4,10-Dibromoanthanthrone - 4378-61-4

4,10-Dibromoanthanthrone

Catalog Number: EVT-314421
CAS Number: 4378-61-4
Molecular Formula: C22H8Br2O2
Molecular Weight: 464.1 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
4,10-Dibromoanthanthrone (DBAA) is a synthetic organic compound that belongs to the family of anthraquinone derivatives. It is a yellow crystalline powder that is insoluble in water but soluble in organic solvents such as chloroform, benzene, and toluene. DBAA has been used in various fields such as medical research, environmental research, and industrial research due to its unique chemical structure and biological activity.
Applications in Various Fields
4,10-Dibromoanthanthrone has been used in various fields such as medical research, environmental research, and industrial research. In medical research, 4,10-Dibromoanthanthrone has been studied for its potential role in drug development, particularly in the treatment of cancer and viral infections. Clinical trials have shown promising results in the use of 4,10-Dibromoanthanthrone as a chemotherapeutic agent. However, further studies are needed to determine its safety and efficacy in humans. In environmental research, 4,10-Dibromoanthanthrone has been studied for its effects on ecosystems and its role in pollution management. 4,10-Dibromoanthanthrone has been shown to have toxic effects on aquatic organisms, leading to concerns about its environmental impact. In industrial research, 4,10-Dibromoanthanthrone has been used in manufacturing processes to improve product quality and efficiency. Health and safety considerations should be taken into account when using 4,10-Dibromoanthanthrone in industrial settings.

Properties

CAS Number

4378-61-4

Product Name

4,10-Dibromoanthanthrone

IUPAC Name

9,18-dibromohexacyclo[11.7.1.14,20.02,11.03,8.017,21]docosa-1(21),2,4,6,8,10,13,15,17,19-decaene-12,22-dione

Molecular Formula

C22H8Br2O2

Molecular Weight

464.1 g/mol

InChI

InChI=1S/C22H8Br2O2/c23-15-7-14-19-17-9(15)3-1-5-11(17)21(25)13-8-16(24)10-4-2-6-12(22(14)26)18(10)20(13)19/h1-8H

InChI Key

HTENFZMEHKCNMD-UHFFFAOYSA-N

SMILES

C1=CC2=C(C=C3C4=C2C(=C1)C(=O)C5=CC(=C6C=CC=C(C6=C54)C3=O)Br)Br

Synonyms

4378-61-4; C.I. Vat Orange 3; Lionogen Red GD; Monolite Red 2Y; Lake Fast Red G; Helio Brilliant Orange RK

Canonical SMILES

C1=CC2=C(C=C3C4=C2C(=C1)C(=O)C5=CC(=C6C=CC=C(C6=C54)C3=O)Br)Br
Method of Synthesis or Extraction
4,10-Dibromoanthanthrone can be synthesized by several methods, including the oxidation of 4,10-dibromoanthracene with potassium permanganate, the bromination of anthanthrone with bromine, and the reaction of 4,10-dibromoanthrone with sodium hydroxide. The efficiency and yield of each method vary depending on the reaction conditions and the purity of the starting materials. However, the bromination of anthanthrone with bromine is the most commonly used method for the synthesis of 4,10-Dibromoanthanthrone due to its high yield and simplicity. Environmental and safety considerations should be taken into account during the synthesis process, as some of the reactants and by-products can be hazardous to human health and the environment.
Chemical Structure and Biological Activity
4,10-Dibromoanthanthrone has a unique chemical structure that consists of two bromine atoms attached to the anthanthrone skeleton. This structure confers 4,10-Dibromoanthanthrone with several biological activities, including antitumor, antiviral, and antibacterial properties. 4,10-Dibromoanthanthrone exerts its biological activity by inhibiting the activity of topoisomerase II, an enzyme that is essential for DNA replication and cell division. 4,10-Dibromoanthanthrone also induces apoptosis, a programmed cell death mechanism, in cancer cells by activating the caspase cascade.
Biological Effects
4,10-Dibromoanthanthrone has been shown to have a significant impact on cell function and signal transduction. It can induce cell cycle arrest and apoptosis in cancer cells, leading to the inhibition of tumor growth. 4,10-Dibromoanthanthrone also has potential therapeutic effects in the treatment of viral and bacterial infections. However, 4,10-Dibromoanthanthrone can also have toxic effects on normal cells, leading to adverse side effects such as nausea, vomiting, and bone marrow suppression. Therefore, careful consideration should be taken when using 4,10-Dibromoanthanthrone in medical research.
Future Perspectives and Challenges
Despite its potential applications, there are several limitations in the use and study of 4,10-Dibromoanthanthrone. One of the main challenges is its toxicity to normal cells, which limits its therapeutic potential. Another challenge is the lack of understanding of its mechanism of action and its interaction with other drugs. Future studies should focus on addressing these challenges and developing new strategies to improve the safety and efficacy of 4,10-Dibromoanthanthrone. In addition, the development of new synthetic methods and the optimization of existing methods can lead to improved yields and reduced environmental impact. Overall, 4,10-Dibromoanthanthrone has the potential to be a valuable tool in scientific research, but careful consideration should be taken to ensure its safe and effective use.

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