526-34-1

Usage

Uses

Used in Pharmaceutical Industry:
7-Methoxy-1,3-benzodioxide-5-carboxylic acid is utilized as a key intermediate in the synthesis of pharmaceutical compounds for the development of new drugs and medications. Its presence of a methoxy group and carboxylic acid groups allows for versatile chemical reactions, making it a valuable building block in medicinal chemistry.
Used in Organic Synthesis:
In the realm of organic synthesis, 7-Methoxy-1,3-benzodioxide-5-carboxylic acid serves as a versatile reagent and precursor for the creation of a variety of organic compounds. Its unique structure facilitates multiple synthetic pathways, contributing to the advancement of organic chemistry.
Used in Chemical Research:
7-Methoxy-1,3-benzodioxide-5-carboxylic acid is employed as a research tool in chemical studies, where its properties and reactivity are investigated to gain insights into the behavior of similar compounds. This understanding can lead to the discovery of new chemical reactions and the development of innovative synthetic methods.

InChI:InChI=1/C9H8O5/c1-12-6-2-5(9(10)11)3-7-8(6)14-4-13-7/h2-3H,4H2,1H3,(H,10,11)

Upstream product

• 607-91-0 myristicin 
• 18312-21-5 trans-isomyristicin 
• 3934-84-7 3,4-dihydroxy-5-methoxybenzoic acid 
• 5780-07-4 3-methoxy-4,5-methylenedioxybenzaldehyde 
• 89029-10-7 5,6,7,5'-tetramethoxy-3',4'-methylenedioxyflavone 
• 89029-11-8 5,7,5'-trimethoxy-3',4'-methylenedioxyflavone 
• 3934-87-0 5-hydroxyvanillin 
• 22934-58-3 methyl 7-methoxybenzo[d][1,3]dioxole-5-carboxylate 
• 171738-30-0 methyl 3,5-diisopropoxy-4-methoxybenzoate 
• 487-62-7 isomyristicin 
• 6443-68-1 3-methoxy-4,5-methylenedioxybenzonitrile 
• 3934-86-9 methyl 3,4-dihydroxy-5-methoxybenzoate 
• 73340-44-0 3,3′,5,6,7,8-hexamethoxy-4′,5′-methylenedioxyflavone 

Downstream Products

• 22934-58-3 methyl 7-methoxybenzo[d][1,3]dioxole-5-carboxylate 
• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 74-88-4 methyl iodide 
• 1221717-33-4 3-(3-hydroxy-4-methoxyphenyl)-5-(3-methoxy-4,5-methylenedioxyphenyl)-1,2,4-triazole 
• 1257321-38-2 C₁₇H₁₆N₂O₇ 
• 1257321-39-3 C₁₉H₂₀N₂O₈ 
• 1221721-82-9 2-(3-hydroxy-4-methoxyphenyl)-5-(3-methoxy-4,5-methylenedioxyphenyl)-1,3,4-oxadiazole 
• 1221717-58-3 2-(3,4,5-trimethoxyphenyl)-5-(3-methoxy-4,5-methylenedioxyphenyl)-1,3,4-oxadiazole 
• 1293408-39-5 C₂₂H₂₈O₆Si 
• 1221719-65-8 (3-hydroxy-4-methoxyphenyl)(3-methoxy-4,5-methylenedioxyphenyl)methanone 
• 1192928-03-2 N-(3-benzamidophenylcarbamoyl)-7-methoxybenzo[d][1,3]dioxole-5-carboxamide 
• 1192927-96-0 N-(3-benzamidophenylcarbamothioyl)-7-methoxybenzo[d][1,3]dioxole-5-carboxamide 
• 1301751-69-8 4-(4-methoxyphenyl)-5-(3-methoxy-4,5-methylenedioxyphenyl)-1H-pyrazol-3-amine 
• 1240140-17-3 2-(4-methoxyphenyl)-3-oxo-3-(3-methoxy-4,5-methylenedioxyphenyl)propanenitrile 

Relevant academic research and scientific papers

Structural Modification of the 3,4,5-Trimethoxyphenyl Moiety in the Tubulin Inhibitor VERU-111 Leads to Improved Antiproliferative Activities

Colchicine binding site inhibitors (CBSIs) hold great potential in developing new generations of antimitotic drugs. Unlike existing tubulin inhibitors such as paclitaxel, they are generally much less susceptible to resistance caused by the overexpression

Sea Urchin Embryo Model As a Reliable in Vivo Phenotypic Screen to Characterize Selective Antimitotic Molecules. Comparative evaluation of Combretapyrazoles, -isoxazoles, -1,2,3-triazoles, and -pyrroles as Tubulin-Binding Agents

