4230-93-7

Usage

Uses

Used in Organic Synthesis:
3,4-Dimethoxy-beta-nitrostyrene is used as a key intermediate in various organic synthesis processes. Its unique structure and reactivity make it a valuable compound for the creation of complex organic molecules.
Used in Pharmaceutical Industry:
3,4-Dimethoxy-beta-nitrostyrene is used as a building block for the synthesis of pharmaceutical compounds. Its versatility in organic synthesis allows for the development of new drug candidates with potential therapeutic applications.
Used in Chemical Research:
3,4-Dimethoxy-beta-nitrostyrene is used as a research tool in the study of chemical reactions and mechanisms. Its reactivity and structural features provide insights into the behavior of nitroalkenes and their potential applications in various chemical processes.
Used in Material Science:
3,4-Dimethoxy-beta-nitrostyrene is used as a precursor in the development of new materials with unique properties. Its incorporation into polymers or other materials can lead to the creation of novel materials with enhanced performance characteristics.

InChI:InChI=1/C10H11NO4/c1-14-9-4-3-8(5-6-11(12)13)7-10(9)15-2/h3-7H,1-2H3/b6-5+

Upstream product

• 75-52-5 nitromethane 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 631-61-8 ammonium acetate 
• 91-16-7 1,2-dimethoxybenzene 
• 120-80-9 benzene-1,2-diol 
• 121-33-5 vanillin 
• 6380-23-0 3,4-dimethoxystyrene 
• 2316-26-9 3,4-dimethoxycinnamic acid 
• 20583-78-2 ethyl (E)-3,4-dimethoxycinnamate 
• 39220-86-5 2-nitro-1-(3,4-dimethoxyphenyl)ethanol 
• 14737-89-4 3,4-dimethoxy-trans-cinnamic acid 

Downstream Products

• 858784-62-0 N-[1-(3,4-dimethoxy-phenyl)-2-nitro-ethyl]-N'-phenyl-hydrazine 
• 56493-39-1 [2-(3,4-Dimethoxy-phenyl)-3-nitro-propyl]-methyl-amine 
• 56580-12-2 6-Hydroxy-4-(3,4-dimethoxyphenyl)-5-nitrobicyclo<4.3.0>nonan-2-on 
• 56580-13-3 6-Hydroxy-4-(3,4-dimethoxyphenyl)-5-nitrobicyclo<4.4.0>decan-2-on 
• 54210-65-0 2-(3,4-Dimethoxyphenyl)-1-hydroxy-2-nitro-5-oxo-1-cyclohexanessigsaeure-methylester 
• 54210-64-9 2-(3,4-Dimethoxyphenyl)-4-hydroxy-4-methyl-3-nitro-6-oxo-1-cyclohexancarbonsaeure-methylester 
• 55446-63-4 4-(1,2-dibromo-2-nitro-ethyl)-1,2-dimethoxy-benzene 
• 136289-41-3 1-nitro-2-(3,4-dimethoxyphenyl)-3-(phenylsulphonyl)propene 
• 128530-97-2 1-[(1S,4R,5S,6S)-5-(3,4-Dimethoxy-phenyl)-3-methyl-4-(3-methyl-but-2-enyl)-6-nitro-cyclohex-2-enyl]-piperidine 
• 70360-83-7 1,2-dimethoxy-4-(2-nitroethyl)benzene 
• 46729-91-3 1-(3,4-dimethoxyphenyl)-2-nitroethan-1-one 
• 79238-81-6 4-[(3,4-dimethoxyphenyl)ethynyl]-1,2-dimethoxybenzene 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 125103-87-9 c-2,t-4-bis(3,4-dimethoxyphenyl)-r-1,t-3-dinitrocyclobutane 

Relevant academic research and scientific papers

Microwave-assisted rapid synthesis of spirooxindole-pyrrolizidine analogues and their activity as anti-amyloidogenic agents

A library of Sox-pyrrolizidines was rapidly prepared by microwave-assisted, one-pot, three-component, 1,3-dipolar cycloaddition of azomethine ylides from l-proline and isatin, with various β-nitrostyrenes. Nitro-Sox compounds, 4b, 4d and 4e inhibit HEWL amyloid fibril formation by ThT studies with percentages of fluorescence intensity of 55.4, 42.9 and 40.3%, respectively. Further studies with MTT assay, Raman spectroscopy, TEM and molecular docking supported these promising candidates for activity against amyloid misfolding, a phenomenon leading to Alzheimer's disease pathology.

A green metal-free "one-pot" microwave assisted synthesis of 1,4-dihydrochromene triazoles

The synthesis of several 4-aryl-1,4-dihydrochromene-triazoles was achieved via a metal-free "one-pot"procedure using PEG400 as the sole solvent in an eco-friendly process. Using microwave irradiation, the triazole derivatives were obtained in good yields and short reaction times starting from readily accessible building blocks.

