6316-70-7

Usage

Uses

Used in Scientific Research:
1-(3,4,5-Trimethoxyphenyl)-2-nitroethene is used as a research chemical for [application reason] in the field of organic chemistry. It is valuable for studying the properties and reactions of nitroethene derivatives and their potential applications in various chemical processes.
Used in Organic Chemistry:
1-(3,4,5-Trimethoxyphenyl)-2-nitroethene is used as a chemical intermediate for [application reason] in the synthesis of more complex organic molecules. Its unique structure with a nitro group and methoxy-substituted phenyl ring makes it a candidate for further functionalization and exploration in organic synthesis.

InChI:InChI=1/C11H13NO5/c1-15-9-6-8(4-5-12(13)14)7-10(16-2)11(9)17-3/h4-7H,1-3H3/b5-4+

Upstream product

• 75-52-5 nitromethane 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 64-17-5 ethanol 
• 67-56-1 methanol 
• 440667-51-6 3-(3,4,5-trimethoxyphenyl)dihydropyrrolo[1,2-c]oxazole-1,5-dione 
• 34346-90-2 3-(3',4',5'-trimethoxyphenyl)-prop-2-en-1-al 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 14326-13-7 1-(1-hydroxy-2-nitroethyl)-3,4,5-trimethoxybenzene 

Downstream Products

• 128869-27-2 2-(allylthio)-1-nitro-2-(3,4,5-trimethoxyphenyl)ethane 
• 141944-24-3 N,N-dimethyl-6-nitro-5-(3,4,5-trimethoxyphenyl)-2-cyclohexen-1-amine 
• 132557-22-3 (1S,2R,3R,10bS)-8,9-Dimethoxy-1-nitro-2-(3,4,5-trimethoxy-phenyl)-1,2,3,5,6,10b-hexahydro-pyrrolo[2,1-a]isoquinoline-3-carboxylic acid methyl ester 
• 63909-39-7 1,2,3-trimethoxy-5-(2-nitroethyl)benzene 
• 33877-70-2 ethyl 4-nitro-3-(3,4,5-trimethoxyphenyl)butanoate 
• 133116-46-8 3-(3,4,5-Trimethoxy-phenyl)-furo[3,2-c]chromen-4-one 
• 5990-01-2 N-(3,4,5-trimethoxy-phenethyl)-benzamide 
• 6308-78-7 trimethyl-(3,4,5-trimethoxy-phenethyl)-ammonium; iodide 
• 1190132-25-2 (E)-ethyl 2-hydroxy-4-(3,4,5-trimethoxyphenyl)-3-nitrobut-3-enoate 
• 1182279-91-9 (R)-2-(2-nitro-1-(3,4,5-trimethoxyphenyl)ethyl)-1H-pyrrole 
• 1215288-65-5 1-acetylamino-2,2-dibromo-2-nitro-1-(3,4,5-trimethoxyphenyl)ethane 
• 1227148-21-1 (4S)-5-nitro-4-(3,4,5-trimethoxyphenyl)-pentan-2-one 
• 1314296-86-0 3-(phenylsulfonyl)-4-(3,4,5-trimethoxyphenyl)-1H-pyrazole 
• 1323976-08-4 phenyl(5-phenyl-3-(3,4,5-trimethoxyphenyl)-1H-pyrrol-2-yl)methanone 

Relevant academic research and scientific papers

Synthesis, binding, and functional properties of tetrahydroisoquinolino-2-alkyl phenones as selective σ2R/TMEM97 ligands

Sigma-2 receptor (σ2R/TMEM97) has been implicated to play important roles in multiple cellular dysfunctions, such as cell neoplastic proliferation, neuro-inflammation, neurodegeneration, etc. Selective σ2 ligands are believed to be promising pharmacological tools to regulate or diagnose various disorders. As an ongoing effort of discovery of new and selective σ2 ligands, we have synthesized a series of tetrahydroisoquinolino-2-alkyl phenone analogs and identified that 10 of them have moderate to potent affinity and selectivity for σ2R/TMEM97. Especially, 4 analogs showed Ki values ranging from 0.38 to 5.1 nM for σ2R/TMEM97 with no or low affinity for sigma-1 receptor (σ1R). Functional assays indicated that these 4 most potent analogs had no effects on intracellular calcium concentration and were classified as putative σ2R/TMEM97 antagonists according to current understanding. The σ2R/TMEM97 has been suggested to play important roles in the central nervous system. Based on published pharmacological and clinical results from several regarded σ2R/TMEM97 antagonists, these analogs may potentially be useful for the treatment of various neurodegenerative diseases.

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.

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.

Facile Synthesis of 1,3,5-Triarylbenzenes and 4-Aryl-NH-1,2,3-Triazoles Using Mesoporous Pd-MCM-41 as Reusable Catalyst

We report mesoporous nano-Pd-MCM-41 catalyzed rapid and efficient synthesis of 1,3,5-triarylbenzenes via de-nitrative cyclotrimerization of β-nitrostyrenes. All the reactions were very fast and high yielding. The Pd-MCM-41 was also very effective in catalyzing de-nitrative [3+2] cycloaddition of β-nitrostyrenes with TMSN3 to synthesize 4-aryl-NH-1,2,3-triazoles. The catalyst was reused at least up to eight times with minimum loss of catalytic activity.

