206649-07-2

Basic information

• Product Name: Benzene, 1,2,3-trimethoxy-5-[(1E)-2-(4-methoxy-3-nitrophenyl)ethenyl]-
• CAS NO: 206649-07-2
• Molecular Formula: C18H19NO6
• Molecular Weight: 345.352
• Mol File: 206649-07-2.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: Benzene, 1,2,3-trimethoxy-5-[(1E)-2-(4-methoxy-3-nitrophenyl)ethenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,2,3-trimethoxy-5-[(1E)-2-(4-methoxy-3-nitrophenyl)ethenyl]-(206649-07-2)
• EPA Substance Registry System: Benzene, 1,2,3-trimethoxy-5-[(1E)-2-(4-methoxy-3-nitrophenyl)ethenyl]-(206649-07-2)

Safety Data

• Hazardous Substances Data: 206649-07-2(Hazardous Substances Data)

Upstream product

• 134029-74-6 [(3,4,5-trimethoxyphenyl)methyl]phosphoric acid diethyl ester 
• 31680-08-7 4-methoxy-3-nitrobenzaldehyde 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 3840-31-1 (3,4,5-trimethoxyphenyl)methanol 
• 21852-50-6 3,4,5-trimethoxybenzyl bromide 
• 74-83-9 methyl bromide 
• 3011-34-5 4-hydroxy-3-nitrobenzaldehyde 
• 61240-20-8 triphenyl-(3,4,5-trimethoxybenzyl)phosphonium bromide 
• 108683-61-0 triphenyl(3,4,5-trimethoxybenzyl)phosphonium chloride 
• 213113-18-9 3-methoxy-4-nitrobenzyltriphenylphosphonium bromide 
• 61010-34-2 3-nitro-4-methoxybenzyl bromide 
• 119-10-8 4-methoxy-3-nitrotoluene 
• 313673-23-3 (4-methoxy-3-nitrobenzyl)triphenylphosphonium bromide 

Downstream Products

• 213113-12-3 ((E)-1-(3'-amino-4'-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene) 
• 1185996-41-1 C₁₈H₂₁NO₄*ClH 
• 482288-61-9 2-methoxy-5-(3,4,5-trimethoxyphenethyl)benzenamine 
• 482288-62-0 2-(4-methoxy-3-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)ethane 
• 162705-07-9 3-amino-deoxycombretastatin A₄ 
• 206649-13-0 5-(4-Methoxy-3-nitro-phenyl)-4-(3,4,5-trimethoxy-phenyl)-thiazol-2-ylamine 
• 206649-11-8 2-Bromo-2-(4-methoxy-3-nitro-phenyl)-1-(3,4,5-trimethoxy-phenyl)-ethanone 
• 162705-13-7 (Z)-1-(4''-methoxy-3''-nitrophenyl)-2-(3',4',5'-trimethoxyphenyl)ethene 
• 206649-09-4 2-Bromo-2-(4-methoxy-3-nitro-phenyl)-1-(3,4,5-trimethoxy-phenyl)-ethanol 

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.

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 and Synthesis of Aminostilbene-Arylpropenones as Tubulin Polymerization Inhibitors

A series of aminostilbene - arylpropenones were designed and synthesized by Michael addition and were investigated for their cytotoxic activity against various human cancer cell lines. Some of the investigated compounds exhibited significant antiproliferative activity against a panel of 60 human cancer cell lines of the US National Cancer Institute, with 50% growth inhibition (GI50) values in the range from 50 value of 50) values ranging from 0.011 to 8.56μM. A cell cycle assay revealed that these compounds arrested the G2/M phase of the cell cycle. Two compounds exhibited strong inhibitory effects on tubulin assembly with IC50 values of 0.71 and 0.79μM. Moreover, dot-blot analysis of cyclinB1 demonstrated that some of the congeners strongly induced cyclinB1 protein levels. Molecular docking studies indicated that these compounds occupy the colchicine binding site of tubulin.