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6-Bromoisatin, also known as 2-bromoindole-3-carboxaldehyde, is a chemical compound with the molecular formula C8H6BrNO. It is a brominated derivative of isatin, a naturally occurring compound found in various plants. 6-Bromoisatin is recognized for its potential pharmacological properties, including anti-cancer and anti-inflammatory activities, and has been studied for its use in the synthesis of pharmaceutical drugs and organic compounds. Furthermore, it has been explored as a fluorescent probe in biological and cellular imaging studies, making it a versatile and important chemical compound with various potential applications in the fields of medicine, pharmacology, and chemical synthesis.

77603-45-3

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77603-45-3 Usage

Uses

Used in Pharmaceutical Synthesis:
6-Bromoisatin is used as a key intermediate in the synthesis of pharmaceutical drugs and organic compounds. Its unique chemical structure allows for the development of new drugs with potential therapeutic benefits.
Used in Cancer Research:
6-Bromoisatin is used as an anti-cancer agent in cancer research. Its potential pharmacological properties have been studied for their ability to inhibit the growth and proliferation of cancer cells, making it a promising candidate for the development of new cancer treatments.
Used in Inflammation Management:
6-Bromoisatin is used as an anti-inflammatory agent in the study of inflammation management. Its potential to modulate inflammatory pathways and reduce inflammation-related symptoms makes it a valuable compound for the development of new anti-inflammatory drugs.
Used in Biological and Cellular Imaging:
6-Bromoisatin is used as a fluorescent probe in biological and cellular imaging studies. Its fluorescent properties allow researchers to visualize cellular structures and processes, contributing to a better understanding of cell biology and the development of new diagnostic tools.
Used in Drug Delivery Systems:
6-Bromoisatin is used in the development of drug delivery systems to improve the bioavailability and therapeutic outcomes of drugs. Its chemical properties can be utilized to enhance the delivery of pharmaceutical compounds to target tissues, increasing their efficacy and reducing side effects.

Check Digit Verification of cas no

The CAS Registry Mumber 77603-45-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,7,6,0 and 3 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 77603-45:
(7*7)+(6*7)+(5*6)+(4*0)+(3*3)+(2*4)+(1*5)=143
143 % 10 = 3
So 77603-45-3 is a valid CAS Registry Number.

77603-45-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-Bromo-1H-benzo[d][1,3]oxazine-2,4-dione

1.2 Other means of identification

Product number -
Other names 6-BROMOISATIN

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:77603-45-3 SDS

77603-45-3Relevant academic research and scientific papers

QUINAZOLINONE HSD17B13 INHIBITORS AND USES THEREOF

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Paragraph 00147-00148; 00168; 00179, (2022/02/05)

Described herein are HSD17B13 inhibitors and pharmaceutical compositions comprising said inhibitors. The subject compounds and compositions are useful for the treatment of liver disease, metabolic disease, or cardiovascular disease, such as NAFLD or NASH,

Synthesis and Nematicidal Activities of 1,2,3-Benzotriazin-4-one Derivatives against Meloidogyne incognita

Wang, Gaolei,Chen, Xiulei,Deng, Yayun,Li, Zhong,Xu, Xiaoyong

, p. 6883 - 6889 (2015/08/18)

A series of novel 1,2,3-benzotriazin-4-one derivatives were synthesized by the reaction of 3-bromoalkyl-1,2,3-benzotriazin-4-ones with potassium salt of 2-cyanoimino-4-oxothiazolidine in the presence of potassium iodide. Nematicidal assays in vivo showed that some of them exhibited good control efficacy against the cucumber root-knot nematode disease caused by Meloidogyne incognita, up to 100% at the concentration of 10.0 mg L-1, which indicated that 1,2,3-benzotriazin-4-one derivatives might be potential for novel promising nematicides. The nematicidal activity was influenced by the combination of substituent type, substituted position, and linker length in the molecule. The inhibition rate data at the concentrations of 5.0 and 1.0 mg L-1 for the compounds with high inhibitory activities were also provided. When tested in vitro, none of them showed direct inhibition against M. incognita. The investigation of a significant difference between in vivo and in vitro data is in progress.

Recyclable (PhSe)2-catalyzed selective oxidation of isatin by H2O2: a practical and waste-free access to isatoic anhydride under mild and neutral conditions

Yu, Lei,Ye, Jianqing,Zhang, Xu,Ding, Yuanhua,Xu, Qing

, p. 4830 - 4838 (2015/10/05)

After a series of careful conditional optimizations and catalyst screenings, a methodology to prepare isatoic anhydrides through organoselenium-catalyzed selective oxidation of isatins by H2O2 under mild and neutral conditions was developed. The reactions were very practical because of the recyclability of the catalyst and solvent and the convenient isolation procedures of the products. This work reports the organoselenium-catalyzed oxidation of heterocycles that greatly expands the application scopes of organoselenium catalysis. It also indicates that the organoselenium catalysts are robust enough to be recycled in industrial production if suitable isolation procedures are developed.

