Category: 4230-93-7

Sun, Mianmian published the artcileTotal syntheses of benzylisoquinoline alkaloids Neolitacumoine, Mollinedine and Papaverine, Recommanded Product: 1,2-Dimethoxy-4-(2-nitrovinyl)benzene, the publication is Youji Huaxue (2020), 40(1), 149-155, database is CAplus.

A new general synthetic route towards benzylisoquinoline alkaloids was developed. The key step of this route is Cu-catalyzed cascade oxidation-aromatization of 1-benzyl-3,4-dihydroisoquinolines. The three benzylisoquinoline alkaloids such as Neolitacumoine, Mollinedine and Papaverine were synthesized starting from piperonaldehyde and 3,4-dimethoxybenzaldehyde by 8 steps in 42%, 37% and 37% overall yields, resp.

Youji Huaxue published new progress about 4230-93-7. 4230-93-7 belongs to catalysis-chemistry, auxiliary class Alkenyl,Nitro Compound,Benzene,Ether, name is 1,2-Dimethoxy-4-(2-nitrovinyl)benzene, and the molecular formula is C16H24BNO2, Recommanded Product: 1,2-Dimethoxy-4-(2-nitrovinyl)benzene.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Pottie, Eline published the artcileSynthesis and Functional Characterization of 2-(2,5-Dimethoxyphenyl)-N-(2-fluorobenzyl)ethanamine (25H-NBF) Positional Isomers, Quality Control of 4230-93-7, the publication is ACS Chemical Neuroscience (2021), 12(9), 1667-1673, database is CAplus and MEDLINE.

Synthes of positional isomers of 25H-NBF, with two methoxy groups placed on different positions of the Ph group of the phenethylamine moiety. These isomers were then functionally characterized in an in vitro bioassay monitoring the recruitment of ¦Â-arrestin 2 to the 5-HT2AR through luminescent readout via the NanoBiT technol. The obtained results provide insight into the optimal substitution pattern of the Ph group of the phenethylamine moiety of N-benzyl derived substances, a feature so far mostly explored in the phenethylamines underived at the N-position. In the employed bioassay, the most potent substances were 24H-NBF (EC₅₀ value of 158 nM), 26H-NBF (397 nM), and 25H-NBF (448 nM), with 23H-NBF, 35H-NBF, and 34H-NBF yielding ¦ÌM EC50 values. A similar ranking was obtained for the compounds’ efficacy: taking as a reference LSD (lysergic acid diethylamide), 24H-, 26H-, and 25H-NBF had an efficacy of 106-107%, followed by 23H-NBF (96.1%), 34H-NBF (75.2%), and 35H-NBF (58.9%). The stronger activity of 24H-, 25H-, and 26H-NBF emphasizes the important role of the methoxy group at position 2 of the phenethylamine moiety for the in vitro functionality of NBF substances.

ACS Chemical Neuroscience published new progress about 4230-93-7. 4230-93-7 belongs to catalysis-chemistry, auxiliary class Alkenyl,Nitro Compound,Benzene,Ether, name is 1,2-Dimethoxy-4-(2-nitrovinyl)benzene, and the molecular formula is C10H11NO4, Quality Control of 4230-93-7.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Sharma, Pankaj published the artcileEffect of sulfamic acid on 1,3-dipolar cycloaddition reaction: mechanistic studies and synthesis of 4-aryl-NH-1,2,3-triazoles from nitroolefins, Recommanded Product: 1,2-Dimethoxy-4-(2-nitrovinyl)benzene, the publication is Journal of the Brazilian Chemical Society (2017), 28(4), 589-597, database is CAplus.

A facile and new metal-free 1,3-dipolar cycloaddition reaction for the synthesis of 4-aryl-NH-1,2,3-triazoles, e.g., I from nitroolefins, e.g., 3-nitro-2-phenyl-2H-1-benzopyran and NaN₃ employing NH₂SO₃H has been developed. Sulfamic acid proved to be an efficient additive in this transformation by inhibiting the formation of triaryl benzene. Mechanistic aspects and key intermediates associated with this transformation have also been characterized by online monitoring of the reaction using electrospray ionization tandem mass spectrometry method (ESI-MS/MS). The protocol emphasizes broad substrate scope for many functionalities, simple reaction conditions such as stability to open air, less reaction time, easy work-up, eco-friendly and with good to excellent yields.

