21753-16-2

Usage

Uses

Used in Pharmaceutical Synthesis:
5-(1H-indol-3-ylmethyl)imidazolidine-2,4-dione is utilized as a key building block for the creation of various pharmaceuticals and bioactive compounds. Its diverse reactivity and pharmacological properties contribute to the development of new drugs with potential therapeutic applications.
Used in Antiepileptic Applications:
In the field of medicinal chemistry, 5-(1H-indol-3-ylmethyl)imidazolidine-2,4-dione is studied for its potential as an antiepileptic agent, highlighting its capacity to address neurological conditions through modulation of neurotransmitter receptors in the central nervous system.
Used in Antimicrobial Applications:
5-(1H-indol-3-ylmethyl)imidazolidine-2,4-dione is also being investigated for its antimicrobial properties, suggesting its use in combating microbial infections by disrupting essential cellular processes in bacteria or other microorganisms.
Used in Antitumor Applications:
5-(1H-indol-3-ylmethyl)imidazolidine-2,4-dione has shown promise in antitumor research, indicating its potential to be developed into an agent that can target and inhibit the growth of cancer cells, contributing to cancer treatment strategies.
Used in Neurotransmitter Receptor Modulation:
Due to its ability to modulate neurotransmitter receptors, 5-(1H-indol-3-ylmethyl)imidazolidine-2,4-dione is considered for applications in the treatment of central nervous system disorders, where receptor modulation can have therapeutic benefits.

Upstream product

• 117490-34-3 5-(3-indolylmethylene)hydantoin 
• 1118-02-1 trimethylsilyl isocyanate 
• 7303-49-3 DL-tryptophan methyl ester 
• 2290-65-5 trimethylsilyl isothiocyanate 

Downstream Products

• 54-12-6 Trp 
• 69243-99-8 5-indol-3-ylmethyl-3-[3-(4-phenyl-piperidin-1-yl)-propyl]-imidazolidine-2,4-dione 
• 73-22-3 L-Tryptophan 

Relevant academic research and scientific papers

The indole-hydantoin derivative exhibits anti-inflammatory activity by preventing the transactivation of NF-κB through the inhibition of NF-κB p65 phosphorylation at Ser276

Indole- and hydantoin-based derivatives both exhibit anti-inflammatory activity, suggesting that the structures of indole and hydantoin are functional for this activity. In the present study, we synthesized two types of indole-hydantoin derivatives, IH-1 (5-(1H-indole-3-ylmethylene) imidazolidine-2,4-dione) and IH-2 (5-(1H-indole-3-ylmethyl) imidazolidine-2,4-dione) and examined their effects on LPS-induced inflammatory responses in murine macrophage-like RAW264.7 cells. LPS-induced inflammatory responses were not affected by indole, hydantoin, or IH-2. In contrast, IH-1 significantly inhibited the LPS-induced production of nitric oxide (NO) and secretion of CCL2 and CXCL1 by suppressing the mRNA expression of inducible NO synthase (iNOS), CCL2, and CXCL1. IH-1 markedly inhibited the LPS-induced activation of NF-κB without affecting the degradation of IκBα or nuclear translocation of NF-κB. IH-1 markedly attenuated the transcriptional activity of NF-κB by suppressing the LPS-induced phosphorylation of the NF-κB p65 subunit at Ser276. Furthermore, IH-1 prevented the LPS-induced interaction of NF-κB p65 subunit with a transcriptional coactivator, cAMP response element-binding protein (CBP). Collectively, these results revealed the potential of the novel indole-hydantoin derivative, IH-1 as an anti-inflammatory drug.

Structure-activity relationship study of novel necroptosis inhibitors

Necroptosis is a regulated caspase-independent cell death mechanism that results in morphological features resembling necrosis. It can be induced in a FADD-deficient variant of human Jurkat T cells treated with TNF-α. 5-(1H-Indol-3-ylmethyl)-2-thiohydantoins and 5-(1H-indol-3-ylmethyl)hydantoins were found to be potent necroptosis inhibitors (called necrostatins). A SAR study revealed that several positions of the indole were intolerant of substitution, while small substituents at the 7-position resulted in increased inhibitory activity. The hydantoin ring was also quite sensitive to structural modifications. A representative member of this compound class demonstrated moderate pharmacokinetic characteristics and readily entered the central nervous system upon intravenous administration.

Inhibitors of cellular necrosis

The present invention relates to compounds and pharmaceutical preparations and their use in therapy for preventing or treating trauma, ischemia, stroke and degenerative diseases associated with cell death. Methods and compositions of the invention are particularly useful for treating neurological disorders associated with cellular necrosis.