81575-48-6

Usage

Structure

2,5-Cyclohexadiene-1,4-dione core with various substituents

Derivative

2,5-Cyclohexadiene-1,4-dione

Bromodecyl group

A ten-carbon aliphatic chain with a bromine atom attached

Dimethoxy groups

Two methoxy groups (-OCH3) attached to the aromatic ring

Methyl group

A single carbon atom with three hydrogen atoms attached (-CH3) as a substituent

Potential applications

Organic synthesis and medicinal chemistry

Unique structure

The combination of bromodecyl, dimethoxy, and methyl groups with the 2,5-cyclohexadiene-1,4-dione core

Possible uses

Development of new drugs or creation of novel materials with specialized properties

Further research

Necessary to fully understand the potential uses and properties of the compound

Upstream product

• 605-94-7 2,3-Dimethoxy-5-methyl-1,4-benzoquinone 
• 82413-47-6 11-bromoperoxyundecanoic acid 
• 2834-05-1 11-bromoundecanoic acid 
• 15949-84-5 11-bromoundecanoyl chloride 

Downstream Products

• 336184-90-8 C₁₉H₃₁BrO₄ 
• 1594439-30-1 6,6'-(10,10'-(piperazine-1,4-diyl)bis(decane-10,1-diyl))bis(2,3-dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione) 
• 1594439-34-5 6,6'-(10,10'-(1,4-diazepane-1,4-diyl)bis(decane-10,1-diyl))bis(2,3-dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione) 
• 1594439-40-3 2-(10-(4-(biphenylcarbonyl)-1,4-diazepan-1-yl)decyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione 
• 1608464-07-8 2-(10-(4-((S)-3-(2-((S)-3-(biphenyl-4-yl)-2-hydroxypropoxy)ethoxy)-2-hydroxypropyl)-1H-1,2,3-triazol-1-yl)decyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione 
• 1319741-67-7 6-(10-thioacetyldecyl)-ubiquinone 
• 1319741-66-6 2,3,4,5-tetramethoxy-6-(10-thioacetyldecyl)-toluene 
• 1319741-65-5 2,3,4,5-tetramethoxy-6-(10-bromodecyl)-toluene 
• 1309779-63-2 Bis-6-(10-mercaptodecyl)-bisubiquinone 

Relevant academic research and scientific papers

Identification of novel bivalent mimetics of annonaceous acetogenins via a scaffold-hopping strategy

A series of novel bivalent mimetics of annonaceous acetogenins have been designed, synthesized, and evaluated. Among these, compound 7 bearing a homopiperazine ring in the middle region exhibited more potent growth inhibitory activity and higher selectivity against cancer cells over normal cells by comparison with AA005. This work indicates that modification of the middle piperazine ring is a useful optimizing tool for the simplified acetogenin mimetics.

Biological evaluation of new mimetics of annonaceous acetogenins: Alteration of right scaffold by click linkage with aromatic functionalities

A small library of analogues of annonaceous acetogenins through click linkage with aromatic moieties is established using a convergent modular fragment-assembly approach. These analogues exhibited low micromolar inhibitory activities against the proliferation of several human cancer cell lines. Structure-activity relationship (SAR) of these analogues indicates that replacement of the methoxy groups of ubiquinone ring with methyl groups is proved to be a useful strategy for improving the anticancer activity of quinone-acetogenin hybrids.

In situ spectroeletrochemistry and cytotoxic activities of natural ubiquinone analogues

Quinones are a group of potent antineoplastic agents. Here we described effective and facile routes to synthesize a series of ubiquinone analogues (UQAs). These unique compounds have been investigated by electrochemistry and in situ UV-vis spectroelectrochemistry to explore their electron-transfer processes and radical properties in aprotic media. The structure-activities relationships of inhibiting cancer cell proliferation of UQAs were examined in murine melanoma B16F10 cells using a 72 h continuous exposure MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Our results revealed that UQAs had improved antiproliferative activity and displayed better inhibitory effects than natural ubiquinone 10. The cytotoxic activities of UQAs were correlated to the semiubiquinone radicals, which were confirmed by in situ electron spin resonance (ESR). In the cytotoxicity test, 6-vinylubiquinone 5 and 6-(4′-fluorophenyl) ubiquinone 7 that possess half maximal inhibitory concentration value (IC50) of 6.1 μM and 6.2 μM. This would make them as valuable candidates for future pharmacological studies.

Reversible redox of NADH and NAD+ at a hybrid lipid bilayer membrane using ubiquinone

Here, we report the reversible interconversion between NADH and NAD + at a low overpotential, which is in part mediated by ubiquinone embedded in a biomimetic membrane to mimic the initial stages of respiration. This system can be used as a platform to examine biologically relevant electroactive molecules embedded in a natural membrane environment and provide new insights into the mechanism of biological redox cycling.

Synthesis and characterization of mitoQ and idebenone analogues as mediators of oxygen consumption in mitochondria

Analogues of mitoQ and idebenone were synthesized to define the structural elements that support oxygen consumption in the mitochondrial respiratory chain. Eight analogues were prepared and fully characterized, then evaluated for their ability to support oxygen consumption in the mitochondrial respiratory chain. While oxygen consumption was strongly inhibited by mitoQ analogues 2-4 in a chain length-dependent manner, modification of idebenone by replacement of the quinone methoxy groups by methyl groups (analogues 6-8) reduced, but did not eliminate, oxygen consumption. Idebenone analogues 6-8 also displayed significant cytoprotective properties toward cultured mammalian cells in which glutathione had been depleted by treatment with diethyl maleate.

METHODS FOR REDUCING ANTHRACYCLINE-INDUCED TOXICITY

Methods for treating cancers/tumors, including administering to a subject an effective amount of a mitochondria-targeted antioxidant alone or in combination with a chemotherapeutic agents. Likewise, methods for mitigating toxicity associated with a chemot