyrrole-1-oxides I. The developed methodol. was successfully applied to the asym. synthesis of Methdilazine.

ChemistrySelect 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 C8H17Br, HPLC of Formula: 5153-73-1.

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

Singh, Shivendra published the artcileRapid access of 2,3,4-trisubstituted-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole derivatives via one-pot three component catalytic reaction, Synthetic Route of 5153-73-1, the publication is Tetrahedron Letters (2012), 53(45), 6087-6090, database is CAplus.

A simple, green, and efficient one-pot three component strategy for the synthesis of 2-aryl-3-nitro-4-hydroxy-2,3,4,9-tetrahydrothiopyrano[2,3-b]indoles I [R = Boc, EtO₂C; R¹ = Ph, 4-MeC₆H₄, 2-ClC₆H₄, etc.; R² = H, Me] has been achieved by the combination of N-protected-2-chloro-3-formylindoles, sodium hydrosulfide with β-nitrostyrenes R¹CH:C(R²)NO₂ at room temperature in ethanol using DABCO as a catalyst. Furthermore, high enantio- and diastereoselectives’ syntheses of title compounds have been achieved for the first time using cupreidine (5 mol %) as catalyst, providing good to excellent yields.

Tetrahedron Letters 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 C10H15ClO3S, Synthetic Route of 5153-73-1.

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

Ambala, Srinivas published the artcileMetal-free, room temperature, acid-K₂S₂O₈ mediated method for the nitration of olefins: an easy approach for the synthesis of nitroolefins, Quality Control of 5153-73-1, the publication is RSC Advances (2019), 9(52), 30428-30431, database is CAplus and MEDLINE.

A simple, room temperature method for the nitration of olefins by using inexpensive sodium nitrite as a source of nitro groups in the presence of trifluoroacetic acid (TFA) and potassium persulfate (K₂S₂O₈) under an open atm. Styrenes and mono-substituted olefins give stereo-selective corresponding E-nitroolefins under optimized conditions, however, 1,1-bisubstituted olefins give a mixture of E- and Z-nitroolefins. The optimized conditions work well with electron-donating, electron-withdrawing, un-substituted and heterocyclic styrenes and mono-substituted olefins and gave corresponding nitroolefins with good to excellent yields.

RSC Advances 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, Quality Control of 5153-73-1.

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