122-47-4

Usage

Uses

Used in Pharmaceutical Synthesis:
3,4-Dimethoxy-beta-methyl-beta-nitrostyrene is utilized as a precursor in the pharmaceutical industry for the synthesis of various organic compounds and pharmaceuticals. Its unique chemical structure allows it to be a key component in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Forensic Science:
In the forensic science field, 3,4-Dimethoxy-beta-methyl-beta-nitrostyrene is employed as a precursor in the production of forensic reference standards for drug analysis. Its role in creating these standards is crucial for accurate identification and quantification of drugs in forensic investigations, thereby aiding in the pursuit of justice and the resolution of legal cases.

InChI:InChI=1/C11H13NO4/c1-8(12(13)14)6-9-4-5-10(15-2)11(7-9)16-3/h4-7H,1-3H3/b8-6-

Upstream product

• 110-86-1 pyridine 
• 509-14-8 tetranitromethane 
• 67-64-1 acetone 
• 93-16-3 Methylisoeugenol 
• 79-24-3 Nitroethane 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 75-04-7 ethylamine 

Downstream Products

• 17254-09-0 3.4-Dimethoxy-1-(2-propionylaminopropyl)-benzol 
• 51920-75-3 N-[2-(3,4-dimethoxy-phenyl)-1-methyl-ethyl]-acetamide 
• 776-99-8 3,4-dimethoxyphenylacetone 
• 87095-02-1 2-nitro-1-(3,4-dimethoxyphenyl)propane 
• 14382-91-3 2-hydroxy-4,5-dimethoxybenzaldehyde 
• 120-26-3 2-(3,4-dimethoxyphenyl)-1-methylethylamine 
• 52987-31-2 N-[2-(3,4-dimethoxyphenyl)-1-methyl-ethyl]formamide 
• 1315060-74-2 2-(3,4-dimethoxyphenyl)-3-methyl-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-1-carbonitrile 
• 1210053-75-0 C₁₅H₁₈N₂O₄ 
• 4156-24-5 3-(3',4'-dimethoxyphenyl)butan-2-one 
• 103266-52-0 1-(3,4-bis-benzyloxy-phenyl)-2-[2-(3,4-dimethoxy-phenyl)-1-methyl-ethylamino]-ethanone 

Relevant academic research and scientific papers

Synthesis, antimicrobial study, and molecular docking simulation of 3,4-dimethoxy-β-nitrostyrene derivatives as candidate ptp1b inhibitor

A derivative series of 3,4-dimethoxy-β-nitrostyrene was synthesized through nitroaldol reaction, including a new compound of 3,4-ethylenedioxy-β-bromo-β-nitrostyrene. The antimicrobial activity effect of 3,4-alkyloxy modification of β-nitrostyrene was investigated. A molecular docking study was also performed to obtain information about their interactions with protein tyrosine phosphatase 1B (PTP1B). The active residues of cysteine-215 and arginine-221 of PTP1B play a key role in signaling pathways that regulate various microorganism cell functions. It also acts as a negative regulator in signaling pathways of insulin that are involved in type 2 diabetes and other metabolic diseases. These derivatives exhibited potential antifungal activity. The studied compounds were also had potential as fragments to be PTP1B inhibitors by interacting with serine-216 and arginine-221 residues, according to their molecular docking. 3,4-Ethylenedioxy-β-methyl-β-nitrostyrene was the most successful potential candidate as a PTP1B inhibitor. However, further research is needed to investigate their potential for medicinal use.

Novel dihydroquinolizinones for the treatment and prophylaxis of hepatitis B virus infection

The invention provides novel compounds having the general formula: wherein R1, R2, R3, R4, R5 and R6 are as described herein, compositions including the compounds and methods of using the compounds.

NOVEL DIHYDROQUINOLIZINONES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION

The invention provides novel compounds having the general formula (I) wherein R1, R2 R3, R4, R5 and R6 are as described herein, compositions including the compounds and methods of using the compounds in the treatment of the hepatitis B virus.

Exploring nitrostyrene as a scaffold for a new class a of monoamine oxidase inhibitors

With the ultimate purpose of finding out the structural features that are relevant for MAO inhibitory activity and selectivity towards MAO-B isoform, a series of compounds encompassing a β-nitrostyrene moiety was designed and the in vitro inhibitory activity was evaluated. In the present work, we report the synthesis and the pharmacological evaluation of a series of functionalized derivatives of β-methyl-β-nitrostyrene with distinct substitution patterns in the phenyl ring, namely hydroxyl, methoxy, benzyloxy and methylenedioxy. All the studied compounds were substituted in meta and para positions of the phenyl ring related to the nitrovinyl side chain. The synthesized compounds were evaluated towards both human MAO isoforms, displaying some of them activities in the low micromolar range. Particularly compound 6 (a methylenedioxy derivative) exhibits high potency and selectivity towards MAO-B.

UV-absorbers for ophthalmic lens materials

UV absorbing monomers that are particularly useful in ophthalmic devices are disclosed.

Oxidative aromatic C-O bond formation: synthesis of 3-functionalized benzo[b]furans by FeCl3-mediated ring closure of a-Aryl ketones

A variety of 3-functionalized benzo[b]furans were achieved by way of a FeCl3-medlated Intramolecular cyclization of electron-rich a-aryl ketones. The alkoxy substituent on the benzene ring In the substrates was essential for an efficient cyclization to occur. This novel method allows the construction of benzo[b]furan rings by joining the O-atom on the side chain to the benzene ring via direct oxidative aromatic C-O bond formation.

1,2,3,4-TETRAHYDROISOQUINOLINE DERIVATIVES, PREPARATIONS THEREOF AND USES THEREOF

Compounds of general formula (I) wherein D, E, R1, R2, R3, R4, R5, R6 and R7 are as defined in the specification, as well as salts, enantiomers thereof and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.

Catalytic N-sulfonyliminium ion-mediated cyclizations to α-vinyl-substituted isoquinolines and β-carbolines and applications in metathesis

Catalytic Sn(OTf)2-induced cyclization of linear, aryl-containing allylic N,O-acetals produced vinyl-substituted tetrahydroisoquinolines and tetrahydro-1H-β-carbolines. The usefulness of the vinyl moiety in the resulting products was demonstrated via the synthesis of various key building blocks for alkaloid structures. The α-vinyl moiety was utilized in a [2,3] sigmatropic rearrangement, in ring-closing metathesis and a cross-metathesis-based synthesis of vincantril, an antianoxia agent, and a synthetic member of the vincamine type natural products.

Synthesis and bovine β3-adrenergic agonistic activities of a novel series of aryloxypropanolamines

We synthesized a novel series of 21 aryloxypropanolamine compounds characterized by N-alkyl, aralkyl, and aryl substituents. The compounds showed potent β3-adrenergic agonistic activities in Chinese hamster ovary cells expressing the bovine β3-adrenoceptors with Kact and Ki values of 4.2 ± 3.0 nM and 459 ± 169 nM respectively, for the ligand with the best compromise between potency and affinity. Structure-activity relationships are discussed.

REDUCTION OF ARYLALKYLAZOMETHINES WITH SODIUM BOROHYDRIDE

The secondary amines R1R2C6H3CH2CH(CH3)NHCHR5CHR6(CH2)nC6H3R3R4 were synthesized by the reduction of the respective azomethines with sodium borohydride.The reaction was conducted in anhydrous methanol in the presence of hydrogen chloride with the azomethine and hydrogen chloride in a molar ratio of 1:1.The yield was 50-90percent.The erythro and threo isomers were isolated, and the data from the IR spectra of the isomers are given.