6940-49-4

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromophthalide is used as a pharmaceutical intermediate for its potential medicinal properties. It is being studied for its anti-inflammatory and anti-tumor activities, which could lead to the development of new drugs for treating various diseases.
Used in Materials Science:
3-Bromophthalide is used as a photo-responsive material in optoelectronic devices due to its unique physical and chemical properties. Its potential applications in this field could contribute to the advancement of optoelectronic technology.
Used in Organic Synthesis:
3-Bromophthalide is used as a building block in the synthesis of various organic compounds. Its versatility in chemical reactions allows for the creation of a wide range of compounds with different properties and applications.

InChI:InChI=1/C8H5BrO2/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-4,7H

Upstream product

• 87-41-2 2-benzofuran-1(3H)-one 
• 7726-95-6 bromine 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 144-55-8 sodium hydrogencarbonate 
• 65-85-0 benzoic acid 
• 6295-21-2 3-chloro-1(3H)-isobenzofuranone 
• 85-44-9 phthalic anhydride 
• 118-90-1 ortho-methylbenzoic acid 
• 764-28-3 (E)-3,3'-(diazene-1,2-diyl)bis(2-methylpropanenitrile) 

Downstream Products

• 16824-02-5 3-ethoxy-3H-isobenzofuran-1-one 
• 119-39-1 phthalazone 
• 65543-72-8 3,3'-oxy-di-phthalide 
• 119-67-5 o-carboxybenzaldehyde 
• 26486-93-1 3-hydroxy-2,3-dihydro-isoindol-1-one 
• 4195-21-5 3-morpholin-4-yl-3H-isobenzofuran-1-one 
• 5467-92-5 isoquinolin-1-yl(diphenyl)methanol 
• 16576-23-1 1-benzoylisoquinoline 
• 491-30-5 1-hydroxyisoquinoline 
• 24223-06-1 1-(3-oxo-1,3-dihydroisobenzofuran-1-yl)isoquinoline 
• 132455-09-5 3-(3-methylphenoxy)-1,3-dihydro-1-isobenzofuranone 
• 131387-55-8 3-(Toluene-4-sulfonyl)-3H-isobenzofuran-1-one 
• 61133-42-4 3-phenoxy-1,3-dihydro-1-isobenzofuranone 
• 82027-09-6 3-<(p-toluenesulfonyl)oxy>phthalide 

Relevant academic research and scientific papers

Enantioselective synthesis of 3-aryl-phthalides through a nickel-catalyzed stereoconvergent cross-coupling reaction

A nickel-catalyzed asymmetric Suzuki-Miyaura cross-coupling of racemic 3-bromo-phthalides and arylboronic acids was realized for the synthesis of diverse chiral 3-aryl-phthalides in moderate to excellent reaction yields. The reaction proceeded in a stereoconvergent manner and high enantioselectivities were observed for most examined examples. A number of functional groups like aldehyde, ester and bromide were well tolerated. Heteroaromatic boronic acids were also competent coupling partners in this reaction.

NOVEL COMPOUNDS USEFUL AS POLY(ADP-RIBOSE) POLYMERASE (PARP) INHIBITORS

The present invention provides novel poly(ADP-ribose) polymerase (PARP) inhibitors, methods of preparing them, pharmaceutical compositions containing them and methods for the treatment, prevention and/or amelioration of PARP mediated diseases or disorders using them. In particular, the compounds described herein are useful for the treatment of carcinoma of the breast, ovarian cancer, carcinoma of the liver, carcinoma of the lung, small cell lung cancer, esophageal cancer, gall bladder cancer, pancreatic cancer and stomach cancer.

Chiral Bicyclic Imidazole-Catalyzed Acylative Dynamic Kinetic Resolution for the Synthesis of Chiral Phthalidyl Esters

Utilizing a chiral bicyclic imidazole organocatalyst and adopting a continuous injection process, an alternative route has been developed for the efficient synthesis of chiral phthalidyl ester prodrugs via dynamic kinetic resolution of 3-hydroxyphthalides through enantioselective acylation (up to 99 % ee). The computational studies suggest a general base catalytic mechanism differing from the widely accepted nucleophilic catalytic mechanism. The structure analysis of the key transition states shows that the CH-π interactions and not the previously considered cation/π-π interactions between the catalyst and substrate is the dominant factor giving rise to the observed stereocontrol.

Synthesis and biological profiling of novel isocoumarin derivatives and related compounds

In the continuation of our study of substituted isocoumarins a series of novel 3-azolyl isocoumarin and their thio derivatives, including some related lactone compounds was prepared and biologically profiled against C. albicans showing moderate activity with MIC values in range of 4-60 μg mL-1, in general. The additional characterisation of selected compounds was carried out by exploring their activity on CYP3A4 and CYP2D6 enzymes, while experiments on mutagenicity were performed by AMES test. The representative isocoumarins 3b, 4a and 4b showed lower inhibitory activity on CYP enzymes, when compared to the reference inhibitors, ketoconazole and quinidine. Compound 4a showed a higher mutagenic potential than the other two compounds. Further characterization included cytotoxicity profiling against normal MRC5 cells.

