2206-43-1

Usage

Uses

Used in Chemical Synthesis:
4-Methoxyisophthalic acid is used as a key intermediate in the synthesis of various chemical compounds, including pharmaceuticals, dyes, and other specialty chemicals. Its unique structure allows for versatile reactions and functional group manipulations, making it a valuable building block in the chemical industry.
Used in Pharmaceutical Industry:
4-Methoxyisophthalic acid is used as a starting material for the development of new drugs, particularly those targeting specific diseases. Its chemical properties enable the creation of novel molecular structures with potential therapeutic benefits.
Used in Dye Manufacturing:
In the dye industry, 4-Methoxyisophthalic acid is used as a precursor for the production of various types of dyes, including those used in textiles, plastics, and other materials. Its ability to form colored compounds makes it an essential component in the development of new and improved dyes.
Used in Polymer Production:
4-Methoxyisophthalic acid is utilized in the production of certain types of polymers, such as polyesters and polyamides. Its chemical properties contribute to the formation of polymer chains with specific characteristics, making it a valuable component in the development of new materials with tailored properties.
Used in Coatings and Adhesives:
In the coatings and adhesives industry, 4-Methoxyisophthalic acid is used to improve the performance of these materials. Its chemical properties can enhance the durability, adhesion, and other properties of coatings and adhesives, making it a valuable additive in the formulation of these products.
Used in Agriculture:
4-Methoxyisophthalic acid is employed in the agricultural industry, where it is used as a component in the development of new agrochemicals, such as pesticides and herbicides. Its unique chemical properties allow for the creation of compounds with improved efficacy and selectivity, contributing to more effective and environmentally friendly agricultural practices.

InChI:InChI=1/C9H8O5/c1-14-7-3-2-5(8(10)11)4-6(7)9(12)13/h2-4H,1H3,(H,10,11)(H,12,13)

Upstream product

• 6123-02-0 5-Chloromethyl-2-methoxybenzaldehyde 
• 25445-34-5 1-methoxy-2,4-bis(chloromethyl)benzene 
• 857599-49-6 2-methoxy-5-(2,2,2-trichloro-1-hydroxy-ethyl)-benzoic acid 
• 124-38-9 carbon dioxide 
• 38474-03-2 1-(isopropylthio)-3-methoxybenzene 
• 117658-57-8 methyl 4-methyl-2-(tetrahydro-2H-pyran-2-yl)phenyl ether 
• 7722-84-1 dihydrogen peroxide 
• 548-19-6 isoginkgetin 
• 74-88-4 methyl iodide 
• 74901-08-9 5-hydroxymethylsalicylaldehyde 
• 145742-54-7 2-methoxy-5-propyl-benzaldehyde 
• 883541-44-4 2-methoxy-5-methoxymethyl-benzaldehyde 
• 7732-18-5 water 
• 531-99-7 5-acetyl-2-methoxybenzaldehyde 

Downstream Products

• 22955-73-3 dimethyl 4-methoxyisophthalate 
• 479579-02-7 methyl 4-methoxy-3-(3-pyridinylmethylaminocarbonyl)benzoate 
• 1029440-58-1 N,N'-di(2-fluorophenyl)-4-methoxyl-isophthalamide 
• 1007588-88-6 C₂₁H₁₆Cl₂N₂O₃ 
• 1029440-60-5 C₂₁H₁₆Br₂N₂O₃ 
• 1029440-62-7 C₂₁H₁₆I₂N₂O₃ 
• 929637-59-2 N¹,N³-bis(2-methylphenyl)-4-methoxyisophthalamide 
• 1029441-03-9 C₂₃H₂₂N₂O₅ 
• 1029440-91-2 C₂₃H₁₈N₂O₇ 
• 1029440-88-7 N¹,N³-bis(2-benzylphenyl)-4-methoxyisophthalamide 
• 1029440-77-4 C₂₅H₂₀N₄O₃ 
• 1007588-82-0 C₂₁H₁₆F₂N₂O₃ 
• 1007588-84-2 C₂₁H₁₆Cl₂N₂O₃ 
• 1007588-85-3 C₂₁H₁₆Br₂N₂O₃ 