A phosgene and peroxide-free one-pot tandem synthesis of isatoic anhydrides involving anthranilic acid, boc anhydride and 2-chloro-N-methyl pyridinium iodide

Verma, Chhaya,Sharma, Somesh,Pathak, Arunendra

supporting information, p. 6897 - 6899 (2019/04/10)

A phosgene and peroxide-free approach for the synthesis of isatoic anhydrides has been described. The synthesis involves the carbamate formation with boc anhydride followed by in situ cyclization to afford the isatoic anhydride. The importance of this synthetic strategy is in the ease of operation, scalability and preparation from readily available raw materials.

Is the 2,3-carbon-carbon bond of indole really inert to oxidative cleavage by Oxone?-Synthesis of isatoic anhydrides from indoles

Nelson, Amber C.,Kalinowski, Emily S.,Czerniecki, Nikolas J.,Jacobson, Taylor L.,Grundt, Peter

supporting information, p. 7455 - 7457 (2013/11/06)

A recent report has indicated that the oxidizing agent Oxone does not possess the ability to cleave the 2,3-carbon-carbon bond of indole. Work in our laboratory shows that this is not the case. Indole and a variety of aryl ring substituted derivatives readily react to form synthetically important isatoic anhydrides.

Synthesis of 123I-labelled analogues of imidazobenzodiazepine receptor ligands

Katsifis, Andrew G.,McPhee, Meredith E.,Mattner, Filomena,Ridley, Damon D.

, p. 1061 - 1069 (2007/10/03)

Reaction of bromo- or iodo-substituted isatoic anhydrides with N-methylglycine, L-proline or D-proline afforded bromo- or iodo-substituted 1,4-benzodiazepinediones which on condensation with ethyl or t-butyl isocyanoacetates gave ethyl or t-butyl bromo- or iodo-imidazobenzodiazepine carboxylates. These aryl halides were converted into the corresponding tributylstannanes with bis(tributyltin) in the presence of (triphenylphosphine)palladium(0), and the stannanes were treated with sodium (123I)iodide in the presence of chloramine-T to give the required 123I-labelled analogues of the imidazobenzodiazepine receptor ligands flumazenil and bretazenil.

Pyridazinedione compounds useful in treating neurological disorders

-

, (2008/06/13)

The present invention relates to pyridazino[4,5-b]quinolines, and pharmaceutically useful salts thereof, which are excitatory amino acid antagonists and which are useful when such antagonism is desired such as in the treatment of neurological disorders. The invention further provides pharmaceutical compositions containing pyridazino[4,5-b]quinolines as active ingredient, and methods for the treatment of neurological disorders.

Glycine receptor antagonist pharmacophore

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, (2008/06/13)

Methods of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neurodegenerative diseases including Alzheimer''s disease, amyotrophic lateral sclerosis, Huntington''s disease and Down''s syndrome, treating or preventing the adverse consequences of the hyperactivity of the excitatory amino acids, as well as treating anxiety, chronic pain, convulsions and inducing anesthesia are disclosed by administering to an animal in need of such treatment a compound which has high binding to the glycine receptor.

Synthesis of iodine-123 labelled analogues of the partial agonist (S)- and (R)-bretazenil for the study of CNS benzodiazepine receptors using SPECT

Katsifis, Andrew,Mattner, Filomena,McPhee, Meredith,Kassiou, Michael,Najdovski, Ljubco,Dikic, Branko

, p. 835 - 845 (2007/10/03)

The (S) and (R)-[123I]iodinated analogues of the benzodiazepine receptor partial agonist bretazenil have been synthesised for study of the central benzodiazepine receptor using SPECT. (S)- and (R)-[123I]iodobretazenil were prepared from the appropriate tin precursors by electrophilic iododestannylation with Na[123I] in the presence of Chloramine-T. The products were purified by semi-preparative reverse-phase HPLC with radiochemical yields of 80% in a total synthesis time of 50 minutes. The specific activity was determined to be greater than 2500 Ci/mmol. The radiochemical and chemical purity assessed by radio-TLC and HPLC were found to be 98%. The enantiomeric purity of the (S) and (R) isomers were greater than 97% as assessed by analytical chiral HPLC analysis.

Tricyclic heterocyclic compounds as psychopharmaceuticals

-

, (2008/06/13)

New heterocyclic compounds having the general formula STR1 wherein STR2 CO2 R' or CONR'R", wherein R' and R" independently are C1-6 -alkyl, C3-7 -cycloalkyl or C1-6 -alkoxymethyl; --A-- is --C(=O)--NR'"--, --NR'"--C(=O)--, or STR3 wherein R'" is C1-6 -alkyl; X is C or N; and R4 is hydrogen, halogen, CN, C1-6 -alkyl, C1-6 -alkynyl, trimethylsilyl-C1-6 -alkynyl, aryloxy which may be substituted with halogen, aralkoxy, C3-7 -cycloalkoxy which may be substituted with one or more C1-6 -alkyl groups, or NR""R'"", wherein R"" and R'"" independently are C1-6 -alkoxy or together with the nitrogen atom form a 3-7 membered heterocyclic ring. The compounds are useful in psychopharmaceutical preparations as anticonvulsants, anxiolytics, hypnotics, and nootropics.

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