23994-65-2

Usage

Uses

Used in Pharmaceutical Synthesis:
5-(2-Thienyl)-1,3-cyclohexanedione is utilized as a key intermediate in the synthesis of various pharmaceuticals due to its unique structure and reactivity. It plays a crucial role in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Synthesis:
In the agrochemical industry, 5-(2-Thienyl)-1,3-cyclohexanedione is employed as a precursor in the production of various agrochemicals. Its properties make it suitable for the creation of compounds that can be used in agricultural applications to protect crops and enhance yields.
Used in Organic Synthesis:
5-(2-Thienyl)-1,3-cyclohexanedione is used as a versatile building block in organic synthesis. Its ability to participate in various chemical reactions makes it an important component in the creation of complex organic molecules and materials.
Used in Biological Research:
5-(2-Thienyl)-1,3-cyclohexanedione is studied for its potential biological activities, such as anti-inflammatory and antioxidant properties. This research is valuable for understanding its therapeutic potential and for developing new treatments based on its pharmacological effects.
Used in Material Science:
5-(2-Thienyl)-1,3-cyclohexanedione's structural features and reactivity also make it a candidate for use in material science, where it could contribute to the development of new materials with specific properties for various applications.

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 874-83-9 2-thenylideneacetone 
• 105-53-3 diethyl malonate 
• 874-83-9 (E)-4-(2-thienyl)but-3-en-2-one 
• 71637-34-8 3-hydroxymethyl-thiophene 

Downstream Products

• 21403-77-0 2-acetyl-5-(thiophen-2-yl)cyclohexane-1,3-dione 
• 1625672-21-0 1-((4-cyanophenyl)(2-hydroxy-6-oxo-4-(thiophen-2-yl)cyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea 

Relevant academic research and scientific papers

Inhibition of Autophagy by a Small Molecule through Covalent Modification of the LC3 Protein

The autophagic ubiquitin-like protein LC3 functions through interactions with LC3-interaction regions (LIRs) of other autophagy proteins, including autophagy receptors, which stands out as a promising protein–protein interaction (PPI) target for the intervention of autophagy. Post-translational modifications like acetylation of Lys49 on the LIR-interacting surface could disrupt the interaction, offering an opportunity to design covalent small molecules interfering with the interface. Through screening covalent compounds, we discovered a small molecule modulator of LC3A/B that covalently modifies LC3A/B protein at Lys49. Activity-based protein profiling (ABPP) based evaluations reveal that a derivative molecule DC-LC3in-D5 exhibits a potent covalent reactivity and selectivity to LC3A/B in HeLa cells. DC-LC3in-D5 compromises LC3B lipidation in vitro and in HeLa cells, leading to deficiency in the formation of autophagic structures and autophagic substrate degradation. DC-LC3in-D5 could serve as a powerful tool for autophagy research as well as for therapeutic interventions.

New Insight into the Structure-Activity Relationships of the Selective Excitatory Amino Acid Transporter Subtype 1 (EAAT1) Inhibitors UCPH-101 and UCPH-102

In the present study, we made further investigations on the structure-activity requirements of the selective excitatory amino acid transporter 1 (EAAT1) inhibitor, 2-amino-4-(4-methoxyphenyl)-7-(naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile (UCPH-101), by exploring 15 different substituents (R1) at the 7-position in combination with eight different substituents (R2) at the 4-position. Among the 63 new analogues synthesized, we identified a number of compounds that unexpectedly displayed inhibitory activities at EAAT1 in light of understanding the structure-activity relationship (SAR) of this inhibitor class extracted from previous studies. Moreover, the nature of the R1 and R2 substituents were observed to contribute to the functional properties of the various analogues in additive and non-additive ways. Finally, separation of the four stereoisomers of analogue 14 g (2-amino-4-([1,1′-biphenyl]-4-yl)-3-cyano-7-isopropyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene) was carried out, and in agreement with a study of a related scaffold, the R configuration at C4 was found to be mandatory for inhibitory activity, while both the C7 diastereomers were found to be active as EAAT1 inhibitors. A study of the stereochemical stability of the four pure stereoisomers 14 g-A-D showed that epimerization takes places at C7 via a ring-opening, C-C bond rotation, ring-closing mechanism. Inhibition of glutamate uptake: 63 new analogues of the selective EAAT1 inhibitor UCPH-101 were synthesized and characterized pharmacologically. Analogues that unexpectedly displayed inhibitory activities at EAAT1 were identified. Furthermore, separation of the four stereoisomers of analogue 14 g revealed that, in agreement with a study of a related scaffold, the R configuration at C4 is mandatory for inhibitory activity, whereas both C7 diastereomers are active as EAAT1 inhibitors.

COMPOUNDS AND METHODS FOR ALTERING LIFESPAN OF EUKARYOTIC ORGANISMS

Provided are compounds which generally have a triketone structure. Examples of the compounds include derivatives of 1,3-cyclohexanedione, such as: 1,3-cyclohexanedione, 2-propanoyl-5-cyclohexyl-; 1,3-cyclohexanedione, 2-propanoyl-5-[4-fluorophenyl]-; 1,3-cyclohexanedione, 2-acetyl-5-[thien-2-yl]-; 1,3-cyclohexanedione, 2-acetyl-5 -butyl-; and 1,3-cyclohexanedione, 2-propanoyl-5-[bicyclo[2.2.1]hept-2-en-5-yl]-. The compounds can be used to alter the lifespan of eukaryotic organisms and treat inflammation.

PROCESS FOR THE PRODUCTION OF OPTICALLY ACTIVE CYCLIC ENAMINONE DERIVATIVES

A process for the production of optically active cyclic enaminone derivatives characterized by aminating one of the carbonyl groups of a cyclic 1,3-diketone derivative having a symmetry plane to obtain an optically isomeric mixture of chiral cyclic enamin