A series of both novel and reported combretastatin analogues, including diarylpyrazoles, -isoxazoles, -1,2,3-triazoles, and -pyrroles, were synthesized via improved protocols to evaluate their antimitotic antitubulin activity using in vivo sea urchin embryo assay and a panel of human cancer cells. A systematic comparative structure-activity relationship studies of these compounds were conducted. Pyrazoles 1i and 1p, isoxazole 3a, and triazole 7b were found to be the most potent antimitotics across all tested compounds causing cleavage alteration of the sea urchin embryo at 1, 0.25, 1, and 0.5 nM, respectively. These agents exhibited comparable cytotoxicity against human cancer cells. Structure-activity relationship studies revealed that compounds substituted with 3,4,5-trimethoxyphenyl ring A and 4-methoxyphenyl ring B displayed the highest activity. 3-Hydroxy group in the ring B was essential for the antiproliferative activity in the diarylisoxazole series, whereas it was not required for potency of diarylpyrazoles. Isoxazoles 3 with 3,4,5-trimethoxy-substituted ring A and 3-hydroxy-4-methoxy-substituted ring B were more active than the respective pyrazoles 1. Of the azoles substituted with the same set of other aryl pharmacophores, diarylpyrazoles 1, 4,5-diarylisoxazoles 3, and 4,5-diaryl-1,2,3-triazoles 7 displayed similar strongest antimitotic antitubulin effect followed by 3,4-diarylisoxazoles 5, 1,5-diaryl-1,2,3-triazoles 8, and pyrroles 10 that showed the lowest activity. Introduction of the amino group into the heterocyclic core decreased the antimitotic antitubulin effect of pyrazoles, triazoles, and to a lesser degree of 4,5-diarylisoxazoles, whereas potency of the respective 3,4-diarylisoxazoles was increased.

Cis -restricted 3-aminopyrazole analogues of combretastatins: Synthesis from plant polyalkoxybenzenes and biological evaluation in the cytotoxicity and phenotypic sea urchin embryo assays

We have synthesized a series of novel cis-restricted 4,5-polyalkoxydiaryl- 3-aminopyrazole analogues of combretastatins via short synthetic sequences using building blocks isolated from dill and parsley seed extracts. The resulting compounds were tested in vivo in the phenotypic sea urchin embryo assay to reveal their antimitotic and antitubulin effects. The most potent aminopyrazole, 14a, altered embryonic cell division at 10 nM concentration, exhibiting microtubule-destabilizing properties. Compounds 12a and 14a displayed pronounced cytotoxicity in the NCI60 anticancer drug screen, with the ability to inhibit growth of multi-drug-resistant cancer cells.

Application of plant allylpolyalkoxybenzenes in synthesis of antimitotic phenstatin analogues

Phenstatin and its derivatives with the modified ring A have been synthesized, using plant allylpolyalkoxybenzenes as a starting material. The targeted molecules were evaluated in a phenotypic sea urchin embryo assay for antiproliferative activity. It was found that phenstatin ring A modifications yielded antimitotic compounds. The most effective myristicin derivative 7d (combretastatin A-2 analogue) was determined to be ca. 10 times more potent than phenstatin, displaying antimitotic tubulin-destabilizing activity at the same concentration range as combretastatins. In contrast to combretastatins, 7d featured the steric stability with potential for further design as anticancer agent.

Polyalkoxybenzenes from plant raw materials 4. Parsley and dill seed extracts in the synthesis of polyalkoxy-3,5-diaryl-1,2,4-oxadiazoles with antiproliferative activity

Polyalkoxy-5-(4-hydroxyphenyl)-3-phenyl-1,2,4-oxadiazoles were prepared from allylpolyalkoxybenzenes, the main metabolites of parsley and dill seeds. Due to the spatial arrangement of the aryl substituents provided by 1,2,4-oxadiozole fragment, these compounds can be considered as structural analogs of natural antimitotic combretastatins. The antimitotic activity of the synthesized compounds was evaluated in vivo using sea urchin embryo test.

Bis(5-aryl-2-pyridyl) derivatives

A bis(5-aryl-2-pyridyl) compound represented by formula (1) or a salt thereof: wherein A is a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, and X is a group selected from the group consisting of moieties having formulas (2) to (5): wherein, in formula (2), m is an integer of 1 or 2; in formula (3), n is an integer of 1 to 6; and in formula (4), R is hydrogen or a lower alkyl group and p is an integer of 1 to 6.

SUBSTITUTED 4-(1H-BENZIMIDAZOL-2-YL)[1,4]DIAZEPANES USEFUL FOR THE TREATMENT ALLERGIC DISEASES

The present invention relates to novel 4-(1H-benzimidazol-2-yl)[1,4] diazepane derivatives of formula (1): and stereoisomers thereof, and pharmaceutically acceptable salts thereof which are useful as histamine receptor antagonists and tachykinin receptor antagonist. Such antagonists are useful in the treatment of allergic rhinitis, including seasonal rhinitis and sinusitis; inflammatory bowel diseases, including Crohn's disease and ulcerative colitis; asthma; bronchitis; and emesis.

Novel substituted 4-(1H-benzimidazol-2-yl) [1,4]diazepanes useful for the treatment of allergic diseases

The present invention relates to novel 4-(1H-benzimidazol-2-yl)[1,4]diazepane derivatives of formula and stereoisomers thereof, and pharmaceutically acceptable salts thereof which are useful as histamine receptor antagonists and tachykinin receptor antagonist. Such antagonists are useful in the treatment of allergic rhinitis, including seasonal rhinitis and sinusitis; inflammatory bowel diseases, including Crohn's disease and ulcerative colitis; asthma; bronchitis; and emesis.

Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic disease

The present invention relates to novel 4-(1H-benzimidazol-2-yl)[1,4]diazepane derivatives of formula (1): and stereoisomers thereof, and pharmaceutically acceptable salts thereof which are useful as histamine receptor antagonists and tachykinin receptor antagonist. Such antagonists are useful in the treatment of allergic rhinitis, including seasonal rhinitis and sinusitis; inflammatory bowel diseases, including Crohn's disease and ulcerative colitis; asthma; bronchitis; and emesis.