Journal of the Brazilian Chemical Society published new progress about 4230-93-7. 4230-93-7 belongs to catalysis-chemistry, auxiliary class Alkenyl,Nitro Compound,Benzene,Ether, name is 1,2-Dimethoxy-4-(2-nitrovinyl)benzene, and the molecular formula is C15H12O6, Recommanded Product: 1,2-Dimethoxy-4-(2-nitrovinyl)benzene.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Puerto Galvis, Carlos E. published the artcileRegio- and stereoselective synthesis of spirooxindole 1′-nitro pyrrolizidines with five concurrent stereocenters under aqueous medium and their bioprospection using the zebrafish (Danio rerio) embryo model, Category: catalysis-chemistry, the publication is Organic & Biomolecular Chemistry (2013), 11(42), 7372-7386, database is CAplus and MEDLINE.

A highly regio- and stereoselective method has been developed and expanded for the synthesis of a 20-membered library of spirooxindole 1′-nitro pyrrolizidines, e.g. I, via 1,3-dipolar cycloaddition of azomethine ylides, generated in situ by a decarboxylative route from a common set of diverse isatins and L-proline derivatives, with substituted ¦Â-nitrostyrenes under aqueous medium. Among various reaction conditions, water proved to be necessary for the interaction of the reagents as well as heating the reaction at 90¡ã for one hour, during which time the desired products were obtained in good yields and with excellent regio- and stereoselectivities. We subsequently applied in silico drug discovery computational methods to (i) identify the ADME properties, based on Lipinski’s rule, (ii) screen the toxicol. profile, and (iii) predict the penetration through the blood brain barrier (BBB) of the synthesized compounds Next, the LC₅₀ values of all these spirocyclic oxindoles were determined in zebrafish embryos cultured individually in buffer solutions of each compound and, finally, the phenotypes induced by these mols. in the zebrafish embryos at concentrations below their LC₅₀ were analyzed at 48, 72 and 96 h post fertilization.

Organic & Biomolecular Chemistry published new progress about 4230-93-7. 4230-93-7 belongs to catalysis-chemistry, auxiliary class Alkenyl,Nitro Compound,Benzene,Ether, name is 1,2-Dimethoxy-4-(2-nitrovinyl)benzene, and the molecular formula is C10H11NO4, Category: catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Brand, Yaneth M. published the artcileCombretastatin A-4: the antitubulin agent that inspired the design and synthesis of styrene and spiroisatin hybrids as promising cytotoxic, antifungal and antiviral compounds, COA of Formula: C10H11NO4, the publication is Journal of the Brazilian Chemical Society (2020), 31(5), 999-1010, database is CAplus.

The design of a series of styrene and spiroisatin hybrids was based on the structure of combretastatin A-4 1. This library of 20 compounds were synthesized with the pharmacophoric units: 3,4,5-trimethoxy or/and 4-hydroxy-3-methoxy Ph moities in their structure. Thereby, the libraries of beta-nitrostyrenes 10a-10c, spiroisatin-dihydroquinolines 14a-14c, spiroisatinthiazolidinones 17a-17c and spiroisatin-nitropyrrolizidines 20a-20k were evaluated for their in vitro cytotoxic, anti-proliferative, antifungal and antiviral activities. Biol. results revealed that among these compounds, beta-nitrostyrenes 10a-10c exhibited significant cytotoxicity (HeLa and Jurkat tumor cells) and antifungal (T. mentagrophytes) activities. Moreover, the spiroisatindihydroquinoline 14a and 14c showed promising cytotoxicity (U937 cells). 14a-14c mols. were active against human herpesviruses serotypes 1 and 2 (HHV-1 and HHV-2), but only 14a and 14b were effective against dengue virus serotype 2 (DENV-2). The spiroisatin-nitropyrrolizidine 20c exhibited moderate anti-herpetic activity, while 17c spiroisatin-thiazolidinone derivative also reduced the infection of HHV-1 and DENV-2. Finally, the mol. docking showed that these kind of mols. interact with the subunit a/beta-tubulin.

