135586-17-3

Basic information

• Product Name: 2-BroMo-3-benzyloxy-4-Methoxybenzoic Acid
• Synonyms: 2-BroMo-3-benzyloxy-4-Methoxybenzoic Acid;2-BroMo-4-Methoxy-3-(phenylMethoxy)-benzoic Acid;3-(benzyloxy)-2-bromo-4-methoxybenzoic acid
• CAS NO: 135586-17-3
• Molecular Formula: C₁₅H₁₃BrO₄
• Molecular Weight: 337.16532
• Product Categories: Aromatics;Intermediate
• Mol File: 135586-17-3.mol

Chemical Properties

• Melting Point: 159-161 °C
• Boiling Point: 440.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.486±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 2.97±0.10(Predicted)
• CAS DataBase Reference: 2-BroMo-3-benzyloxy-4-Methoxybenzoic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BroMo-3-benzyloxy-4-Methoxybenzoic Acid(135586-17-3)
• EPA Substance Registry System: 2-BroMo-3-benzyloxy-4-Methoxybenzoic Acid(135586-17-3)

Safety Data

• Hazardous Substances Data: 135586-17-3(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Taspine intermediate.

Upstream product

• 621-59-0 isovanillin 
• 100-39-0 benzyl bromide 
• 2973-58-2 2-bromoisovanillin 
• 38849-38-6 3-(benzyloxy)-2-bromo-4-methoxybenzaldehyde 

Downstream Products

• 1233979-40-2 C₁₅H₁₂BrClO₃ 
• 1233979-39-9 3-(benzyloxy)-2-bromo-4-methoxy-N-methylbenzamide 
• 1233979-41-3 6,6'-bis(benzyloxy)-5,5'-dimethoxy-N,N'-dimethylbiphenyl-2,2'-dicarboxamide 
• 1326579-33-2 5,5'-dimethoxy-N,N'-dimethyl-6,6'-bis(2-oxo-2-{[3-(trifluoromethyl)phenyl]amino}ethoxy)biphenyl-2,2'-dicarboxamide 
• 1326579-34-3 6,6'-bis{2-[(3,4-dichlorophenyl)amino]-2-oxoethoxy}-5,5'-dimethoxy-N,N'-dimethylbiphenyl-2,2'-dicarboxamide 
• 1326579-35-4 5,5'-dimethoxy-6,6'-bis{2-[(4-methoxyphenyl)amino]-2-oxoethoxy}-N,N'-dimethylbiphenyl-2,2'-dicarboxamide 
• 1326579-38-7 6,6'-bis{2-[(4-bromophenyl)amino]-2-oxoethoxy}-5,5'-dimethoxy-N,N'-dimethylbiphenyl-2,2'-dicarboxamide 
• 1326579-40-1 C₃₄H₃₂F₂N₄O₈ 
• 1326579-42-3 6,6'-bis{2-[(3-fluorophenyl)amino]-2-oxoethoxy}-5,5'-dimethoxy-N,N'-dimethylbiphenyl-2,2'-dicarboxamide 
• 1326579-43-4 6,6'-bis(2-anilino-2-oxoethoxy)-5,5'-dimethoxy-N,N'-dimethylbiphenyl-2,2'-dicarboxamide 
• 1326579-45-6 6,6'-bis{2-[(6-fluoropyridin-3-yl)amino]-2-oxoethoxy}-5,5'-dimethoxy-N,N'-dimethylbiphenyl-2,2'-dicarboxamide 
• 1285535-52-5 C₁₈H₂₀BrNO₃ 
• 1285535-49-0 C₁₉H₂₂BrNO₃ 
• 1285535-50-3 C₃₈H₄₄N₂O₆ 

Relevant articles and documents

With anti-tumor activity of a biphenyl amide compound and its preparation method and application

The invention discloses a biphenyl amide compound with antitumor activity as well as a preparation method and application thereof. The structural formula of the compound is shown in the specification, wherein in the structural formula, R1 is hydrogen or halogen; R2 is alkoxy with carbon number of 1-4; the terminal of R2 is replaced by tert-amido; R2 is linked to the para-position of amide via an oxygen atom. The compound has good tumor cell inhibiting activity in vitro and can be used for preparing antitumor drugs, especially anti-hepatoma drugs and anti-breast cancer drugs. The preparation method of the biphenyl amide compound, provided by the invention, has the advantages that the raw materials are accessible, the reaction conditions are mild, the reaction process is simple to operate, and the used reagent is cheap.

