Related Experiment Video
Updated: Feb 6, 2026
08:12
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
10.6K
Tariquidar-Related Chalcones and Ketones as ABCG2 Modulators
Diana Peña-Solórzano1,2, Matthias Scholler2, Günther Bernhardt2
1Laboratorio de Síntesis Orgánica Sostenible, Departamento de Química, Universidad Nacional de Colombia-Sede Bogotá, 5997 Bogotá, Colombia.
ACS Medicinal Chemistry Letters
|August 22, 2018
Summary
Novel chalcone-based compounds effectively modulate ABCG2 transporters, showing promise for overcoming cancer drug resistance. These selective modulators offer new tools for studying ABCG2 function in cancer therapy.
Area of Science:
- Biochemistry
- Pharmacology
- Medicinal Chemistry
Background:
- ATP-binding cassette (ABC) transporters, such as ABCG2, are crucial for xenobiotic defense but contribute to cancer multidrug resistance.
- Existing ABCG2 modulators, like tariquidar analogues, face limitations due to hydrolysis, hindering their clinical application.
Purpose of the Study:
- To design and synthesize novel chalcone- and ketone-based compounds as selective ABCG2 modulators.
- To evaluate the synthesized compounds for their ABCG2 modulatory activity and selectivity against other ABC transporters (ABCB1, ABCC1).
Main Methods:
- Synthesis of novel chalcone- and ketone-based compounds inspired by tariquidar analogues.
- Characterization of synthesized compounds.
- Evaluation of ABCG2 modulatory activity and selectivity across ABCB1 and ABCC1 transporters.
Main Results:
- Chalcone-based compounds demonstrated selectivity for ABCG2 over ABCB1 and ABCC1.
- Chalcone compound 16d (UR-DP48) exhibited comparable maximal effects to fumitremorgin C and marked antiproliferative activity.
- Ketone-based compound 17f showed less pronounced cytotoxicity.
Conclusions:
- Chalcone-containing tariquidar analogues are promising selective modulators for ABCG2.
- These novel compounds can aid in functional investigations of ABCG2 transporters and potentially overcome cancer drug resistance.
Related Concept Videos
01:04Structures of Aldehydes and Ketones
12.2K
Vanillin—a flavoring agent in vanilla, cinnamaldehyde—a molecule responsible for the distinct smell of cinnamon, and acetone—a strong-smelling ingredient in nail polish removers, all belong to a class of carbonyl compounds called aldehydes and ketones (Figure 1). Although both aldehydes and ketones contain the characteristic carbonyl (C=O) bond, their chemical structures vary with respect to the groups directly attached to the carbonyl carbon.
In aldehydes (Figures 1a and 1b), the...
In aldehydes (Figures 1a and 1b), the...
12.2K
01:09IUPAC Nomenclature of Ketones
7.7K
Like aldehydes, ketones are named using IUPAC rules; in this case, by replacing “e” in the name of the longest hydrocarbon chain with “one.” In acyclic ketones, the ketonic carbon is given the lowest locant value. For instance, as shown below, a simple five-carbon ketone is named pentan-2-one, instead of pentan-4-one. IUPAC rules also allow the placing of the locant value before the parent name to give an alternate name, 2-pentanone.
7.7K
01:11Common Names of Aldehydes and Ketones
5.0K
Some common aldehydes and ketones are popularly known by their common names used historically and predate the IUPAC nomenclature.
Common names of aldehydes are derived from the names of their corresponding acid. For instance, the two-carbon aldehyde–acetaldehyde derives its name from the corresponding acid–acetic acid. Similarly, formaldehyde derives its name from formic acid and benzaldehyde from benzoic acid.
Aliphatic ketones are named by suffixing the word “ketone” to the...
Common names of aldehydes are derived from the names of their corresponding acid. For instance, the two-carbon aldehyde–acetaldehyde derives its name from the corresponding acid–acetic acid. Similarly, formaldehyde derives its name from formic acid and benzaldehyde from benzoic acid.
Aliphatic ketones are named by suffixing the word “ketone” to the...
5.0K
00:57Nitriles to Ketones: Grignard Reaction
6.2K
Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the Grignard...
The mechanism begins with a nucleophilic attack by the Grignard...
6.2K
01:23Protecting Groups for Aldehydes and Ketones: Introduction
9.0K
Protecting groups are compounds that can bind to a specific functional group in the presence of other functional groups to protect them from undesired chemical reactions. These compounds can selectively bind to particular functional groups and advance chemoselective reactions in polyfunctional systems (Figure 1). After the functional group has served its purpose, it is removed by reacting it with specific compounds.
9.0K
01:09Mass Spectrometry: Aldehyde and Ketone Fragmentation
4.9K
In mass spectrometry, the fragmentation of aliphatic aldehydes and ketones generally occurs through three key mechanisms: α-cleavage, inductive cleavage, and the McLafferty rearrangement.
4.9K