39816-35-8

Usage

Uses

Used in Organic Synthesis:
1-(3-Hydroxy-4-methoxyphenyl)-2-nitroethene is used as a key intermediate in organic synthesis for the production of various organic compounds. Its unique structure and reactivity allow for the formation of a wide range of chemical products, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Chemical Reactions as a Reagent:
In the realm of chemical reactions, 1-(3-Hydroxy-4-methoxyphenyl)-2-nitroethene serves as a versatile reagent. Its ability to participate in various types of reactions, such as addition, substitution, and rearrangement, makes it a useful tool for chemists in the development of new synthetic routes and methodologies.
Used in Pharmaceutical Industry:
1-(3-Hydroxy-4-methoxyphenyl)-2-nitroethene is used as a starting material or a functional group in the design and synthesis of pharmaceutical compounds. Its presence in a molecule can impart specific biological activities, such as anti-inflammatory, analgesic, or antimicrobial properties, depending on the context of the molecule's structure.
Used in Materials Science:
In the field of materials science, 1-(3-Hydroxy-4-methoxyphenyl)-2-nitroethene has potential applications in the development of new materials with unique properties. Its incorporation into polymers, for example, can lead to materials with enhanced thermal stability, mechanical strength, or other desirable characteristics.
Overall, 1-(3-Hydroxy-4-methoxyphenyl)-2-nitroethene is a multifaceted compound with a broad spectrum of applications in various industries, including organic synthesis, pharmaceuticals, and materials science, owing to its distinctive structure and chemical reactivity.

InChI:InChI=1/C9H9NO4/c1-14-9-3-2-7(6-8(9)11)4-5-10(12)13/h2-6,11H,1H3/b5-4+

Upstream product

• 621-59-0 isovanillin 
• 75-52-5 nitromethane 
• 74-89-5 methylamine 
• 63909-29-5 (E)-2-(benzyloxy)-1-methoxy-4-(2-nitrovinyl)benzene 

Downstream Products

• 3213-30-7 5-(2-amino-ethyl)-2-methoxy-phenol 
• 645-33-0 3-hydroxy-4-methoxy-β-phenethylamine hydrochloride 
• 101293-33-8 7-methoxy-1-phenyl-1,2,3,4-tetrahydro-isoquinolin-6-ol; hydrochloride 
• 18034-35-0 1-(3,4-dimethoxy-phenyl)-7-methoxy-1,2,3,4-tetrahydro-isoquinolin-6-ol; hydrochloride 
• 75491-93-9 dehydrodiscretine 
• 322474-09-9 2-(3-hydroxy-4-methoxyphenyl)-1-nitroethane 
• 38411-82-4 2-(2-amino-ethyl)-5-methoxy-hydroquinone 
• 39816-38-1 N₂-(4-methoxy-3-hydroxyphenyl)ethylformamide 
• 1199-18-4 6-Hydroxydopamin 
• 39816-43-8 (2,5-dihydroxy-4-methoxy-phenethyl)-carbamic acid benzyl ester 
• 39816-39-2 [2-(4-methoxy-3,6-dioxo-cyclohexa-1,4-dienyl)-ethyl]-carbamic acid benzyl ester 
• 39816-36-9 [2-(3-Hydroxy-4-methoxy-phenyl)-ethyl]-carbamic acid benzyl ester 
• 39816-44-9 N-(2,5-Dihydroxy-4-methoxyphenetyl)-acetamid 
• 39816-40-5 2-(2-Acetamidoethyl)-5-methoxy-p-benzochinon 

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.

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, antiproliferative and pro-apoptotic effects of nitrostyrenes and related compounds in Burkitt’s lymphoma

Background: Cancers of the lymphatic cells (lymphomas) account for approximately 12% of malignant diseases worldwide. The nitrostyrene scaffold is identified as a lead target structure for the development of particularly effective compounds targeting Burkitt’s lymphoma (BL). Objectives: The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt’s lymphoma (BL). Methods: A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions. Single crystal X-Ray analysis confirmed the E configuration for six examples of these novel structures. A number of nitrostyrene-related compounds were also investigated including 1,3-bis(aryl)-2-nitropropenes together with heterocyclic scaffolds containing the nitrovinyl pharmacophore such as 3-nitro-2-phenyl-2H-chromenes. The antiproliferative activities of the compounds were evaluated using the BL cell lines EBV- MUTU-1 and EBV+ DG-75 (chemoresistant) to establish preliminary structure-activity relationships. Results: Lead compounds with optimized nitrostyrene scaffolds and 3-nitro-2-phenyl-2Hchromene structures were successfully established with typical IC50 values of 0.45 μM and 0.47 μM in MUTU-1 cells and 1.41 μM and 1.92 μM, respectively, in DG-75 cells. The mechanism of cell death was identified as apoptotic and the lead compound was found to elicit comparable apoptotic effects to Taxol in Burkitt’s lymphoma cell lines MUTU-1 and DG-75. Conclusion: This class of pharmaceutically active compounds with potential for the treatment of Burkitt’s lymphoma suggest a potential role for nitrostyrene based agents in chemotherapy.