Industrial synthesis method of o-aldehyde phenyl fatty acid

The invention provides an industrial synthesis method of o-aldehyde phenyl fatty acid, which comprises the following steps: by using aromatic lactone or o-methylphenyl fatty acid as a raw material, carrying out halogenation reaction and hydrolysis to obtain the o-aldehyde phenyl fatty acid. In the method, halogen is used in the production process; however, if haloid acid or haloid salt formed byhydrolysis is directly discharged to the environment, the cost of a halogen source accounts for most of the cost of the whole process, and severe environmental pollution is caused; by means of the method, an activated halogen source can be obtained in real time by adding a specific oxidant in the reaction process, so that the closed cycle of halogen elements is realized by means of the subsequenthydrolysis process; therefore, a large amount of raw material cost is saved on the whole, environmental pollution is reduced, the product yield is high, and large-scale production is facilitated.

Synthesis and antifungal activities of 3-substituted phthalide derivatives

In order to obtain novel bioactive compounds with significant antifungal activities, two series of 3-substituted phthalide derivatives were designed and synthesized via reduction, bromine substitution, and etherification. In addition, the antifungal activities of all target compounds against nine phytopathogenic fungi in vitro were tested by using the mycelial growth rate method at the concentration of 50 μg mL-1. Preliminary bioassay tests showed that some compounds exhibited more potent antifungal activities as compared with hymexazol. The preliminary structure-activity relationships (SARs) of all target compounds were also investigated.

Synthesis and Investigation of Phthalazinones as Antitubercular Agents

A series of 2- and 7-substituted phthalazinones was synthesised and their potential as anti-tubercular drugs assessed via Mycobacterium tuberculosis (mc26230) growth inhibition assays. All phthalazinones tested showed growth inhibitory activity (MIC 100 μm), and those compounds containing lipophilic and electron-withdrawing groups generally exhibited better anti-tubercular activity. Several lead compounds were identified, including 7-((2-amino-6-(4-fluorophenyl)pyrimidin-4-yl)amino)-2-heptylphthalazin-1(2H)-one (MIC=1.6 μm), 4-tertbutylphthalazin-2(1H)-one (MIC=3 μm), and 7-nitro-phthalazin-1(2H)-one (MIC=3 μm). Mode of action studies indicated that selected pyrimidinyl-phthalazinones may interfere with NADH oxidation, however, the mode of action of the lead compound is independent of this enzyme. MIC=minimum inhibitory concentration.

DL-3-n-butylphthalide-Edaravone hybrids as novel dual inhibitors of amyloid-β aggregation and monoamine oxidases with high antioxidant potency for Alzheimer's therapy

Considering the complex etiology of Alzheimer's disease (AD), multifunctional agents may be beneficial for the treatment of this disease. A series of DL-3-n-butylphthalide-Edaravone hybrids were designed, synthesized and evaluated as novel dual inhibitors of amyloid-β aggregation and monoamine oxidases. Among them, compounds 9a–d exhibited good inhibition of self-induced Aβ1-42aggregation with inhibition ratio 57.7–71.5%. For MAO, these new hybrids exhibited good balance of inhibition for MAO-A and MAO-B. In addition, all target compounds retained the antioxidant activity of edaravone, showed equal or better antioxidant activity than edaravone. The results of the parallel artificial membrane permeability assay for blood-brain barrier indicated that compounds 9a–d would be able to cross the blood-brain barrier and reach their biological targets in the central nervous system. The promising results in all assays demonstrated that the strategy behind the designing of compounds was rational and favourable. Taken together, these preliminary findings suggested that the compounds with the strongest bioactivity deserves further investigated for pharmacological development in AD therapy.

Facile construction of pyrrolo[1,2-: B] isoquinolin-10(5 H)-ones via a redox-amination-aromatization-Friedel-Crafts acylation cascade reaction and discovery of novel topoisomerase inhibitors

An efficient redox-amination-aromatization-Friedel-Crafts acylation cascade process from trans-4-hydroxyproline and 2-formylbenzoic acids has been developed for the synthesis of pyrrolo[1,2-b]isoquinolin-10(5H)-ones. Compound 3h was identified as a new potent dual topoisomerase I/II inhibitor.

Studies on the phthalidation of heteroarenes: A facile preparation of 3-(heteroaryl)phthalides via triflic acid mediated phthalidation

A triflic acid mediated heteroarylation of phthalaldehydic acid in 1,2-dichloroethane at reflux temperature leads to the formation of 3-heteroarylphthalides. This method for the phthalidation of heteroarenes can be utilized for the successful preparation of mono-, bis- and tris- heteroarylphthalides. Georg Thieme Verlag Stuttgart. New York.