Discovery of biphenyl-based VEGFR-2 inhibitors. Part 3: Design, synthesis and 3D-QSAR studies

VEGFR-2 plays an essential role in angiogenesis and is a central target for anticancer drug discovery. In order to develop novel VEGFR-2 inhibitors, we designed and synthesized 33 biphenyl amides based on our previously reported lead compound. The biological results indicated that four compounds (18b, 20e, 20h and 20j) are potent VEGFR-2 inhibitors which are comparable to positive control. Compound 18b displayed the most potent VEGFR-2 inhibition with IC50 value of 2.02 nM. Moreover, it exhibited promising antiproliferative activity against MCF-7 and SMMC-7721 cells with IC50 values of 1.47 μM and 5.98 μM, respectively. Molecular docking and 3D-QSAR studies were also carried out. The results indicated that these biphenyl amides could serve as promising leads for further optimization as novel VEGFR-2 inhibitors.

Synthesis of novel taspine diphenyl derivatives as fluorescence probes and inhibitors of breast cancer cell proliferation

Two novel taspine diphenyl derivatives (Ta-dD) were designed and synthesized by introducing different coumarin fluorescent groups into the basic structure of Ta-dD. The main advantage of these two compounds is that they can be used as fluorescence probes and inhibitors simultaneously. In the present study, the fluorescent properties of the probes were measured and their inhibition of four breast cancer cell lines was tested. Different concentrations of the fluorescence probe were added to MCF-7 breast cancer cells for fluorescence imaging analysis under normal conditions. The results suggested that both of the new compounds have not only fluorescence but also the ability to inhibit effects on different breast cancer cell lines, which indicates their possible further use as dual functional fluorescence probes in tracer analysis. Copyright

Synthesis and cytotoxic evaluation of novel symmetrical taspine derivatives as anticancer agents

It has been demonstrated that taspine derivatives act as anticancer agents, thus we designed and synthesized a novel class of symmetrical biphenyl derivatives. We evaluated the cytotoxicity and antitumor activity of biphenyls against five human tumor and normal cell lines. The results indicated that the majority of the compounds exhibited anticancer activity equivalent to or greater than the positive control. Compounds (11) and (12) demonstrated the most potent cytotoxic activity with IC50 values between 19.41 μM and 29.27 μM. The potent antiproliferative capabilities of these compounds against ECV304 human transformed endothelial cells indicated that these biphenyls could potentially serve as antiangiogenic agents. We also reviewed the relationship between structure and activity based on the experimental results. Our findings provide a good starting point for further development of symmetrical biphenyl derivatives as potential novel anticancer agents.

Synthesis and preliminary biological evaluation of novel taspine derivatives as anticancer agents

Antiangiogenic therapy might represent a new promising anticancer therapeutic strategy. Taspine can significantly inhibit cell proliferation of human umbilical vein endothelial cells (HUVECs) induced by vascular endothelial growth factor-165, which is crucial for angiogenesis. In this study, a series of novel taspine derivatives were synthesized and screened for in vitro anticancer and antiangiogenesis activities. The majority of the derivatives demonstrated a moderate degree of cytotoxicity against human cancer cell lines. One of them (14) exhibited much better antiproliferative activity against CACO-2 (IC 50 = 52.5 μM) and ECV304 (IC50 = 2.67 μM) cells than taspine did. Some of them were also effective in antiproliferative assays against HUVECs. The in silico estimate of solubility of title compounds were higher than that of taspine.

Facile and efficient total synthesis of taspine

The facile and efficient total synthesis of taspine was achieved in 10 steps in high yield (16.5% overall) from commercially available isovanillin. Key steps in the synthesis are preparation of a symmetrical homodimer employing a classical Ullmann coupling reaction, and introduction of an allyl substituent by the Claisen rearrangement reaction. Significantly, the facile synthetic scheme proposed in this work has the characteristics of mild reaction conditions, inexpensive reagents, higher yield, and simple operation. Georg Thieme Verlag Stuttgart.