Journal of the Brazilian Chemical Society published new progress about 4230-93-7. 4230-93-7 belongs to catalysis-chemistry, auxiliary class Alkenyl,Nitro Compound,Benzene,Ether, name is 1,2-Dimethoxy-4-(2-nitrovinyl)benzene, and the molecular formula is C10H11NO4, COA of Formula: C10H11NO4.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Kang, Ki-Tae published the artcileOne-Pot Catalytic Enantioselective Synthesis of Functionalized Tetrahydroquinolines by Aza-Michael/Michael Cascade Reactions of N-Protected 2-Aminophenyl ¦Á,¦Â-Unsaturated Esters with Nitroolefins, Application of 1,2-Dimethoxy-4-(2-nitrovinyl)benzene, the publication is Synthesis (2014), 46(24), 3365-3373, database is CAplus.

A highly enantioselective synthesis of functionalized tetrahydroquinolines with useful biol. properties was developed by asym. organocatalytic aza-Michael/Michael cascade reactions of nitroolefins with N-protected 2-aminophenyl ¦Á,¦Â-unsaturated esters in the presence of a chiral thiourea catalyst. The reaction gave the corresponding highly functionalized tetrahydroquinolines in good yields, excellent diastereoselectivities (>30:1 dr), and high enantioselectivities (¡Ü99% ee).

Synthesis published new progress about 4230-93-7. 4230-93-7 belongs to catalysis-chemistry, auxiliary class Alkenyl,Nitro Compound,Benzene,Ether, name is 1,2-Dimethoxy-4-(2-nitrovinyl)benzene, and the molecular formula is C10H11NO4, Application of 1,2-Dimethoxy-4-(2-nitrovinyl)benzene.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Alsharif, Meshari A. published the artcilePharmacological Activities of Novel Chromene Derivatives as Calcium/Calmodulin Dependent Protein Kinase IV (CAMKIV) Inhibitors, Safety of 1,2-Dimethoxy-4-(2-nitrovinyl)benzene, the publication is ChemistrySelect (2020), 5(2), 498-505, database is CAplus.

A series of 3-nitro-2-phenyl-2H-chromenes I (R = 4-fluorophenyl, 2-nitrophenyl, naphthalen-1-yl, etc.; R¹ = H, 3-OMe, 4-Me; R² = 3-OMe, 4-F, 4-Cl, etc.) has been synthesized, characterized and tested for their inhibition potential and binding affinity with the CAMKIV. Among the synthesized compounds, the IC₅₀ value (50% of ATPase activity) for compounds I (R = 2-nitrophenyl, R¹ = H, R² = 4-F; R = 4-chlorophenyl, R¹ = 4-Me, R² = H) was observed as 12.22 ¡À 1.12¦ÌM and 16.10 ¡À 1.30¦ÌM resp. The fluorescence binding and dot-blot assay further complements inhibitory potential, indicating a better binding affinity. These compounds were tested against human cancerous cells (HepG2) and observed a significant inhibition of cell viability, induced apoptosis and lowered tau-phosphorylation. In cell viability studies, the IC₅₀ values for compounds I (R = 2-nitrophenyl, R¹ = H, R² = 4-F; R = 4-chlorophenyl, R¹ = 4-Me, R² = H) were 18.33 ¡À 1.12 and 26.22 ¡À 1.30¦ÌM resp. These results suggested that the compounds I (R = 2-nitrophenyl, R¹ = H, R² = 4-F; R = 4-chlorophenyl, R¹ = 4-Me, R² = H) are non-toxic to the normal cells and specifically inhibit the proliferation of cancerous cells.

ChemistrySelect published new progress about 4230-93-7. 4230-93-7 belongs to catalysis-chemistry, auxiliary class Alkenyl,Nitro Compound,Benzene,Ether, name is 1,2-Dimethoxy-4-(2-nitrovinyl)benzene, and the molecular formula is C10H11NO4, Safety of 1,2-Dimethoxy-4-(2-nitrovinyl)benzene.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Kim, Shinae published the artcileAsymmetric domino aza-Michael-Michael reaction of o-N-protected aminophenyl ¦Á,¦Â-unsaturated ketones: construction of chiral functionalized tetrahydroquinolines, Name: 1,2-Dimethoxy-4-(2-nitrovinyl)benzene, the publication is Tetrahedron (2014), 70(34), 5114-5121, database is CAplus.