Design, synthesis and evaluation of thiourea derivatives as antimicrobial and antiviral agents

Background: The development of drug-resistant by bacteria appears rapidly and thus making the effectiveness of antibiotics severely limited. Methods: A series of thiourea derivatives was synthesized, characterized and evaluated for their in vitro antibacterial, antifungal and antiviral activities. Results: Structures of the newly synthesized compounds were confirmed by elemental and spectral analysis. The biological results showed that some of the target compounds displayed comparable antimicrobial and antiviral activities with reference drugs. Structure-activity relationship studies revealed that the ortho-chloro or fluoro substituted phenyl at Ar1 and substituted pyridinyl at Ar2 positions of the thiourea nucleus are essential for their in vitro antimicrobial and anti-HIV activity. In particular, compounds 8 and 10 showed better activity against the tested bacteria, fungi and viral strains than other synthesized PET derivatives reported in the present study. Conclusion: These results provide an encouraging lead that could be used for the development of new potent antiviral and antimicrobial agents.

Synthesis of Benzo[4,5]imidazo[2,1-b]thiazole by Copper(II)-Catalyzed Thioamination of Nitroalkene with 1H-Benzo[d]imidazole-2-thiol

A Copper(II)-catalyzed thioamination of β-nitroalkene with 1H-benzo[d]imidazole-2-thiol has been developed for the synthesis of benzo[4,5]imidazo[2,1-b]thiazole derivatives. A variety of N-fused benzoimidazothiazole derivatives are obtained in high yields through successive C?N and C?S bond formations. This protocol is also applicable to β-substituted β-nitroalkenes to afford 2,3-disubstituted benzoimidazothiazoles. (Figure presented.).

Method for synthesizing nitroolefin compound

The invention relates to a method for synthesizing an organic compound. The method is used for solving the problem of current synthesis of nitroolefin compounds that reaction byproducts are numerous,raw materials are expensive, and some methods are relatively troublesome in aftertreatment. The invention provides a method for preparing a nitroolefin compound. The nitroolefin compound is prepared through subjecting a cinnamyl aldehyde compound, which serves as a starting material, to a reaction with a nitrate and a solvent for 1 to 24 hours at the temperature of 25 DEG C to 150 DEG C. A methodfor direct nitration by using a cheap nitrate is achieved. The method is a new route for synthesizing the nitroolefin compound.

ZrCl4-mediated synthesis of 1,2,3-triazoles from vinyl nitrates and their biological evaluation

A ZrCl4-mediated simple method for the conversion of vinyl nitrates to 1,2,3-triazoles in excellent yields is developed. The obtained new triazoles were evaluated for their antimicrobial activity.

Iodine catalyzed one-pot synthesis of highly substituted N-methyl pyrroles via [3 + 2] annulation and their in vitro evaluation as antibacterial agents

A new class of highly substituted pyrroles have been synthesized via a simple, fast, and efficient method using environmentally friendly iodine catalyzed [3 + 2] annulation. N-Methyl-N-[(E)-1-(methylsulfanyl)-2-nitro-1-ethenyl]amine (NMSM) 1 and β-nitrostyrenes 3 underwent cycloaddition to afford the desired products 4 in excellent yields under solvent and metal free conditions. All the pyrrole derivatives were evaluated for their in vitro anti-bacterial activity. Among the synthesized pyrrole derivatives, 4b, 4c, 4e, 4g, 4i, 4j, 4l, 4m and 4n displayed good inhibitory properties against a panel of Gram positive and negative infectious pathogens.

Synthesis, in vitro cytotoxicity and apoptosis inducing study of 2-aryl-3-nitro-2 H -chromene derivatives as potent anti-breast cancer agents

A series of 2-aryl-3-nitro-2H-chromenes 4a-u were designed as hybrid analogs of flavanone, β-nitrostyrene and nitrovinylstilbene scaffolds. They were synthesized from the reaction of appropriate β-nitrostyrenes and salicylaldehydes in good yields. In vitro cytotoxic activities of compounds 4a-u were tested against breast cancer cell lines including MCF-7, T-47D and MDA-MB-231. Most compounds exhibited good cytotoxic activity against selected cell lines, being more potent than standard drug etoposide. Representatively, 8-methoxy-3-nitro-2-(4-chlorophenyl)-2H-chromene (4l) with IC50 Combining double low line 0.2 μ4M against MCF-7 cells, was 36-times more potent than etoposide. Apoptosis as a mechanism of cell death for selected compounds 4h and 4l was confirmed morphologically by acridine orange/ethidium bromide double staining and TUNEL analysis, as well as caspase-3 activation assay.