162705-07-9

Basic information

• Product Name: (Z)-2-Methoxy-5-(3,4,5-Trimethoxystyryl)Aniline
• Synonyms: (Z)-2-Methoxy-5-(3,4,5-Trimethoxystyryl)Aniline;2-Methoxy-5-[(1Z)-2-(3,4,5-TriMethoxyphenyl)Ethenyl]-BenzenaMine;(Z)-1-(3'-amino-4'-methoxyphenyl)-2-(3'',4'',5''-trimethoxyphenyl)ethene;AVE-8063;2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]aniline
• CAS NO: 162705-07-9
• Molecular Formula: C₁₈H₂₁NO₄
• Molecular Weight: 315.36364
• Mol File: 162705-07-9.mol

Chemical Properties

• Boiling Point: 496.377 °C at 760 mmHg
• Flash Point: 271.603 °C
• Appearance: /
• Density: 1.164g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.615
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 4.17±0.10(Predicted)
• CAS DataBase Reference: (Z)-2-Methoxy-5-(3,4,5-Trimethoxystyryl)Aniline(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-2-Methoxy-5-(3,4,5-Trimethoxystyryl)Aniline(162705-07-9)
• EPA Substance Registry System: (Z)-2-Methoxy-5-(3,4,5-Trimethoxystyryl)Aniline(162705-07-9)

Safety Data

• Hazardous Substances Data: 162705-07-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Electronics:
(Z)-2-Methoxy-5-(3,4,5-Trimethoxystyryl)Aniline is used as a building block for the synthesis of organic semiconductors, contributing to the development of advanced electronic devices and materials.
Used in Material Science:
In the field of material science, (Z)-2-Methoxy-5-(3,4,5-Trimethoxystyryl)Aniline is utilized for the synthesis of dyes and other functional materials, enhancing their properties and performance.
Used in Pharmaceutical Research:
(Z)-2-Methoxy-5-(3,4,5-Trimethoxystyryl)Aniline may have potential biological activity, making it a candidate for pharmaceutical research. Further studies are required to explore its potential applications in drug development.

InChI:InChI=1/C18H21NO4/c1-20-15-8-7-12(9-14(15)19)5-6-13-10-16(21-2)18(23-4)17(11-13)22-3/h5-11H,19H2,1-4H3/b6-5-

Upstream product

• 162705-13-7 (Z)-1-(4''-methoxy-3''-nitrophenyl)-2-(3',4',5'-trimethoxyphenyl)ethene 
• 119-10-8 4-methoxy-3-nitrotoluene 
• 61010-34-2 3-nitro-4-methoxybenzyl bromide 
• 313673-23-3 (4-methoxy-3-nitrobenzyl)triphenylphosphonium bromide 
• 61240-20-8 triphenyl-(3,4,5-trimethoxybenzyl)phosphonium bromide 
• 31680-08-7 4-methoxy-3-nitrobenzaldehyde 
• 612542-09-3 (4-methoxy-3-aminobenzyl)triphenylphosphonium bromide hydrochloride salt 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 351003-10-6 3-amino-4-methoxy-benzaldehyde 
• 206649-07-2 (E)-1-(4-methoxy-3-nitrophenyl)-2-(3',4',5'-trimethoxyphenyl)ethene 
• 21852-50-6 3,4,5-trimethoxybenzyl bromide 
• 3840-31-1 (3,4,5-trimethoxyphenyl)methanol 
• 942912-87-0 (E)-2-(3-amino-4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)acrylic acid 
• 869497-70-1 (E)-2-(3'-bromo-4'-methoxyphenyl)-3-(3'',4'',5''-trimethoxyphenyl)acrylic acid 

Downstream Products

• 863116-52-3 2-((2-Hydroxy-ethyl)-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxy-phenyl)-vinyl]-phenyl}-amino)-ethanol 
• 286463-65-8 (S,Z)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((2-methoxy-5-(3,4,5-trimethoxystyryl)phenyl)amino)-3-oxopropyl acetate 
• 1181256-89-2 C₄₉H₇₄N₁₀O₁₅ 
• 1181256-90-5 C₅₂H₇₉N₁₁O₁₆ 
• 1181256-91-6 C₅₄H₈₃N₁₁O₁₆ 
• 1181256-92-7 C₅₂H₇₉N₁₁O₁₆ 
• 1181256-83-6 C₄₉H₇₄N₁₀O₁₅ 
• 1425495-87-9 3'-N-(1-oxyl-2,2,5,5-tetramethyl-3-pyrrolinylcarbonyl)-amido-AVE8063 
• 1425495-88-0 3'-N-(1-oxyl-2,2,5,5-tetramethyl-3-pyrrolidinylcarbonyl)-amido-AVE8063 
• 1425495-89-1 3'-N-(1-oxyl-2,2,6,6-tetramethyl-4-tetrahydropyridinylcarbonyl)-amido-AVE8063 
• 1425495-90-4 3'-N-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinylcarbonyl)-amido-AVE8063 
• 1350766-44-7 3'-N-[N-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinylcarbonyl)-L-glycinyl]-amido-AVE8063 
• 1350766-45-8 3'-N-[N-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinylcarbonyl)-L-alaninyl]-amido-AVE8063 
• 1350766-47-0 3'-N-[N-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinylcarbonyl)-L-valinyl]-amido-AVE8063 

Relevant articles and documents

Design, synthesis and biological evaluation of combretastatin A-4 sulfamate derivatives as potential anti-cancer agents

A series of combretastatin A-4 (CA-4) sulfamate derivatives were synthesized and their structure-activity relationship on tubulin, arylsulfatase and tumor cell antiproliferation inhibition was studied. Among them, compound 16a showed excellent potency as well as CA-4 under the same conditions against six tumor cells including HTC-116, HeLa, HepG2, MGC803, MKN45 and MCF-7 cells, respectively. Molecular docking revealed that several important hydrogen bond interactions were formed between the sulfamate group of 16a and the colchicine binding site of tubulin and steroid sulfatase respectively. Although compound 16a was less active than CA-4 in regard to its in vitro activity as an inhibitor of tubulin polymerization, it was effective as an inhibitor of arylsulfatase. This novel combretastatin A-4 sulfamate derivative has the potential to be developed as a dual inhibitor of tubulin polymerization and arylsulfatase for cancer therapy.

Compositions and Methods for Treatment of Cancer

Resistance of randomly dispersed and oxygen-starved lung tumor cells to chemo- and radiotherapy constitutes the vast majority recurrences and death from lung cancer. We use sickle cells derived from humans with sickle cell anemia to target oxygen-deprived

Prodrug Activation by a Viral Protease: Evaluating Combretastatin Peptide Hybrids to Selectively Target Infected Cells

Infections with flaviviruses such as dengue virus (DENV) are prevalent throughout tropical regions worldwide. Replication of these viruses depends on tubulin, a host cell factor that can be targeted to obtain broad-spectrum antiviral agents. Targeting of tubulin does, however, require specific measures to avoid toxic side-effects. Herein, we report the synthesis and biological evaluation of combretastatin peptide hybrids that incorporate the cleavage site of the DENV protease to allow activation of the tubulin ligand within infected cells. The prodrug candidates have no effect on tubulin polymerization in vitro and are 20-2000-fold less toxic than combretastatin A-4. Several of the prodrug candidates were cleaved by the DENV protease in vitro with similar efficiency as the natural viral substrates. Selected compounds were studied in DENV and Zika virus replication assays and had antiviral activity at subcytotoxic concentrations.

Pt(IV) prodrugs containing microtubule inhibitors displayed potent antitumor activity and ability to overcome cisplatin resistance

It is well-known that cisplatin exhibited a broad spectrum of anticancer activities against many solid tumors, but its severe toxicity and drug resistance have largely limited wider clinical applications. Various strategies have been tried to discover new Pt (II) drugs with at least equal activity as well as low toxicity compared to cisplatin, but the inherent problem remains unsolved. Here we report that Pt (IV) complexes comprising a CA-4 analogue, as dual-targeting Pt (IV) prodrug, were synthesized and evaluated for anti-proliferative activity using MTT assay. Among them, complex 19 displayed most potent activity against the tested cancer cell lines, and simultaneously exhibited better cell selectivity between cancer cells and normal cells than that of cisplatin. Mechanism studies revealed that complex 19 effectively induced cell cycle arrest at the G2/M phase and dramatically disrupted the microtubule organization. Moreover, complex 19 significantly induced cell apoptosis and decreased MMP. Importantly, complex 19 significantly inhibited tumor growth in SK-OV-3 xenograft model in vivo without apparent toxicity.