The diastereo- and enantioselective synthesis of 2,3,4-trisubstituted tetrahydroquinolines e. g., I, has been developed through organocatalytic domino aza-Michael-Michael reaction of o-N-tosylaminophenyl ¦Á,¦Â-unsaturated ketones with nitroalkenes. This useful and simple domino process afforded diverse highly functionalized tetrahydroquinolines, some of which are not easily accessible using other methodologies, in good yields and with excellent diastereo- and enantioselectivities (up to >30:1 dr, >99% ee).

Tetrahedron published new progress about 4230-93-7. 4230-93-7 belongs to catalysis-chemistry, auxiliary class Alkenyl,Nitro Compound,Benzene,Ether, name is 1,2-Dimethoxy-4-(2-nitrovinyl)benzene, and the molecular formula is C10H11NO4, Name: 1,2-Dimethoxy-4-(2-nitrovinyl)benzene.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Bhagat, Ujjawal Kumar published the artcileDABCO-mediated aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to cycloalkenones. Regioselective synthesis of disubstituted 1,2,3-triazoles, Computed Properties of 4230-93-7, the publication is Tetrahedron Letters (2017), 58(4), 298-301, database is CAplus.

Aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to 2-cycloalken-1-ones was studied in the presence of DABCO as organic base. The reactions were carried out in acetonitrile at room temperature to provide 2,4-disubstituted 2H-1,2,3-triazoles I [R = H, Me; Ar = C₆H₅, 4-MeC₆H₄, 2-MeO-1-naphthyl, etc.; n = 1] as major adducts and 1,4-disubstituted 1H-1,2,3-triazoles II [n = 0] as minor adducts. Though the reaction times are longer (4-8 days), the two regioisomers were separated by using column chromatog. and the adducts were obtained in very good to excellent combined chem. yields. The electron-rich and electron-poor substituents on aryl moiety of 4-aryl-triazoles could tolerate the reaction conditions to afford the title adducts.

Tetrahedron Letters published new progress about 4230-93-7. 4230-93-7 belongs to catalysis-chemistry, auxiliary class Alkenyl,Nitro Compound,Benzene,Ether, name is 1,2-Dimethoxy-4-(2-nitrovinyl)benzene, and the molecular formula is C10H11NO4, Computed Properties of 4230-93-7.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Xi, Bao-Min published the artcileDrug metabolism-based design, synthesis, and bioactivities of 1-(2,6-dimethylphenoxy)-2-(3,4-dimethoxyphenylethylamino)propane hydrochloride (DDPH) analogs as ¦Á₁-adrenoceptors antagonists, Synthetic Route of 4230-93-7, the publication is Bioorganic & Medicinal Chemistry (2011), 19(2), 783-788, database is CAplus and MEDLINE.

1-(2,6-Dimethylphenoxy)-2-(3,4-dimethoxyphenylethylamino)propane hydrochloride (DDPH) is a potent ¦Á₁-adrenoceptor antagonist that is currently under Phase II clinic trials. However, the fast metabolism has restricted its further use. In this paper, 11 DDPH analogs were designed according to the probable metabolism pathways of DDPH, and featured the structures of halogen, Me, and cyano groups at the 3-, or 4-position of aromatic ring A to block the hydroxylation, and one hydroxyl group at the 3-, or 4-position of aromatic ring B to extend the duration time. These compounds were synthesized in moderate to good yields from the reductive amination of substituted phenoxyacetones with substituted phenylethylamines, and fully characterized with ¹H NMR, IR, and HRMS. Biol. evaluation indicated that most of the compounds exhibited strong blocking and moderate to good antihypertensive activities. It is clear that the compounds having 4-OH/3-OMe on group B exhibited higher blocking activities and longer duration time than their corresponding analogs having 4-OMe/3-OMe (and also 3-OH/4-OMe). Among them, compound 13 having bromo group at the 4-position of ring A and 4-OH/3-OMe on group B, exhibited the highest blocking activity, whereas compound 17 that had a Me group at the 4-position of ring A and a hydroxyl group at the 4-position of ring B, was more active than potent DDPH in terms of both blocking and antihypertensive activities. In addition, the possible correlations between the blocking and antihypertensive activities are also briefly discussed.

Bioorganic & Medicinal Chemistry published new progress about 4230-93-7. 4230-93-7 belongs to catalysis-chemistry, auxiliary class Alkenyl,Nitro Compound,Benzene,Ether, name is 1,2-Dimethoxy-4-(2-nitrovinyl)benzene, and the molecular formula is C20H23N3O2S, Synthetic Route of 4230-93-7.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia