95041-90-0

Basic information

• Product Name: PHENOL, 2-METHOXY-5-[2-(3,4,5-TRIMETHOXYPHENYL)ETHYL]-
• Synonyms: PHENOL, 2-METHOXY-5-[2-(3,4,5-TRIMETHOXYPHENYL)ETHYL]-;3'-Hydroxy-3,4,4',5-tetraMethoxybibenzyl
• CAS NO: 95041-90-0
• Molecular Formula: C₁₈H₂₂O₅
• Molecular Weight: 318.36
• EINECS: 1312995-182-4
• Mol File: 95041-90-0.mol

Chemical Properties

• Boiling Point: 439.1°Cat760mmHg
• Flash Point: 219.4°C
• Appearance: /
• Density: 1.147
• Vapor Pressure: 2.54E-08mmHg at 25°C
• Refractive Index: 1.553
• Storage Temp.: 2-8°C
• PKA: 9.99±0.10(Predicted)
• CAS DataBase Reference: PHENOL, 2-METHOXY-5-[2-(3,4,5-TRIMETHOXYPHENYL)ETHYL]-(CAS DataBase Reference)
• NIST Chemistry Reference: PHENOL, 2-METHOXY-5-[2-(3,4,5-TRIMETHOXYPHENYL)ETHYL]-(95041-90-0)
• EPA Substance Registry System: PHENOL, 2-METHOXY-5-[2-(3,4,5-TRIMETHOXYPHENYL)ETHYL]-(95041-90-0)

Safety Data

• Hazardous Substances Data: 95041-90-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
PHENOL, 2-METHOXY-5-[2-(3,4,5-TRIMETHOXYPHENYL)ETHYL]is used as a cytotoxic compound for its ability to strongly inhibit tubulin polymerization in cell mitosis. This property makes it a promising anticancer agent, as it can potentially disrupt the cell division process in cancer cells, thereby limiting their proliferation and growth.
Used in Anticancer Applications:
As a promising anticancer agent, PHENOL, 2-METHOXY-5-[2-(3,4,5-TRIMETHOXYPHENYL)ETHYL]may be employed in the development of novel therapeutics targeting various types of cancer. Its mechanism of action, which involves the inhibition of tubulin polymerization, could be harnessed to create treatments that are effective against a range of malignancies.

InChI:InChI=1/C18H22O5/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/h7-11,19H,5-6H2,1-4H3

Upstream product

• 51458-25-4 (3-benzyloxy-4-methoxybenzyl)triphenylphosphonium chloride 
• 61240-20-8 triphenyl-(3,4,5-trimethoxybenzyl)phosphonium bromide 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 21852-50-6 3,4,5-trimethoxybenzyl bromide 
• 621-59-0 isovanillin 
• 50773-56-3 3-benzyloxy-4-hydroxybenzaldehyde 
• 203448-30-0 (3-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)(3,4,5-trimethoxyphenyl)methanone 
• 203448-32-2 phenstatin 
• 185698-54-8 2-[3-(tert-butyldimethylsilyloxy)-4-methoxyphenyl]-1-(3,4,5-trimethoxyphenyl)ethyne 
• 185698-55-9 2-(3-hydroxy-4-methoxyphenyl)-1-(3',4',5'-trimethoxyphenyl)ethyne 
• 90-05-1 2-methoxy-phenol 
• 30287-15-1 2-methoxyphenyl 2-chloroacetate 
• 874812-62-1 2-methoxy-5-(3,4,5-trimethoxybenzoyl)phenyl 2-chloroacetate 
• 116518-95-7 <3-(benzyloxy)-4-methoxybenzyl>triphenylphosphonium bromide 

Downstream Products

• 922527-87-5 3,4,5,4'-tetramethoxyl-α,β-diphenylethane-3'-O-sodium sulphate 
• 911193-51-6 C₁₈H₂₃O₈P 
• 95041-91-1 erianin acetate 

Relevant articles and documents

Dichloroacetic acid coupled diphenylethane compound as well as preparation method and application thereof

The invention belongs to the technical field of medicine synthesis, and particularly relates to a dichloroacetic acid coupled diphenylethane compound as well as a preparation method and application thereof. The structure of the dichloroacetic acid coupled diphenylethane compound is shown as a general formula (I), R1, R2 and R3 are respectively selected from but not limited to any one of-OH,-OMe and H, R4 is selected from but not limited to any one of-OMe and-OEt, R5 and R6 are selected from chlorine atoms or fluorine atoms, m is 0 or 1, and n is a positive integer selected from 1-8 or 11-12. The dichloroacetic acid coupled diphenylethane compound disclosed by the invention is stable in structure, low in toxicity, simple and convenient in preparation process and high in yield, does not need to be stored in a dark place, has obvious anti-tumor activity on various tumor cells cultured in vitro, and is obvious in in-vivo anti-tumor effect. The general formula (I) is shown in the specification.

Orchid heterocyclic derivative as well as preparation method and application thereof

The invention relates to a lansamine heterocyclic derivative as well as a preparation method and application thereof. Wherein, X is O or NH. R Is one of a furanyl heterocyclic substituent, a thiophenyl heterocyclic substituent, a thiazolyl heterocyclic substituent, a pyrimidinyl heterocyclic substituent, a pyridazinyl heterocycle substituent, an indolyl heterocyclic substituent, and an indolyl heterocyclic substituent. The preparation method comprises the following steps: carrying out condensation reaction on crude orchid and a carboxylic acid compound containing the substituent R. Or, 4 - methoxy -3 - nitrobenzaldehyde and 3,trimethoxy - triphenyl benzyl bromide salt is used as a raw material, and after Wittig reaction and reduction reaction, the tetracarboxylic acid compound containing the substituent R is subjected to a condensation reaction. Compared with the prior art, heterocyclic compounds such as crude orchid and nicotinic acid are connected through an ester bond to form a twin medicine, and a new way is provided for improving the pharmacological activity of the crude orchid.

5-FLUOROURACIL DERIVATIVES, PREPARATION METHODS AND USES THEREOF

Disclosed is a 5-fluorouracil derivative having the molecular structure shown in general formula VI, in which Ra and Rb groups are an alkoxy group or a fluorine-substituted alkoxy group having 1, 2, 3, or 4 carbon atoms, and are mono-, bis-, tri-, tetra- or penta-substituted on a phenyl group; a linking group L1 is an alkyl or alkenyl group having 1, 2, 3, or 4 carbon atoms, a linking group L2 is oxygen, or an alkyl or alkoxy group having 1, 2, 3, or 4 carbon atoms, or an amino acid, or an alkyl group having 1, 2, 3, or 4 carbon atoms containing an amino moiety, or a furyl group, and an X group is O or —NH—. Further disclosed is a method for preparing such a derivative and a use of the same in the treatment of cancer, tumor diseases, and diseases caused by abnormal neovascularization in a human or non-human mammal, and a medicament or a composition containing the 5-fluorouracil derivative.

Identification of Pyruvate Carboxylase as the Cellular Target of Natural Bibenzyls with Potent Anticancer Activity against Hepatocellular Carcinoma via Metabolic Reprogramming

Cancer cell proliferation in some organs often depends on conversion of pyruvate to oxaloacetate via pyruvate carboxylase (PC) for replenishing the tricarboxylic acid cycle to support biomass production. In this study, PC was identified as the cellular target of erianin using the photoaffinity labeling-click chemistry-based probe strategy. Erianin potently inhibited the enzymatic activity of PC, which mediated the anticancer effect of erianin in human hepatocellular carcinoma (HCC). Erianin modulated cancer-related gene expression and induced changes in metabolic intermediates. Moreover, erianin promotes mitochondrial oxidative stress and inhibits glycolysis, leading to insufficient energy required for cell proliferation. Analysis of 14 natural analogs of erianin showed that some compounds exhibited potent inhibitory effects on PC. These results suggest that PC is a cellular target of erianin and reveal the unrecognized function of PC in HCC tumorigenesis; erianin along with its analogs warrants further development as a novel therapeutic strategy for the treatment of HCC.

Erianin, a novel dibenzyl compound in Dendrobium extract, inhibits bladder cancer cell growth via the mitochondrial apoptosis and JNK pathways

Erianin, a component extracted from the traditional Chinese herbal medicine Dendrobium, has shown significant anti-tumour activity in various cancers but not in bladder cancer. In this study, we assessed the effects of Erianin on bladder cancer growth and elucidated the related mechanisms. First, Erianin was synthesized with high yields, and markedly suppressed EJ and T24 cell proliferation. It induced G2/M-phase arrest in vitro. Furthermore, Erianin triggered apoptosis via caspase cascades activation and the mitochondrial-mediated apoptotic pathway. Bim up-regulation and Bcl-2 down-regulation as the symbol of apoptosis which were found to play the dominant role in the effects of Erianin. We further showed that JNK pathway activation is necessary for the Erianin-mediated anti-proliferation and apoptotic response. Finally, Erianin exhibited anti-tumour activity and induced apoptosis in tumour tissue in vivo. Collectively, these results suggest that Erianin induced cell cycle G2/M-phase arrest and apoptosis via the JNK signalling pathway in bladder cancer, indicating the potential usefulness of Erianin for the therapy of bladder cancer.

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.

Discovery of Isoerianin Analogues as Promising Anticancer Agents

The cytotoxic activity of a series of 23 new isoerianin derivatives with modifications on both the A and B rings was studied. Several compounds exhibited excellent antiproliferative activity at nanomolar concentrations against a panel of human cancer cell lines. The most cytotoxic compound, isoerianin (3), strongly inhibits tubulin polymerization in the micromolar range. Moreover, isoerianin leads to G2/M phase cell-cycle arrest in H1299 and K562 cancer cells, and strongly induces apoptosis. Isoerianin also disrupts the vessel-like structures formed by human umbilical vein endothelial cells (HUVECs) invitro, suggesting that this compound may act as a vascular disrupting agent. It clearly appears that in this compound series, the 1,1-ethane bridge encountered in isoerianin derivatives can replace the 1,2-ethane bridge of natural erianin with no loss of activity. This reinforces the bioisosteric replacement approach in the combretastatin series previously reported by our research group.

New efficient synthesis of combretastatin A-4 via Colvin rearrangement

A new four-step approach for the synthesis of anticancer agent combretastatin A-4 (CA-4) has been developed. The method includes the Colvin rearrangement of the benzophenone derivative phenstatin to the key diarylalkyne followed by stereoselective semi-reduction to CA-4 in good overall yield.

PROCESS FOR PREPARING ERIANIN

A process for preparing Erianin (Dihydro Combretastation A-4), wherein 3,4,5-trimethoxy benzaldehyde is converted to phosphonium salt or phosphonate ester or the likes thereof, then reacted with isovanillin (3-hydroxyl-4-methoxyl benzaldehyde) including a protected hydroxyl in the 3-position, followed by hydrogenation and deprotection.