Preparation and application for 5-fluorouracil substituted carboxylic acid derivative

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Design, Synthesis, and in vitro and in vivo Evaluations of (Z)-3,4,5-Trimethoxystyrylbenzenesulfonamides/sulfonates as Highly Potent Tubulin Polymerization Inhibitors

Newer therapeutics can be developed in drug discovery by adopting the strategy of scaffold hopping of the privileged scaffolds from known bioactive compounds. This strategy has been widely employed in drug-discovery processes. Structure-based docking studies illustrate the basic underlying concepts and reveal that interactions of the sulfonamide group and hydrophobic interactions are crucial. On the basis of this strategy, over 60 synthetic analogues were synthesized and evaluated for their cytotoxicity against the NCI panel of 60 human cancer cell lines; the majority of these compounds exhibited promising cytotoxicity with GI50 values ranging between 18 and 50 nm. Among these compounds, (Z)-N-[2,3-dimethoxy-5-(3,4,5-trimethoxystyryl)phenyl]-4-methoxybenzenesulfonamide (7 a) and (Z)-N-[2-hydroxy-3-methoxy-6-(3,4,5-trimethoxystyryl)phenyl]-4-methoxybenzenesulfonamide (9 a) were found to be potent. Similar results were obtained against three human cancer cell lines with IC50 values ranging between 0.04 and 3.0 μm. Studies aimed at elucidating the mechanism of action of these new analogues revealed that they inhibited the in vitro polymerization of tubulin and disorganized the assembly of microtubules in HeLa and MCF-7cancer cells. Lead compounds 7 a and 9 a displayed notable in vivo antitumor activity in a HeLa tumor xenograft model. Our studies have resulted in the identification of a scaffold that can target tubulin polymerization, which should have significant potential toward the development of new antitumor drugs.

CA-4 antitumor drug, synthesizing method and application thereof

The invention discloses a CA-4 antitumor drug, a synthesizing method and an application thereof. The CA-4 antitumor drug is formed in the manner of introducing the alkoxy or fluorine-containing alkoxy into 4' site of natural product combretastatin and functionally chemical modifying 3' site thereof. The CA-4 antitumor drug disclosed by the invention has higher capacity of restraining tubulin gathering and can be used for anti-tumor therapy.

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Targeting tumor vasculature represents an intriguing therapeutic strategy in the treatment of cancer. In an effort to discover new vascular disrupting agents with improved water solubility and potentially greater bioavailability, various amino acid prodru

Combretastatin A-4 and Derivatives: Potential Fungicides Targeting Fungal Tubulin

Combretastatin A-4, first isolated from the African willow tree Combretum caffrum, is a tubulin polymerization inhibitor in medicine. It was first postulated as a potential fungicide targeting fungal tubulin for plant disease control in this study. Combretastatin A-4 and its derivatives were synthesized and tested against Rhizoctonia solani and Pyricularia oryzae. Several compounds have EC50 values similar to or better than that of isoprothiolane, which is widely used for rice disease control. Structure-activity relationship study indicated the the cis configuration and hydroxyl group in combretastatin A-4 are crucial to the antifungal effect. Molecular modeling indicated the binding sites of combretastatin A-4 and carbendazim on fungal tubulin are totally different. The bioactivity of combretastatin A-4 and its derivatives against carbendazim-resistant strains was demonstrated in this study. The results provide a new approach for fungicide discovery and fungicide resistance management.

Design, synthesis and anti-proliferative effects in tumor cells of new combretastatin A-4 analogs

Abstract A total of 11 novel combretastatin A-4 (CA-4) analogs were designed, synthesized, and evaluated for the anti-proliferative effects in tumor cells. The compounds represent four structural classes: (i) hydrogenated derivatives, (ii) ethoxyl derivatives, (iii) amino derivatives and (iv) pro-drugs. Biological evaluations demonstrate that multiple structural features control the biological potency. Three of the compounds, sit-1, sit-2 and sit-3, have potent anti-proliferative activity against multiple cancer cell lines. Their pro-drugs were synthesized to increase water solubility. Structure-activity relationship study and Surflex-Docking were studied in this paper. These results will be useful for the design of new CA-4 analogs that are structurally related to the SAR study.