Structure–activity relationship and biological evaluation of berberine derivatives as PCSK9 down-regulating agents

Proprotein convertase subtilisin/kexin type 9 (PCSK9) is a secreted protein and its deficiency markedly enhanced the survival rate of patient with cardiovascular diseases (CVDs). Forty berberine (BBR) derivatives were synthesized and evaluated for their activities on down-regulating the transcription of PCSK9 in HepG2 cells, taking BBR as the lead. Structure–activity relationship (SAR) analysis revealed that 2,3-dimethoxy moiety might be beneficial for activity. Among them, 9k displayed the most potent activity with IC50 value of 9.5 ± 0.5 μM, better than that of BBR. Also, it significantly decreased PCSK9 protein level at cellular level, as well as in the liver and serum of mice in vivo. Furthermore, 9k markedly increased LDLR expression and LDL-C clearance via down-regulating PCSK9 protein. The mechanism of action of 9k is targeting HNF1α and/or Sp1 cluster modulation upstream of PCSK9, a different one from BBR. Therefore, 9k might have the potential to be a novel PCSK9 transcriptional inhibitor for the treatment of atherosclerosis, worthy for further investigation.

Synthesis and Functional Characterization of 2-(2,5-Dimethoxyphenyl)-N-(2-fluorobenzyl)ethanamine (25H-NBF) Positional Isomers

Serotonergic psychedelics, substances exerting their pharmacological action through activation of the serotonin 2A receptor (5-HT2AR), have continuously comprised a substantial fraction of the over 1000 reported New Psychoactive Substances (NPS) so far. Within this category, N-benzyl derived phenethylamines, such as NBOMes and NBFs, have shown to be of particular relevance. As these substances remain incompletely characterized, this study aimed at synthesizing positional isomers of 25H-NBF, with two methoxy groups placed on different positions of the phenyl group of the phenethylamine moiety. These isomers were then functionally characterized in an in vitro bioassay monitoring the recruitment of β-Arrestin 2 to the 5-HT2AR through luminescent readout via the NanoBiT technology. The obtained results provide insight into the optimal substitution pattern of the phenyl 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 μM 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.

A covalent p97/VCP ATPase inhibitor can overcome resistance to CB-5083 and NMS-873 in colorectal cancer cells

Small-molecule inhibitors of p97 are useful tools to study p97 function. Human p97 is an important AAA ATPase due to its diverse cellular functions and implication in mediating the turnover of proteins involved in tumorigenesis and virus infections. Multi

Dipolar HCP materials as alternatives to DMF solvent for azide-based synthesis

Hypercrosslinked polymers HCP-DMF and HCP-DMF-SO3H containing abundant and flexible DMF moieties were designed and synthesized. Benefitting from the solvation microenvironment provided by the pseudo-DMF moities, the polar HCPs manifested outstanding performances in the conversions of NaN3 to benzylic azides and 1,2,3-triazoles in EtOH (95%), respectively, avoiding the use of risky DMF and improving the separation processes of the products.

DIHYDRO-SPIRO[INDOLINE-3:1'-ISOQUINOLIN]-2-ONES AND THEIR ANALOGUES AND DERIVATIVES AND METHODS OF TREATING CANCER AND OTHER DISEASES

The present invention is directed to various 3',4'-dihydro-2'H-spiro[indoline-3:1'-isoquinolin]-2-one compounds and methods for treating disease states and/or conditions which are mediated through sphingosine-1-phosphate receptor(s). The present invention

Preparation method of dopamine hydrochloride

The invention provides a method which comprises the following steps: taking veratraldehyde as a starting raw material, firstly carrying out condensation reaction with nitromethane to generate 3, 4-dimethoxy-beta-nitrostyrolene, carrying out catalytic reduction to obtain 3, 4-dimethoxy phenylethylamine, carrying out reaction with hydrobromic acid to remove methoxy, and finally salifying with hydrochloric acid to obtain dopamine hydrochloride. The preparation method has the advantages of cheap and easily available initial raw materials, simple process, no high-temperature and high-pressure steps, low cost, high purity and high yield, and is suitable for industrial production.

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.

Combretastatin A-4: The Antitubulin Agent that Inspired the Design and Synthesis of Styrene and Spiroisatin Hybrids as Promising Cytotoxic, Antifungal and Antiviral Compounds

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 phenyl moities in their structure. Thereby, the libraries of β-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. Biological results revealed that among these compounds, β-nitrostyrenes 10a-10c exhibited significant cytotoxicity (HeLa and Jurkat tumor cells) and antifungal (T. mentagrophytes) activities. Moreover, the spiroisatin-dihydroquinoline 14a and 14c showed promising cytotoxicity (U937 cells). 14a-14c molecules 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 molecular docking showed that these kind of molecules interact with the subunit α/β-tubulin.