In vitro and in vivo biological evaluation of new 4,5-disubstituted 1,2,3-triazoles as cis-constrained analogs of combretastatin A4

To find new and better antivascular agents for cancer therapy, a series of combretastatin A4 (CA4) analogs were prepared from 1,3-diaryl-2-nitroprop-1-enes (6-12) obtained in a two-step synthesis from appropriate arylaldehydes and 2-aryl-1-nitroethanes (4 or 5). Treatment of these 1,3-diaryl-2-nitroprop-1-enes 6-12 by sodium azide in DMSO yielded the targeted compounds. The synthesized 1,2,3-triazoles disubstituted in 4- and 5-positions by one benzyl group and one aryl nucleus have also been tested for biological activities involved in antivascular action. It was found that several new compounds exhibited interesting biological activities in the nanomolar or low micromolar range, in terms of rounding up of endothelial cells, inhibition of tubulin polymerization, and cytotoxicity on B16 melanoma cancer cells. In silico docking studies of 11 and 19 within the active site of tubulin were also carried out in order to rationalize the inhibitory properties of these compounds and further understand their inhibition mechanism. In vivo evaluation of compounds 11 and 19 in mice bearing colon 26 carcinoma indicated modest anticancer activity.

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.

Drug metabolism-based design, synthesis, and bioactivities of 1-(2,6-dimethylphenoxy)-2-(3,4-dimethoxyphenylethylamino)propane hydrochloride (DDPH) analogs as α1-adrenoceptors antagonists

1-(2,6-dimethylphenoxy)-2-(3,4-dimethoxyphenylethylamino)propane hydrochloride (DDPH) is a potent α1-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, methyl, 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. Biological 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 methyl 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.

The synthesis and biologic evaluation of anti-platelet and cytotoxic β-nitrostyrenes

Our previous studies demonstrated that two cytotoxic β-nitrostyrene derivatives, 3,4-methylenedioxy-β-nitrostyrene (MNS) and 4-O-benzoyl-3-methoxy-β-nitrostyrene (BMNS) exhibit potent anti-platelet activities. In this study, a series of β-nitrostyrenes we

E-Combretastatin and E-resveratrol structural modifications: Antimicrobial and cancer cell growth inhibitory β-E-nitrostyrenes

As part of a broad-based SAR investigation of E-resveratrol (strong sirtuin activator and antineoplastic) and the anticancer vascular-targeting combretastatin-type stilbenes, a series of twenty-three β-E-nitrostyrenes was synthesized in order to evaluate potential antineoplastic, antitubulin, and antimicrobial activities. The β-E-nitrostyrenes evaluated ranged from monosubstituted phenols to trimethoxy and 3-methoxy-4,5-methylenedioxy derivatives. Two of the β-nitrostyrenes were synthesized as water-soluble sodium phosphate derivatives (4t, 4v). All except four (4r, 4s, 4t, 4u) of the series significantly inhibited a minipanel of human cancer cell lines. All but eight led to an IC50 of 10 μM for inhibition of tubulin polymerization, and all except three (4l, 4t, 4v) displayed antimicrobial activity.

β-Nitrostyrene derivatives as potential antibacterial agents: A structure-property-activity relationship study

A multidisciplinary project was developed, combining the synthesis of a series of β-nitrostyrene derivatives and the determination of their physicochemical parameters (redox potentials, partition coefficients), to the evaluation of the corresponding antibacterial activity. A complete conformational analysis was also performed, in order to get relevant structural information. Subsequently, a structure-property-activity (SPAR) approach was applied, through linear regression analysis, aiming at obtaining a putative correlation between the physicochemical parameters of the compounds investigated and their antibacterial activity (both against standard strains and clinical isolates). The β-nitrostyrene compounds displayed a lower activity towards all the tested bacteria relative to the β-methyl-β-nitrostyrene analogues. This was observed particularly for the 3-hydroxy-4-methoxy-β-methyl-β-nitrostyrene (IVb) against the Gram-positive bacteria (Staphylococcus aureus, Enterococcus faecalis and Enterococcus faecium). The SPAR results revealed the existence of a clear correlation between the redox potentials and the antibacterial activity of the series of β-nitrostyrene derivatives under study.

Solid-supported acids for debenzylation of aryl benzyl ethers

Solid-supported acids have been investigated for aromatic debenzylation reactions. Stoichiometric amounts of solid-supported acids in refluxing toluene with or without 4 equiv of methanol effectively provided the desired aromatic debenzylation products of various systems in moderate to excellent yields (up to 98%).