Relevant academic research and scientific papers

Preparation method of picotamide

The invention provides a method for preparing picotamide, which comprises the following steps: taking dimethyl 4-hydroxyl isophthalate as a raw material, carrying out methyl etherification reaction toobtain dimethyl 4-methoxy isophthalate; then, carrying out hydrolysis reaction to obtain 4-methoxy isophthalic acid; and finally, carrying out amidation reaction to obtain picotamide. Compared with atraditional method, the preparation method has the advantages of short synthesis steps, simplicity and convenience in operation, high reaction speed, high yield and the like. Besides, the raw materials required by the method are extracted from waste residues generated in industrial production, the extraction method is simple, the resource utilization rate is increased, the environmental pollutionis reduced, the production cost is reduced, and the method is suitable for large-scale industrial production.

Synthesis and in vitro activities on anti-platelet aggregation of 4-methoxy-1,3-phthalamidesamides and benzenedisulfonamides

Cardiovascular diseases are the most frequent cause of morbidity and mortality worldwide. In order to discover novel compounds with anti-platelet aggregation activities, a series of novel 4-methoxy-1,3-phthalamidesamides (1a–1i) and a series of novel 4-methoxy-1,3-benzenedisulfon-amides (2a–2i) were synthesized and their anti-platelet aggregation activities were evaluated by the turbidimetric method in response to the following agonists: adenosine diphosphate (ADP), arachidonic acid (AA), and Collagen. Those compounds that have better in vitro activities were subjected to cell toxicity tests via cell counting kit-8 (CCK-8) assay. The inhibition rates of anti-platelet in vitro of five compounds 1g (39.45%), 2d (38.87%), 2g (38.55%), 2h (44.56%), and 2i (43.93%) were higher than that of two reference drugs picotamide (36.12%) and aspirin (38.45%) when ADP was selected as an inducer. The inhibition rates of seven compounds 1c (43.63%), 1d (40.02%), 1g (47.42%), 1i (40.45%), 2c (40.11%), 2d (40.45%), and 2i (49.05%) were higher than that of picotamide (34.89%) and aspirin (39.43%) when AA was selected as inducer. And the inhibition rates of five compounds 1d (47.22%), 1i (45.01%), 2d (38.74%), 2e (42.21%), and 2f (39.94%) were higher than picotamide (38.45%) and aspirin (37.08%) when collagen was selected as inducer. Moreover, the effect of cell toxicity exhibited that none of the compounds had obvious cell toxicity against L-929 cells. Therefore, 4-methoxy-1,3-phthalamidesamides (1a–1i) and 4-methoxy-1,3-benzenedisulfon-amides (2a–2i) have the potential to become a novel kind of anti-platelet drugs and deserve further study.

Design, synthesis and biological evaluation of 4-methoxy diaryl isophthalates as antiplatelet agents

A series of 4-methoxy diphenyl isophthalates, which are the isosturctural analogs of picotamide, were designed and synthesized using the concept of isosterism. The structures of these new analogs were characterized by all means of spectroscopy, including 1H NMR, 13C NMR, and MS spectra. In vitro antiplatelet aggregation activities of these compounds were investigated by using Born’s test method. Among the 19 compounds tested for both ADP and collagen inducers, six of them (P216–P219 and P220–P221) were found to exhibit higher activity in vitro antiplatelet aggregation than Picotamide. In particular, the compound P220 bearing a nitrooxyl group showed the highest acitivity 72.1% (induced by collagen) and 72.5% (induced by ADP), with IC50 values of 0.30 μM/L induced by ADP (1.3 μM/L) and LD50 CloseSPigtSPi 2500 mg/kg, could have dual mechanism of action. Evaluation of cytotoxic activity of the compounds against L929 cell line revealed that none of the compounds have significant cytotoxicity. Through the careful analysis of in vitro activity data, the SAR of these compounds was preliminarily deduced. The results of this study showed that 4-methoxy diaryl isophthalates derivatives are potential to become an antiplatelet aggregation agents.

