10258-18-1

Basic information

• Product Name: 4-Imidazolidinone, 5-(1H-indol-3-ylmethylene)-2-thioxo-
• Synonyms: 4-Imidazolidinone,5-(1H-indol-3-ylmethylene)-2-thioxo;5-(3'-indolal)-2-thiohydantoin;5-Indol-3-ylmethylen-2-thioxo-imidazolidin-4-on;5-(3-indolylmethylene)-2-thiohydantoin;5-indol-3-ylmethylene-2-thioxo-imidazolidin-4-one;(Z)-5-((1H-indol-3-yl)methylene)-2-thioxoimidazolidin-4-one;5-[(E)-1H-indol-3-ylmethylidene]-2-thioxotetrahydro-4H-imidazol-4-one;(5Z)-5-((1H-indol-3-yl)methylene)-2-thioxoimidazolidin-4-one
• CAS NO: 10258-18-1
• Molecular Formula: C12H9N3OS
• Molecular Weight: 243.28400
• Mol File: 10258-18-1.mol
• Article Data: 13

Chemical Properties

• Melting Point: 310-315 °C
• Density: 1.50±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 4-Imidazolidinone, 5-(1H-indol-3-ylmethylene)-2-thioxo-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Imidazolidinone, 5-(1H-indol-3-ylmethylene)-2-thioxo-(10258-18-1)
• EPA Substance Registry System: 4-Imidazolidinone, 5-(1H-indol-3-ylmethylene)-2-thioxo-(10258-18-1)

Safety Data

• Hazardous Substances Data: 10258-18-1(Hazardous Substances Data)

Upstream product

• 503-87-7 2-thiohydantoin 
• 487-89-8 Indole-3-carboxaldehyde 
• 6286-56-2 2-cyano-3-(2,3-dihydro-1H-indol-3-yl)acrilic acid ethyl ester 
• 120-72-9 indole 

Downstream Products

• 117490-34-3 5-(3-indolylmethylene)hydantoin 
• 1190367-67-9 C₁₉H₁₆N₄O 
• 1190367-68-0 C₂₁H₂₀N₄O₃ 
• 488829-41-0 5-[1-(1H-Indol-3-yl)-meth-(Z)-ylidene]-2-{[1-phenyl-meth-(E)-ylidene]-hydrazono}-imidazolidin-4-one 

Relevant articles and documents

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A convenient synthesis of glycosylated hydantoins as potential antiviral agents

Reaction of 5-arylidene-2-thiohydantoins 3a-d with glycosyl halides 4a,b under alkaline conditions gave the respective bisglycosylated derivatives 5a-h. Deacetylation with ammonia in methanol caused a change of the S-glycosyl residue and gave the N-3 glyc

In vitro structure-activity relationships of aplysinopsin analogs and their in vivo evaluation in the chick anxiety-depression model

Aplysinopsins are tryptophan-derived natural products that have been isolated from a variety of marine organisms and have been shown to possess a range of biological activities. In vitro receptor binding assays showed that of the 12 serotonin receptor subtypes, analogues showed a high affinity for the 5-HT2B and 5-HT2C receptor subtypes, with selectivity for 5-HT2B over 5-HT2C. While no conclusions could be drawn about the number and position of N-methylations, bromination at C-4 and C-5 of the indole ring resulted in greater binding affinities, with Ki's as low as 35 nM. This data, combined with previous knowledge of the CNS activity of aplysinopsin analogs, suggested that these compounds may have potential as leads for antidepressant drugs. Compounds 3c, 3u, and 3x were evaluated in the chick anxiety-depression model to assess their in vivo efficacy. Compound 3c showed a modest antidepressant effect at a dose of 30 nM/kg in the animal model.

Synthesis and evaluation of aplysinopsin analogs as inhibitors of human monoamine oxidase A and B

Aplysinopsins are tryptophan-derived natural products that have been isolated from a variety of marine organisms. Previous studies have shown aplysinopsin analogs to possess a variety of biological activities, including modulation of neurotransmissions. A series of fifty aplysinopsin analogs was synthesized and assayed for monoamine oxidase A and B inhibitory activity. Three compounds displayed significant MAO inhibitory activity and selectivity. The compound (E)-5-[(6-bromo-1H-indol-3-yl)methylene]-2-imino-1,3- dimethylimidazolidin-4-one (3x) possessed an IC50 of 5.6 nM at MAO-A and had a selectivity index of 80.24. An SAR study revealed that multiple N-methylations, one of which should be at position N-2′, and bromination at C-5 or C-6 are important factors for MAO-A potency and selectivity.