Synthesis and in vitro activities on anti-platelet aggregation of 4-methoxyisophthalamides

A series of 4-methoxyisophthalamides (1d–1w) were designed and synthesized and their chemical structures were confirmed by IR, MS, 1H-NMR, and 13C-NMR. The in vitro on anti-platelet aggregation activities of these compounds were assessed by using Born method. Compounds with higher activities were selected to continue research via Cell Counting Kit-8 (CCK-8) assays of their cytotoxicities. Biological screening results revealed four compounds 1h, 1i, 1q, and 1v exhibited higher activities than the control drugs on against the platelet aggregation induced by adenosine triphosphate (ADP). Moreover, compounds 1p and 1q exhibited higher in vitro activities than picotamide induced by collagen at the concentration of 1.3 μM. Compound 1p also possessed anti-platelet aggregation activity superior to the control drug picotamide induced by arachidonic acid (AA) at the concentration of 1.3 μM. At the same time, the result of cytotoxicities exhibited that none of the compounds have significant cytotoxicities. Therefore, 4-methoxyisophthalamides are potential to become novel anti-platelet drugs with high activities and minimum toxicities.

Preparation method for 4-methoxy-1,3-phthalic acid

The invention provides a preparation method for 4-methoxy-1,3-phthalic acid. 4-methoxy-1,3-phthalic acid is key intermediate for preparation of an anti-platelet aggregation drug picotamide (with a trade name of plactidil). According to the preparation method, 4-methoxy-1,3-phthalic acid is prepared from the starting raw material p-methylphenol or o-methylphenol through esterification, Fries rearrangement, methylation, oxidation and acidification. Compared with traditional preparation methods, the preparation method provided by the invention has the advantages of low equipment investment, simple operation, quick reaction, high yield, low synthesis cost, greatly reduced environmental pollution and the like, and is particularly suitable for large-scale industrial production.

New synthesis of 4-methoxyisophthalic acid

A new synthetic route to 4-methoxyisophthalic acid, the key intermediate in the synthesis of Picotamide, is reported. The new protocol starts from commercially available and cheap 4-methylphenol and includes four steps: esterification, Fries rearrangement, methylation, and oxidation; the overall yield is 49%. Unlike the traditional Blanc chloromethylation/oxidation scheme, the proposed procedure avoids using volatile and corrosive hydrochloric acid.

Design, synthesis and in vitro activities on anti-platelet aggregation of 4-methoxybenzene-1,3-isophthalamides

On the purpose of searching for the structure-activity relationship (SAR) and obtaining novel anti-platelet drugs, 41 4-methoxybenzene-1,3-isophthalamides have been described the synthesis process and in vitro activities on anti-platelet aggregation. The target compounds have been classified into four series: series 1 (ortho-substituted phenyl: 1a-1j), series 2 (meta-substituted phenyl: 2a-2k), series 3 (para-substituted phenyl: 3a-3l) and series 4 (aromatic of no substituted group and aromatic heterocyclic substituted groups: 4a-4h). The chemical structures of the target compounds were confirmed by MS, IR, 1H NMR, and their in vitro activities on anti-platelet aggregation were tested and assessed by using Born test. The result showed that thirteen compounds 1c, 1d, 1i, 1j, 2g, 3a, 3c, 3d, 3f, 3h, 3l, 4b and 4c have superior anti-platelet aggregation activities than the reference drug Picotamide.

Synthesis and mesomorphism of 1,3-benzenedicarboxylic acid derivatives

4-Methoxy-l,3-benzenedicarboxylic acid esters and 4-(4- hexyloxybenzoylamino)phenyl 1,3-benzenedicarboxylate, each containing five aromatic rings, were synthesized. The influence of the structure of the synthesized banana-like compounds on their mesogenic activity was examined.

Compound for the treatment of atherosclerotic-thrombotic pathological conditions

4-Methoxy-N1-(4-trans-nitrooxycyclohexyl)-N3-(3-pyridinylmethyl)-1,3-benzenedicarboxamide and acid addition salts thereof with pharmaceutically acceptable organic and inorganic acids, and a pharmaceutical composition containing the same, for the treatment of vascular diseases involving atherosclerotic-thrombotic conditions and of other pathological conditions as shown in the description.

"Compound for the treatment of atherosclerotic-thrombotic pathological conditions"

4-Methoxy-N1-(4-trans-nitrooxycyclohexyl)-N3-(3-pyridinylmethyl)-1,3-benzenedicarboxamide of following formula 1: and acid addition salts thereof with pharmaceutically acceptable organic and inorganic acids, and a pharmaceutical composition containing the same, for the treatment of vascular diseases involving atherosclerotic-thrombotic conditions and of other pathological conditions as shown in the description.